# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2017

####################################################################### 
# 
# 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_20161010-1
_database_code_depnum_ccdc_archive 'CCDC 1521255'
_audit_update_record             
;
2016-12-07 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 N2'
_chemical_formula_weight         350.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1532(5)
_cell_length_b                   10.2921(7)
_cell_length_c                   12.9838(11)
_cell_angle_alpha                66.763(7)
_cell_angle_beta                 88.564(6)
_cell_angle_gamma                73.285(6)
_cell_volume                     953.99(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2396
_cell_measurement_theta_min      3.7230
_cell_measurement_theta_max      72.0570
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.547
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.95928
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5962
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.812
_diffrn_reflns_theta_max         72.337
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3648
_reflns_number_gt                3028
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0639P)²+0.0745P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3648
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.08426(15) 0.28295(13) 0.10410(10) 0.0490(3) Uani 1 1 d . . . . .
C13 C 0.54951(16) 0.35383(14) -0.25686(12) 0.0453(3) Uani 1 1 d . . . . .
C19 C 0.43824(17) 0.31879(15) -0.32479(11) 0.0453(3) Uani 1 1 d . . . . .
C22 C 0.22905(18) 0.25626(15) -0.46011(11) 0.0468(3) Uani 1 1 d . . . . .
N25 N 0.12565(17) 0.22661(16) -0.52612(11) 0.0588(3) Uani 1 1 d . . . . .
C2 C 0.20022(18) 0.20365(15) 0.06184(11) 0.0481(3) Uani 1 1 d . . . . .
C18 C 0.53480(16) 0.32262(14) -0.14175(12) 0.0456(3) Uani 1 1 d . . . . .
C20 C 0.25970(18) 0.36104(16) -0.32714(12) 0.0488(3) Uani 1 1 d . . . . .
H20 H 0.2078 0.4107 -0.2829 0.059 Uiso 1 1 calc R U . . .
C12 C 0.41124(17) 0.24740(15) -0.08047(11) 0.0475(3) Uani 1 1 d . . . . .
H12 H 0.3891 0.1770 -0.1014 0.057 Uiso 1 1 calc R U . . .
C10 C -0.04682(18) 0.22930(16) 0.15228(11) 0.0473(3) Uani 1 1 d . . . . .
C5 C -0.05960(19) 0.09065(16) 0.16202(12) 0.0523(3) Uani 1 1 d . . . . .
C11 C 0.32903(18) 0.27295(16) 0.00274(12) 0.0512(3) Uani 1 1 d . . . . .
H11 H 0.3554 0.3404 0.0254 0.061 Uiso 1 1 calc R U . . .
C17 C 0.64290(19) 0.36144(17) -0.08465(13) 0.0529(3) Uani 1 1 d . . . . .
H17 H 0.6347 0.3399 -0.0084 0.063 Uiso 1 1 calc R U . . .
C23 C 0.40830(19) 0.21485(18) -0.45896(13) 0.0558(4) Uani 1 1 d . . . . .
H23 H 0.4606 0.1659 -0.5036 0.067 Uiso 1 1 calc R U . . .
C21 C 0.15721(17) 0.33171(16) -0.39301(12) 0.0496(3) Uani 1 1 d . . . . .
H21 H 0.0383 0.3627 -0.3927 0.060 Uiso 1 1 calc R U . . .
C14 C 0.67024(18) 0.42458(16) -0.30972(13) 0.0522(3) Uani 1 1 d . . . . .
H14 H 0.6804 0.4463 -0.3858 0.063 Uiso 1 1 calc R U . . .
C16 C 0.76184(19) 0.43112(18) -0.13870(14) 0.0558(4) Uani 1 1 d . . . . .
H16 H 0.8323 0.4563 -0.0992 0.067 Uiso 1 1 calc R U . . .
C4 C 0.0723(2) 0.00608(16) 0.12127(14) 0.0615(4) Uani 1 1 d . . . . .
H4 H 0.0723 -0.0877 0.1291 0.074 Uiso 1 1 calc R U . . .
C24 C 0.50905(18) 0.24530(18) -0.39280(13) 0.0544(3) Uani 1 1 d . . . . .
H24 H 0.6279 0.2158 -0.3937 0.065 Uiso 1 1 calc R U . . .
C9 C -0.1764(2) 0.31774(19) 0.19172(13) 0.0589(4) Uani 1 1 d . . . . .
H9 H -0.1690 0.4087 0.1863 0.071 Uiso 1 1 calc R U . . .
C6 C -0.2022(2) 0.0462(2) 0.20977(15) 0.0679(4) Uani 1 1 d . . . . .
H6 H -0.2121 -0.0445 0.2164 0.081 Uiso 1 1 calc R U . . .
C3 C 0.1992(2) 0.06198(16) 0.07065(14) 0.0586(4) Uani 1 1 d . . . . .
H3 H 0.2849 0.0078 0.0419 0.070 Uiso 1 1 calc R U . . .
C15 C 0.77491(19) 0.46301(17) -0.25188(14) 0.0565(4) Uani 1 1 d . . . . .
H15 H 0.8540 0.5103 -0.2890 0.068 Uiso 1 1 calc R U . . .
C8 C -0.3128(2) 0.2708(2) 0.23786(15) 0.0680(4) Uani 1 1 d . . . . .
H8 H -0.3973 0.3299 0.2637 0.082 Uiso 1 1 calc R U . . .
C27 C -0.0479(2) 0.2293(2) -0.49908(16) 0.0681(4) Uani 1 1 d . . . . .
H27A H -0.0450 0.1599 -0.4230 0.102 Uiso 1 1 calc R U . . .
H27B H -0.1015 0.2027 -0.5496 0.102 Uiso 1 1 calc R U . . .
H27C H -0.1125 0.3272 -0.5067 0.102 Uiso 1 1 calc R U . . .
C7 C -0.3255(2) 0.1345(2) 0.24629(15) 0.0730(5) Uani 1 1 d . . . . .
H7 H -0.4190 0.1038 0.2771 0.088 Uiso 1 1 calc R U . . .
C26 C 0.2062(3) 0.1333(2) -0.58313(18) 0.0793(5) Uani 1 1 d . . . . .
H26A H 0.2807 0.1781 -0.6342 0.119 Uiso 1 1 calc R U . . .
H26B H 0.1192 0.1218 -0.6244 0.119 Uiso 1 1 calc R U . . .
H26C H 0.2722 0.0378 -0.5287 0.119 Uiso 1 1 calc R U . . .


_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 C2 1.3208(18) . ?
N1 C10 1.3682(18) . ?
C13 C14 1.3979(19) . ?
C13 C18 1.4092(19) . ?
C13 C19 1.4868(18) . ?
C19 C24 1.3912(19) . ?
C19 C20 1.3916(19) . ?
C22 N25 1.3890(18) . ?
C22 C21 1.397(2) . ?
C22 C23 1.398(2) . ?
N25 C26 1.440(2) . ?
N25 C27 1.444(2) . ?
C2 C3 1.419(2) . ?
C2 C11 1.4694(19) . ?
C18 C17 1.3982(19) . ?
C18 C12 1.4730(18) . ?
C20 C21 1.3803(19) . ?
C12 C11 1.331(2) . ?
C10 C9 1.412(2) . ?
C10 C5 1.416(2) . ?
C5 C4 1.411(2) . ?
C5 C6 1.411(2) . ?
C17 C16 1.384(2) . ?
C23 C24 1.381(2) . ?
C14 C15 1.382(2) . ?
C16 C15 1.382(2) . ?
C4 C3 1.358(2) . ?
C9 C8 1.370(2) . ?
C6 C7 1.360(3) . ?
C8 C7 1.398(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
C2 N1 C10 118.23(12) . . ?
C14 C13 C18 118.45(12) . . ?
C14 C13 C19 118.89(12) . . ?
C18 C13 C19 122.62(12) . . ?
C24 C19 C20 116.51(12) . . ?
C24 C19 C13 120.88(12) . . ?
C20 C19 C13 122.58(12) . . ?
N25 C22 C21 121.03(13) . . ?
N25 C22 C23 121.99(13) . . ?
C21 C22 C23 116.97(12) . . ?
C22 N25 C26 118.83(13) . . ?
C22 N25 C27 118.98(12) . . ?
C26 N25 C27 116.52(14) . . ?
N1 C2 C3 122.48(13) . . ?
N1 C2 C11 115.63(12) . . ?
C3 C2 C11 121.89(13) . . ?
C17 C18 C13 118.87(12) . . ?
C17 C18 C12 119.73(12) . . ?
C13 C18 C12 121.39(12) . . ?
C21 C20 C19 122.14(12) . . ?
C11 C12 C18 124.70(13) . . ?
N1 C10 C9 118.34(13) . . ?
N1 C10 C5 122.77(13) . . ?
C9 C10 C5 118.87(14) . . ?
C4 C5 C6 124.10(15) . . ?
C4 C5 C10 117.00(13) . . ?
C6 C5 C10 118.90(15) . . ?
C12 C11 C2 125.57(13) . . ?
C16 C17 C18 121.66(14) . . ?
C24 C23 C22 121.19(13) . . ?
C20 C21 C22 121.14(13) . . ?
C15 C14 C13 121.73(14) . . ?
C15 C16 C17 119.41(13) . . ?
C3 C4 C5 119.83(14) . . ?
C23 C24 C19 122.04(13) . . ?
C8 C9 C10 120.61(16) . . ?
C7 C6 C5 120.79(16) . . ?
C4 C3 C2 119.56(14) . . ?
C14 C15 C16 119.88(13) . . ?
C9 C8 C7 120.23(16) . . ?
C6 C7 C8 120.59(16) . . ?

_refine_diff_density_max         0.132
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049

_shelxl_version_number           2014-1

