# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_exp_5506
_database_code_depnum_ccdc_archive 'CCDC 1863990'
_audit_update_record             
;
2018-09-13 deposited with the CCDC.
2018-09-19 downloaded from the CCDC.
;
_audit_creation_date             2018-06-08
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H20 N2'
_chemical_formula_sum            'C20 H20 N2'
_chemical_formula_weight         288.38
_chemical_melting_point          ?
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.2034(5)
_cell_length_b                   10.7772(7)
_cell_length_c                   10.7933(7)
_cell_angle_alpha                103.292(6)
_cell_angle_beta                 93.266(5)
_cell_angle_gamma                105.419(6)
_cell_volume                     779.86(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2045
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1760
_cell_measurement_theta_min      3.7340
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5833
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.96
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.8281
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -47.00   45.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -77.0000    0.0000 92

#__ type_ start__ end____ width___ exp.time_
  2 omega   59.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335 -178.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -36.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -57.0000 -150.0000 69

#__ type_ start__ end____ width___ exp.time_
  4 omega   10.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   57.0000  -60.0000 67

#__ type_ start__ end____ width___ exp.time_
  5 omega   58.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  178.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   -8.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000  120.0000 93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0220436000
_diffrn_orient_matrix_UB_12      0.0490044000
_diffrn_orient_matrix_UB_13      0.0482745000
_diffrn_orient_matrix_UB_21      -0.0716182000
_diffrn_orient_matrix_UB_22      -0.0504299000
_diffrn_orient_matrix_UB_23      0.0170495000
_diffrn_orient_matrix_UB_31      0.0706143000
_diffrn_orient_matrix_UB_32      -0.0062932000
_diffrn_orient_matrix_UB_33      0.0448555000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2562
_reflns_number_total             3068
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3068
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0480P)²+0.2440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1132
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.15475(17) 0.64336(12) 0.76777(11) 0.0173(3) Uani 1 1 d . . .
N2 N 0.11922(19) 0.35535(13) 0.86060(13) 0.0239(3) Uani 1 1 d . . .
C16 C -0.0482(2) 0.76120(15) 0.68269(15) 0.0208(3) Uani 1 1 d . . .
H16 H -0.1060 0.7715 0.7578 0.025 Uiso 1 1 calc R . .
C7 C 0.6463(2) 0.88609(15) 1.16723(15) 0.0212(3) Uani 1 1 d . . .
H7 H 0.7667 0.8719 1.1558 0.025 Uiso 1 1 calc R . .
C20 C 0.1806(2) 0.68330(15) 0.55473(14) 0.0196(3) Uani 1 1 d . . .
H20 H 0.2764 0.6399 0.5435 0.023 Uiso 1 1 calc R . .
C3 C 0.3191(2) 0.86813(14) 1.07935(14) 0.0177(3) Uani 1 1 d . . .
C4 C 0.2857(2) 0.92450(15) 1.20274(14) 0.0205(3) Uani 1 1 d . . .
H4 H 0.1648 0.9371 1.2160 0.025 Uiso 1 1 calc R . .
C15 C 0.0957(2) 0.69448(14) 0.66938(14) 0.0173(3) Uani 1 1 d . . .
C8 C 0.5036(2) 0.84927(14) 1.06215(14) 0.0185(3) Uani 1 1 d . . .
C13 C 0.1730(2) 0.43460(15) 0.80583(14) 0.0186(3) Uani 1 1 d . . .
C9 C 0.5279(2) 0.78427(15) 0.93019(14) 0.0191(3) Uani 1 1 d . . .
H9 H 0.5395 0.8341 0.8697 0.023 Uiso 1 1 calc R . .
C12 C 0.2459(2) 0.53628(14) 0.73473(14) 0.0178(3) Uani 1 1 d . . .
H12 H 0.2054 0.4930 0.6433 0.021 Uiso 1 1 calc R . .
C1 C 0.0914(2) 0.67815(14) 0.89536(14) 0.0172(3) Uani 1 1 d . . .
H1A H 0.1378 0.6288 0.9488 0.021 Uiso 1 1 calc R . .
H1B H -0.0493 0.6491 0.8859 0.021 Uiso 1 1 calc R . .
C18 C -0.0194(2) 0.80030(16) 0.47136(15) 0.0242(4) Uani 1 1 d . . .
H18 H -0.0578 0.8350 0.4062 0.029 Uiso 1 1 calc R . .
C6 C 0.6101(2) 0.94375(15) 1.28862(15) 0.0227(3) Uani 1 1 d . . .
H6 H 0.7067 0.9700 1.3580 0.027 Uiso 1 1 calc R . .
C10 C 0.5343(2) 0.65901(15) 0.89216(14) 0.0186(3) Uani 1 1 d . . .
H10 H 0.5765 0.6191 0.9517 0.022 Uiso 1 1 calc R . .
C19 C 0.1241(2) 0.73587(15) 0.45813(15) 0.0218(3) Uani 1 1 d . . .
H19 H 0.1832 0.7279 0.3834 0.026 Uiso 1 1 calc R . .
C2 C 0.1614(2) 0.82868(15) 0.96630(14) 0.0192(3) Uani 1 1 d . . .
H2A H 0.2088 0.8786 0.9047 0.023 Uiso 1 1 calc R . .
H2B H 0.0502 0.8554 0.9967 0.023 Uiso 1 1 calc R . .
C11 C 0.4745(2) 0.58166(15) 0.75525(14) 0.0189(3) Uani 1 1 d . . .
H11 H 0.5191 0.6424 0.7010 0.023 Uiso 1 1 calc R . .
C5 C 0.4298(2) 0.96213(15) 1.30606(15) 0.0224(3) Uani 1 1 d . . .
H5 H 0.4050 1.0000 1.3876 0.027 Uiso 1 1 calc R . .
C17 C -0.1044(2) 0.81176(16) 0.58412(16) 0.0252(4) Uani 1 1 d . . .
H17 H -0.2013 0.8543 0.5939 0.030 Uiso 1 1 calc R . .
C14 C 0.5540(2) 0.46243(16) 0.71359(16) 0.0259(4) Uani 1 1 d . . .
H14A H 0.5281 0.4078 0.7730 0.039 Uiso 1 1 calc R . .
H14B H 0.6916 0.4934 0.7122 0.039 Uiso 1 1 calc R . .
H14C H 0.4924 0.4112 0.6293 0.039 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
N1 C15 1.3980(18) . ?
N1 C12 1.4598(18) . ?
N1 C1 1.4733(18) . ?
N2 C13 1.1452(19) . ?
C16 H16 0.9300 . ?
C16 C15 1.407(2) . ?
C16 C17 1.388(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.394(2) . ?
C7 C6 1.386(2) . ?
C20 H20 0.9300 . ?
C20 C15 1.406(2) . ?
C20 C19 1.385(2) . ?
C3 C4 1.394(2) . ?
C3 C8 1.413(2) . ?
C3 C2 1.519(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(2) . ?
C8 C9 1.478(2) . ?
C13 C12 1.480(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.332(2) . ?
C12 H12 0.9800 . ?
C12 C11 1.575(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.556(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(2) . ?
C18 C17 1.388(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.381(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.495(2) . ?
C19 H19 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C11 H11 0.9800 . ?
C11 C14 1.529(2) . ?
C5 H5 0.9300 . ?
C17 H17 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C15 N1 C12 118.34(12) . . ?
C15 N1 C1 120.00(12) . . ?
C12 N1 C1 120.57(11) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C17 C16 C15 120.28(14) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.48(14) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C19 C20 C15 121.15(14) . . ?
C4 C3 C8 118.30(13) . . ?
C4 C3 C2 120.78(13) . . ?
C8 C3 C2 120.92(13) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.04(14) . . ?
C5 C4 H4 119.5 . . ?
N1 C15 C16 121.10(13) . . ?
N1 C15 C20 121.22(13) . . ?
C20 C15 C16 117.67(13) . . ?
C7 C8 C3 120.01(14) . . ?
C7 C8 C9 124.10(13) . . ?
C3 C8 C9 115.83(13) . . ?
N2 C13 C12 178.94(15) . . ?
C8 C9 H9 117.8 . . ?
C10 C9 C8 124.30(13) . . ?
C10 C9 H9 117.8 . . ?
N1 C12 C13 110.33(12) . . ?
N1 C12 H12 107.1 . . ?
N1 C12 C11 115.28(12) . . ?
C13 C12 H12 107.1 . . ?
C13 C12 C11 109.51(12) . . ?
C11 C12 H12 107.1 . . ?
N1 C1 H1A 108.4 . . ?
N1 C1 H1B 108.4 . . ?
N1 C1 C2 115.30(11) . . ?
H1A C1 H1B 107.5 . . ?
C2 C1 H1A 108.4 . . ?
C2 C1 H1B 108.4 . . ?
C19 C18 H18 120.8 . . ?
C19 C18 C17 118.46(14) . . ?
C17 C18 H18 120.8 . . ?
C7 C6 H6 120.1 . . ?
C5 C6 C7 119.75(14) . . ?
C5 C6 H6 120.1 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 120.97(13) . . ?
C11 C10 H10 119.5 . . ?
C20 C19 C18 120.87(14) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C3 C2 C1 115.98(12) . . ?
C3 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
C1 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C12 C11 H11 107.9 . . ?
C10 C11 C12 106.54(11) . . ?
C10 C11 H11 107.9 . . ?
C10 C11 C14 115.50(13) . . ?
C14 C11 C12 110.78(12) . . ?
C14 C11 H11 107.9 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.41(15) . . ?
C6 C5 H5 119.8 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.56(14) . . ?
C18 C17 H17 119.2 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
N1 C12 C11 C10 55.50(15) . . . . ?
N1 C12 C11 C14 -178.13(12) . . . . ?
N1 C1 C2 C3 -107.39(14) . . . . ?
N2 C13 C12 N1 -157(9) . . . . ?
N2 C13 C12 C11 -29(9) . . . . ?
C7 C8 C9 C10 71.3(2) . . . . ?
C7 C6 C5 C4 -0.6(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C3 C8 C9 C10 -105.93(17) . . . . ?
C4 C3 C8 C7 0.3(2) . . . . ?
C4 C3 C8 C9 177.67(13) . . . . ?
C4 C3 C2 C1 -118.07(15) . . . . ?
C15 N1 C12 C13 -138.47(13) . . . . ?
C15 N1 C12 C11 96.86(15) . . . . ?
C15 N1 C1 C2 -62.43(17) . . . . ?
C15 C16 C17 C18 -1.1(2) . . . . ?
C15 C20 C19 C18 -0.5(2) . . . . ?
C8 C7 C6 C5 1.5(2) . . . . ?
C8 C3 C4 C5 0.5(2) . . . . ?
C8 C3 C2 C1 62.23(18) . . . . ?
C8 C9 C10 C11 153.46(14) . . . . ?
C13 C12 C11 C10 -69.59(15) . . . . ?
C13 C12 C11 C14 56.77(16) . . . . ?
C9 C10 C11 C12 -77.63(16) . . . . ?
C9 C10 C11 C14 158.89(14) . . . . ?
C12 N1 C15 C16 157.69(13) . . . . ?
C12 N1 C15 C20 -23.55(19) . . . . ?
C12 N1 C1 C2 129.75(13) . . . . ?
C1 N1 C15 C16 -10.4(2) . . . . ?
C1 N1 C15 C20 168.36(13) . . . . ?
C1 N1 C12 C13 29.54(17) . . . . ?
C1 N1 C12 C11 -95.13(15) . . . . ?
C6 C7 C8 C3 -1.3(2) . . . . ?
C6 C7 C8 C9 -178.41(14) . . . . ?
C19 C20 C15 N1 -178.96(13) . . . . ?
C19 C20 C15 C16 -0.2(2) . . . . ?
C19 C18 C17 C16 0.4(2) . . . . ?
C2 C3 C4 C5 -179.24(13) . . . . ?
C2 C3 C8 C7 -179.96(13) . . . . ?
C2 C3 C8 C9 -2.62(19) . . . . ?
C17 C16 C15 N1 179.75(13) . . . . ?
C17 C16 C15 C20 1.0(2) . . . . ?
C17 C18 C19 C20 0.4(2) . . . . ?

