# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_MR-KG-N2
_database_code_depnum_ccdc_archive 'CCDC 1051021'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2'
_chemical_formula_sum            'C22 H18 N2'
_chemical_formula_weight         310.38

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                   8.440(2)
_cell_length_b                   9.676(2)
_cell_length_c                   10.316(3)
_cell_angle_alpha                75.506(9)
_cell_angle_beta                 87.977(11)
_cell_angle_gamma                79.212(9)
_cell_volume                     801.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1601
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      30.9

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9850
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724+'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5833
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.90
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2743
_reflns_number_gt                2673
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0'

_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)+(0.0678P)²+2.6699P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2743
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0876
_refine_ls_wR_factor_ref         0.2317
_refine_ls_wR_factor_gt          0.2310
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_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
C1 C 0.0644(4) -0.0502(4) 0.2236(3) 0.0219(8) Uani 1 1 d . . .
C2 C -0.0780(4) -0.0061(4) 0.2802(3) 0.0223(8) Uani 1 1 d . . .
C3 C 0.1783(4) 0.0513(4) 0.1700(4) 0.0222(8) Uani 1 1 d . . .
C4 C 0.2347(4) 0.0644(4) 0.0387(4) 0.0262(8) Uani 1 1 d . . .
H4 H 0.1966 0.0116 -0.0161 0.031 Uiso 1 1 calc R . .
C5 C 0.3444(5) 0.1527(4) -0.0121(4) 0.0298(9) Uani 1 1 d . . .
H5 H 0.3797 0.1615 -0.1018 0.036 Uiso 1 1 calc R . .
C6 C 0.4033(5) 0.2285(4) 0.0665(4) 0.0294(9) Uani 1 1 d . . .
H6 H 0.4799 0.2885 0.0319 0.035 Uiso 1 1 calc R . .
C7 C 0.3493(5) 0.2159(4) 0.1966(4) 0.0287(9) Uani 1 1 d . . .
H7 H 0.3897 0.2676 0.2513 0.034 Uiso 1 1 calc R . .
C8 C 0.2369(4) 0.1290(4) 0.2483(4) 0.0241(8) Uani 1 1 d . . .
H8 H 0.2001 0.1225 0.3373 0.029 Uiso 1 1 calc R . .
C9 C -0.1402(4) 0.1513(4) 0.2746(4) 0.0230(8) Uani 1 1 d . . .
C10 C -0.1621(5) 0.2574(4) 0.1548(4) 0.0269(8) Uani 1 1 d . . .
H10 H -0.1341 0.2319 0.0727 0.032 Uiso 1 1 calc R . .
C11 C -0.2246(5) 0.4003(4) 0.1544(4) 0.0333(9) Uani 1 1 d . . .
H11 H -0.2395 0.4720 0.0718 0.040 Uiso 1 1 calc R . .
C12 C -0.2656(5) 0.4402(5) 0.2724(4) 0.0350(10) Uani 1 1 d . . .
H12 H -0.3086 0.5386 0.2711 0.042 Uiso 1 1 calc R . .
C13 C -0.2439(5) 0.3373(5) 0.3909(5) 0.0382(10) Uani 1 1 d . . .
H13 H -0.2699 0.3642 0.4726 0.046 Uiso 1 1 calc R . .
C14 C -0.1841(5) 0.1940(4) 0.3924(4) 0.0303(9) Uani 1 1 d . . .
H14 H -0.1727 0.1229 0.4755 0.036 Uiso 1 1 calc R . .
C15 C 0.1265(4) -0.1992(4) 0.2124(4) 0.0229(8) Uani 1 1 d . . .
C16 C 0.2858(4) -0.2678(4) 0.2136(4) 0.0258(8) Uani 1 1 d . . .
H16 H 0.3773 -0.2260 0.2207 0.031 Uiso 1 1 calc R . .
C17 C 0.2889(5) -0.4093(4) 0.2027(4) 0.0292(9) Uani 1 1 d . . .
H17 H 0.3827 -0.4810 0.2024 0.035 Uiso 1 1 calc R . .
C18 C 0.1340(5) -0.4262(4) 0.1924(4) 0.0320(9) Uani 1 1 d . . .
H18 H 0.0998 -0.5114 0.1830 0.038 Uiso 1 1 calc R . .
C19 C -0.1840(4) -0.1044(4) 0.3510(4) 0.0235(8) Uani 1 1 d . . .
C20 C -0.3498(4) -0.0588(4) 0.3457(4) 0.0239(8) Uani 1 1 d . . .
H20 H -0.4030 0.0337 0.2959 0.029 Uiso 1 1 calc R . .
C21 C -0.4266(6) -0.1616(6) 0.4194(5) 0.0445(11) Uani 1 1 d . . .
H21 H -0.5399 -0.1529 0.4313 0.053 Uiso 1 1 calc R . .
C22 C -0.3159(8) -0.2773(6) 0.4725(5) 0.0558(16) Uani 1 1 d . . .
H22 H -0.3372 -0.3667 0.5267 0.067 Uiso 1 1 calc R . .
N1 N 0.0360(4) -0.2979(4) 0.1981(4) 0.0302(8) Uani 1 1 d . . .
N2 N -0.1496(7) -0.2435(5) 0.4326(4) 0.0572(12) Uani 1 1 d . . .
H1W H -0.066(7) -0.283(6) 0.196(5) 0.056(16) Uiso 1 1 d . . .
H2W H -0.019(9) -0.305(8) 0.468(8) 0.10(2) Uiso 1 1 d . . .


_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
C1 C2 1.361(5) . ?
C1 C15 1.470(5) . ?
C1 C3 1.496(5) . ?
C2 C19 1.471(5) . ?
C2 C9 1.502(5) . ?
C3 C8 1.390(5) . ?
C3 C4 1.403(5) . ?
C4 C5 1.379(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.388(5) . ?
C9 C14 1.396(5) . ?
C10 C11 1.383(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.363(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(6) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N1 1.367(5) . ?
C15 C16 1.383(5) . ?
C16 C17 1.397(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.359(6) . ?
C17 H17 0.9500 . ?
C18 N1 1.370(5) . ?
C18 H18 0.9500 . ?
C19 N2 1.381(5) . ?
C19 C20 1.385(5) . ?
C20 C21 1.348(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.328(8) . ?
C21 H21 0.9500 . ?
C22 N2 1.520(7) . ?
C22 H22 0.9500 . ?
N1 H1W 0.85(6) . ?
N2 H2W 1.17(8) . ?

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 C1 C15 125.2(3) . . ?
C2 C1 C3 121.9(3) . . ?
C15 C1 C3 112.8(3) . . ?
C1 C2 C19 124.3(3) . . ?
C1 C2 C9 121.6(3) . . ?
C19 C2 C9 114.1(3) . . ?
C8 C3 C4 118.2(3) . . ?
C8 C3 C1 122.1(3) . . ?
C4 C3 C1 119.6(3) . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 119.1(4) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C8 121.0(4) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C3 120.2(3) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
C10 C9 C14 117.8(3) . . ?
C10 C9 C2 122.4(3) . . ?
C14 C9 C2 119.8(3) . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 121.0(4) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 119.4(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.2(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 121.4(4) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
N1 C15 C16 106.1(3) . . ?
N1 C15 C1 126.2(3) . . ?
C16 C15 C1 127.7(3) . . ?
C15 C16 C17 108.3(3) . . ?
C15 C16 H16 125.9 . . ?
C17 C16 H16 125.9 . . ?
C18 C17 C16 107.8(3) . . ?
C18 C17 H17 126.1 . . ?
C16 C17 H17 126.1 . . ?
C17 C18 N1 107.5(3) . . ?
C17 C18 H18 126.3 . . ?
N1 C18 H18 126.3 . . ?
N2 C19 C20 108.3(4) . . ?
N2 C19 C2 131.4(4) . . ?
C20 C19 C2 120.2(3) . . ?
C21 C20 C19 111.8(4) . . ?
C21 C20 H20 124.1 . . ?
C19 C20 H20 124.1 . . ?
C22 C21 C20 107.8(4) . . ?
C22 C21 H21 126.1 . . ?
C20 C21 H21 126.1 . . ?
C21 C22 N2 109.0(4) . . ?
C21 C22 H22 125.5 . . ?
N2 C22 H22 125.5 . . ?
C15 N1 C18 110.3(3) . . ?
C15 N1 H1W 125(4) . . ?
C18 N1 H1W 125(4) . . ?
C19 N2 C22 102.9(4) . . ?
C19 N2 H2W 124(4) . . ?
C22 N2 H2W 133(4) . . ?

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
C15 C1 C2 C19 6.4(6) . . . . ?
C3 C1 C2 C19 -171.1(3) . . . . ?
C15 C1 C2 C9 -173.5(3) . . . . ?
C3 C1 C2 C9 8.9(5) . . . . ?
C2 C1 C3 C8 55.5(5) . . . . ?
C15 C1 C3 C8 -122.4(4) . . . . ?
C2 C1 C3 C4 -127.6(4) . . . . ?
C15 C1 C3 C4 54.5(4) . . . . ?
C8 C3 C4 C5 -0.5(5) . . . . ?
C1 C3 C4 C5 -177.5(3) . . . . ?
C3 C4 C5 C6 1.1(6) . . . . ?
C4 C5 C6 C7 -0.8(6) . . . . ?
C5 C6 C7 C8 -0.2(6) . . . . ?
C6 C7 C8 C3 0.8(5) . . . . ?
C4 C3 C8 C7 -0.5(5) . . . . ?
C1 C3 C8 C7 176.5(3) . . . . ?
C1 C2 C9 C10 55.5(5) . . . . ?
C19 C2 C9 C10 -124.5(4) . . . . ?
C1 C2 C9 C14 -127.1(4) . . . . ?
C19 C2 C9 C14 53.0(5) . . . . ?
C14 C9 C10 C11 0.4(5) . . . . ?
C2 C9 C10 C11 177.9(3) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 -1.2(6) . . . . ?
C12 C13 C14 C9 1.9(6) . . . . ?
C10 C9 C14 C13 -1.5(6) . . . . ?
C2 C9 C14 C13 -179.1(4) . . . . ?
C2 C1 C15 N1 31.4(6) . . . . ?
C3 C1 C15 N1 -150.8(4) . . . . ?
C2 C1 C15 C16 -148.8(4) . . . . ?
C3 C1 C15 C16 28.9(5) . . . . ?
N1 C15 C16 C17 -1.2(4) . . . . ?
C1 C15 C16 C17 179.0(4) . . . . ?
C15 C16 C17 C18 1.1(5) . . . . ?
C16 C17 C18 N1 -0.5(5) . . . . ?
C1 C2 C19 N2 36.0(6) . . . . ?
C9 C2 C19 N2 -144.1(4) . . . . ?
C1 C2 C19 C20 -146.7(4) . . . . ?
C9 C2 C19 C20 33.2(5) . . . . ?
N2 C19 C20 C21 -0.3(5) . . . . ?
C2 C19 C20 C21 -178.2(3) . . . . ?
C19 C20 C21 C22 -1.3(5) . . . . ?
C20 C21 C22 N2 2.2(5) . . . . ?
C16 C15 N1 C18 0.9(4) . . . . ?
C1 C15 N1 C18 -179.3(3) . . . . ?
C17 C18 N1 C15 -0.2(5) . . . . ?
C20 C19 N2 C22 1.5(4) . . . . ?
C2 C19 N2 C22 179.1(4) . . . . ?
C21 C22 N2 C19 -2.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         1.002
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.075
