# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_r150713e1
_database_code_depnum_ccdc_archive 'CCDC 1439492'
_audit_update_record             
;
2015-11-29 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 N2'
_chemical_formula_weight         332.39

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                   17.318(4)
_cell_length_b                   6.2349(12)
_cell_length_c                   7.3422(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.81(3)
_cell_angle_gamma                90.00
_cell_volume                     787.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    2459
_cell_measurement_theta_min      2.3688
_cell_measurement_theta_max      27.9785

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9837
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8756
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         27.95
_reflns_number_total             1882
_reflns_number_gt                1606
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.0714P)²+0.0918P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1882
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
N1 N 0.15627(5) 0.50136(15) 0.74732(12) 0.0165(2) Uani 1 1 d . . .
C1 C 0.08734(6) 0.43064(18) 0.67019(15) 0.0184(3) Uani 1 1 d . . .
H1 H 0.0489 0.5344 0.6298 0.022 Uiso 1 1 calc R . .
C2 C 0.06811(6) 0.21696(19) 0.64515(15) 0.0196(3) Uani 1 1 d . . .
H2 H 0.0181 0.1759 0.5888 0.023 Uiso 1 1 calc R . .
C3 C 0.12335(6) 0.06411(18) 0.70395(15) 0.0194(3) Uani 1 1 d . . .
H3 H 0.1121 -0.0845 0.6900 0.023 Uiso 1 1 calc R . .
C4 C 0.19520(6) 0.13319(18) 0.78345(14) 0.0168(2) Uani 1 1 d . . .
H4 H 0.2344 0.0320 0.8252 0.020 Uiso 1 1 calc R . .
C5 C 0.21001(6) 0.35160(17) 0.80218(14) 0.0136(2) Uani 1 1 d . . .
C6 C 0.28673(6) 0.43386(16) 0.88277(13) 0.0134(2) Uani 1 1 d . . .
C7 C 0.35363(6) 0.32307(16) 0.86468(14) 0.0134(2) Uani 1 1 d . . .
H7 H 0.3506 0.1873 0.8055 0.016 Uiso 1 1 calc R . .
C8 C 0.42764(6) 0.40833(16) 0.93334(13) 0.0124(2) Uani 1 1 d . . .
C9 C 0.43154(6) 0.61343(17) 1.02276(13) 0.0129(2) Uani 1 1 d . . .
C10 C 0.36056(6) 0.72185(17) 1.04296(14) 0.0148(2) Uani 1 1 d . . .
H10 H 0.3620 0.8562 1.1042 0.018 Uiso 1 1 calc R . .
C11 C 0.29106(6) 0.63578(17) 0.97590(14) 0.0145(2) Uani 1 1 d . . .
H11 H 0.2445 0.7108 0.9910 0.017 Uiso 1 1 calc R . .
C12 C 0.50351(6) 0.70061(17) 1.08786(14) 0.0134(2) Uani 1 1 d . . .
H12 H 0.5059 0.8360 1.1475 0.016 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 C1 1.3341(14) . ?
N1 C5 1.3459(14) . ?
C1 C2 1.3803(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.3828(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.3793(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3895(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.4807(14) . ?
C6 C7 1.3687(14) . ?
C6 C11 1.4304(14) . ?
C7 C8 1.4236(14) . ?
C7 H7 0.9500 . ?
C8 C12 1.3969(14) 3_667 ?
C8 C9 1.4354(15) . ?
C9 C12 1.3915(14) . ?
C9 C10 1.4259(14) . ?
C10 C11 1.3559(14) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C8 1.3968(14) 3_667 ?
C12 H12 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 116.74(10) . . ?
N1 C1 C2 124.42(10) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C1 C2 C3 118.46(10) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 118.23(11) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 119.64(10) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 122.50(10) . . ?
N1 C5 C6 115.80(9) . . ?
C4 C5 C6 121.69(9) . . ?
C7 C6 C11 119.58(9) . . ?
C7 C6 C5 121.08(9) . . ?
C11 C6 C5 119.31(9) . . ?
C6 C7 C8 120.94(10) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C12 C8 C7 121.58(10) 3_667 . ?
C12 C8 C9 119.32(9) 3_667 . ?
C7 C8 C9 119.09(9) . . ?
C12 C9 C10 121.82(10) . . ?
C12 C9 C8 119.79(9) . . ?
C10 C9 C8 118.39(9) . . ?
C11 C10 C9 120.91(10) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C6 121.06(9) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C9 C12 C8 120.90(10) . 3_667 ?
C9 C12 H12 119.6 . . ?
C8 C12 H12 119.6 3_667 . ?

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 0.52(16) . . . . ?
N1 C1 C2 C3 0.25(17) . . . . ?
C1 C2 C3 C4 -0.50(16) . . . . ?
C2 C3 C4 C5 0.01(15) . . . . ?
C1 N1 C5 C4 -1.04(15) . . . . ?
C1 N1 C5 C6 178.40(9) . . . . ?
C3 C4 C5 N1 0.80(16) . . . . ?
C3 C4 C5 C6 -178.61(9) . . . . ?
N1 C5 C6 C7 -148.81(10) . . . . ?
C4 C5 C6 C7 30.63(15) . . . . ?
N1 C5 C6 C11 29.18(13) . . . . ?
C4 C5 C6 C11 -151.38(10) . . . . ?
C11 C6 C7 C8 -1.54(15) . . . . ?
C5 C6 C7 C8 176.44(8) . . . . ?
C6 C7 C8 C12 -178.50(9) . . . 3_667 ?
C6 C7 C8 C9 0.07(15) . . . . ?
C12 C8 C9 C12 -0.32(17) 3_667 . . . ?
C7 C8 C9 C12 -178.92(8) . . . . ?
C12 C8 C9 C10 180.00(9) 3_667 . . . ?
C7 C8 C9 C10 1.40(15) . . . . ?
C12 C9 C10 C11 178.91(9) . . . . ?
C8 C9 C10 C11 -1.41(15) . . . . ?
C9 C10 C11 C6 -0.05(16) . . . . ?
C7 C6 C11 C10 1.56(15) . . . . ?
C5 C6 C11 C10 -176.46(9) . . . . ?
C10 C9 C12 C8 179.99(9) . . . 3_667 ?
C8 C9 C12 C8 0.32(17) . . . 3_667 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.95
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_sa
_database_code_depnum_ccdc_archive 'CCDC 1439493'
_audit_update_record             
;
2015-11-29 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 N2'
_chemical_formula_weight         332.39

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           Orthorhombic
_symmetry_space_group_name_H-M   Pca2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   7.4367(15)
_cell_length_b                   6.2803(13)
_cell_length_c                   35.030(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1636.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    109
_cell_measurement_theta_min      1.7435
_cell_measurement_theta_max      27.8784

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
???? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8767
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_sigmaI/netI    0.0884
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2986
_reflns_number_gt                2155
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.1270P)²+0.0000P] 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       0.024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(8)
_refine_ls_number_reflns         2986
_refine_ls_number_parameters     236
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0816
_refine_ls_wR_factor_ref         0.2145
_refine_ls_wR_factor_gt          0.1974
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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 0.6826(5) -0.2178(8) 0.41033(14) 0.0304(12) Uani 1 1 d . . .
N2 N 1.0584(6) 0.7118(8) 0.04532(14) 0.0318(13) Uani 1 1 d . . .
C1 C 0.7395(6) -0.1243(9) 0.37812(16) 0.0225(12) Uani 1 1 d . . .
H1 H 0.7758 -0.2159 0.3580 0.027 Uiso 1 1 calc R . .
C2 C 0.7503(6) 0.0874(8) 0.37144(14) 0.0170(12) Uani 1 1 d . . .
C3 C 0.6988(6) 0.2245(8) 0.40077(15) 0.0214(12) Uani 1 1 d . . .
H3 H 0.7054 0.3746 0.3977 0.026 Uiso 1 1 calc R . .
C4 C 0.6379(7) 0.1352(10) 0.43442(15) 0.0285(13) Uani 1 1 d . . .
H4 H 0.6007 0.2243 0.4549 0.034 Uiso 1 1 calc R . .
C5 C 0.6310(7) -0.0814(11) 0.43832(17) 0.0323(15) Uani 1 1 d . . .
H5 H 0.5882 -0.1390 0.4617 0.039 Uiso 1 1 calc R . .
C6 C 0.8100(6) 0.1765(7) 0.33339(13) 0.0182(10) Uani 1 1 d . . .
C7 C 0.9057(6) 0.3752(7) 0.33172(13) 0.0215(10) Uani 1 1 d . . .
H7 H 0.9343 0.4469 0.3548 0.026 Uiso 1 1 calc R . .
C8 C 0.9561(7) 0.4630(7) 0.29794(14) 0.0146(10) Uani 1 1 d . . .
H8 H 1.0206 0.5935 0.2978 0.017 Uiso 1 1 calc R . .
C9 C 0.9124(6) 0.3589(7) 0.26172(13) 0.0184(9) Uani 1 1 d . . .
C10 C 0.9603(7) 0.4485(7) 0.22672(14) 0.0185(10) Uani 1 1 d . . .
H10 H 1.0225 0.5805 0.2260 0.022 Uiso 1 1 calc R . .
C11 C 0.9162(5) 0.3429(6) 0.19246(12) 0.0149(9) Uani 1 1 d . . .
C12 C 0.9664(6) 0.4305(8) 0.15606(13) 0.0183(9) Uani 1 1 d . . .
H12 H 1.0261 0.5642 0.1551 0.022 Uiso 1 1 calc R . .
C13 C 0.9293(6) 0.3235(7) 0.12254(13) 0.0185(10) Uani 1 1 d . . .
C14 C 0.8338(6) 0.1261(7) 0.12450(12) 0.0179(10) Uani 1 1 d . . .
H14 H 0.8025 0.0548 0.1015 0.021 Uiso 1 1 calc R . .
C15 C 0.7866(7) 0.0376(8) 0.15880(18) 0.0227(11) Uani 1 1 d . . .
H15 H 0.7260 -0.0955 0.1592 0.027 Uiso 1 1 calc R . .
C16 C 0.8262(6) 0.1403(6) 0.19358(12) 0.0165(9) Uani 1 1 d . . .
C17 C 0.7814(7) 0.0530(8) 0.22906(14) 0.0189(9) Uani 1 1 d . . .
H17 H 0.7226 -0.0812 0.2298 0.023 Uiso 1 1 calc R . .
C18 C 0.8201(5) 0.1570(7) 0.26351(13) 0.0177(10) Uani 1 1 d . . .
C19 C 0.7692(6) 0.0711(7) 0.29976(13) 0.0177(9) Uani 1 1 d . . .
H19 H 0.7063 -0.0604 0.3008 0.021 Uiso 1 1 calc R . .
C20 C 0.9988(8) 0.6275(9) 0.07861(18) 0.0271(13) Uani 1 1 d . . .
H20 H 0.9618 0.7203 0.0985 0.033 Uiso 1 1 calc R . .
C21 C 0.9901(6) 0.4011(8) 0.08454(14) 0.0194(12) Uani 1 1 d . . .
C22 C 1.0461(6) 0.2694(9) 0.05507(15) 0.0252(13) Uani 1 1 d . . .
H22 H 1.0413 0.1191 0.0579 0.030 Uiso 1 1 calc R . .
C23 C 1.1087(7) 0.3584(11) 0.02172(16) 0.0309(14) Uani 1 1 d . . .
H23 H 1.1481 0.2705 0.0013 0.037 Uiso 1 1 calc R . .
C24 C 1.1135(7) 0.5807(11) 0.01835(16) 0.0341(15) Uani 1 1 d . . .
H24 H 1.1589 0.6402 -0.0046 0.041 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 C1 1.340(6) . ?
N1 C5 1.357(8) . ?
N2 C24 1.319(7) . ?
N2 C20 1.355(7) . ?
C1 C2 1.352(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(6) . ?
C2 C6 1.512(7) . ?
C3 C4 1.382(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(9) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C19 1.385(6) . ?
C6 C7 1.438(6) . ?
C7 C8 1.358(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.464(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(6) . ?
C9 C18 1.443(6) . ?
C10 C11 1.410(6) . ?
C10 H10 0.9500 . ?
C11 C16 1.438(6) . ?
C11 C12 1.438(6) . ?
C12 C13 1.381(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.431(6) . ?
C13 C21 1.488(7) . ?
C14 C15 1.369(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.410(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.399(6) . ?
C17 C18 1.402(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.431(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.439(8) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(7) . ?
C22 C23 1.376(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.401(9) . ?
C23 H23 0.9500 . ?
C24 H24 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 114.9(5) . . ?
C24 N2 C20 118.3(5) . . ?
N1 C1 C2 126.5(5) . . ?
N1 C1 H1 116.7 . . ?
C2 C1 H1 116.7 . . ?
C1 C2 C3 117.6(4) . . ?
C1 C2 C6 122.3(4) . . ?
C3 C2 C6 120.1(4) . . ?
C4 C3 C2 117.9(5) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C5 C4 C3 120.1(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 123.0(5) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C19 C6 C7 119.3(4) . . ?
C19 C6 C2 120.6(4) . . ?
C7 C6 C2 120.1(4) . . ?
C8 C7 C6 121.6(4) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C18 120.9(4) . . ?
C10 C9 C8 121.6(4) . . ?
C18 C9 C8 117.4(4) . . ?
C9 C10 C11 119.9(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C16 120.1(4) . . ?
C10 C11 C12 120.9(4) . . ?
C16 C11 C12 118.9(3) . . ?
C13 C12 C11 121.0(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 118.7(4) . . ?
C12 C13 C21 122.7(4) . . ?
C14 C13 C21 118.5(4) . . ?
C15 C14 C13 121.4(4) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 121.3(4) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 122.6(4) . . ?
C17 C16 C11 118.8(4) . . ?
C15 C16 C11 118.6(4) . . ?
C16 C17 C18 122.2(4) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C17 C18 C19 122.3(4) . . ?
C17 C18 C9 118.0(4) . . ?
C19 C18 C9 119.7(4) . . ?
C6 C19 C18 121.1(4) . . ?
C6 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
N2 C20 C21 121.7(5) . . ?
N2 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C22 C21 C20 117.9(4) . . ?
C22 C21 C13 124.2(4) . . ?
C20 C21 C13 117.8(4) . . ?
C23 C22 C21 119.4(5) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 119.0(5) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
N2 C24 C23 123.6(5) . . ?
N2 C24 H24 118.2 . . ?
C23 C24 H24 118.2 . . ?

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 0.3(7) . . . . ?
N1 C1 C2 C3 0.5(7) . . . . ?
N1 C1 C2 C6 -177.6(4) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C6 C2 C3 C4 177.2(4) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?
C1 N1 C5 C4 -0.7(7) . . . . ?
C3 C4 C5 N1 0.2(7) . . . . ?
C1 C2 C6 C19 33.5(6) . . . . ?
C3 C2 C6 C19 -144.5(4) . . . . ?
C1 C2 C6 C7 -148.3(4) . . . . ?
C3 C2 C6 C7 33.7(6) . . . . ?
C19 C6 C7 C8 0.4(7) . . . . ?
C2 C6 C7 C8 -177.9(4) . . . . ?
C6 C7 C8 C9 0.9(7) . . . . ?
C7 C8 C9 C10 178.8(4) . . . . ?
C7 C8 C9 C18 -2.2(7) . . . . ?
C18 C9 C10 C11 0.9(6) . . . . ?
C8 C9 C10 C11 179.8(4) . . . . ?
C9 C10 C11 C16 -1.7(6) . . . . ?
C9 C10 C11 C12 -179.1(4) . . . . ?
C10 C11 C12 C13 177.6(4) . . . . ?
C16 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 2.1(6) . . . . ?
C11 C12 C13 C21 -175.6(4) . . . . ?
C12 C13 C14 C15 -3.1(7) . . . . ?
C21 C13 C14 C15 174.8(4) . . . . ?
C13 C14 C15 C16 1.6(7) . . . . ?
C14 C15 C16 C17 -179.4(5) . . . . ?
C14 C15 C16 C11 0.7(7) . . . . ?
C10 C11 C16 C17 1.0(6) . . . . ?
C12 C11 C16 C17 178.5(4) . . . . ?
C10 C11 C16 C15 -179.0(4) . . . . ?
C12 C11 C16 C15 -1.6(6) . . . . ?
C15 C16 C17 C18 -179.5(5) . . . . ?
C11 C16 C17 C18 0.4(6) . . . . ?
C16 C17 C18 C19 178.0(4) . . . . ?
C16 C17 C18 C9 -1.1(6) . . . . ?
C10 C9 C18 C17 0.5(6) . . . . ?
C8 C9 C18 C17 -178.5(4) . . . . ?
C10 C9 C18 C19 -178.6(4) . . . . ?
C8 C9 C18 C19 2.4(6) . . . . ?
C7 C6 C19 C18 -0.2(6) . . . . ?
C2 C6 C19 C18 178.1(4) . . . . ?
C17 C18 C19 C6 179.6(4) . . . . ?
C9 C18 C19 C6 -1.3(6) . . . . ?
C24 N2 C20 C21 -1.7(7) . . . . ?
N2 C20 C21 C22 0.4(7) . . . . ?
N2 C20 C21 C13 177.8(5) . . . . ?
C12 C13 C21 C22 143.5(5) . . . . ?
C14 C13 C21 C22 -34.3(6) . . . . ?
C12 C13 C21 C20 -33.6(6) . . . . ?
C14 C13 C21 C20 148.6(4) . . . . ?
C20 C21 C22 C23 0.6(6) . . . . ?
C13 C21 C22 C23 -176.6(5) . . . . ?
C21 C22 C23 C24 -0.3(7) . . . . ?
C20 N2 C24 C23 2.0(8) . . . . ?
C22 C23 C24 N2 -1.1(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.113
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1439496'
_audit_update_record             
;
2015-11-29 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;
_audit_creation_date             2014-12-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H16 N2'
_chemical_formula_sum            'C24 H16 N2'
_chemical_formula_weight         332.39
_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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.582(10)
_cell_length_b                   5.997(5)
_cell_length_c                   10.882(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.308(13)
_cell_angle_gamma                90
_cell_volume                     799.1(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2697
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4500
_cell_measurement_theta_min      1.6632
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6164
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.397
_diffrn_reflns_theta_min         3.328
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             1987
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0002
_diffrn_orient_matrix_UB_12      0.0350
_diffrn_orient_matrix_UB_13      0.0877
_diffrn_orient_matrix_UB_21      -0.0052
_diffrn_orient_matrix_UB_22      0.1548
_diffrn_orient_matrix_UB_23      -0.0618
_diffrn_orient_matrix_UB_31      -0.0794
_diffrn_orient_matrix_UB_32      0.0047
_diffrn_orient_matrix_UB_33      0.0185
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1645
_reflns_number_total             1810
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1810
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0746
_refine_ls_restrained_S_all      1.194
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0669P)²+0.4633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.1775
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.06526(16) 0.4041(3) -0.15880(17) 0.0374(5) Uani 1 1 d . . . . .
C1 C 0.0815(2) 0.2697(4) -0.0587(2) 0.0437(6) Uani 1 1 d . . . . .
H1 H 0.0435 0.1354 -0.0672 0.052 Uiso 1 1 calc R . . . .
C2 C 0.1510(2) 0.3160(4) 0.0571(2) 0.0391(6) Uani 1 1 d . . . . .
H2 H 0.1571 0.2160 0.1237 0.047 Uiso 1 1 calc R . . . .
C3 C 0.21148(15) 0.5122(3) 0.07366(17) 0.0245(5) Uani 1 1 d . . . . .
C4 C 0.19479(19) 0.6530(4) -0.0307(2) 0.0369(6) Uani 1 1 d . . . . .
H4 H 0.2329 0.7868 -0.0259 0.044 Uiso 1 1 calc R . . . .
C5 C 0.1215(2) 0.5943(4) -0.1421(2) 0.0402(6) Uani 1 1 d . . . . .
H5 H 0.1109 0.6940 -0.2093 0.048 Uiso 1 1 calc R . . . .
C6 C 0.29446(16) 0.5648(3) 0.19256(17) 0.0238(5) Uani 1 1 d . . . . .
C7 C 0.35116(16) 0.7741(3) 0.20448(17) 0.0258(5) Uani 1 1 d . . . . .
H7 H 0.3306 0.8807 0.1414 0.031 Uiso 1 1 calc R . . . .
C8 C 0.43436(16) 0.8210(3) 0.30572(17) 0.0237(5) Uani 1 1 d . . . . .
H8 H 0.4695 0.9583 0.3102 0.028 Uiso 1 1 calc R . . . .
C9 C 0.46848(16) 0.6626(3) 0.40499(17) 0.0219(4) Uani 1 1 d . . . . .
C10 C 0.40963(16) 0.4558(3) 0.39744(17) 0.0224(4) Uani 1 1 d . . . . .
C11 C 0.32256(16) 0.4137(3) 0.28962(17) 0.0242(4) Uani 1 1 d . . . . .
H11 H 0.2840 0.2805 0.2851 0.029 Uiso 1 1 calc R . . . .
C12 C 0.55779(16) 0.7016(3) 0.50617(17) 0.0236(4) Uani 1 1 d . . . . .
H12 H 0.5963 0.8347 0.5094 0.028 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 C1 1.332(3) . ?
N1 C5 1.332(3) . ?
C1 C2 1.387(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.392(3) . ?
C3 C6 1.497(3) . ?
C4 C5 1.389(3) . ?
C6 C7 1.435(3) . ?
C6 C11 1.375(3) . ?
C7 C8 1.363(3) . ?
C8 C9 1.428(3) . ?
C9 C10 1.437(3) . ?
C9 C12 1.400(3) . ?
C10 C11 1.431(3) . ?
C10 C12 1.401(3) 3_666 ?
C12 C10 1.401(3) 3_666 ?

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 115.48(19) . . ?
N1 C1 C2 124.6(2) . . ?
C1 C2 C3 119.9(2) . . ?
C2 C3 C4 115.61(19) . . ?
C2 C3 C6 122.83(18) . . ?
C4 C3 C6 121.46(19) . . ?
C5 C4 C3 120.3(2) . . ?
N1 C5 C4 124.1(2) . . ?
C7 C6 C3 119.71(17) . . ?
C11 C6 C3 122.00(19) . . ?
C11 C6 C7 118.21(18) . . ?
C8 C7 C6 121.80(18) . . ?
C7 C8 C9 121.02(18) . . ?
C8 C9 C10 118.01(17) . . ?
C12 C9 C8 122.07(18) . . ?
C12 C9 C10 119.91(17) . . ?
C11 C10 C9 119.09(17) . . ?
C12 C10 C9 118.74(17) 3_666 . ?
C12 C10 C11 122.12(18) 3_666 . ?
C6 C11 C10 121.75(19) . . ?
C9 C12 C10 121.34(18) . 3_666 ?

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 C1 C2 C3 -1.5(4) . . . . ?
C1 N1 C5 C4 1.5(4) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
C1 C2 C3 C6 -175.1(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C6 C7 -177.9(2) . . . . ?
C2 C3 C6 C11 5.4(3) . . . . ?
C3 C4 C5 N1 -1.6(4) . . . . ?
C3 C6 C7 C8 -173.80(18) . . . . ?
C3 C6 C11 C10 173.55(17) . . . . ?
C4 C3 C6 C7 5.9(3) . . . . ?
C4 C3 C6 C11 -170.8(2) . . . . ?
C5 N1 C1 C2 0.1(4) . . . . ?
C6 C3 C4 C5 176.5(2) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C6 C11 C10 -3.2(3) . . . . ?
C7 C8 C9 C10 -2.4(3) . . . . ?
C7 C8 C9 C12 176.16(18) . . . . ?
C8 C9 C10 C11 2.2(3) . . . . ?
C8 C9 C10 C12 179.83(17) . . . 3_666 ?
C8 C9 C12 C10 -179.80(18) . . . 3_666 ?
C9 C10 C11 C6 0.6(3) . . . . ?
C10 C9 C12 C10 -1.2(3) . . . 3_666 ?
C11 C6 C7 C8 3.1(3) . . . . ?
C12 C9 C10 C11 -176.41(17) . . . . ?
C12 C9 C10 C12 1.2(3) . . . 3_666 ?
C12 C10 C11 C6 -176.89(19) 3_666 . . . ?

