# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_r-3
_database_code_depnum_ccdc_archive 'CCDC 1432637'
_audit_update_record             
;
2015-10-21 deposited with the CCDC.
2016-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H18 N6'
_chemical_formula_sum            'C28 H18 N6'
_chemical_formula_weight         438.48

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           Trigonal
_symmetry_space_group_name_H-M   R-3:h
_space_group_name_Hall           '-R 3'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   31.5821(12)
_cell_length_b                   31.5821(12)
_cell_length_c                   5.8362(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     5041.3(5)
_cell_formula_units_Z            9
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    930
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      17.72

_exptl_crystal_description       needle
_exptl_crystal_colour            translucent
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2052
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9548
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23120
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_sigmaI/netI    0.0824
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2071
_reflns_number_gt                809
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'Bruker Instrument Service v2011.12.3.0 (Bruker 2011)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2014)'
_computing_structure_solution    'SIR2004 (Burla, M. C.et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 3.2i (Crystal Impact, 2014)'
_computing_publication_material  'APEX2 (version 2014.9-0; Bruker, 2014)'

_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)+(0.0592P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2071
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.0906
_refine_ls_goodness_of_fit_ref   0.713
_refine_ls_restrained_S_all      0.719
_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
H15 H 0.4418(7) 0.0810(8) 1.453(3) 0.083(8) Uiso 1 1 d . . .
H16 H 0.4919(7) 0.0946(7) 1.145(3) 0.074(7) Uiso 1 1 d . . .
H23 H 0.6716(7) 0.1829(6) 0.183(3) 0.067(7) Uiso 1 1 d . . .
H24 H 0.6941(8) 0.2513(8) 0.438(3) 0.089(8) Uiso 1 1 d . . .
H25 H 0.6466(7) 0.2390(8) 0.783(3) 0.080(7) Uiso 1 1 d . . .
H26 H 0.5806(7) 0.1626(7) 0.835(3) 0.061(7) Uiso 1 1 d . . .
H1 H 0.5380(9) 0.0567(8) 0.510(4) 0.133(11) Uiso 1 1 d D . .
H13 H 0.3593(7) -0.0634(7) 1.258(3) 0.063(7) Uiso 1 1 d . . .
H14 H 0.3768(7) 0.0004(8) 1.517(3) 0.082(8) Uiso 1 1 d . . .
C1 C 0.40748(7) -0.06092(9) 0.8992(4) 0.0656(7) Uani 1 1 d . . .
C2 C 0.60176(8) 0.09509(9) 0.2199(4) 0.0644(6) Uani 1 1 d . . .
C11 C 0.45515(8) 0.02559(8) 1.0113(3) 0.0568(6) Uani 1 1 d . . .
C12 C 0.41650(8) -0.02150(9) 1.0496(4) 0.0606(6) Uani 1 1 d . . .
C13 C 0.38659(10) -0.03069(11) 1.2402(4) 0.0721(7) Uani 1 1 d . . .
C14 C 0.39576(11) 0.00602(12) 1.3902(5) 0.0795(8) Uani 1 1 d . . .
C15 C 0.43450(10) 0.05288(12) 1.3547(4) 0.0739(7) Uani 1 1 d . . .
C16 C 0.46386(9) 0.06240(10) 1.1659(4) 0.0679(7) Uani 1 1 d . . .
C21 C 0.58581(8) 0.12869(8) 0.5665(4) 0.0581(6) Uani 1 1 d . . .
C22 C 0.61373(8) 0.13523(8) 0.3693(4) 0.0614(6) Uani 1 1 d . . .
C23 C 0.65378(9) 0.18135(10) 0.3244(5) 0.0734(7) Uani 1 1 d . . .
C24 C 0.66642(10) 0.21918(11) 0.4706(5) 0.0808(8) Uani 1 1 d . . .
C25 C 0.63913(10) 0.21249(11) 0.6657(5) 0.0832(8) Uani 1 1 d . . .
C26 C 0.59933(10) 0.16765(10) 0.7143(5) 0.0725(7) Uani 1 1 d . . .
N11 N 0.48432(6) 0.03211(7) 0.8141(3) 0.0619(5) Uani 1 1 d . . .
N12 N 0.51840(7) 0.07676(7) 0.7871(3) 0.0624(5) Uani 1 1 d . . .
N13 N 0.54563(7) 0.08228(7) 0.6065(3) 0.0639(5) Uani 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0538(15) 0.0767(18) 0.0605(16) 0.0173(14) 0.0060(12) 0.0283(14)
C2 0.0525(15) 0.0732(18) 0.0622(16) 0.0115(14) 0.0048(12) 0.0275(14)
C11 0.0541(15) 0.0693(17) 0.0537(15) 0.0065(13) 0.0018(12) 0.0359(14)
C12 0.0594(15) 0.0707(17) 0.0563(15) 0.0066(13) 0.0006(13) 0.0361(14)
C13 0.0635(17) 0.082(2) 0.0710(19) 0.0130(16) 0.0109(15) 0.0370(17)
C14 0.084(2) 0.112(3) 0.0647(19) 0.0126(19) 0.0180(17) 0.065(2)
C15 0.084(2) 0.085(2) 0.0671(19) 0.0024(17) 0.0042(16) 0.0535(19)
C16 0.0708(18) 0.0743(19) 0.0659(17) 0.0056(15) 0.0048(14) 0.0418(16)
C21 0.0538(14) 0.0575(16) 0.0597(15) 0.0052(13) -0.0053(12) 0.0252(13)
C22 0.0553(14) 0.0619(17) 0.0629(16) 0.0080(13) -0.0009(13) 0.0262(14)
C23 0.0657(17) 0.072(2) 0.074(2) 0.0083(16) 0.0043(15) 0.0279(16)
C24 0.0597(17) 0.0644(19) 0.100(2) 0.0121(18) 0.0038(17) 0.0171(16)
C25 0.078(2) 0.070(2) 0.091(2) -0.0116(18) -0.0122(18) 0.0291(17)
C26 0.0659(18) 0.075(2) 0.071(2) 0.0007(16) 0.0044(16) 0.0308(16)
N11 0.0528(11) 0.0646(13) 0.0611(12) 0.0095(10) 0.0056(9) 0.0241(11)
N12 0.0574(12) 0.0745(14) 0.0574(12) 0.0060(10) 0.0034(10) 0.0346(11)
N13 0.0570(12) 0.0665(15) 0.0623(14) 0.0031(12) 0.0048(11) 0.0266(12)

_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 1.191(3) 10_656 ?
C1 C12 1.431(3) . ?
C2 C1 1.191(3) 10_656 ?
C2 C22 1.425(3) . ?
C11 C16 1.386(3) . ?
C11 C12 1.391(3) . ?
C11 N11 1.424(2) . ?
C12 C13 1.393(3) . ?
C13 C14 1.363(3) . ?
C14 C15 1.386(3) . ?
C15 C16 1.373(3) . ?
C21 C26 1.384(3) . ?
C21 N13 1.397(2) . ?
C21 C22 1.401(3) . ?
C22 C23 1.396(3) . ?
C23 C24 1.356(3) . ?
C24 C25 1.379(3) . ?
C25 C26 1.373(3) . ?
N11 N12 1.2861(19) . ?
N12 N13 1.315(2) . ?

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 C12 177.0(2) 10_656 . ?
C1 C2 C22 177.6(2) 10_656 . ?
C16 C11 C12 119.5(2) . . ?
C16 C11 N11 124.2(2) . . ?
C12 C11 N11 116.3(2) . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 C1 121.2(2) . . ?
C13 C12 C1 119.3(2) . . ?
C14 C13 C12 120.1(3) . . ?
C13 C14 C15 120.7(3) . . ?
C16 C15 C14 119.5(3) . . ?
C15 C16 C11 120.6(3) . . ?
C26 C21 N13 122.9(2) . . ?
C26 C21 C22 119.3(2) . . ?
N13 C21 C22 117.8(2) . . ?
C23 C22 C21 118.9(2) . . ?
C23 C22 C2 120.8(2) . . ?
C21 C22 C2 120.3(2) . . ?
C24 C23 C22 121.0(3) . . ?
C23 C24 C25 119.9(3) . . ?
C26 C25 C24 120.5(3) . . ?
C25 C26 C21 120.3(3) . . ?
N12 N11 C11 112.58(18) . . ?
N11 N12 N13 112.14(18) . . ?
N12 N13 C21 117.6(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
C16 C11 C21 C26 2.52(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.030
####################################################################### 
# 
# 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_to3
_database_code_depnum_ccdc_archive 'CCDC 1432703'
_audit_update_record             
;
2015-10-22 deposited with the CCDC.
2016-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H18 N6'
_chemical_formula_weight         438.48

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.8253(14)
_cell_length_b                   6.2971(5)
_cell_length_c                   15.069(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.900(5)
_cell_angle_gamma                90.00
_cell_volume                     1101.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prismatic
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9564
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9709
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_av_sigmaI/netI    0.0940
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         27.43
_reflns_number_total             2483
_reflns_number_gt                978
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'Bruker Instrument Service v2011.12.3.0 (Bruker 2011)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2014)'
_computing_structure_solution    'SIR2004 (Burla, M. C.et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 3.2i (Crystal Impact, 2014)'
_computing_publication_material  'APEX2 (version 2014.9-0; Bruker, 2014)'

_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)+(0.1243P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.004(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2483
_refine_ls_number_parameters     190
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1892
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.2376
_refine_ls_wR_factor_gt          0.1811
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.965
_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 0.2225(3) 0.8565(5) 0.0284(3) 0.0591(10) Uani 1 1 d . . .
C2 C 0.2433(3) 0.7187(5) -0.0190(3) 0.0594(10) Uani 1 1 d . . .
C11 C 0.2734(3) 1.1887(5) 0.1107(2) 0.0525(9) Uani 1 1 d D . .
C12 C 0.1936(3) 1.0292(5) 0.0835(2) 0.0545(9) Uani 1 1 d . . .
C13 C 0.0864(3) 1.0417(6) 0.1061(3) 0.0624(10) Uani 1 1 d . . .
C14 C 0.0571(3) 1.2073(6) 0.1548(3) 0.0681(11) Uani 1 1 d . . .
C15 C 0.1351(3) 1.3656(7) 0.1828(3) 0.0695(12) Uani 1 1 d . . .
C16 C 0.2438(3) 1.3587(6) 0.1615(3) 0.0657(11) Uani 1 1 d . . .
C21 C 0.2663(3) 0.5436(4) -0.0754(2) 0.0532(9) Uani 1 1 d . . .
C22 C 0.3703(3) 0.5257(5) -0.1029(2) 0.0513(9) Uani 1 1 d . . .
C23 C 0.3921(3) 0.3466(6) -0.1519(3) 0.0647(10) Uani 1 1 d . . .
C24 C 0.3081(4) 0.1947(6) -0.1755(3) 0.0678(11) Uani 1 1 d . . .
C25 C 0.2035(4) 0.2176(6) -0.1511(3) 0.0684(11) Uani 1 1 d . . .
C26 C 0.1819(3) 0.3877(6) -0.1008(3) 0.0631(10) Uani 1 1 d . . .
N11 N 0.3818(2) 1.1722(4) 0.0850(2) 0.0632(9) Uani 1 1 d D . .
N12 N 0.5455(2) 0.6705(4) -0.1097(2) 0.0619(9) Uani 1 1 d D . .
N13 N 0.4513(2) 0.6924(4) -0.0776(2) 0.0611(9) Uani 1 1 d . . .
H13 H 0.035(3) 0.922(6) 0.087(3) 0.086(12) Uiso 1 1 d . . .
H14 H -0.016(3) 1.211(5) 0.174(2) 0.065(9) Uiso 1 1 d . . .
H15 H 0.118(3) 1.480(5) 0.210(2) 0.065(10) Uiso 1 1 d . . .
H16 H 0.293(3) 1.455(6) 0.181(3) 0.083(13) Uiso 1 1 d . . .
H23 H 0.470(3) 0.336(5) -0.162(2) 0.067(10) Uiso 1 1 d . . .
H24 H 0.324(3) 0.086(6) -0.203(3) 0.073(12) Uiso 1 1 d . . .
H25 H 0.155(3) 0.109(6) -0.164(3) 0.085(13) Uiso 1 1 d . . .
H26 H 0.112(3) 0.402(4) -0.0824(19) 0.043(8) Uiso 1 1 d . . .
H1 H 0.396(3) 1.051(3) 0.0404(12) 0.090 Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.058(2) 0.0541(19) 0.064(3) -0.0008(18) 0.0099(18) -0.0144(16)
C2 0.056(2) 0.058(2) 0.066(3) 0.0094(19) 0.0159(18) -0.0072(16)
C11 0.0429(18) 0.069(2) 0.047(2) 0.0064(17) 0.0110(16) 0.0019(16)
C12 0.059(2) 0.0548(19) 0.050(2) 0.0038(16) 0.0099(17) -0.0065(16)
C13 0.064(2) 0.067(2) 0.057(3) -0.0008(19) 0.0123(19) -0.0153(19)
C14 0.053(2) 0.089(3) 0.066(3) -0.001(2) 0.021(2) -0.004(2)
C15 0.071(3) 0.073(3) 0.067(3) -0.018(2) 0.019(2) 0.006(2)
C16 0.063(2) 0.067(2) 0.065(3) -0.005(2) 0.004(2) -0.0185(19)
C21 0.063(2) 0.0485(18) 0.047(2) 0.0032(16) 0.0095(17) -0.0012(16)
C22 0.059(2) 0.0478(18) 0.044(2) 0.0046(15) 0.0029(16) -0.0160(15)
C23 0.059(2) 0.075(2) 0.062(3) 0.004(2) 0.015(2) 0.0010(19)
C24 0.095(3) 0.051(2) 0.058(3) -0.0092(19) 0.014(2) -0.008(2)
C25 0.076(3) 0.059(2) 0.070(3) 0.002(2) 0.011(2) -0.026(2)
C26 0.061(2) 0.064(2) 0.066(3) 0.003(2) 0.017(2) -0.0103(18)
N11 0.0578(17) 0.0612(16) 0.071(2) -0.0102(15) 0.0147(16) -0.0133(14)
N12 0.0574(17) 0.0675(17) 0.059(2) 0.0062(15) 0.0074(15) -0.0120(14)
N13 0.0537(17) 0.0626(16) 0.068(2) -0.0004(15) 0.0138(15) -0.0124(13)

_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 1.179(5) . ?
C1 C12 1.448(5) . ?
C2 C21 1.449(5) . ?
C11 C12 1.386(4) . ?
C11 C16 1.399(5) . ?
C11 N11 1.411(4) . ?
C12 C13 1.375(5) . ?
C13 C14 1.357(5) . ?
C13 H13 0.98(4) . ?
C14 C15 1.369(5) . ?
C14 H14 0.96(3) . ?
C15 C16 1.383(5) . ?
C15 H15 0.87(3) . ?
C16 H16 0.85(4) . ?
C21 C22 1.375(4) . ?
C21 C26 1.400(4) . ?
C22 C23 1.398(5) . ?
C22 N13 1.423(4) . ?
C23 C24 1.376(5) . ?
C23 H23 0.96(3) . ?
C24 C25 1.363(5) . ?
C24 H24 0.84(4) . ?
C25 C26 1.364(5) . ?
C25 H25 0.89(4) . ?
C26 H26 0.93(3) . ?
N11 N12 1.318(4) 3_675 ?
N11 H1 1.051(18) . ?
N12 N13 1.304(4) . ?
N12 N11 1.318(4) 3_675 ?

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 C12 177.6(4) . . ?
C1 C2 C21 177.7(3) . . ?
C12 C11 C16 119.3(3) . . ?
C12 C11 N11 117.9(3) . . ?
C16 C11 N11 122.8(3) . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 C1 120.9(3) . . ?
C11 C12 C1 119.5(3) . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 H13 123(2) . . ?
C12 C13 H13 116(2) . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 121.1(19) . . ?
C15 C14 H14 118.7(19) . . ?
C14 C15 C16 120.5(4) . . ?
C14 C15 H15 123(2) . . ?
C16 C15 H15 116(2) . . ?
C15 C16 C11 119.4(3) . . ?
C15 C16 H16 120(3) . . ?
C11 C16 H16 121(3) . . ?
C22 C21 C26 119.5(3) . . ?
C22 C21 C2 121.1(3) . . ?
C26 C21 C2 119.4(3) . . ?
C21 C22 C23 119.3(3) . . ?
C21 C22 N13 117.0(3) . . ?
C23 C22 N13 123.6(3) . . ?
C24 C23 C22 120.1(4) . . ?
C24 C23 H23 125.3(19) . . ?
C22 C23 H23 114.4(19) . . ?
C25 C24 C23 120.3(4) . . ?
C25 C24 H24 121(2) . . ?
C23 C24 H24 119(2) . . ?
C24 C25 C26 120.5(4) . . ?
C24 C25 H25 116(2) . . ?
C26 C25 H25 123(2) . . ?
C25 C26 C21 120.2(4) . . ?
C25 C26 H26 121.1(17) . . ?
C21 C26 H26 118.7(17) . . ?
N12 N11 C11 116.4(3) 3_675 . ?
N12 N11 H1 123.7(18) 3_675 . ?
C11 N11 H1 119.4(18) . . ?
N13 N12 N11 111.9(3) . 3_675 ?
N12 N13 C22 113.7(3) . . ?

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
C12 C1 C2 C21 -106(12) . . . . ?
C16 C11 C12 C13 0.7(5) . . . . ?
N11 C11 C12 C13 -178.9(3) . . . . ?
C16 C11 C12 C1 178.0(3) . . . . ?
N11 C11 C12 C1 -1.6(5) . . . . ?
C2 C1 C12 C13 67(8) . . . . ?
C2 C1 C12 C11 -110(8) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C1 C12 C13 C14 -177.4(3) . . . . ?
C12 C13 C14 C15 -0.3(6) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C14 C15 C16 C11 0.2(6) . . . . ?
C12 C11 C16 C15 -0.7(5) . . . . ?
N11 C11 C16 C15 178.9(3) . . . . ?
C1 C2 C21 C22 -143(10) . . . . ?
C1 C2 C21 C26 36(10) . . . . ?
C26 C21 C22 C23 -3.1(5) . . . . ?
C2 C21 C22 C23 175.5(3) . . . . ?
C26 C21 C22 N13 178.0(3) . . . . ?
C2 C21 C22 N13 -3.4(5) . . . . ?
C21 C22 C23 C24 2.7(5) . . . . ?
N13 C22 C23 C24 -178.5(3) . . . . ?
C22 C23 C24 C25 -0.2(6) . . . . ?
C23 C24 C25 C26 -2.0(6) . . . . ?
C24 C25 C26 C21 1.6(6) . . . . ?
C22 C21 C26 C25 1.0(5) . . . . ?
C2 C21 C26 C25 -177.6(3) . . . . ?
C12 C11 N11 N12 178.1(3) . . . 3_675 ?
C16 C11 N11 N12 -1.4(5) . . . 3_675 ?
N11 N12 N13 C22 180.0(3) 3_675 . . . ?
C21 C22 N13 N12 -176.7(3) . . . . ?
C23 C22 N13 N12 4.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.049
