# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_exp_3085
_database_code_depnum_ccdc_archive 'CCDC 1441236'
_audit_update_record             
;
2015-12-08 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;
_audit_creation_date             2015-04-24
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        2,4-2CzBN
_chemical_formula_moiety         'C31 H19 N3'
_chemical_formula_sum            'C31 H19 N3'
_chemical_formula_weight         433.49
_chemical_absolute_configuration unk
_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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'
3 'x+1/2, y+1/2, z'
4 'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   16.7003(9)
_cell_length_b                   14.0892(12)
_cell_length_c                   9.3429(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.029(6)
_cell_angle_gamma                90.00
_cell_volume                     2186.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2032
_cell_measurement_temperature    101.8
_cell_measurement_theta_max      29.3952
_cell_measurement_theta_min      3.4514
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5192
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.63
_diffrn_ambient_temperature      101.8
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -63.00    5.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      -13.6043  -37.0000   30.0000 68

#__ type_ start__ end____ width___ exp.time_
  2 omega   32.00   82.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       18.9168   37.0000    0.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega  -44.00   34.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       18.9168  -77.0000   60.0000 78

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00   86.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       18.9168   71.0000 -169.0000 52
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0154440000
_diffrn_orient_matrix_UB_12      0.0230504000
_diffrn_orient_matrix_UB_13      0.0587109000
_diffrn_orient_matrix_UB_21      -0.0204270000
_diffrn_orient_matrix_UB_22      0.0330545000
_diffrn_orient_matrix_UB_23      -0.0481336000
_diffrn_orient_matrix_UB_31      -0.0341980000
_diffrn_orient_matrix_UB_32      -0.0301511000
_diffrn_orient_matrix_UB_33      -0.0078463000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3343
_reflns_number_total             3569
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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         0.148
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0416P)²+0.1982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0806
_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 0.27317(9) 0.21496(10) 0.16071(17) 0.0195(4) Uani 1 1 d . . .
N2 N 0.24811(8) 0.53626(11) 0.33933(16) 0.0178(3) Uani 1 1 d . . .
N3 N 0.44202(9) 0.59667(12) 0.51719(18) 0.0235(4) Uani 1 1 d . . .
C19 C 0.17877(10) 0.53763(14) 0.41251(19) 0.0196(4) Uani 1 1 d . . .
C26 C 0.18531(11) 0.09333(14) 0.1004(2) 0.0204(4) Uani 1 1 d . . .
C14 C 0.14485(11) 0.62937(14) 0.3985(2) 0.0215(4) Uani 1 1 d . . .
C3 C 0.42361(11) 0.37241(13) 0.3596(2) 0.0196(4) Uani 1 1 d . . .
H3 H 0.4789 0.3719 0.3959 0.024 Uiso 1 1 calc R . .
C8 C 0.25672(11) 0.62555(13) 0.2767(2) 0.0191(4) Uani 1 1 d . . .
C18 C 0.14732(10) 0.46668(14) 0.4926(2) 0.0210(4) Uani 1 1 d . . .
H18 H 0.1709 0.4053 0.5004 0.025 Uiso 1 1 calc R . .
C2 C 0.37683(11) 0.45300(13) 0.37660(19) 0.0179(4) Uani 1 1 d . . .
C31 C 0.19837(11) 0.17606(13) 0.1842(2) 0.0200(4) Uani 1 1 d . . .
C12 C 0.18667(13) 0.77610(14) 0.2523(2) 0.0263(5) Uani 1 1 d . . .
H12 H 0.1439 0.8167 0.2726 0.032 Uiso 1 1 calc R . .
C21 C 0.38080(11) 0.16735(14) 0.0028(2) 0.0220(4) Uani 1 1 d . . .
H21 H 0.4153 0.2199 0.0269 0.026 Uiso 1 1 calc R . .
C7 C 0.41202(10) 0.53382(14) 0.4544(2) 0.0182(4) Uani 1 1 d . . .
C20 C 0.30869(11) 0.15627(13) 0.06311(19) 0.0202(4) Uani 1 1 d . . .
C22 C 0.40023(12) 0.09895(15) -0.0934(2) 0.0264(5) Uani 1 1 d . . .
H22 H 0.4494 0.1044 -0.1356 0.032 Uiso 1 1 calc R . .
C1 C 0.29554(10) 0.45448(13) 0.32003(19) 0.0175(4) Uani 1 1 d . . .
C17 C 0.07977(11) 0.48893(16) 0.5610(2) 0.0273(5) Uani 1 1 d . . .
H17 H 0.0566 0.4417 0.6165 0.033 Uiso 1 1 calc R . .
C13 C 0.19316(11) 0.68439(14) 0.3098(2) 0.0202(4) Uani 1 1 d . . .
C6 C 0.26227(11) 0.37652(13) 0.24644(19) 0.0185(4) Uani 1 1 d . . .
H6 H 0.2078 0.3782 0.2053 0.022 Uiso 1 1 calc R . .
C4 C 0.38932(11) 0.29329(13) 0.2900(2) 0.0188(4) Uani 1 1 d . . .
H4 H 0.4206 0.2377 0.2812 0.023 Uiso 1 1 calc R . .
C5 C 0.30854(10) 0.29551(13) 0.2326(2) 0.0184(4) Uani 1 1 d . . .
C25 C 0.25557(12) 0.08049(13) 0.0236(2) 0.0208(4) Uani 1 1 d . . .
C10 C 0.30695(12) 0.74751(15) 0.1358(2) 0.0269(5) Uani 1 1 d . . .
H10 H 0.3457 0.7707 0.0769 0.032 Uiso 1 1 calc R . .
C30 C 0.14397(11) 0.20559(14) 0.2784(2) 0.0235(4) Uani 1 1 d . . .
H30 H 0.1536 0.2609 0.3358 0.028 Uiso 1 1 calc R . .
C16 C 0.04520(12) 0.57948(17) 0.5499(2) 0.0298(5) Uani 1 1 d . . .
H16 H -0.0008 0.5928 0.5982 0.036 Uiso 1 1 calc R . .
C23 C 0.34953(13) 0.02163(14) -0.1308(2) 0.0278(5) Uani 1 1 d . . .
H23 H 0.3653 -0.0251 -0.1956 0.033 Uiso 1 1 calc R . .
C9 C 0.31465(12) 0.65588(14) 0.1902(2) 0.0226(4) Uani 1 1 d . . .
H9 H 0.3576 0.6157 0.1692 0.027 Uiso 1 1 calc R . .
C27 C 0.11557(12) 0.04044(15) 0.1088(2) 0.0259(5) Uani 1 1 d . . .
H27 H 0.1056 -0.0150 0.0518 0.031 Uiso 1 1 calc R . .
C28 C 0.06075(12) 0.06965(15) 0.2014(2) 0.0283(5) Uani 1 1 d . . .
H28 H 0.0130 0.0339 0.2080 0.034 Uiso 1 1 calc R . .
C15 C 0.07693(11) 0.64954(15) 0.4698(2) 0.0257(5) Uani 1 1 d . . .
H15 H 0.0531 0.7108 0.4629 0.031 Uiso 1 1 calc R . .
C29 C 0.07525(12) 0.15133(15) 0.2853(2) 0.0277(5) Uani 1 1 d . . .
H29 H 0.0371 0.1700 0.3485 0.033 Uiso 1 1 calc R . .
C24 C 0.27704(12) 0.01282(14) -0.0744(2) 0.0258(5) Uani 1 1 d . . .
H24 H 0.2421 -0.0387 -0.1018 0.031 Uiso 1 1 calc R . .
C11 C 0.24347(13) 0.80650(15) 0.1656(2) 0.0292(5) Uani 1 1 d . . .
H11 H 0.2394 0.8685 0.1256 0.035 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 C31 1.402(2) . ?
N1 C20 1.407(2) . ?
N1 C5 1.416(2) . ?
N2 C19 1.405(2) . ?
N2 C8 1.401(2) . ?
N2 C1 1.420(2) . ?
N3 C7 1.148(2) . ?
C19 C14 1.412(3) . ?
C19 C18 1.385(3) . ?
C26 C31 1.408(3) . ?
C26 C25 1.450(3) . ?
C26 C27 1.392(3) . ?
C14 C13 1.441(3) . ?
C14 C15 1.404(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.397(3) . ?
C3 C4 1.384(3) . ?
C8 C13 1.407(3) . ?
C8 C9 1.392(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.390(3) . ?
C2 C7 1.442(3) . ?
C2 C1 1.404(2) . ?
C31 C30 1.393(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.399(3) . ?
C12 C11 1.379(3) . ?
C21 H21 0.9500 . ?
C21 C20 1.391(3) . ?
C21 C22 1.380(3) . ?
C20 C25 1.412(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.401(3) . ?
C1 C6 1.381(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.400(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(2) . ?
C25 C24 1.394(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.388(3) . ?
C10 C11 1.398(3) . ?
C30 H30 0.9500 . ?
C30 C29 1.386(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.378(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.376(3) . ?
C9 H9 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.387(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.399(3) . ?
C15 H15 0.9500 . ?
C29 H29 0.9500 . ?
C24 H24 0.9500 . ?
C11 H11 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
C31 N1 C20 108.35(15) . . ?
C31 N1 C5 124.96(16) . . ?
C20 N1 C5 126.53(15) . . ?
C19 N2 C1 124.89(15) . . ?
C8 N2 C19 108.47(15) . . ?
C8 N2 C1 126.31(15) . . ?
N2 C19 C14 108.08(16) . . ?
C18 C19 N2 129.16(17) . . ?
C18 C19 C14 122.68(17) . . ?
C31 C26 C25 107.00(16) . . ?
C27 C26 C31 119.57(18) . . ?
C27 C26 C25 133.37(18) . . ?
C19 C14 C13 107.61(16) . . ?
C15 C14 C19 118.53(19) . . ?
C15 C14 C13 133.84(18) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 119.96(17) . . ?
N2 C8 C13 108.93(16) . . ?
C9 C8 N2 128.78(17) . . ?
C9 C8 C13 122.25(17) . . ?
C19 C18 H18 121.4 . . ?
C19 C18 C17 117.25(18) . . ?
C17 C18 H18 121.4 . . ?
C3 C2 C7 119.72(16) . . ?
C3 C2 C1 119.97(17) . . ?
C1 C2 C7 120.30(17) . . ?
N1 C31 C26 108.97(17) . . ?
C30 C31 N1 129.26(17) . . ?
C30 C31 C26 121.68(17) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C11 C12 C13 118.83(19) . . ?
C20 C21 H21 121.4 . . ?
C22 C21 H21 121.4 . . ?
C22 C21 C20 117.29(18) . . ?
N3 C7 C2 178.04(19) . . ?
N1 C20 C25 108.52(15) . . ?
C21 C20 N1 129.66(17) . . ?
C21 C20 C25 121.72(18) . . ?
C21 C22 H22 119.1 . . ?
C21 C22 C23 121.86(19) . . ?
C23 C22 H22 119.1 . . ?
C2 C1 N2 119.62(17) . . ?
C6 C1 N2 120.51(15) . . ?
C6 C1 C2 119.87(17) . . ?
C18 C17 H17 119.3 . . ?
C18 C17 C16 121.3(2) . . ?
C16 C17 H17 119.3 . . ?
C8 C13 C14 106.86(16) . . ?
C12 C13 C14 133.78(17) . . ?
C12 C13 C8 119.31(18) . . ?
C1 C6 H6 120.0 . . ?
C1 C6 C5 120.00(16) . . ?
C5 C6 H6 120.0 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.80(17) . . ?
C5 C4 H4 120.1 . . ?
C6 C5 N1 119.56(15) . . ?
C6 C5 C4 120.35(17) . . ?
C4 C5 N1 120.09(16) . . ?
C20 C25 C26 107.16(16) . . ?
C24 C25 C26 133.45(19) . . ?
C24 C25 C20 119.39(18) . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.53(19) . . ?
C11 C10 H10 119.2 . . ?
C31 C30 H30 121.2 . . ?
C29 C30 C31 117.57(18) . . ?
C29 C30 H30 121.2 . . ?
C17 C16 H16 119.5 . . ?
C15 C16 C17 120.95(19) . . ?
C15 C16 H16 119.5 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.52(19) . . ?
C24 C23 H23 119.7 . . ?
C8 C9 H9 121.5 . . ?
C10 C9 C8 117.05(18) . . ?
C10 C9 H9 121.5 . . ?
C26 C27 H27 120.4 . . ?
C28 C27 C26 119.18(18) . . ?
C28 C27 H27 120.4 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.46(18) . . ?
C29 C28 H28 119.8 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.25(19) . . ?
C16 C15 H15 120.4 . . ?
C30 C29 C28 121.54(19) . . ?
C30 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C25 C24 H24 120.4 . . ?
C23 C24 C25 119.15(19) . . ?
C23 C24 H24 120.4 . . ?
C12 C11 C10 121.03(19) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?

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 C31 C30 C29 -177.07(18) . . . . ?
N1 C20 C25 C26 -0.2(2) . . . . ?
N1 C20 C25 C24 179.21(17) . . . . ?
N2 C19 C14 C13 2.1(2) . . . . ?
N2 C19 C14 C15 -176.61(16) . . . . ?
N2 C19 C18 C17 176.38(18) . . . . ?
N2 C8 C13 C14 1.2(2) . . . . ?
N2 C8 C13 C12 -176.70(16) . . . . ?
N2 C8 C9 C10 176.80(18) . . . . ?
N2 C1 C6 C5 -177.71(16) . . . . ?
C19 N2 C8 C13 0.1(2) . . . . ?
C19 N2 C8 C9 -177.48(19) . . . . ?
C19 N2 C1 C2 -119.18(19) . . . . ?
C19 N2 C1 C6 60.7(2) . . . . ?
C19 C14 C13 C8 -2.0(2) . . . . ?
C19 C14 C13 C12 175.4(2) . . . . ?
C19 C14 C15 C16 -0.5(3) . . . . ?
C19 C18 C17 C16 -0.2(3) . . . . ?
C26 C31 C30 C29 -1.1(3) . . . . ?
C26 C25 C24 C23 179.06(19) . . . . ?
C26 C27 C28 C29 0.1(3) . . . . ?
C14 C19 C18 C17 -0.2(3) . . . . ?
C3 C2 C7 N3 -4(6) . . . . ?
C3 C2 C1 N2 179.20(16) . . . . ?
C3 C2 C1 C6 -0.7(3) . . . . ?
C3 C4 C5 N1 179.74(17) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C8 N2 C19 C14 -1.43(19) . . . . ?
C8 N2 C19 C18 -178.43(18) . . . . ?
C8 N2 C1 C2 68.2(2) . . . . ?
C8 N2 C1 C6 -111.9(2) . . . . ?
C18 C19 C14 C13 179.38(17) . . . . ?
C18 C19 C14 C15 0.6(3) . . . . ?
C18 C17 C16 C15 0.3(3) . . . . ?
C2 C3 C4 C5 2.1(3) . . . . ?
C2 C1 C6 C5 2.1(3) . . . . ?
C31 N1 C20 C21 177.09(18) . . . . ?
C31 N1 C20 C25 0.64(19) . . . . ?
C31 N1 C5 C6 -46.7(3) . . . . ?
C31 N1 C5 C4 132.96(18) . . . . ?
C31 C26 C25 C20 -0.3(2) . . . . ?
C31 C26 C25 C24 -179.6(2) . . . . ?
C31 C26 C27 C28 -0.9(3) . . . . ?
C31 C30 C29 C28 0.2(3) . . . . ?
C21 C20 C25 C26 -177.02(17) . . . . ?
C21 C20 C25 C24 2.4(3) . . . . ?
C21 C22 C23 C24 1.6(3) . . . . ?
C7 C2 C1 N2 0.2(3) . . . . ?
C7 C2 C1 C6 -179.62(17) . . . . ?
C20 N1 C31 C26 -0.81(19) . . . . ?
C20 N1 C31 C30 175.58(19) . . . . ?
C20 N1 C5 C6 138.57(18) . . . . ?
C20 N1 C5 C4 -41.8(3) . . . . ?
C20 C21 C22 C23 0.6(3) . . . . ?
C20 C25 C24 C23 -0.2(3) . . . . ?
C22 C21 C20 N1 -178.61(19) . . . . ?
C22 C21 C20 C25 -2.6(3) . . . . ?
C22 C23 C24 C25 -1.7(3) . . . . ?
C1 N2 C19 C14 -175.14(16) . . . . ?
C1 N2 C19 C18 7.9(3) . . . . ?
C1 N2 C8 C13 173.74(16) . . . . ?
C1 N2 C8 C9 -3.9(3) . . . . ?
C1 C2 C7 N3 175(6) . . . . ?
C1 C6 C5 N1 178.12(16) . . . . ?
C1 C6 C5 C4 -1.5(3) . . . . ?
C17 C16 C15 C14 0.1(3) . . . . ?
C13 C14 C15 C16 -178.9(2) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
C13 C12 C11 C10 -0.4(3) . . . . ?
C4 C3 C2 C7 177.48(17) . . . . ?
C4 C3 C2 C1 -1.5(3) . . . . ?
C5 N1 C31 C26 -176.36(16) . . . . ?
C5 N1 C31 C30 0.0(3) . . . . ?
C5 N1 C20 C21 -7.4(3) . . . . ?
C5 N1 C20 C25 176.11(16) . . . . ?
C25 C26 C31 N1 0.7(2) . . . . ?
C25 C26 C31 C30 -176.07(17) . . . . ?
C25 C26 C27 C28 175.8(2) . . . . ?
C9 C8 C13 C14 178.97(17) . . . . ?
C9 C8 C13 C12 1.1(3) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C27 C26 C31 N1 178.19(16) . . . . ?
C27 C26 C31 C30 1.5(3) . . . . ?
C27 C26 C25 C20 -177.3(2) . . . . ?
C27 C26 C25 C24 3.4(4) . . . . ?
C27 C28 C29 C30 0.3(3) . . . . ?
C15 C14 C13 C8 176.4(2) . . . . ?
C15 C14 C13 C12 -6.1(4) . . . . ?
C11 C12 C13 C14 -177.8(2) . . . . ?
C11 C12 C13 C8 -0.6(3) . . . . ?
C11 C10 C9 C8 -0.5(3) . . . . ?

####################################################################### 
# 
# 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_2czbn
_database_code_depnum_ccdc_archive 'CCDC 1441237'
_audit_update_record             
;
2015-12-08 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2,6-2CzBN
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H19 N3'
_chemical_formula_sum            'C31 H19 N3'
_chemical_formula_weight         433.49

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
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   8.4562(16)
_cell_length_b                   7.9666(14)
_cell_length_c                   34.004(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.974(4)
_cell_angle_gamma                90.00
_cell_volume                     2282.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    867
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      18.70

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SAINT (Bruker, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13316
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_sigmaI/netI    0.0931
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.99
_reflns_number_total             4483
_reflns_number_gt                1850
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SAINT (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker,1997)'
_computing_publication_material  'SHELXTL (Bruker,1997)'

_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)+(0.0010P)²+0.8000P] 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         4483
_refine_ls_number_parameters     296
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1834
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.1340
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_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 0.2892(4) 1.0845(4) 0.10234(10) 0.1004(12) Uani 1 1 d . . .
N2 N 0.1068(4) 0.8930(3) 0.17644(8) 0.0641(8) Uani 1 1 d . . .
C1 C 0.2739(4) 0.9489(4) 0.11150(10) 0.0693(11) Uani 1 1 d . . .
C2 C 0.2541(4) 0.7793(4) 0.12454(10) 0.0569(9) Uani 1 1 d . A .
C3 C 0.1717(4) 0.7536(4) 0.15726(10) 0.0640(10) Uani 1 1 d . . .
C4 C 0.1564(5) 0.5938(4) 0.17205(11) 0.1025(15) Uani 1 1 d . . .
H4 H 0.1017 0.5757 0.1943 0.123 Uiso 1 1 calc R . .
C5 C 0.2235(6) 0.4610(5) 0.15336(13) 0.1141(17) Uani 1 1 d . . .
H5 H 0.2122 0.3528 0.1630 0.137 Uiso 1 1 calc R . .
C6 C 0.3063(5) 0.4853(4) 0.12096(12) 0.0840(12) Uani 1 1 d . A .
H6 H 0.3517 0.3943 0.1090 0.101 Uiso 1 1 calc R . .
C7 C 0.3223(4) 0.6446(4) 0.10618(10) 0.0676(10) Uani 1 1 d D . .
C8 C -0.0446(5) 0.9583(4) 0.16813(10) 0.0591(9) Uani 1 1 d . . .
C9 C -0.1642(5) 0.9061(5) 0.14060(11) 0.0781(11) Uani 1 1 d . . .
H9 H -0.1484 0.8177 0.1235 0.094 Uiso 1 1 calc R . .
C10 C -0.3068(6) 0.9887(6) 0.13924(13) 0.0966(14) Uani 1 1 d . . .
H10 H -0.3897 0.9542 0.1213 0.116 Uiso 1 1 calc R . .
C11 C -0.3296(6) 1.1210(6) 0.16388(15) 0.1008(14) Uani 1 1 d . . .
H11 H -0.4272 1.1753 0.1620 0.121 Uiso 1 1 calc R . .
C12 C -0.2115(6) 1.1758(5) 0.19149(13) 0.0833(12) Uani 1 1 d . . .
H12 H -0.2291 1.2651 0.2082 0.100 Uiso 1 1 calc R . .
C13 C -0.0644(5) 1.0935(4) 0.19372(10) 0.0610(9) Uani 1 1 d . . .
C14 C 0.0813(5) 1.1112(4) 0.21829(11) 0.0627(10) Uani 1 1 d . . .
C15 C 0.1347(6) 1.2176(5) 0.24857(12) 0.0848(12) Uani 1 1 d . . .
H15 H 0.0689 1.3020 0.2567 0.102 Uiso 1 1 calc R . .
C16 C 0.2842(6) 1.1987(6) 0.26653(13) 0.1026(15) Uani 1 1 d . . .
H16 H 0.3191 1.2704 0.2870 0.123 Uiso 1 1 calc R . .
C17 C 0.3854(5) 1.0746(6) 0.25484(13) 0.0974(14) Uani 1 1 d . . .
H17 H 0.4870 1.0644 0.2675 0.117 Uiso 1 1 calc R . .
C18 C 0.3358(5) 0.9659(5) 0.22447(12) 0.0800(12) Uani 1 1 d . . .
H18 H 0.4024 0.8823 0.2163 0.096 Uiso 1 1 calc R . .
C19 C 0.1853(5) 0.9860(4) 0.20692(10) 0.0586(9) Uani 1 1 d . . .
N3 N 0.4211(7) 0.6674(8) 0.07692(18) 0.0919(13) Uani 0.642(3) 1 d PD A 1
C20 C 0.3898(7) 0.7310(9) 0.04143(14) 0.076(3) Uani 0.642(3) 1 d PGD A 1
C21 C 0.2484(6) 0.8011(9) 0.02519(17) 0.085(3) Uani 0.642(3) 1 d PG A 1
H21A H 0.1614 0.8077 0.0401 0.102 Uiso 0.642(3) 1 calc PR A 1
C22 C 0.2370(7) 0.8613(8) -0.01332(18) 0.143(5) Uani 0.642(3) 1 d PG A 1
H22A H 0.1424 0.9082 -0.0242 0.172 Uiso 0.642(3) 1 calc PR A 1
C23 C 0.3670(9) 0.8514(9) -0.03559(13) 0.125(4) Uani 0.642(3) 1 d PG A 1
H23A H 0.3594 0.8917 -0.0614 0.150 Uiso 0.642(3) 1 calc PR A 1
C24 C 0.5084(7) 0.7813(9) -0.01934(17) 0.146(5) Uani 0.642(3) 1 d PG A 1
H24A H 0.5954 0.7747 -0.0342 0.176 Uiso 0.642(3) 1 calc PR A 1
C25 C 0.5198(6) 0.7211(8) 0.01917(18) 0.082(3) Uani 0.642(3) 1 d PGD A 1
C26 C 0.6438(6) 0.6374(5) 0.04185(13) 0.091(3) Uani 0.642(3) 1 d PGD A 1
C27 C 0.7995(6) 0.5892(7) 0.03772(16) 0.104(3) Uani 0.642(3) 1 d PG A 1
H27A H 0.8458 0.6136 0.0146 0.124 Uiso 0.642(3) 1 calc PR A 1
C28 C 0.8859(5) 0.5045(7) 0.0682(2) 0.141(3) Uani 0.642(3) 1 d PG A 1
H28A H 0.9900 0.4723 0.0654 0.170 Uiso 0.642(3) 1 calc PR A 1
C29 C 0.8166(6) 0.4680(6) 0.10281(17) 0.114(3) Uani 0.642(3) 1 d PG A 1
H29A H 0.8744 0.4113 0.1232 0.137 Uiso 0.642(3) 1 calc PR A 1
C30 C 0.6609(6) 0.5162(6) 0.10693(13) 0.094(3) Uani 0.642(3) 1 d PG A 1
H30A H 0.6146 0.4917 0.1301 0.112 Uiso 0.642(3) 1 calc PR A 1
C31 C 0.5745(5) 0.6008(6) 0.07645(14) 0.080(2) Uani 0.642(3) 1 d PGD A 1
N3' N 0.3981(6) 0.6672(11) 0.0711(2) 0.0919(13) Uani 0.358(3) 1 d PGD A 2
C20' C 0.3144(13) 0.7522(17) 0.0341(3) 0.076(3) Uani 0.358(3) 1 d PGD A 2
C21' C 0.1583(12) 0.8052(19) 0.0262(3) 0.085(3) Uani 0.358(3) 1 d PG A 2
H21B H 0.0876 0.7973 0.0456 0.102 Uiso 0.358(3) 1 calc PR A 2
C22' C 0.1079(11) 0.8702(17) -0.0107(3) 0.143(5) Uani 0.358(3) 1 d PG A 2
H22B H 0.0035 0.9057 -0.0160 0.172 Uiso 0.358(3) 1 calc PR A 2
C23' C 0.2136(15) 0.8820(16) -0.0397(2) 0.125(4) Uani 0.358(3) 1 d PG A 2
H23B H 0.1799 0.9255 -0.0644 0.150 Uiso 0.358(3) 1 calc PR A 2
C24' C 0.3697(13) 0.8290(18) -0.0318(3) 0.146(5) Uani 0.358(3) 1 d PG A 2
H24B H 0.4404 0.8369 -0.0512 0.176 Uiso 0.358(3) 1 calc PR A 2
C25' C 0.4201(10) 0.7640(16) 0.0051(3) 0.082(3) Uani 0.358(3) 1 d PGD A 2
C26' C 0.5707(10) 0.7045(13) 0.0182(3) 0.091(3) Uani 0.358(3) 1 d PGD A 2
C27' C 0.7179(11) 0.6720(12) 0.0045(3) 0.104(3) Uani 0.358(3) 1 d PG A 2
H27B H 0.7381 0.7042 -0.0208 0.124 Uiso 0.358(3) 1 calc PR A 2
C28' C 0.8350(9) 0.5914(14) 0.0288(4) 0.141(3) Uani 0.358(3) 1 d PG A 2
H28B H 0.9335 0.5697 0.0197 0.170 Uiso 0.358(3) 1 calc PR A 2
C29' C 0.8048(10) 0.5433(13) 0.0668(3) 0.114(3) Uani 0.358(3) 1 d PG A 2
H29B H 0.8831 0.4894 0.0830 0.137 Uiso 0.358(3) 1 calc PR A 2
C30' C 0.6575(12) 0.5758(12) 0.0804(3) 0.094(3) Uani 0.358(3) 1 d PG A 2
H30B H 0.6373 0.5436 0.1058 0.112 Uiso 0.358(3) 1 calc PR A 2
C31' C 0.5405(9) 0.6564(13) 0.0561(3) 0.080(2) Uani 0.358(3) 1 d PGD A 2


_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 1.135(4) . ?
N2 C8 1.388(4) . ?
N2 C19 1.394(4) . ?
N2 C3 1.422(4) . ?
C1 C2 1.436(4) . ?
C2 C3 1.378(4) . ?
C2 C7 1.392(4) . ?
C3 C4 1.379(4) . ?
C4 C5 1.381(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(4) . ?
C6 H6 0.9300 . ?
C7 N3 1.365(5) . ?
C7 N3' 1.414(6) . ?
C8 C9 1.381(4) . ?
C8 C13 1.404(4) . ?
C9 C10 1.371(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.403(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.434(4) . ?
C14 C15 1.379(4) . ?
C14 C19 1.407(4) . ?
C15 C16 1.364(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(4) . ?
C18 H18 0.9300 . ?
N3 C20 1.314(6) . ?
N3 C31 1.403(6) . ?
C20 C21 1.3900 . ?
C20 C25 1.3900 . ?
C21 C22 1.3900 . ?
C21 H21A 0.9300 . ?
C22 C23 1.3900 . ?
C22 H22A 0.9300 . ?
C23 C24 1.3900 . ?
C23 H23A 0.9300 . ?
C24 C25 1.3900 . ?
C24 H24A 0.9300 . ?
C25 C26 1.414(5) . ?
C26 C27 1.3900 . ?
C26 C31 1.3900 . ?
C27 C28 1.3900 . ?
C27 H27A 0.9300 . ?
C28 C29 1.3900 . ?
C28 H28A 0.9300 . ?
C29 C30 1.3900 . ?
C29 H29A 0.9300 . ?
C30 C31 1.3900 . ?
C30 H30A 0.9300 . ?
N3' C31' 1.350(7) . ?
N3' C20' 1.545(8) . ?
C20' C21' 1.3900 . ?
C20' C25' 1.3900 . ?
C21' C22' 1.3900 . ?
C21' H21B 0.9300 . ?
C22' C23' 1.3900 . ?
C22' H22B 0.9300 . ?
C23' C24' 1.3900 . ?
C23' H23B 0.9300 . ?
C24' C25' 1.3900 . ?
C24' H24B 0.9300 . ?
C25' C26' 1.395(8) . ?
C26' C27' 1.3900 . ?
C26' C31' 1.3900 . ?
C27' C28' 1.3900 . ?
C27' H27B 0.9300 . ?
C28' C29' 1.3900 . ?
C28' H28B 0.9300 . ?
C29' C30' 1.3900 . ?
C29' H29B 0.9300 . ?
C30' C31' 1.3900 . ?
C30' H30B 0.9300 . ?

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
C8 N2 C19 108.9(3) . . ?
C8 N2 C3 125.8(3) . . ?
C19 N2 C3 125.3(3) . . ?
N1 C1 C2 177.9(4) . . ?
C3 C2 C7 120.4(3) . . ?
C3 C2 C1 118.0(3) . . ?
C7 C2 C1 121.5(3) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 N2 119.8(3) . . ?
C4 C3 N2 120.1(3) . . ?
C3 C4 C5 118.9(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.4(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
N3 C7 C6 118.3(4) . . ?
N3 C7 C2 121.9(4) . . ?
C6 C7 C2 119.3(3) . . ?
C6 C7 N3' 119.4(5) . . ?
C2 C7 N3' 121.1(4) . . ?
C9 C8 N2 129.3(3) . . ?
C9 C8 C13 122.1(4) . . ?
N2 C8 C13 108.6(3) . . ?
C10 C9 C8 118.0(4) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C11 C10 C9 121.2(4) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 121.9(4) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C13 118.3(4) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C12 C13 C8 118.6(4) . . ?
C12 C13 C14 134.3(4) . . ?
C8 C13 C14 107.1(3) . . ?
C15 C14 C19 118.0(4) . . ?
C15 C14 C13 134.8(4) . . ?
C19 C14 C13 107.2(3) . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 121.4(4) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 117.6(4) . . ?
C19 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
C18 C19 N2 128.9(3) . . ?
C18 C19 C14 122.9(4) . . ?
N2 C19 C14 108.2(3) . . ?
C20 N3 C7 129.3(5) . . ?
C20 N3 C31 104.4(5) . . ?
C7 N3 C31 125.6(5) . . ?
N3 C20 C21 128.1(5) . . ?
N3 C20 C25 111.9(5) . . ?
C21 C20 C25 120.0 . . ?
C22 C21 C20 120.0 . . ?
C22 C21 H21A 120.0 . . ?
C20 C21 H21A 120.0 . . ?
C23 C22 C21 120.0 . . ?
C23 C22 H22A 120.0 . . ?
C21 C22 H22A 120.0 . . ?
C22 C23 C24 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C24 C23 H23A 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24A 120.0 . . ?
C23 C24 H24A 120.0 . . ?
C24 C25 C20 120.0 . . ?
C24 C25 C26 131.6(4) . . ?
C20 C25 C26 108.3(4) . . ?
C27 C26 C31 120.0 . . ?
C27 C26 C25 137.7(4) . . ?
C31 C26 C25 102.3(4) . . ?
C26 C27 C28 120.0 . . ?
C26 C27 H27A 120.0 . . ?
C28 C27 H27A 120.0 . . ?
C29 C28 C27 120.0 . . ?
C29 C28 H28A 120.0 . . ?
C27 C28 H28A 120.0 . . ?
C28 C29 C30 120.0 . . ?
C28 C29 H29A 120.0 . . ?
C30 C29 H29A 120.0 . . ?
C29 C30 C31 120.0 . . ?
C29 C30 H30A 120.0 . . ?
C31 C30 H30A 120.0 . . ?
C30 C31 C26 120.0 . . ?
C30 C31 N3 127.0(4) . . ?
C26 C31 N3 112.9(4) . . ?
C31' N3' C7 142.6(7) . . ?
C31' N3' C20' 94.7(7) . . ?
C7 N3' C20' 122.2(5) . . ?
C21' C20' C25' 120.0 . . ?
C21' C20' N3' 130.7(7) . . ?
C25' C20' N3' 109.2(7) . . ?
C22' C21' C20' 120.0 . . ?
C22' C21' H21B 120.0 . . ?
C20' C21' H21B 120.0 . . ?
C21' C22' C23' 120.0 . . ?
C21' C22' H22B 120.0 . . ?
C23' C22' H22B 120.0 . . ?
C24' C23' C22' 120.0 . . ?
C24' C23' H23B 120.0 . . ?
C22' C23' H23B 120.0 . . ?
C23' C24' C25' 120.0 . . ?
C23' C24' H24B 120.0 . . ?
C25' C24' H24B 120.0 . . ?
C24' C25' C20' 120.0 . . ?
C24' C25' C26' 127.9(9) . . ?
C20' C25' C26' 112.1(9) . . ?
C27' C26' C31' 120.0 . . ?
C27' C26' C25' 140.9(8) . . ?
C31' C26' C25' 98.8(8) . . ?
C28' C27' C26' 120.0 . . ?
C28' C27' H27B 120.0 . . ?
C26' C27' H27B 120.0 . . ?
C27' C28' C29' 120.0 . . ?
C27' C28' H28B 120.0 . . ?
C29' C28' H28B 120.0 . . ?
C30' C29' C28' 120.0 . . ?
C30' C29' H29B 120.0 . . ?
C28' C29' H29B 120.0 . . ?
C29' C30' C31' 120.0 . . ?
C29' C30' H30B 120.0 . . ?
C31' C30' H30B 120.0 . . ?
N3' C31' C30' 114.7(7) . . ?
N3' C31' C26' 125.0(8) . . ?
C30' C31' C26' 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_czbn
_database_code_depnum_ccdc_archive 'CCDC 1441238'
_audit_update_record             
;
2015-12-08 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3,5-2CzBN
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H19 N3'
_chemical_formula_sum            'C31 H19 N3'
_chemical_formula_weight         433.49

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)/n
_symmetry_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                   9.1838(15)
_cell_length_b                   13.264(2)
_cell_length_c                   18.172(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.142(4)
_cell_angle_gamma                90.00
_cell_volume                     2196.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1620
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      20.37

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Bruker SMART'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15026
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0716
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         28.00
_reflns_number_total             5283
_reflns_number_gt                2805
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0010P)²+0.2000P] 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         5283
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.004
_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 0.6613(2) 0.86568(17) 0.12483(10) 0.0892(7) Uani 1 1 d . . .
N2 N 0.20345(15) 0.65121(13) 0.26440(7) 0.0539(4) Uani 1 1 d . . .
N3 N 0.14279(14) 0.64041(12) -0.00417(7) 0.0475(4) Uani 1 1 d . . .
C1 C 0.5584(2) 0.81918(18) 0.12712(10) 0.0607(6) Uani 1 1 d . . .
C2 C 0.42676(18) 0.76005(15) 0.12899(10) 0.0485(5) Uani 1 1 d . . .
C3 C 0.37812(19) 0.73638(15) 0.19611(9) 0.0530(5) Uani 1 1 d . . .
H3 H 0.4307 0.7573 0.2405 0.064 Uiso 1 1 calc R . .
C4 C 0.25075(19) 0.68149(15) 0.19611(9) 0.0477(5) Uani 1 1 d . . .
C5 C 0.17278(18) 0.64985(14) 0.13015(9) 0.0465(5) Uani 1 1 d . . .
H5 H 0.0874 0.6123 0.1308 0.056 Uiso 1 1 calc R . .
C6 C 0.22150(17) 0.67385(14) 0.06326(9) 0.0418(4) Uani 1 1 d . . .
C7 C 0.34857(18) 0.72889(14) 0.06242(9) 0.0463(5) Uani 1 1 d . . .
H7 H 0.3818 0.7451 0.0176 0.056 Uiso 1 1 calc R . .
C8 C 0.2797(2) 0.58398(15) 0.31467(10) 0.0532(5) Uani 1 1 d . . .
C9 C 0.4174(2) 0.54232(18) 0.31419(11) 0.0699(6) Uani 1 1 d . . .
H9 H 0.4747 0.5576 0.2769 0.084 Uiso 1 1 calc R . .
C10 C 0.4666(3) 0.47717(19) 0.37110(14) 0.0793(7) Uani 1 1 d . . .
H10 H 0.5589 0.4480 0.3724 0.095 Uiso 1 1 calc R . .
C11 C 0.3810(3) 0.45455(18) 0.42621(13) 0.0816(7) Uani 1 1 d . . .
H11 H 0.4171 0.4107 0.4641 0.098 Uiso 1 1 calc R . .
C12 C 0.2446(3) 0.49519(18) 0.42623(11) 0.0711(6) Uani 1 1 d . . .
H12 H 0.1883 0.4794 0.4638 0.085 Uiso 1 1 calc R . .
C13 C 0.1906(2) 0.56056(15) 0.36943(10) 0.0533(5) Uani 1 1 d . . .
C14 C 0.0557(2) 0.61512(16) 0.35152(9) 0.0519(5) Uani 1 1 d . . .
C15 C -0.0727(2) 0.62291(18) 0.38462(11) 0.0660(6) Uani 1 1 d . . .
H15 H -0.0836 0.5857 0.4269 0.079 Uiso 1 1 calc R . .
C16 C -0.1826(2) 0.6855(2) 0.35471(13) 0.0729(7) Uani 1 1 d . . .
H16 H -0.2680 0.6911 0.3771 0.088 Uiso 1 1 calc R . .
C17 C -0.1681(2) 0.74064(18) 0.29127(12) 0.0680(6) Uani 1 1 d . . .
H17 H -0.2437 0.7833 0.2720 0.082 Uiso 1 1 calc R . .
C18 C -0.0437(2) 0.73371(16) 0.25604(10) 0.0592(5) Uani 1 1 d . . .
H18 H -0.0344 0.7706 0.2134 0.071 Uiso 1 1 calc R . .
C19 C 0.06646(19) 0.66981(15) 0.28667(9) 0.0478(5) Uani 1 1 d . . .
C20 C 0.20185(19) 0.58954(14) -0.06067(9) 0.0454(5) Uani 1 1 d . . .
C21 C 0.3438(2) 0.55646(15) -0.06362(11) 0.0567(5) Uani 1 1 d . . .
H21 H 0.4175 0.5683 -0.0247 0.068 Uiso 1 1 calc R . .
C22 C 0.3722(2) 0.50538(17) -0.12619(13) 0.0717(6) Uani 1 1 d . . .
H22 H 0.4665 0.4813 -0.1291 0.086 Uiso 1 1 calc R . .
C23 C 0.2635(3) 0.48905(18) -0.18498(13) 0.0785(7) Uani 1 1 d . . .
H23 H 0.2863 0.4558 -0.2271 0.094 Uiso 1 1 calc R . .
C24 C 0.1225(2) 0.52154(17) -0.18164(11) 0.0666(6) Uani 1 1 d . . .
H24 H 0.0496 0.5099 -0.2210 0.080 Uiso 1 1 calc R . .
C25 C 0.09011(19) 0.57183(14) -0.11886(9) 0.0492(5) Uani 1 1 d . . .
C26 C -0.04334(19) 0.61150(15) -0.09624(10) 0.0480(5) Uani 1 1 d . . .
C27 C -0.1887(2) 0.61516(16) -0.12942(11) 0.0591(6) Uani 1 1 d . . .
H27 H -0.2148 0.5882 -0.1764 0.071 Uiso 1 1 calc R . .
C28 C -0.2924(2) 0.65902(17) -0.09178(12) 0.0671(6) Uani 1 1 d . . .
H28 H -0.3898 0.6608 -0.1132 0.080 Uiso 1 1 calc R . .
C29 C -0.2543(2) 0.70041(18) -0.02271(13) 0.0707(6) Uani 1 1 d . . .
H29 H -0.3266 0.7306 0.0014 0.085 Uiso 1 1 calc R . .
C30 C -0.1127(2) 0.69852(16) 0.01177(11) 0.0608(6) Uani 1 1 d . . .
H30 H -0.0881 0.7270 0.0584 0.073 Uiso 1 1 calc R . .
C31 C -0.00795(18) 0.65276(14) -0.02536(9) 0.0457(5) Uani 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
N1 C1 1.134(2) . ?
N2 C19 1.391(2) . ?
N2 C8 1.400(2) . ?
N2 C4 1.423(2) . ?
N3 C20 1.394(2) . ?
N3 C31 1.400(2) . ?
N3 C6 1.4144(19) . ?
C1 C2 1.445(3) . ?
C2 C3 1.386(2) . ?
C2 C7 1.391(2) . ?
C3 C4 1.378(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(2) . ?
C5 C6 1.383(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.381(3) . ?
C8 C13 1.399(2) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.363(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.437(3) . ?
C14 C15 1.393(2) . ?
C14 C19 1.398(2) . ?
C15 C16 1.366(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(2) . ?
C18 H18 0.9300 . ?
C20 C21 1.383(2) . ?
C20 C25 1.399(2) . ?
C21 C22 1.376(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.374(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.385(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.440(2) . ?
C26 C27 1.396(2) . ?
C26 C31 1.400(2) . ?
C27 C28 1.369(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.375(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.372(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.382(2) . ?
C30 H30 0.9300 . ?

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
C19 N2 C8 108.68(14) . . ?
C19 N2 C4 126.09(15) . . ?
C8 N2 C4 124.52(15) . . ?
C20 N3 C31 108.43(14) . . ?
C20 N3 C6 125.89(14) . . ?
C31 N3 C6 125.67(14) . . ?
N1 C1 C2 179.2(2) . . ?
C3 C2 C7 120.67(16) . . ?
C3 C2 C1 120.38(16) . . ?
C7 C2 C1 118.94(16) . . ?
C4 C3 C2 119.09(16) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.56(16) . . ?
C3 C4 N2 120.04(15) . . ?
C5 C4 N2 119.27(16) . . ?
C4 C5 C6 120.16(16) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 119.90(16) . . ?
C7 C6 N3 119.91(15) . . ?
C5 C6 N3 120.18(15) . . ?
C6 C7 C2 119.61(16) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
C9 C8 C13 122.17(19) . . ?
C9 C8 N2 129.39(18) . . ?
C13 C8 N2 108.43(16) . . ?
C10 C9 C8 117.4(2) . . ?
C10 C9 H9 121.3 . . ?
C8 C9 H9 121.3 . . ?
C9 C10 C11 121.1(2) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.3(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C8 118.69(19) . . ?
C12 C13 C14 134.38(19) . . ?
C8 C13 C14 106.92(16) . . ?
C15 C14 C19 118.6(2) . . ?
C15 C14 C13 133.82(19) . . ?
C19 C14 C13 107.63(16) . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 121.5(2) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 117.42(19) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 H18 121.3 . . ?
C18 C19 N2 129.42(17) . . ?
C18 C19 C14 122.17(17) . . ?
N2 C19 C14 108.33(16) . . ?
C21 C20 N3 129.60(16) . . ?
C21 C20 C25 121.59(17) . . ?
N3 C20 C25 108.79(15) . . ?
C22 C21 C20 117.70(19) . . ?
C22 C21 H21 121.1 . . ?
C20 C21 H21 121.1 . . ?
C21 C22 C23 121.43(19) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 120.7(2) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 119.17(19) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C24 C25 C20 119.42(18) . . ?
C24 C25 C26 133.51(17) . . ?
C20 C25 C26 107.05(15) . . ?
C27 C26 C31 118.95(18) . . ?
C27 C26 C25 133.76(18) . . ?
C31 C26 C25 107.29(15) . . ?
C28 C27 C26 119.09(19) . . ?
C28 C27 H27 120.5 . . ?
C26 C27 H27 120.5 . . ?
C27 C28 C29 120.77(18) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C30 C29 C28 122.0(2) . . ?
C30 C29 H29 119.0 . . ?
C28 C29 H29 119.0 . . ?
C29 C30 C31 117.56(19) . . ?
C29 C30 H30 121.2 . . ?
C31 C30 H30 121.2 . . ?
C30 C31 N3 129.91(16) . . ?
C30 C31 C26 121.66(16) . . ?
N3 C31 C26 108.42(15) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.031
