# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_140619a_0m
_database_code_depnum_ccdc_archive 'CCDC 1403580'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 B F2 N4'
_chemical_formula_weight         364.20

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6636(9)
_cell_length_b                   9.9831(10)
_cell_length_c                   11.0281(11)
_cell_angle_alpha                97.3640(10)
_cell_angle_beta                 91.1370(10)
_cell_angle_gamma                108.7930(10)
_cell_volume                     893.62(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4603
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.69

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9857
_exptl_absorpt_correction_T_max  0.9885
_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            7793
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         27.69
_reflns_number_total             4062
_reflns_number_gt                3370
_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)+(0.0679P)²+0.2730P] 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         4062
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.026
_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
B1 B 1.22302(18) 0.40722(18) 0.44655(15) 0.0340(3) Uani 1 1 d . . .
C1 C 1.27998(17) 0.60201(16) 0.29152(14) 0.0393(3) Uani 1 1 d . . .
C2 C 1.17452(18) 0.62687(16) 0.20835(14) 0.0404(3) Uani 1 1 d . . .
H2 H 1.2030 0.6989 0.1590 0.048 Uiso 1 1 calc R . .
C3 C 1.01787(17) 0.52700(15) 0.20959(13) 0.0351(3) Uani 1 1 d . . .
C4 C 1.03369(16) 0.43930(15) 0.29520(12) 0.0331(3) Uani 1 1 d . . .
C5 C 0.94291(16) 0.32335(14) 0.35556(12) 0.0308(3) Uani 1 1 d . . .
C6 C 0.77478(16) 0.23156(15) 0.33663(12) 0.0327(3) Uani 1 1 d . . .
C7 C 0.67632(16) 0.22902(15) 0.22592(13) 0.0344(3) Uani 1 1 d . . .
C8 C 0.69348(17) 0.18047(16) 0.10633(14) 0.0385(3) Uani 1 1 d . . .
C9 C 0.56020(18) 0.19178(17) 0.03658(14) 0.0423(3) Uani 1 1 d . . .
H9 H 0.5390 0.1654 -0.0476 0.051 Uiso 1 1 calc R . .
C10 C 0.46804(18) 0.24779(18) 0.11356(15) 0.0424(3) Uani 1 1 d . . .
C11 C 1.45740(19) 0.6784(2) 0.32337(19) 0.0554(5) Uani 1 1 d . . .
H11A H 1.4767 0.6995 0.4108 0.083 Uiso 1 1 calc R . .
H11B H 1.4905 0.7659 0.2885 0.083 Uiso 1 1 calc R . .
H11C H 1.5192 0.6191 0.2912 0.083 Uiso 1 1 calc R . .
C12 C 0.87108(19) 0.52851(18) 0.13725(15) 0.0457(4) Uani 1 1 d . . .
H12A H 0.8424 0.4514 0.0704 0.069 Uiso 1 1 calc R . .
H12B H 0.8950 0.6178 0.1057 0.069 Uiso 1 1 calc R . .
H12C H 0.7814 0.5174 0.1891 0.069 Uiso 1 1 calc R . .
C13 C 0.8265(2) 0.1269(2) 0.05938(16) 0.0559(5) Uani 1 1 d . . .
H13A H 0.9109 0.2036 0.0317 0.084 Uiso 1 1 calc R . .
H13B H 0.7828 0.0512 -0.0076 0.084 Uiso 1 1 calc R . .
H13C H 0.8713 0.0916 0.1238 0.084 Uiso 1 1 calc R . .
C14 C 0.3206(2) 0.2885(3) 0.08731(19) 0.0634(5) Uani 1 1 d . . .
H14A H 0.2375 0.2482 0.1410 0.095 Uiso 1 1 calc R . .
H14B H 0.2802 0.2528 0.0038 0.095 Uiso 1 1 calc R . .
H14C H 0.3494 0.3908 0.1003 0.095 Uiso 1 1 calc R . .
C15 C 0.80375(17) 0.13159(15) 0.51073(13) 0.0364(3) Uani 1 1 d . . .
C16 C 0.7332(2) 0.03647(17) 0.59339(15) 0.0458(4) Uani 1 1 d . . .
H16 H 0.6213 -0.0121 0.5864 0.055 Uiso 1 1 calc R . .
C17 C 0.8289(2) 0.01556(18) 0.68389(16) 0.0522(4) Uani 1 1 d . . .
H17 H 0.7818 -0.0462 0.7394 0.063 Uiso 1 1 calc R . .
C18 C 0.9980(2) 0.08669(18) 0.69372(16) 0.0506(4) Uani 1 1 d . . .
H18 H 1.0621 0.0694 0.7546 0.061 Uiso 1 1 calc R . .
C19 C 1.07081(19) 0.18083(17) 0.61566(14) 0.0425(3) Uani 1 1 d . . .
H19 H 1.1831 0.2276 0.6234 0.051 Uiso 1 1 calc R . .
C20 C 0.97347(17) 0.20585(15) 0.52371(13) 0.0336(3) Uani 1 1 d . . .
F1 F 1.27327(11) 0.48988(10) 0.55855(8) 0.0448(2) Uani 1 1 d . . .
F2 F 1.32438(10) 0.32781(10) 0.41728(9) 0.0456(2) Uani 1 1 d . . .
N1 N 1.19427(13) 0.48856(13) 0.34490(11) 0.0359(3) Uani 1 1 d . . .
N2 N 1.03770(13) 0.30268(12) 0.44548(10) 0.0324(3) Uani 1 1 d . . .
N3 N 0.70840(14) 0.14405(13) 0.41441(11) 0.0378(3) Uani 1 1 d . . .
N4 N 0.53802(15) 0.26790(14) 0.22944(11) 0.0400(3) Uani 1 1 d . . .
H4 H 0.5011 0.3000 0.2947 0.048 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
B1 F1 1.3718(18) . ?
B1 F2 1.3776(18) . ?
B1 N1 1.527(2) . ?
B1 N2 1.6073(18) . ?
C1 N1 1.3516(18) . ?
C1 C2 1.382(2) . ?
C1 C11 1.491(2) . ?
C2 C3 1.403(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(2) . ?
C3 C12 1.493(2) . ?
C4 N1 1.3920(17) . ?
C4 C5 1.4259(19) . ?
C5 N2 1.3527(17) . ?
C5 C6 1.4436(18) . ?
C6 N3 1.3106(18) . ?
C6 C7 1.4683(19) . ?
C7 C8 1.374(2) . ?
C7 N4 1.3731(18) . ?
C8 C9 1.417(2) . ?
C8 C13 1.494(2) . ?
C9 C10 1.365(2) . ?
C9 H9 0.9300 . ?
C10 N4 1.3660(19) . ?
C10 C14 1.494(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N3 1.3753(19) . ?
C15 C16 1.406(2) . ?
C15 C20 1.4121(19) . ?
C16 C17 1.364(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.403(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.403(2) . ?
C19 H19 0.9300 . ?
C20 N2 1.3692(18) . ?
N4 H4 0.8600 . ?

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
F1 B1 F2 110.18(12) . . ?
F1 B1 N1 114.39(13) . . ?
F2 B1 N1 114.02(12) . . ?
F1 B1 N2 111.15(11) . . ?
F2 B1 N2 109.74(12) . . ?
N1 B1 N2 96.61(10) . . ?
N1 C1 C2 107.82(12) . . ?
N1 C1 C11 122.23(14) . . ?
C2 C1 C11 129.96(14) . . ?
C1 C2 C3 109.68(13) . . ?
C1 C2 H2 125.2 . . ?
C3 C2 H2 125.2 . . ?
C4 C3 C2 105.00(12) . . ?
C4 C3 C12 130.78(13) . . ?
C2 C3 C12 124.12(13) . . ?
N1 C4 C3 108.63(12) . . ?
N1 C4 C5 108.37(11) . . ?
C3 C4 C5 142.83(12) . . ?
N2 C5 C4 110.53(11) . . ?
N2 C5 C6 118.29(12) . . ?
C4 C5 C6 131.18(12) . . ?
N3 C6 C5 121.17(12) . . ?
N3 C6 C7 118.31(12) . . ?
C5 C6 C7 120.44(12) . . ?
C8 C7 N4 108.12(12) . . ?
C8 C7 C6 128.84(13) . . ?
N4 C7 C6 122.87(13) . . ?
C7 C8 C9 106.28(13) . . ?
C7 C8 C13 126.76(14) . . ?
C9 C8 C13 126.96(14) . . ?
C10 C9 C8 108.67(13) . . ?
C10 C9 H9 125.7 . . ?
C8 C9 H9 125.7 . . ?
C9 C10 N4 107.22(13) . . ?
C9 C10 C14 130.70(15) . . ?
N4 C10 C14 122.05(15) . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C16 119.47(13) . . ?
N3 C15 C20 121.13(13) . . ?
C16 C15 C20 119.28(14) . . ?
C17 C16 C15 119.92(15) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.31(15) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 121.40(15) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 118.96(15) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
N2 C20 C19 121.89(13) . . ?
N2 C20 C15 118.03(12) . . ?
C19 C20 C15 120.08(13) . . ?
C1 N1 C4 108.85(12) . . ?
C1 N1 B1 137.81(12) . . ?
C4 N1 B1 113.25(11) . . ?
C5 N2 C20 121.20(11) . . ?
C5 N2 B1 111.06(11) . . ?
C20 N2 B1 127.72(11) . . ?
C6 N3 C15 119.40(12) . . ?
C10 N4 C7 109.68(13) . . ?
C10 N4 H4 125.2 . . ?
C7 N4 H4 125.2 . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        27.69
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.047
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_140526b_0m
_database_code_depnum_ccdc_archive 'CCDC 1403581'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-22 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 H27 B F2 N4'
_chemical_formula_weight         420.31

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7229(14)
_cell_length_b                   9.6603(15)
_cell_length_c                   15.144(2)
_cell_angle_alpha                91.398(2)
_cell_angle_beta                 106.187(2)
_cell_angle_gamma                112.231(2)
_cell_volume                     1122.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    987
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9881
_exptl_absorpt_correction_T_max  0.9915
_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            8109
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_sigmaI/netI    0.1424
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3926
_reflns_number_gt                1603
_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)+(0.0140P)²+0.3602P] 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       0.0044(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3926
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1781
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_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
B1 B -0.2090(6) 0.5727(5) 0.5498(3) 0.0446(12) Uani 1 1 d . . .
C1 C -0.2213(5) 0.3795(5) 0.6739(3) 0.0502(11) Uani 1 1 d . . .
C2 C -0.0893(6) 0.3623(4) 0.7425(3) 0.0542(12) Uani 1 1 d . . .
C3 C 0.0711(5) 0.4683(4) 0.7383(3) 0.0512(11) Uani 1 1 d . . .
C4 C 0.0305(5) 0.5514(4) 0.6678(3) 0.0438(10) Uani 1 1 d . . .
C5 C 0.1054(5) 0.6699(4) 0.6194(3) 0.0404(10) Uani 1 1 d . . .
C6 C 0.2834(5) 0.7710(4) 0.6316(3) 0.0405(10) Uani 1 1 d . . .
C7 C 0.1941(5) 0.8692(4) 0.4976(3) 0.0417(10) Uani 1 1 d . . .
C8 C 0.2372(5) 0.9670(4) 0.4335(3) 0.0536(12) Uani 1 1 d . . .
H8 H 0.3534 1.0207 0.4377 0.064 Uiso 1 1 calc R . .
C9 C 0.1091(6) 0.9834(4) 0.3650(3) 0.0581(12) Uani 1 1 d . . .
H9 H 0.1376 1.0495 0.3229 0.070 Uiso 1 1 calc R . .
C10 C -0.0636(6) 0.9019(5) 0.3579(3) 0.0609(13) Uani 1 1 d . . .
H10 H -0.1494 0.9151 0.3108 0.073 Uiso 1 1 calc R . .
C11 C -0.1128(5) 0.8030(5) 0.4172(3) 0.0535(12) Uani 1 1 d . . .
H11 H -0.2298 0.7491 0.4113 0.064 Uiso 1 1 calc R . .
C12 C 0.0183(5) 0.7851(4) 0.4872(3) 0.0401(10) Uani 1 1 d . . .
C13 C 0.4254(4) 0.7796(4) 0.7146(3) 0.0402(10) Uani 1 1 d . . .
C14 C 0.4624(5) 0.8392(4) 0.8043(3) 0.0513(11) Uani 1 1 d . . .
C15 C 0.6205(5) 0.8306(4) 0.8564(3) 0.0501(11) Uani 1 1 d . . .
C16 C 0.6758(5) 0.7668(4) 0.7971(3) 0.0470(11) Uani 1 1 d . . .
C17 C -0.4149(5) 0.2971(4) 0.6483(3) 0.0722(14) Uani 1 1 d . . .
H17A H -0.4574 0.3391 0.6894 0.108 Uiso 1 1 calc R . .
H17B H -0.4436 0.1920 0.6536 0.108 Uiso 1 1 calc R . .
H17C H -0.4679 0.3072 0.5855 0.108 Uiso 1 1 calc R . .
C18 C -0.1172(5) 0.2502(5) 0.8102(3) 0.0724(14) Uani 1 1 d . . .
H18A H -0.0238 0.2150 0.8238 0.087 Uiso 1 1 calc R . .
H18B H -0.2260 0.1636 0.7816 0.087 Uiso 1 1 calc R . .
C19 C -0.1225(8) 0.3169(6) 0.9002(3) 0.134(2) Uani 1 1 d . . .
H19A H -0.0168 0.4049 0.9277 0.200 Uiso 1 1 calc R . .
H19B H -0.1336 0.2434 0.9422 0.200 Uiso 1 1 calc R . .
H19C H -0.2203 0.3446 0.8878 0.200 Uiso 1 1 calc R . .
C20 C 0.2437(5) 0.4765(5) 0.7962(3) 0.0756(15) Uani 1 1 d . . .
H20A H 0.3229 0.5023 0.7602 0.113 Uiso 1 1 calc R . .
H20B H 0.2310 0.3803 0.8160 0.113 Uiso 1 1 calc R . .
H20C H 0.2887 0.5524 0.8496 0.113 Uiso 1 1 calc R . .
C21 C 0.3543(6) 0.9015(5) 0.8407(3) 0.0974(18) Uani 1 1 d . . .
H21A H 0.4270 1.0007 0.8751 0.146 Uiso 1 1 calc R . .
H21B H 0.3030 0.8363 0.8808 0.146 Uiso 1 1 calc R . .
H21C H 0.2638 0.9075 0.7896 0.146 Uiso 1 1 calc R . .
C22 C 0.7107(5) 0.8795(5) 0.9598(3) 0.0760(14) Uani 1 1 d . . .
H22A H 0.8341 0.9039 0.9728 0.091 Uiso 1 1 calc R . .
H22B H 0.6981 0.9704 0.9785 0.091 Uiso 1 1 calc R . .
C23 C 0.6390(7) 0.7602(6) 1.0168(3) 0.117(2) Uani 1 1 d . . .
H23A H 0.5172 0.7368 1.0052 0.176 Uiso 1 1 calc R . .
H23B H 0.7001 0.7971 1.0816 0.176 Uiso 1 1 calc R . .
H23C H 0.6538 0.6707 0.9999 0.176 Uiso 1 1 calc R . .
C24 C 0.8306(5) 0.7281(5) 0.8138(3) 0.0776(15) Uani 1 1 d . . .
H24A H 0.9259 0.8001 0.8631 0.116 Uiso 1 1 calc R . .
H24B H 0.8632 0.7308 0.7582 0.116 Uiso 1 1 calc R . .
H24C H 0.8025 0.6287 0.8311 0.116 Uiso 1 1 calc R . .
F1 F -0.3005(3) 0.4818(2) 0.46512(15) 0.0580(7) Uani 1 1 d . . .
F2 F -0.3006(2) 0.6531(2) 0.56870(14) 0.0560(6) Uani 1 1 d . . .
N1 N -0.1494(4) 0.4933(4) 0.6282(2) 0.0455(9) Uani 1 1 d . . .
N2 N -0.0206(4) 0.6863(3) 0.5497(2) 0.0385(8) Uani 1 1 d . . .
N3 N 0.3248(4) 0.8622(3) 0.5710(2) 0.0446(9) Uani 1 1 d . . .
N4 N 0.5564(4) 0.7374(3) 0.7102(2) 0.0486(9) Uani 1 1 d . . .
H4 H 0.5631 0.6982 0.6606 0.058 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
B1 F1 1.377(5) . ?
B1 F2 1.382(4) . ?
B1 N1 1.507(5) . ?
B1 N2 1.593(5) . ?
C1 N1 1.355(4) . ?
C1 C2 1.386(5) . ?
C1 C17 1.496(5) . ?
C2 C3 1.407(5) . ?
C2 C18 1.509(5) . ?
C3 C4 1.399(5) . ?
C3 C20 1.488(5) . ?
C4 N1 1.389(4) . ?
C4 C5 1.420(5) . ?
C5 N2 1.356(4) . ?
C5 C6 1.443(5) . ?
C6 N3 1.316(4) . ?
C6 C13 1.474(5) . ?
C7 N3 1.377(4) . ?
C7 C12 1.398(4) . ?
C7 C8 1.399(5) . ?
C8 C9 1.358(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.361(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.394(4) . ?
C11 H11 0.9300 . ?
C12 N2 1.379(4) . ?
C13 C14 1.363(4) . ?
C13 N4 1.368(4) . ?
C14 C15 1.419(5) . ?
C14 C21 1.504(5) . ?
C15 C16 1.364(5) . ?
C15 C22 1.513(5) . ?
C16 N4 1.374(4) . ?
C16 C24 1.491(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.513(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.505(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N4 H4 0.8600 . ?

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
F1 B1 F2 109.4(3) . . ?
F1 B1 N1 114.8(4) . . ?
F2 B1 N1 114.1(4) . . ?
F1 B1 N2 110.7(3) . . ?
F2 B1 N2 109.9(3) . . ?
N1 B1 N2 97.3(3) . . ?
N1 C1 C2 108.9(4) . . ?
N1 C1 C17 120.7(4) . . ?
C2 C1 C17 130.3(4) . . ?
C1 C2 C3 108.1(4) . . ?
C1 C2 C18 124.9(4) . . ?
C3 C2 C18 127.0(4) . . ?
C4 C3 C2 106.1(3) . . ?
C4 C3 C20 129.8(4) . . ?
C2 C3 C20 124.0(4) . . ?
N1 C4 C3 108.5(3) . . ?
N1 C4 C5 108.2(3) . . ?
C3 C4 C5 143.2(4) . . ?
N2 C5 C4 110.4(3) . . ?
N2 C5 C6 117.3(3) . . ?
C4 C5 C6 132.3(4) . . ?
N3 C6 C5 121.7(3) . . ?
N3 C6 C13 117.4(3) . . ?
C5 C6 C13 120.9(3) . . ?
N3 C7 C12 121.6(4) . . ?
N3 C7 C8 119.5(4) . . ?
C12 C7 C8 118.8(4) . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.0(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 122.5(4) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 117.7(4) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
N2 C12 C11 121.3(4) . . ?
N2 C12 C7 117.7(3) . . ?
C11 C12 C7 121.0(4) . . ?
C14 C13 N4 107.7(3) . . ?
C14 C13 C6 129.4(3) . . ?
N4 C13 C6 122.7(3) . . ?
C13 C14 C15 107.4(3) . . ?
C13 C14 C21 125.9(4) . . ?
C15 C14 C21 126.7(4) . . ?
C16 C15 C14 107.8(3) . . ?
C16 C15 C22 125.6(4) . . ?
C14 C15 C22 126.5(4) . . ?
C15 C16 N4 107.2(3) . . ?
C15 C16 C24 131.1(4) . . ?
N4 C16 C24 121.8(3) . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C18 C19 112.6(4) . . ?
C2 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C2 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C15 112.9(4) . . ?
C23 C22 H22A 109.0 . . ?
C15 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C15 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16 C24 H24A 109.5 . . ?
C16 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C16 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 C4 108.3(3) . . ?
C1 N1 B1 138.3(4) . . ?
C4 N1 B1 113.4(3) . . ?
C5 N2 C12 122.0(3) . . ?
C5 N2 B1 110.7(3) . . ?
C12 N2 B1 127.3(3) . . ?
C6 N3 C7 119.2(3) . . ?
C13 N4 C16 109.9(3) . . ?
C13 N4 H4 125.1 . . ?
C16 N4 H4 125.1 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.044
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_141121a
_database_code_depnum_ccdc_archive 'CCDC 1403582'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 N4'
_chemical_formula_weight         260.30

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   Pna2(1)

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

_cell_length_a                   6.8864(6)
_cell_length_b                   19.4648(16)
_cell_length_c                   9.6124(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1288.47(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5970
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.51

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9859
_exptl_absorpt_correction_T_max  0.9884
_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            10492
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.58
_reflns_number_total             2964
_reflns_number_gt                2701
_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)+(0.0599P)²+0.0614P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(18)
_refine_ls_number_reflns         2964
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.035
_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 0.8508(2) 0.42657(7) 0.25896(15) 0.0433(3) Uani 1 1 d . . .
C2 C 0.9706(2) 0.42124(8) 0.37377(17) 0.0490(4) Uani 1 1 d . . .
H2 H 0.9456 0.3960 0.4540 0.059 Uiso 1 1 calc R . .
C3 C 1.1371(2) 0.46096(9) 0.34717(18) 0.0541(4) Uani 1 1 d . . .
H3 H 1.2418 0.4670 0.4070 0.065 Uiso 1 1 calc R . .
C4 C 1.1173(2) 0.48882(9) 0.2184(2) 0.0574(4) Uani 1 1 d . . .
H4 H 1.2069 0.5171 0.1742 0.069 Uiso 1 1 calc R . .
C5 C 0.6642(2) 0.39769(7) 0.21796(14) 0.0406(3) Uani 1 1 d . . .
C6 C 0.55565(18) 0.35061(6) 0.30428(14) 0.0360(3) Uani 1 1 d . . .
C7 C 0.61722(18) 0.33452(7) 0.44770(14) 0.0370(3) Uani 1 1 d . . .
C8 C 0.5839(2) 0.36910(8) 0.56974(15) 0.0440(3) Uani 1 1 d . . .
H8 H 0.5081 0.4083 0.5807 0.053 Uiso 1 1 calc R . .
C9 C 0.6864(2) 0.33405(8) 0.67580(15) 0.0473(3) Uani 1 1 d . . .
H9 H 0.6908 0.3460 0.7694 0.057 Uiso 1 1 calc R . .
C10 C 0.7770(2) 0.27996(8) 0.61552(16) 0.0487(3) Uani 1 1 d . . .
H10 H 0.8552 0.2482 0.6611 0.058 Uiso 1 1 calc R . .
C11 C 0.3305(2) 0.33816(7) 0.12954(15) 0.0433(3) Uani 1 1 d . . .
C12 C 0.1614(3) 0.30719(10) 0.07684(19) 0.0594(4) Uani 1 1 d . . .
H12 H 0.0951 0.2749 0.1300 0.071 Uiso 1 1 calc R . .
C13 C 0.0941(3) 0.32447(11) -0.0525(2) 0.0673(5) Uani 1 1 d . . .
H13 H -0.0163 0.3031 -0.0877 0.081 Uiso 1 1 calc R . .
C14 C 0.1899(3) 0.37384(11) -0.13142(18) 0.0646(5) Uani 1 1 d . . .
H14 H 0.1411 0.3857 -0.2184 0.078 Uiso 1 1 calc R . .
C15 C 0.3539(3) 0.40508(10) -0.08381(16) 0.0566(4) Uani 1 1 d . . .
H15 H 0.4157 0.4382 -0.1376 0.068 Uiso 1 1 calc R . .
C16 C 0.4302(2) 0.38681(8) 0.04864(14) 0.0434(3) Uani 1 1 d . . .
N1 N 0.59835(19) 0.41593(7) 0.09355(13) 0.0478(3) Uani 1 1 d . . .
N2 N 0.39551(17) 0.32126(6) 0.25963(12) 0.0422(3) Uani 1 1 d . . .
N3 N 0.73448(18) 0.27969(6) 0.47700(13) 0.0436(3) Uani 1 1 d . . .
H3A H 0.7749 0.2499 0.4177 0.052 Uiso 1 1 calc R . .
N4 N 0.9444(2) 0.46826(7) 0.16548(16) 0.0530(3) Uani 1 1 d . . .
H4A H 0.9000 0.4797 0.0851 0.064 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
C1 N4 1.3717(19) . ?
C1 C2 1.381(2) . ?
C1 C5 1.457(2) . ?
C2 C3 1.406(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(3) . ?
C3 H3 0.9300 . ?
C4 N4 1.355(2) . ?
C4 H4 0.9300 . ?
C5 N1 1.3273(18) . ?
C5 C6 1.4446(19) . ?
C6 N2 1.3140(17) . ?
C6 C7 1.4760(18) . ?
C7 N3 1.3676(17) . ?
C7 C8 1.3718(19) . ?
C8 C9 1.415(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.354(2) . ?
C9 H9 0.9300 . ?
C10 N3 1.3633(18) . ?
C10 H10 0.9300 . ?
C11 N2 1.3684(17) . ?
C11 C16 1.405(2) . ?
C11 C12 1.406(2) . ?
C12 C13 1.369(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.422(2) . ?
C15 H15 0.9300 . ?
C16 N1 1.360(2) . ?
N3 H3A 0.8600 . ?
N4 H4A 0.8600 . ?

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
N4 C1 C2 106.69(13) . . ?
N4 C1 C5 117.74(13) . . ?
C2 C1 C5 135.53(13) . . ?
C1 C2 C3 107.47(15) . . ?
C1 C2 H2 126.3 . . ?
C3 C2 H2 126.3 . . ?
C4 C3 C2 107.66(16) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
N4 C4 C3 108.22(15) . . ?
N4 C4 H4 125.9 . . ?
C3 C4 H4 125.9 . . ?
N1 C5 C6 120.70(13) . . ?
N1 C5 C1 116.22(13) . . ?
C6 C5 C1 123.07(12) . . ?
N2 C6 C5 121.49(12) . . ?
N2 C6 C7 116.99(12) . . ?
C5 C6 C7 121.50(11) . . ?
N3 C7 C8 107.80(12) . . ?
N3 C7 C6 121.84(12) . . ?
C8 C7 C6 130.28(12) . . ?
C7 C8 C9 107.22(12) . . ?
C7 C8 H8 126.4 . . ?
C9 C8 H8 126.4 . . ?
C10 C9 C8 107.23(13) . . ?
C10 C9 H9 126.4 . . ?
C8 C9 H9 126.4 . . ?
C9 C10 N3 108.80(13) . . ?
C9 C10 H10 125.6 . . ?
N3 C10 H10 125.6 . . ?
N2 C11 C16 120.53(13) . . ?
N2 C11 C12 119.83(14) . . ?
C16 C11 C12 119.64(13) . . ?
C13 C12 C11 120.16(17) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.30(18) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 121.25(15) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 119.69(17) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
N1 C16 C11 121.44(12) . . ?
N1 C16 C15 119.64(14) . . ?
C11 C16 C15 118.92(15) . . ?
C5 N1 C16 117.74(13) . . ?
C6 N2 C11 117.95(13) . . ?
C10 N3 C7 108.95(12) . . ?
C10 N3 H3A 125.5 . . ?
C7 N3 H3A 125.5 . . ?
C4 N4 C1 109.96(15) . . ?
C4 N4 H4A 125.0 . . ?
C1 N4 H4A 125.0 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.034
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_150116a_0m
_database_code_depnum_ccdc_archive 'CCDC 1403583'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N4'
_chemical_formula_weight         316.40

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/c

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

_cell_length_a                   30.722(5)
_cell_length_b                   10.9071(18)
_cell_length_c                   15.974(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.161(2)
_cell_angle_gamma                90.00
_cell_volume                     5268.7(16)
_cell_formula_units_Z            10
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8193
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      23.94

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.997
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1680
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9903
_exptl_absorpt_correction_T_max  0.9921
_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            44304
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_sigmaI/netI    0.0794
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         27.65
_reflns_number_total             12168
_reflns_number_gt                5458
_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)+(0.1628P)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         12168
_refine_ls_number_parameters     551
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1551
_refine_ls_R_factor_gt           0.0933
_refine_ls_wR_factor_ref         0.3024
_refine_ls_wR_factor_gt          0.2764
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.007
_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 0.43140(10) 0.2920(3) 0.3435(2) 0.0478(8) Uani 1 1 d . . .
C2 C 0.45971(13) 0.3224(4) 0.4190(2) 0.0642(10) Uani 1 1 d . . .
H2 H 0.4892 0.2983 0.4265 0.077 Uiso 1 1 calc R . .
C3 C 0.44543(15) 0.3856(4) 0.4813(3) 0.0746(12) Uani 1 1 d . . .
H3 H 0.4651 0.4086 0.5298 0.090 Uiso 1 1 calc R . .
C4 C 0.40052(16) 0.4165(4) 0.4722(3) 0.0741(12) Uani 1 1 d . . .
H4 H 0.3902 0.4535 0.5173 0.089 Uiso 1 1 calc R . .
C5 C 0.37209(13) 0.3938(4) 0.3997(3) 0.0639(10) Uani 1 1 d . . .
H5 H 0.3429 0.4199 0.3941 0.077 Uiso 1 1 calc R . .
C6 C 0.38614(11) 0.3307(3) 0.3317(2) 0.0493(8) Uani 1 1 d . . .
C7 C 0.37475(9) 0.2560(3) 0.1941(2) 0.0447(8) Uani 1 1 d . . .
C8 C 0.41696(10) 0.1926(3) 0.2137(2) 0.0452(8) Uani 1 1 d . . .
C9 C 0.42932(10) 0.0923(3) 0.1608(2) 0.0477(8) Uani 1 1 d . . .
C10 C 0.40456(11) -0.0026(3) 0.1202(2) 0.0539(9) Uani 1 1 d . . .
C11 C 0.43547(12) -0.0813(4) 0.0927(3) 0.0663(11) Uani 1 1 d . . .
H11 H 0.4287 -0.1543 0.0631 0.080 Uiso 1 1 calc R . .
C12 C 0.47668(12) -0.0341(4) 0.1161(3) 0.0607(10) Uani 1 1 d . . .
C13 C 0.35462(12) -0.0284(4) 0.1116(3) 0.0785(13) Uani 1 1 d . . .
H13A H 0.3452 -0.0107 0.1645 0.118 Uiso 1 1 calc R . .
H13B H 0.3489 -0.1130 0.0972 0.118 Uiso 1 1 calc R . .
H13C H 0.3386 0.0225 0.0676 0.118 Uiso 1 1 calc R . .
C14 C 0.52210(14) -0.0771(5) 0.1060(4) 0.0958(16) Uani 1 1 d . . .
H14A H 0.5344 -0.0206 0.0704 0.144 Uiso 1 1 calc R . .
H14B H 0.5200 -0.1569 0.0803 0.144 Uiso 1 1 calc R . .
H14C H 0.5408 -0.0810 0.1608 0.144 Uiso 1 1 calc R . .
C15 C 0.34863(10) 0.2637(3) 0.1083(2) 0.0453(8) Uani 1 1 d . . .
C16 C 0.36036(10) 0.2722(3) 0.0289(2) 0.0489(8) Uani 1 1 d . . .
C17 C 0.32208(11) 0.2917(4) -0.0290(2) 0.0570(9) Uani 1 1 d . . .
H17 H 0.3201 0.3025 -0.0873 0.068 Uiso 1 1 calc R . .
C18 C 0.28761(10) 0.2925(3) 0.0143(2) 0.0513(8) Uani 1 1 d . . .
C19 C 0.23827(11) 0.3007(4) -0.0148(3) 0.0682(11) Uani 1 1 d . . .
H19A H 0.2238 0.2423 0.0160 0.102 Uiso 1 1 calc R . .
H19B H 0.2312 0.2833 -0.0745 0.102 Uiso 1 1 calc R . .
H19C H 0.2284 0.3818 -0.0042 0.102 Uiso 1 1 calc R . .
C20 C 0.40678(12) 0.2663(4) 0.0062(3) 0.0696(11) Uani 1 1 d . . .
H20A H 0.4281 0.2938 0.0538 0.104 Uiso 1 1 calc R . .
H20B H 0.4080 0.3180 -0.0419 0.104 Uiso 1 1 calc R . .
H20C H 0.4133 0.1833 -0.0074 0.104 Uiso 1 1 calc R . .
C21 C 0.17689(10) 0.0937(3) 0.2137(2) 0.0495(8) Uani 1 1 d . . .
C22 C 0.15376(13) -0.0140(3) 0.1810(3) 0.0677(11) Uani 1 1 d . . .
H22 H 0.1267 -0.0315 0.1967 0.081 Uiso 1 1 calc R . .
C23 C 0.16951(13) -0.0901(4) 0.1289(3) 0.0707(11) Uani 1 1 d . . .
H23 H 0.1537 -0.1596 0.1081 0.085 Uiso 1 1 calc R . .
C24 C 0.21045(14) -0.0640(4) 0.1058(3) 0.0730(11) Uani 1 1 d . . .
H24 H 0.2223 -0.1192 0.0715 0.088 Uiso 1 1 calc R . .
C25 C 0.23337(12) 0.0399(3) 0.1320(3) 0.0601(9) Uani 1 1 d . . .
H25 H 0.2600 0.0567 0.1143 0.072 Uiso 1 1 calc R . .
C26 C 0.21641(10) 0.1210(3) 0.1855(2) 0.0475(8) Uani 1 1 d . . .
C27 C 0.21933(10) 0.3059(3) 0.2585(2) 0.0456(8) Uani 1 1 d . . .
C28 C 0.18512(10) 0.2633(3) 0.3019(2) 0.0444(8) Uani 1 1 d . . .
C29 C 0.17645(10) 0.3169(3) 0.3791(2) 0.0467(8) Uani 1 1 d . . .
C30 C 0.20457(11) 0.3618(3) 0.4509(2) 0.0505(8) Uani 1 1 d . . .
C31 C 0.17824(12) 0.3828(3) 0.5137(2) 0.0583(9) Uani 1 1 d . . .
H31 H 0.1882 0.4123 0.5684 0.070 Uiso 1 1 calc R . .
C32 C 0.13451(11) 0.3513(3) 0.4793(2) 0.0559(9) Uani 1 1 d . . .
C33 C 0.25420(11) 0.3701(4) 0.4639(3) 0.0665(11) Uani 1 1 d . . .
H33A H 0.2656 0.3010 0.4374 0.100 Uiso 1 1 calc R . .
H33B H 0.2660 0.3701 0.5236 0.100 Uiso 1 1 calc R . .
H33C H 0.2626 0.4445 0.4388 0.100 Uiso 1 1 calc R . .
C34 C 0.09374(14) 0.3537(5) 0.5168(3) 0.0828(13) Uani 1 1 d . . .
H34A H 0.0734 0.4123 0.4869 0.124 Uiso 1 1 calc R . .
H34B H 0.1010 0.3766 0.5757 0.124 Uiso 1 1 calc R . .
H34C H 0.0804 0.2739 0.5123 0.124 Uiso 1 1 calc R . .
C35 C 0.23456(10) 0.4318(3) 0.2621(2) 0.0478(8) Uani 1 1 d . . .
C36 C 0.21117(11) 0.5432(3) 0.2659(2) 0.0488(8) Uani 1 1 d . . .
C37 C 0.24127(12) 0.6366(3) 0.2514(2) 0.0595(10) Uani 1 1 d . . .
H37 H 0.2354 0.7203 0.2499 0.071 Uiso 1 1 calc R . .
C38 C 0.28057(12) 0.5830(3) 0.2398(2) 0.0562(9) Uani 1 1 d . . .
C39 C 0.16542(11) 0.5635(3) 0.2758(3) 0.0627(10) Uani 1 1 d . . .
H39A H 0.1473 0.4979 0.2491 0.094 Uiso 1 1 calc R . .
H39B H 0.1552 0.6399 0.2496 0.094 Uiso 1 1 calc R . .
H39C H 0.1637 0.5662 0.3352 0.094 Uiso 1 1 calc R . .
C40 C 0.32234(13) 0.6400(4) 0.2228(3) 0.0758(12) Uani 1 1 d . . .
H40A H 0.3451 0.6312 0.2720 0.114 Uiso 1 1 calc R . .
H40B H 0.3174 0.7255 0.2102 0.114 Uiso 1 1 calc R . .
H40C H 0.3314 0.5999 0.1752 0.114 Uiso 1 1 calc R . .
C41 C 0.02140(15) 0.5963(4) 0.2675(4) 0.1002(17) Uani 1 1 d . . .
H41 H 0.0360 0.6710 0.2778 0.120 Uiso 1 1 calc R . .
C42 C 0.04467(13) 0.4896(3) 0.2890(3) 0.0783(13) Uani 1 1 d . . .
H42 H 0.0743 0.4916 0.3148 0.094 Uiso 1 1 calc R . .
C43 C 0.02203(11) 0.3760(3) 0.2705(3) 0.0562(9) Uani 1 1 d . . .
C44 C 0.02140(10) 0.1671(3) 0.2774(2) 0.0462(8) Uani 1 1 d . . .
C45 C 0.04109(10) 0.0560(3) 0.3186(2) 0.0487(8) Uani 1 1 d . . .
C46 C 0.02138(12) -0.0419(3) 0.3549(3) 0.0615(10) Uani 1 1 d . . .
C47 C 0.05833(13) -0.1145(4) 0.3927(3) 0.0753(12) Uani 1 1 d . . .
H47 H 0.0561 -0.1869 0.4225 0.090 Uiso 1 1 calc R . .
C48 C 0.09783(12) -0.0641(4) 0.3797(3) 0.0649(10) Uani 1 1 d . . .
C49 C -0.02414(15) -0.0666(5) 0.3649(4) 0.0974(16) Uani 1 1 d . . .
H49A H -0.0401 0.0093 0.3635 0.146 Uiso 1 1 calc R . .
H49B H -0.0242 -0.1068 0.4183 0.146 Uiso 1 1 calc R . .
H49C H -0.0381 -0.1185 0.3194 0.146 Uiso 1 1 calc R . .
C50 C 0.14394(14) -0.0995(5) 0.4069(4) 0.0967(16) Uani 1 1 d . . .
H50A H 0.1551 -0.1341 0.3597 0.145 Uiso 1 1 calc R . .
H50B H 0.1460 -0.1591 0.4516 0.145 Uiso 1 1 calc R . .
H50C H 0.1611 -0.0286 0.4273 0.145 Uiso 1 1 calc R . .
N1 N 0.44514(8) 0.2193(3) 0.28432(17) 0.0472(7) Uani 1 1 d . . .
N2 N 0.35955(8) 0.3158(3) 0.25468(18) 0.0514(7) Uani 1 1 d . . .
N3 N 0.47254(8) 0.0720(3) 0.15686(17) 0.0488(7) Uani 1 1 d . . .
H3A H 0.4940 0.1198 0.1774 0.059 Uiso 1 1 calc R . .
N4 N 0.30443(8) 0.2774(2) 0.09759(17) 0.0456(6) Uani 1 1 d . . .
H4A H 0.2892 0.2767 0.1379 0.055 Uiso 1 1 calc R . .
N5 N 0.23661(8) 0.2324(2) 0.20665(18) 0.0479(7) Uani 1 1 d . . .
N6 N 0.16170(8) 0.1649(2) 0.27366(19) 0.0519(7) Uani 1 1 d . . .
N7 N 0.27554(9) 0.4620(2) 0.24435(18) 0.0495(7) Uani 1 1 d . . .
H7 H 0.2954 0.4093 0.2371 0.059 Uiso 1 1 calc R . .
N8 N 0.13454(8) 0.3114(3) 0.40065(19) 0.0503(7) Uani 1 1 d . . .
H8 H 0.1114 0.2854 0.3671 0.060 Uiso 1 1 calc R . .
N9 N 0.04297(8) 0.2706(3) 0.29498(19) 0.0531(7) Uani 1 1 d . . .
N10 N 0.08629(9) 0.0425(3) 0.3345(2) 0.0605(8) Uani 1 1 d . . .
H10 H 0.1047 0.0931 0.3186 0.073 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
C1 N1 1.357(4) . ?
C1 C2 1.397(5) . ?
C1 C6 1.433(4) . ?
C2 C3 1.346(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.345(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.416(5) . ?
C5 H5 0.9300 . ?
C6 N2 1.361(4) . ?
C7 N2 1.318(4) . ?
C7 C8 1.454(4) . ?
C7 C15 1.463(4) . ?
C8 N1 1.328(4) . ?
C8 C9 1.473(4) . ?
C9 N3 1.358(4) . ?
C9 C10 1.377(5) . ?
C10 C11 1.408(5) . ?
C10 C13 1.542(5) . ?
C11 C12 1.357(5) . ?
C11 H11 0.9300 . ?
C12 N3 1.345(5) . ?
C12 C14 1.508(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N4 1.347(4) . ?
C15 C16 1.381(5) . ?
C16 C17 1.378(5) . ?
C16 C20 1.534(5) . ?
C17 C18 1.364(5) . ?
C17 H17 0.9300 . ?
C18 N4 1.350(4) . ?
C18 C19 1.508(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N6 1.377(4) . ?
C21 C26 1.400(4) . ?
C21 C22 1.423(5) . ?
C22 C23 1.326(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.401(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.361(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.394(5) . ?
C25 H25 0.9300 . ?
C26 N5 1.379(4) . ?
C27 N5 1.328(4) . ?
C27 C28 1.435(4) . ?
C27 C35 1.449(4) . ?
C28 N6 1.326(4) . ?
C28 C29 1.431(5) . ?
C29 N8 1.392(4) . ?
C29 C30 1.398(5) . ?
C30 C31 1.414(5) . ?
C30 C33 1.505(5) . ?
C31 C32 1.402(5) . ?
C31 H31 0.9300 . ?
C32 N8 1.330(5) . ?
C32 C34 1.481(5) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 N7 1.378(4) . ?
C35 C36 1.418(5) . ?
C36 C37 1.421(5) . ?
C36 C39 1.459(5) . ?
C37 C38 1.383(5) . ?
C37 H37 0.9300 . ?
C38 N7 1.333(4) . ?
C38 C40 1.493(5) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C41 1.335(9) 2 ?
C41 C42 1.377(6) . ?
C41 H41 0.9300 . ?
C42 C43 1.426(5) . ?
C42 H42 0.9300 . ?
C43 N9 1.342(4) . ?
C43 C43 1.395(7) 2 ?
C44 N9 1.314(4) . ?
C44 C44 1.445(6) 2 ?
C44 C45 1.459(5) . ?
C45 N10 1.375(4) . ?
C45 C46 1.402(5) . ?
C46 C47 1.428(5) . ?
C46 C49 1.460(6) . ?
C47 C48 1.381(5) . ?
C47 H47 0.9300 . ?
C48 N10 1.381(5) . ?
C48 C50 1.458(5) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
N3 H3A 0.8600 . ?
N4 H4A 0.8600 . ?
N7 H7 0.8600 . ?
N8 H8 0.8600 . ?
N10 H10 0.8600 . ?

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
N1 C1 C2 121.2(3) . . ?
N1 C1 C6 119.6(3) . . ?
C2 C1 C6 119.1(3) . . ?
C3 C2 C1 121.7(4) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 119.3(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 121.5(4) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
N2 C6 C5 122.4(3) . . ?
N2 C6 C1 119.9(3) . . ?
C5 C6 C1 117.5(3) . . ?
N2 C7 C8 119.7(3) . . ?
N2 C7 C15 116.9(3) . . ?
C8 C7 C15 123.3(3) . . ?
N1 C8 C7 120.1(3) . . ?
N1 C8 C9 117.0(3) . . ?
C7 C8 C9 122.7(3) . . ?
N3 C9 C10 108.6(3) . . ?
N3 C9 C8 120.1(3) . . ?
C10 C9 C8 130.7(3) . . ?
C9 C10 C11 105.0(3) . . ?
C9 C10 C13 129.6(3) . . ?
C11 C10 C13 125.2(3) . . ?
C12 C11 C10 109.3(3) . . ?
C12 C11 H11 125.4 . . ?
C10 C11 H11 125.4 . . ?
N3 C12 C11 107.3(3) . . ?
N3 C12 C14 119.2(4) . . ?
C11 C12 C14 133.5(4) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 C16 107.2(3) . . ?
N4 C15 C7 120.0(3) . . ?
C16 C15 C7 132.5(3) . . ?
C17 C16 C15 107.3(3) . . ?
C17 C16 C20 124.5(3) . . ?
C15 C16 C20 128.2(3) . . ?
C18 C17 C16 107.9(3) . . ?
C18 C17 H17 126.0 . . ?
C16 C17 H17 126.0 . . ?
N4 C18 C17 107.6(3) . . ?
N4 C18 C19 120.0(3) . . ?
C17 C18 C19 132.3(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C21 C26 121.5(3) . . ?
N6 C21 C22 120.8(3) . . ?
C26 C21 C22 117.6(3) . . ?
C23 C22 C21 122.2(4) . . ?
C23 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
C22 C23 C24 118.8(4) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C25 C24 C23 121.9(4) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C24 C25 C26 119.2(4) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
N5 C26 C25 120.6(3) . . ?
N5 C26 C21 119.2(3) . . ?
C25 C26 C21 120.1(3) . . ?
N5 C27 C28 120.9(3) . . ?
N5 C27 C35 115.8(3) . . ?
C28 C27 C35 123.2(3) . . ?
N6 C28 C29 116.8(3) . . ?
N6 C28 C27 119.9(3) . . ?
C29 C28 C27 123.2(3) . . ?
N8 C29 C30 106.0(3) . . ?
N8 C29 C28 121.1(3) . . ?
C30 C29 C28 132.0(3) . . ?
C29 C30 C31 106.9(3) . . ?
C29 C30 C33 126.7(3) . . ?
C31 C30 C33 125.8(3) . . ?
C32 C31 C30 108.1(3) . . ?
C32 C31 H31 125.9 . . ?
C30 C31 H31 125.9 . . ?
N8 C32 C31 106.9(3) . . ?
N8 C32 C34 122.0(3) . . ?
C31 C32 C34 131.1(4) . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N7 C35 C36 107.0(3) . . ?
N7 C35 C27 121.2(3) . . ?
C36 C35 C27 130.6(3) . . ?
C35 C36 C37 104.9(3) . . ?
C35 C36 C39 129.8(3) . . ?
C37 C36 C39 125.1(3) . . ?
C38 C37 C36 109.1(3) . . ?
C38 C37 H37 125.4 . . ?
C36 C37 H37 125.4 . . ?
N7 C38 C37 107.4(3) . . ?
N7 C38 C40 122.3(3) . . ?
C37 C38 C40 130.4(3) . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C41 C41 C42 122.3(2) 2 . ?
C41 C41 H41 118.9 2 . ?
C42 C41 H41 118.9 . . ?
C41 C42 C43 118.0(4) . . ?
C41 C42 H42 121.0 . . ?
C43 C42 H42 121.0 . . ?
N9 C43 C43 120.81(18) . 2 ?
N9 C43 C42 119.5(3) . . ?
C43 C43 C42 119.6(2) 2 . ?
N9 C44 C44 120.03(19) . 2 ?
N9 C44 C45 117.6(3) . . ?
C44 C44 C45 122.26(18) 2 . ?
N10 C45 C46 109.8(3) . . ?
N10 C45 C44 119.8(3) . . ?
C46 C45 C44 130.1(3) . . ?
C45 C46 C47 103.2(3) . . ?
C45 C46 C49 132.6(3) . . ?
C47 C46 C49 123.8(4) . . ?
C48 C47 C46 111.7(3) . . ?
C48 C47 H47 124.2 . . ?
C46 C47 H47 124.2 . . ?
C47 C48 N10 105.2(3) . . ?
C47 C48 C50 133.1(4) . . ?
N10 C48 C50 121.7(4) . . ?
C46 C49 H49A 109.5 . . ?
C46 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C46 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C48 C50 H50A 109.5 . . ?
C48 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C48 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C8 N1 C1 118.9(3) . . ?
C7 N2 C6 119.2(3) . . ?
C12 N3 C9 109.8(3) . . ?
C12 N3 H3A 125.1 . . ?
C9 N3 H3A 125.1 . . ?
C15 N4 C18 109.9(3) . . ?
C15 N4 H4A 125.0 . . ?
C18 N4 H4A 125.0 . . ?
C27 N5 C26 118.2(3) . . ?
C28 N6 C21 117.6(3) . . ?
C38 N7 C35 111.5(3) . . ?
C38 N7 H7 124.2 . . ?
C35 N7 H7 124.2 . . ?
C32 N8 C29 112.0(3) . . ?
C32 N8 H8 124.0 . . ?
C29 N8 H8 124.0 . . ?
C44 N9 C43 118.4(3) . . ?
C45 N10 C48 110.1(3) . . ?
C45 N10 H10 124.9 . . ?
C48 N10 H10 124.9 . . ?

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 -174.2(4) . . . . ?
C6 C1 C2 C3 0.9(6) . . . . ?
C1 C2 C3 C4 3.3(7) . . . . ?
C2 C3 C4 C5 -5.8(7) . . . . ?
C3 C4 C5 C6 4.0(7) . . . . ?
C4 C5 C6 N2 -173.9(4) . . . . ?
C4 C5 C6 C1 0.3(6) . . . . ?
N1 C1 C6 N2 -13.1(5) . . . . ?
C2 C1 C6 N2 171.7(3) . . . . ?
N1 C1 C6 C5 172.5(3) . . . . ?
C2 C1 C6 C5 -2.7(5) . . . . ?
N2 C7 C8 N1 -17.2(5) . . . . ?
C15 C7 C8 N1 159.2(3) . . . . ?
N2 C7 C8 C9 158.7(3) . . . . ?
C15 C7 C8 C9 -24.9(5) . . . . ?
N1 C8 C9 N3 -32.7(5) . . . . ?
C7 C8 C9 N3 151.3(3) . . . . ?
N1 C8 C9 C10 136.7(4) . . . . ?
C7 C8 C9 C10 -39.3(6) . . . . ?
N3 C9 C10 C11 0.7(4) . . . . ?
C8 C9 C10 C11 -169.7(4) . . . . ?
N3 C9 C10 C13 175.6(4) . . . . ?
C8 C9 C10 C13 5.2(7) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C13 C10 C11 C12 -175.4(4) . . . . ?
C10 C11 C12 N3 -0.4(5) . . . . ?
C10 C11 C12 C14 178.8(5) . . . . ?
N2 C7 C15 N4 -30.2(4) . . . . ?
C8 C7 C15 N4 153.3(3) . . . . ?
N2 C7 C15 C16 142.0(4) . . . . ?
C8 C7 C15 C16 -34.4(5) . . . . ?
N4 C15 C16 C17 0.2(4) . . . . ?
C7 C15 C16 C17 -172.8(3) . . . . ?
N4 C15 C16 C20 178.2(3) . . . . ?
C7 C15 C16 C20 5.2(6) . . . . ?
C15 C16 C17 C18 -1.2(4) . . . . ?
C20 C16 C17 C18 -179.3(3) . . . . ?
C16 C17 C18 N4 1.8(4) . . . . ?
C16 C17 C18 C19 -175.1(4) . . . . ?
N6 C21 C22 C23 -174.0(4) . . . . ?
C26 C21 C22 C23 3.3(6) . . . . ?
C21 C22 C23 C24 0.4(7) . . . . ?
C22 C23 C24 C25 -3.1(7) . . . . ?
C23 C24 C25 C26 2.0(6) . . . . ?
C24 C25 C26 N5 -173.8(4) . . . . ?
C24 C25 C26 C21 1.8(6) . . . . ?
N6 C21 C26 N5 -11.4(5) . . . . ?
C22 C21 C26 N5 171.4(3) . . . . ?
N6 C21 C26 C25 172.9(3) . . . . ?
C22 C21 C26 C25 -4.3(5) . . . . ?
N5 C27 C28 N6 -19.2(5) . . . . ?
C35 C27 C28 N6 155.5(3) . . . . ?
N5 C27 C28 C29 156.3(3) . . . . ?
C35 C27 C28 C29 -29.0(5) . . . . ?
N6 C28 C29 N8 -31.2(4) . . . . ?
C27 C28 C29 N8 153.1(3) . . . . ?
N6 C28 C29 C30 136.5(4) . . . . ?
C27 C28 C29 C30 -39.2(5) . . . . ?
N8 C29 C30 C31 -0.3(4) . . . . ?
C28 C29 C30 C31 -169.3(4) . . . . ?
N8 C29 C30 C33 171.9(3) . . . . ?
C28 C29 C30 C33 2.9(6) . . . . ?
C29 C30 C31 C32 -0.4(4) . . . . ?
C33 C30 C31 C32 -172.8(3) . . . . ?
C30 C31 C32 N8 1.1(4) . . . . ?
C30 C31 C32 C34 179.2(4) . . . . ?
N5 C27 C35 N7 -26.4(4) . . . . ?
C28 C27 C35 N7 158.6(3) . . . . ?
N5 C27 C35 C36 139.8(4) . . . . ?
C28 C27 C35 C36 -35.1(5) . . . . ?
N7 C35 C36 C37 -1.2(4) . . . . ?
C27 C35 C36 C37 -168.9(3) . . . . ?
N7 C35 C36 C39 174.5(3) . . . . ?
C27 C35 C36 C39 6.8(6) . . . . ?
C35 C36 C37 C38 -0.2(4) . . . . ?
C39 C36 C37 C38 -176.1(3) . . . . ?
C36 C37 C38 N7 1.6(4) . . . . ?
C36 C37 C38 C40 -179.9(4) . . . . ?
C41 C41 C42 C43 1.8(11) 2 . . . ?
C41 C42 C43 N9 -176.1(5) . . . . ?
C41 C42 C43 C43 1.8(8) . . . 2 ?
N9 C44 C45 N10 -34.6(5) . . . . ?
C44 C44 C45 N10 148.9(4) 2 . . . ?
N9 C44 C45 C46 138.2(4) . . . . ?
C44 C44 C45 C46 -38.3(7) 2 . . . ?
N10 C45 C46 C47 -0.4(4) . . . . ?
C44 C45 C46 C47 -173.8(4) . . . . ?
N10 C45 C46 C49 172.7(5) . . . . ?
C44 C45 C46 C49 -0.7(8) . . . . ?
C45 C46 C47 C48 -0.3(5) . . . . ?
C49 C46 C47 C48 -174.2(5) . . . . ?
C46 C47 C48 N10 0.9(5) . . . . ?
C46 C47 C48 C50 177.8(5) . . . . ?
C7 C8 N1 C1 9.8(5) . . . . ?
C9 C8 N1 C1 -166.3(3) . . . . ?
C2 C1 N1 C8 179.8(3) . . . . ?
C6 C1 N1 C8 4.7(5) . . . . ?
C8 C7 N2 C6 8.6(5) . . . . ?
C15 C7 N2 C6 -168.0(3) . . . . ?
C5 C6 N2 C7 180.0(3) . . . . ?
C1 C6 N2 C7 5.9(5) . . . . ?
C11 C12 N3 C9 0.8(4) . . . . ?
C14 C12 N3 C9 -178.5(4) . . . . ?
C10 C9 N3 C12 -1.0(4) . . . . ?
C8 C9 N3 C12 170.6(3) . . . . ?
C16 C15 N4 C18 0.9(4) . . . . ?
C7 C15 N4 C18 174.9(3) . . . . ?
C17 C18 N4 C15 -1.7(4) . . . . ?
C19 C18 N4 C15 175.6(3) . . . . ?
C28 C27 N5 C26 9.8(4) . . . . ?
C35 C27 N5 C26 -165.3(3) . . . . ?
C25 C26 N5 C27 -179.5(3) . . . . ?
C21 C26 N5 C27 4.9(5) . . . . ?
C29 C28 N6 C21 -163.4(3) . . . . ?
C27 C28 N6 C21 12.5(4) . . . . ?
C26 C21 N6 C28 2.2(5) . . . . ?
C22 C21 N6 C28 179.4(3) . . . . ?
C37 C38 N7 C35 -2.4(4) . . . . ?
C40 C38 N7 C35 179.0(3) . . . . ?
C36 C35 N7 C38 2.3(4) . . . . ?
C27 C35 N7 C38 171.4(3) . . . . ?
C31 C32 N8 C29 -1.3(4) . . . . ?
C34 C32 N8 C29 -179.7(3) . . . . ?
C30 C29 N8 C32 1.0(4) . . . . ?
C28 C29 N8 C32 171.5(3) . . . . ?
C44 C44 N9 C43 8.6(6) 2 . . . ?
C45 C44 N9 C43 -168.0(3) . . . . ?
C43 C43 N9 C44 2.0(7) 2 . . . ?
C42 C43 N9 C44 179.9(4) . . . . ?
C46 C45 N10 C48 1.0(4) . . . . ?
C44 C45 N10 C48 175.2(3) . . . . ?
C47 C48 N10 C45 -1.2(5) . . . . ?
C50 C48 N10 C45 -178.5(4) . . . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 -0.166 0.250 471 141 ' '
2 0.500 0.165 0.750 471 143 ' '
3 0.000 0.500 0.000 274 72 ' '
4 1.000 0.500 0.500 274 72 ' '
5 0.097 0.249 0.712 13 0 ' '
6 0.903 0.249 0.788 13 0 ' '
7 0.097 0.751 0.212 13 1 ' '
8 0.903 0.751 0.288 13 0 ' '
_platon_squeeze_details          
;
;
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.65
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.068
