# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_1Ph3tBu6CNBT_263K
_database_code_depnum_ccdc_archive 'CCDC 1524669'
_audit_update_record             
;
2016-12-27 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;
#-------------------------------------------
_chemical_name_systematic        
;
3-tert-Butyl-6-cyano-1,4-dihydro-1-phenyl-1,2,4-benzotriazin-4-yl
;
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H17 N4'
_chemical_formula_sum            'C18 H17 N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         289.35

_chemical_melting_point          453-454
#-------------------------------------------
# CRYSTAL DATA
#-------------------------------------------
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8527(6)
_cell_length_b                   9.1813(9)
_cell_length_c                   13.1091(12)
_cell_angle_alpha                86.834(3)
_cell_angle_beta                 80.616(3)
_cell_angle_gamma                74.983(3)
_cell_volume                     785.88(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3534
_cell_measurement_theta_min      2.7675
_cell_measurement_theta_max      25.0521
_cell_measurement_temperature    263.(2)
#-------------------------------------------
_exptl_crystal_description       plate-like
_exptl_crystal_colour            black
_exptl_crystal_size_max          1.239
_exptl_crystal_size_mid          0.538
_exptl_crystal_size_min          0.062
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             306

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;
#------------------------------------------
#EXPERIMENTAL DATA
#------------------------------------------
_diffrn_ambient_temperature      263.(2)

_diffrn_source                   'micro focus sealed tube'
_diffrn_source_type              'INCOATEC I\mS'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered conforcal mirror'

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scan'

_diffrn_detector_area_resol_mean 7.4074

#-------------------------------------------
#REFINEMENT DATA
#-------------------------------------------
_diffrn_reflns_number            2512
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.940
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
Refinement was based on F² against all reflections. The weighted R-factor
(wR) and goodness of fit (S) were based on F², and conventional R-factor (R)
was calculated on F, with F set to zero for negative F². The threshold
expression of I > 2σ(I) was used only for calculating R-factor (gt).

Refined as a 2-component twin.
;

_reflns_number_total             2512
_reflns_number_gt                1707
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_gt          0.1763
_refine_ls_wR_factor_ref         0.2128
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_number_reflns         2512
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0913P)²+0.2568P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.276
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

#-------------------------------------------
_computing_data_collection       
;
Bruker Instrument Service V6.2.3 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHELL V 6.3.1(Bruker AXS Inc., 2004)'
_computing_publication_material  
;
Generate Report (Bruker AXS Inc., 2013)
;
#-------------------------------------------


loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.2633(4) 0.4524(3) 0.75394(18) 0.0428(6) Uani d . . . 1 . .
N N2 0.3446(4) 0.3059(3) 0.78019(19) 0.0471(7) Uani d . . . 1 . .
N N3 0.3913(4) 0.2413(3) 0.6020(2) 0.0514(7) Uani d . . . 1 . .
C C7 0.2418(4) 0.5006(3) 0.6542(2) 0.0403(7) Uani d . . . 1 . .
C C8 0.2025(5) 0.5540(3) 0.8403(2) 0.0449(8) Uani d . . . 1 . .
C C2 0.3089(4) 0.3890(3) 0.5779(2) 0.0424(8) Uani d . . . 1 . .
C C3 0.2911(4) 0.4327(4) 0.4751(2) 0.0458(8) Uani d . . . 1 . .
H H3 0.3356 0.3608 0.4234 0.055 Uiso calc U . R 1 . .
C C6 0.1615(5) 0.6507(4) 0.6276(2) 0.0470(8) Uani d . . . 1 . .
H H6 0.1199 0.724 0.6783 0.056 Uiso calc U . R 1 . .
C C4 0.2084(4) 0.5811(4) 0.4497(2) 0.0454(8) Uani d . . . 1 . .
C C5 0.1436(5) 0.6906(4) 0.5255(2) 0.0467(8) Uani d . . . 1 . .
H H5 0.0883 0.7905 0.5077 0.056 Uiso calc U . R 1 . .
N N4 0.1684(5) 0.6580(4) 0.2601(3) 0.0806(11) Uani d . . . 1 . .
C C1 0.4033(5) 0.2105(3) 0.7022(2) 0.0473(8) Uani d . . . 1 . .
C C18 0.1873(5) 0.6246(4) 0.3437(3) 0.0571(9) Uani d . . . 1 . .
C C14 0.4856(6) 0.0455(4) 0.7309(3) 0.0585(9) Uani d . . . 1 . .
C C13 0.3500(6) 0.5835(4) 0.8883(3) 0.0579(9) Uani d . . . 1 . .
H H13 0.4876 0.54 0.8653 0.069 Uiso calc U . R 1 . .
C C9 -0.0007(6) 0.6141(4) 0.8741(3) 0.0669(11) Uani d . . . 1 . .
H H9 -0.0992 0.591 0.8413 0.08 Uiso calc U . R 1 . .
C C11 0.0897(8) 0.7417(4) 1.0055(3) 0.0778(13) Uani d . . . 1 . .
H H11 0.0513 0.8065 1.0614 0.093 Uiso calc U . R 1 . .
C C12 0.2914(8) 0.6796(5) 0.9721(3) 0.0745(12) Uani d . . . 1 . .
H H12 0.3901 0.7015 1.0054 0.089 Uiso calc U . R 1 . .
C C10 -0.0579(7) 0.7097(5) 0.9576(3) 0.0806(13) Uani d . . . 1 . .
H H10 -0.1956 0.7522 0.9813 0.097 Uiso calc U . R 1 . .
C C15 0.5219(9) 0.0247(4) 0.8424(3) 0.0950(16) Uani d . . . 1 . .
H H15A 0.6263 0.0727 0.8523 0.142 Uiso calc U . R 1 . .
H H15B 0.565 -0.081 0.8584 0.142 Uiso calc U . R 1 . .
H H15C 0.3976 0.0692 0.8873 0.142 Uiso calc U . R 1 . .
C C16 0.6870(8) -0.0202(5) 0.6589(4) 0.0926(15) Uani d . . . 1 . .
H H16A 0.6644 -0.0063 0.5883 0.139 Uiso calc U . R 1 . .
H H16B 0.7345 -0.1259 0.6737 0.139 Uiso calc U . R 1 . .
H H16C 0.7878 0.0305 0.6699 0.139 Uiso calc U . R 1 . .
C C17 0.3305(8) -0.0388(5) 0.7130(4) 0.1003(16) Uani d . . . 1 . .
H H17A 0.2033 0.001 0.7571 0.15 Uiso calc U . R 1 . .
H H17B 0.3807 -0.144 0.7286 0.15 Uiso calc U . R 1 . .
H H17C 0.3097 -0.0267 0.6421 0.15 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 . 1.364(3) ?
N1 C7 . 1.375(4) ?
N1 C8 . 1.445(3) ?
N2 C1 . 1.325(4) ?
N3 C1 . 1.339(4) ?
N3 C2 . 1.368(4) ?
C7 C6 . 1.394(4) ?
C7 C2 . 1.408(4) ?
C8 C13 . 1.364(5) ?
C8 C9 . 1.366(5) ?
C2 C3 . 1.399(4) ?
C3 C4 . 1.378(4) ?
C3 H3 . 0.93 ?
C6 C5 . 1.384(4) ?
C6 H6 . 0.93 ?
C4 C5 . 1.389(4) ?
C4 C18 . 1.445(5) ?
C5 H5 . 0.93 ?
N4 C18 . 1.141(4) ?
C1 C14 . 1.523(5) ?
C14 C15 . 1.517(5) ?
C14 C17 . 1.520(6) ?
C14 C16 . 1.538(6) ?
C13 C12 . 1.387(5) ?
C13 H13 . 0.93 ?
C9 C10 . 1.383(5) ?
C9 H9 . 0.93 ?
C11 C12 . 1.360(6) ?
C11 C10 . 1.372(6) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C10 H10 . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C7 . . 123.4(2) ?
N2 N1 C8 . . 114.1(2) ?
C7 N1 C8 . . 122.5(2) ?
C1 N2 N1 . . 115.3(3) ?
C1 N3 C2 . . 115.8(2) ?
N1 C7 C6 . . 123.2(3) ?
N1 C7 C2 . . 116.2(3) ?
C6 C7 C2 . . 120.6(3) ?
C13 C8 C9 . . 121.6(3) ?
C13 C8 N1 . . 118.9(3) ?
C9 C8 N1 . . 119.4(3) ?
N3 C2 C3 . . 120.1(3) ?
N3 C2 C7 . . 121.6(3) ?
C3 C2 C7 . . 118.3(3) ?
C4 C3 C2 . . 120.7(3) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C5 C6 C7 . . 119.9(3) ?
C5 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C3 C4 C5 . . 120.6(3) ?
C3 C4 C18 . . 120.2(3) ?
C5 C4 C18 . . 119.1(3) ?
C6 C5 C4 . . 119.9(3) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
N2 C1 N3 . . 127.7(3) ?
N2 C1 C14 . . 115.9(3) ?
N3 C1 C14 . . 116.4(3) ?
N4 C18 C4 . . 179.0(4) ?
C15 C14 C17 . . 109.8(4) ?
C15 C14 C1 . . 112.3(3) ?
C17 C14 C1 . . 107.8(3) ?
C15 C14 C16 . . 109.4(4) ?
C17 C14 C16 . . 108.2(3) ?
C1 C14 C16 . . 109.2(3) ?
C8 C13 C12 . . 118.9(4) ?
C8 C13 H13 . . 120.6 ?
C12 C13 H13 . . 120.6 ?
C8 C9 C10 . . 119.2(4) ?
C8 C9 H9 . . 120.4 ?
C10 C9 H9 . . 120.4 ?
C12 C11 C10 . . 120.8(3) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C11 C12 C13 . . 120.0(4) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C11 C10 C9 . . 119.6(4) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 N2 C1 . . . . 0.1(4) ?
C8 N1 N2 C1 . . . . -179.4(3) ?
N2 N1 C7 C6 . . . . -179.0(3) ?
C8 N1 C7 C6 . . . . 0.4(4) ?
N2 N1 C7 C2 . . . . 0.1(4) ?
C8 N1 C7 C2 . . . . 179.6(3) ?
N2 N1 C8 C13 . . . . 68.6(4) ?
C7 N1 C8 C13 . . . . -110.9(3) ?
N2 N1 C8 C9 . . . . -109.2(3) ?
C7 N1 C8 C9 . . . . 71.3(4) ?
C1 N3 C2 C3 . . . . 179.6(3) ?
C1 N3 C2 C7 . . . . 0.1(4) ?
N1 C7 C2 N3 . . . . -0.3(4) ?
C6 C7 C2 N3 . . . . 178.9(3) ?
N1 C7 C2 C3 . . . . -179.7(3) ?
C6 C7 C2 C3 . . . . -0.5(4) ?
N3 C2 C3 C4 . . . . -180.0(3) ?
C7 C2 C3 C4 . . . . -0.5(4) ?
N1 C7 C6 C5 . . . . -179.7(3) ?
C2 C7 C6 C5 . . . . 1.2(4) ?
C2 C3 C4 C5 . . . . 0.9(4) ?
C2 C3 C4 C18 . . . . -178.9(3) ?
C7 C6 C5 C4 . . . . -0.9(5) ?
C3 C4 C5 C6 . . . . -0.2(4) ?
C18 C4 C5 C6 . . . . 179.6(3) ?
N1 N2 C1 N3 . . . . -0.2(5) ?
N1 N2 C1 C14 . . . . -177.3(3) ?
C2 N3 C1 N2 . . . . 0.1(5) ?
C2 N3 C1 C14 . . . . 177.2(3) ?
N2 C1 C14 C15 . . . . -10.8(5) ?
N3 C1 C14 C15 . . . . 171.8(4) ?
N2 C1 C14 C17 . . . . 110.3(4) ?
N3 C1 C14 C17 . . . . -67.2(4) ?
N2 C1 C14 C16 . . . . -132.4(3) ?
N3 C1 C14 C16 . . . . 50.2(4) ?
C9 C8 C13 C12 . . . . -1.4(5) ?
N1 C8 C13 C12 . . . . -179.1(3) ?
C13 C8 C9 C10 . . . . 1.4(6) ?
N1 C8 C9 C10 . . . . 179.1(3) ?
C10 C11 C12 C13 . . . . 0.4(6) ?
C8 C13 C12 C11 . . . . 0.5(6) ?
C12 C11 C10 C9 . . . . -0.4(7) ?
C8 C9 C10 C11 . . . . -0.5(6) ?

####################################################################### 
# 
# 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_1Ph3tBu7CNBT
_database_code_depnum_ccdc_archive 'CCDC 1524670'
_audit_update_record             
;
2016-12-27 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;
#-------------------------------------------
_chemical_name_systematic        
;
3-tert-Butyl-7-cyano-1,4-dihydro-1-phenyl-1,2,4-benzotriazin-4-yl
;
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H17 N4'
_chemical_formula_sum            'C18 H17 N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         289.35

_chemical_melting_point          390-392
#-------------------------------------------
# CRYSTAL DATA
#-------------------------------------------
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   18.709(3)
_cell_length_b                   7.8316(12)
_cell_length_c                   21.501(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.945(4)
_cell_angle_gamma                90
_cell_volume                     3149.9(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2181
_cell_measurement_theta_min      2.7681
_cell_measurement_theta_max      21.5934
_cell_measurement_temperature    296.(2)
#-------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            black-green
_exptl_crystal_size_max          0.740
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;
#------------------------------------------
#EXPERIMENTAL DATA
#------------------------------------------
_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'micro focus sealed tube'
_diffrn_source_type              'INCOATEC I\mS'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered conforcal mirror'

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scan'

_diffrn_detector_area_resol_mean 10.4167

#-------------------------------------------
#REFINEMENT DATA
#-------------------------------------------
_diffrn_reflns_number            10772
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         23.02
_diffrn_reflns_theta_full        23.02
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
Refinement was based on F² against all reflections. The weighted R-factor
(wR) and goodness of fit (S) were based on F², and conventional R-factor (R)
was calculated on F, with F set to zero for negative F². The threshold
expression of I > 2σ(I) was used only for calculating R-factor (gt).
;

_reflns_number_total             2196
_reflns_number_gt                1422
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_gt          0.1891
_refine_ls_wR_factor_ref         0.2190
_refine_ls_goodness_of_fit_ref   1.380
_refine_ls_restrained_S_all      1.380
_refine_ls_number_reflns         2196
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[σ²(Fo²)+(0.1000P)²+0.4850P]
where P=(Fo²+2Fc²)/3
;

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

#-------------------------------------------
_computing_data_collection       
;
Bruker Instrument Service V3.0.28 (Bruker AXS Inc., 2013)
;
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXTL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V 6.3.1(Bruker AXS Inc., 2004)'
_computing_publication_material  
;
Generate Report (Bruker AXS Inc., 2013)
;
#-------------------------------------------

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C7 0.54527(16) 0.2613(4) 0.32317(14) 0.0464(9) Uani d . . . 1 . .
C C2 0.53772(19) 0.2503(4) 0.38781(15) 0.0562(10) Uani d . . . 1 . .
C C8 0.48276(16) 0.2260(4) 0.22076(14) 0.0462(9) Uani d . . . 1 . .
C C9 0.53538(17) 0.1498(4) 0.18624(15) 0.0527(9) Uani d . . . 1 . .
H H9 0.5738 0.0957 0.2059 0.063 Uiso calc U . R 1 . .
C C6 0.60900(17) 0.3167(4) 0.29869(16) 0.0563(10) Uani d . . . 1 . .
H H6 0.6133 0.3295 0.2559 0.068 Uiso calc U . R 1 . .
C C1 0.42055(19) 0.1748(4) 0.37497(17) 0.0589(10) Uani d . . . 1 . .
C C3 0.5971(2) 0.2870(5) 0.42600(17) 0.0730(12) Uani d . . . 1 . .
H H3 0.5932 0.278 0.4689 0.088 Uiso calc U . R 1 . .
C C4 0.6604(2) 0.3354(5) 0.40134(19) 0.0771(12) Uani d . . . 1 . .
H H4 0.6997 0.3567 0.4273 0.092 Uiso calc U . R 1 . .
C C13 0.42451(17) 0.3009(4) 0.19208(15) 0.0574(10) Uani d . . . 1 . .
H H13 0.3883 0.3484 0.2156 0.069 Uiso calc U . R 1 . .
C C5 0.66623(18) 0.3530(5) 0.33759(17) 0.0619(10) Uani d . . . 1 . .
C C12 0.4206(2) 0.3046(5) 0.12825(17) 0.0705(11) Uani d . . . 1 . .
H H12 0.3814 0.3556 0.1086 0.085 Uiso calc U . R 1 . .
C C10 0.5302(2) 0.1551(5) 0.12237(17) 0.0626(10) Uani d . . . 1 . .
H H10 0.5656 0.1044 0.0987 0.075 Uiso calc U . R 1 . .
C C14 0.34795(19) 0.1383(5) 0.40294(17) 0.0708(11) Uani d . . . 1 . .
C C18 0.7327(2) 0.4043(5) 0.31212(18) 0.0742(12) Uani d . . . 1 . .
C C11 0.4733(2) 0.2345(5) 0.09314(17) 0.0714(12) Uani d . . . 1 . .
H H11 0.4707 0.2404 0.05 0.086 Uiso calc U . R 1 . .
C C16 0.3235(2) 0.3025(6) 0.43445(19) 0.0987(15) Uani d . . . 1 . .
H H16A 0.3232 0.3941 0.4048 0.148 Uiso calc U . R 1 . .
H H16B 0.3557 0.3298 0.4682 0.148 Uiso calc U . R 1 . .
H H16C 0.2762 0.2869 0.4502 0.148 Uiso calc U . R 1 . .
C C15 0.2935(2) 0.0832(7) 0.3540(2) 0.1124(18) Uani d . . . 1 . .
H H15A 0.2867 0.1735 0.3243 0.169 Uiso calc U . R 1 . .
H H15B 0.249 0.0582 0.3735 0.169 Uiso calc U . R 1 . .
H H15C 0.3105 -0.017 0.3332 0.169 Uiso calc U . R 1 . .
C C17 0.3567(3) -0.0006(6) 0.4525(2) 0.1077(17) Uani d . . . 1 . .
H H17A 0.3136 -0.0092 0.4759 0.162 Uiso calc U . R 1 . .
H H17B 0.3959 0.028 0.4799 0.162 Uiso calc U . R 1 . .
H H17C 0.3661 -0.108 0.4327 0.162 Uiso calc U . R 1 . .
N N1 0.48579(13) 0.2199(4) 0.28714(12) 0.0523(8) Uani d . . . 1 . .
N N2 0.42162(14) 0.1782(4) 0.31341(13) 0.0592(8) Uani d . . . 1 . .
N N3 0.47469(17) 0.2062(4) 0.41453(13) 0.0694(9) Uani d . . . 1 . .
N N4 0.78624(19) 0.4421(5) 0.29206(18) 0.1018(13) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C7 N1 . 1.384(4) ?
C7 C2 . 1.402(4) ?
C7 C6 . 1.381(4) ?
C2 N3 . 1.365(4) ?
C2 C3 . 1.400(5) ?
C8 C9 . 1.378(4) ?
C8 C13 . 1.375(4) ?
C8 N1 . 1.428(4) ?
C9 C10 . 1.376(4) ?
C9 H9 . 0.93 ?
C6 C5 . 1.378(4) ?
C6 H6 . 0.93 ?
C1 N2 . 1.324(4) ?
C1 N3 . 1.335(4) ?
C1 C14 . 1.521(5) ?
C3 C4 . 1.360(5) ?
C3 H3 . 0.93 ?
C4 C5 . 1.384(5) ?
C4 H4 . 0.93 ?
C13 C12 . 1.373(4) ?
C13 H13 . 0.93 ?
C5 C18 . 1.425(5) ?
C12 C11 . 1.366(5) ?
C12 H12 . 0.93 ?
C10 C11 . 1.377(5) ?
C10 H10 . 0.93 ?
C14 C15 . 1.514(6) ?
C14 C16 . 1.527(5) ?
C14 C17 . 1.529(5) ?
C18 N4 . 1.137(5) ?
C11 H11 . 0.93 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
N1 N2 . 1.375(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C7 C2 . . 116.6(3) ?
N1 C7 C6 . . 123.5(3) ?
C2 C7 C6 . . 119.9(3) ?
N3 C2 C7 . . 122.3(3) ?
N3 C2 C3 . . 119.2(3) ?
C7 C2 C3 . . 118.5(3) ?
C9 C8 C13 . . 120.7(3) ?
C9 C8 N1 . . 120.5(3) ?
C13 C8 N1 . . 118.7(3) ?
C8 C9 C10 . . 119.1(3) ?
C8 C9 H9 . . 120.5 ?
C10 C9 H9 . . 120.5 ?
C7 C6 C5 . . 120.0(3) ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
N2 C1 N3 . . 127.5(3) ?
N2 C1 C14 . . 115.3(3) ?
N3 C1 C14 . . 117.1(3) ?
C4 C3 C2 . . 121.1(3) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 119.8(4) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C12 C13 C8 . . 119.1(3) ?
C12 C13 H13 . . 120.5 ?
C8 C13 H13 . . 120.5 ?
C6 C5 C4 . . 120.5(3) ?
C6 C5 C18 . . 120.0(3) ?
C4 C5 C18 . . 119.5(3) ?
C11 C12 C13 . . 121.1(4) ?
C11 C12 H12 . . 119.4 ?
C13 C12 H12 . . 119.4 ?
C9 C10 C11 . . 120.7(3) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C15 C14 C1 . . 111.9(3) ?
C15 C14 C16 . . 110.2(3) ?
C1 C14 C16 . . 107.0(3) ?
C15 C14 C17 . . 110.1(4) ?
C1 C14 C17 . . 108.8(3) ?
C16 C14 C17 . . 108.7(3) ?
N4 C18 C5 . . 178.7(5) ?
C12 C11 C10 . . 119.3(3) ?
C12 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
N2 N1 C7 . . 121.7(3) ?
N2 N1 C8 . . 113.5(2) ?
C7 N1 C8 . . 124.7(3) ?
C1 N2 N1 . . 116.3(3) ?
C1 N3 C2 . . 115.5(3) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C7 C2 N3 . . . . -1.9(5) ?
C6 C7 C2 N3 . . . . 176.0(3) ?
N1 C7 C2 C3 . . . . 178.5(3) ?
C6 C7 C2 C3 . . . . -3.7(5) ?
C13 C8 C9 C10 . . . . 2.4(5) ?
N1 C8 C9 C10 . . . . 178.7(3) ?
N1 C7 C6 C5 . . . . -179.0(3) ?
C2 C7 C6 C5 . . . . 3.2(5) ?
N3 C2 C3 C4 . . . . -178.4(4) ?
C7 C2 C3 C4 . . . . 1.3(5) ?
C2 C3 C4 C5 . . . . 1.5(6) ?
C9 C8 C13 C12 . . . . -2.4(5) ?
N1 C8 C13 C12 . . . . -178.9(3) ?
C7 C6 C5 C4 . . . . -0.4(5) ?
C7 C6 C5 C18 . . . . 177.7(3) ?
C3 C4 C5 C6 . . . . -2.0(6) ?
C3 C4 C5 C18 . . . . 179.8(4) ?
C8 C13 C12 C11 . . . . 0.3(5) ?
C8 C9 C10 C11 . . . . -0.2(5) ?
N2 C1 C14 C15 . . . . 9.8(5) ?
N3 C1 C14 C15 . . . . -172.9(4) ?
N2 C1 C14 C16 . . . . -111.1(4) ?
N3 C1 C14 C16 . . . . 66.3(4) ?
N2 C1 C14 C17 . . . . 131.7(4) ?
N3 C1 C14 C17 . . . . -50.9(5) ?
C13 C12 C11 C10 . . . . 1.7(6) ?
C9 C10 C11 C12 . . . . -1.8(6) ?
C2 C7 N1 N2 . . . . 3.0(4) ?
C6 C7 N1 N2 . . . . -174.8(3) ?
C2 C7 N1 C8 . . . . 179.0(3) ?
C6 C7 N1 C8 . . . . 1.2(5) ?
C9 C8 N1 N2 . . . . -134.3(3) ?
C13 C8 N1 N2 . . . . 42.1(4) ?
C9 C8 N1 C7 . . . . 49.4(4) ?
C13 C8 N1 C7 . . . . -134.1(3) ?
N3 C1 N2 N1 . . . . -0.4(5) ?
C14 C1 N2 N1 . . . . 176.6(3) ?
C7 N1 N2 C1 . . . . -1.9(4) ?
C8 N1 N2 C1 . . . . -178.3(3) ?
N2 C1 N3 C2 . . . . 1.5(5) ?
C14 C1 N3 C2 . . . . -175.5(3) ?
C7 C2 N3 C1 . . . . -0.2(5) ?
C3 C2 N3 C1 . . . . 179.4(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_1Ph3tBu6CNBT_300K
_database_code_depnum_ccdc_archive 'CCDC 1524671'
_audit_update_record             
;
2016-12-27 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;
#-------------------------------------------
_chemical_name_systematic        
;
3-tert-Butyl-6-cyano-1,4-dihydro-1-phenyl-1,2,4-benzotriazin-4-yl
;
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H17 N4'
_chemical_formula_sum            'C18 H17 N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         289.35

_chemical_melting_point          453-454
#-------------------------------------------
# CRYSTAL DATA
#-------------------------------------------
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   26.317(4)
_cell_length_b                   6.7524(7)
_cell_length_c                   18.003(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.578(3)
_cell_angle_gamma                90
_cell_volume                     3199.0(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    268
_cell_measurement_theta_min      2.2670
_cell_measurement_theta_max      23.7294
_cell_measurement_temperature    300.(2)
#-------------------------------------------
_exptl_crystal_description       plate-like
_exptl_crystal_colour            black
_exptl_crystal_size_max          1.239
_exptl_crystal_size_mid          0.538
_exptl_crystal_size_min          0.062
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224

_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;
#------------------------------------------
#EXPERIMENTAL DATA
#------------------------------------------
_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'micro focus sealed tube'
_diffrn_source_type              'INCOATEC I\mS'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered conforcal mirror'

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scan'

_diffrn_detector_area_resol_mean 7.4074

#-------------------------------------------
#REFINEMENT DATA
#-------------------------------------------
_diffrn_reflns_number            13670
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         24.44
_diffrn_reflns_theta_full        24.44
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
Refinement was based on F² against all reflections. The weighted R-factor
(wR) and goodness of fit (S) were based on F², and conventional R-factor (R)
was calculated on F, with F set to zero for negative F². The threshold
expression of I > 2σ(I) was used only for calculating R-factor (gt).
;

_reflns_number_total             2605
_reflns_number_gt                1929
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_gt          0.2160
_refine_ls_wR_factor_ref         0.2370
_refine_ls_goodness_of_fit_ref   1.396
_refine_ls_restrained_S_all      1.396
_refine_ls_number_reflns         2605
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.6219P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

#-------------------------------------------
_computing_data_collection       
;
Bruker Instrument Service V6.2.3 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXTL-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHELL V 6.3.1(Bruker AXS Inc., 2004)'
_computing_publication_material  
;
Generate Report (Bruker AXS Inc., 2013)
;
#-------------------------------------------


loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.62199(7) 0.4807(2) 0.27175(10) 0.0556(6) Uani d . . . 1 . .
N N2 0.60874(8) 0.4713(3) 0.34448(10) 0.0607(6) Uani d . . . 1 . .
N N3 0.69659(8) 0.4853(3) 0.37820(12) 0.0660(6) Uani d . . . 1 . .
C C7 0.67152(8) 0.4905(3) 0.24833(13) 0.0518(6) Uani d . . . 1 . .
C C2 0.70922(9) 0.4922(3) 0.30498(14) 0.0548(6) Uani d . . . 1 . .
C C3 0.75994(9) 0.5010(3) 0.28396(16) 0.0608(7) Uani d . . . 1 . .
H H3 0.7853 0.5024 0.3202 0.073 Uiso calc U . R 1 . .
C C8 0.57993(8) 0.4722(3) 0.22027(13) 0.0597(7) Uani d . . . 1 . .
C C6 0.68527(9) 0.4966(3) 0.17412(14) 0.0590(7) Uani d . . . 1 . .
H H6 0.6603 0.4951 0.1372 0.071 Uiso calc U . R 1 . .
C C1 0.64718(10) 0.4750(3) 0.39303(13) 0.0607(7) Uani d . . . 1 . .
C C4 0.77290(8) 0.5077(3) 0.21046(16) 0.0599(7) Uani d . . . 1 . .
N N4 0.86756(10) 0.5282(4) 0.17497(19) 0.1061(10) Uani d . . . 1 . .
C C5 0.73536(9) 0.5050(3) 0.15517(16) 0.0642(7) Uani d . . . 1 . .
H H5 0.7444 0.5089 0.1054 0.077 Uiso calc U . R 1 . .
C C13 0.55215(9) 0.3009(4) 0.21492(15) 0.0807(8) Uani d . . . 1 . .
H H13 0.5609 0.1907 0.2433 0.097 Uiso calc U . R 1 . .
C C18 0.82558(10) 0.5188(3) 0.19014(18) 0.0760(8) Uani d . . . 1 . .
C C14 0.63273(12) 0.4687(4) 0.47375(15) 0.0783(8) Uani d . . . 1 . .
C C9 0.56733(10) 0.6349(5) 0.17928(16) 0.0876(9) Uani d . . . 1 . .
H H9 0.586 0.7511 0.1839 0.105 Uiso calc U . R 1 . .
C C12 0.51097(11) 0.2943(6) 0.16683(18) 0.1013(11) Uani d . . . 1 . .
H H12 0.4918 0.1791 0.1627 0.122 Uiso calc U . R 1 . .
C C11 0.49832(11) 0.4563(7) 0.12532(18) 0.1040(12) Uani d . . . 1 . .
H H11 0.4704 0.4516 0.0932 0.125 Uiso calc U . R 1 . .
C C10 0.52645(12) 0.6250(6) 0.1308(2) 0.1121(12) Uani d . . . 1 . .
H H10 0.5181 0.7342 0.1017 0.134 Uiso calc U . R 1 . .
C C16 0.57677(16) 0.4619(8) 0.4848(2) 0.156(2) Uani d . . . 1 . .
H H16A 0.5615 0.5795 0.4645 0.234 Uiso calc U . R 1 . .
H H16B 0.5697 0.454 0.5369 0.234 Uiso calc U . R 1 . .
H H16C 0.563 0.3477 0.46 0.234 Uiso calc U . R 1 . .
C C15 0.6536(2) 0.6544(8) 0.5110(2) 0.165(2) Uani d . . . 1 . .
H H15A 0.6894 0.6642 0.502 0.248 Uiso calc U . R 1 . .
H H15B 0.6478 0.6474 0.5635 0.248 Uiso calc U . R 1 . .
H H15C 0.6367 0.7687 0.4909 0.248 Uiso calc U . R 1 . .
C C17 0.6593(2) 0.2971(8) 0.5096(2) 0.204(3) Uani d . . . 1 . .
H H17A 0.6423 0.1764 0.496 0.306 Uiso calc U . R 1 . .
H H17B 0.6588 0.3125 0.5626 0.306 Uiso calc U . R 1 . .
H H17C 0.6939 0.2923 0.4931 0.306 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 . 1.360(3) ?
N1 C7 . 1.375(3) ?
N1 C8 . 1.438(3) ?
N2 C1 . 1.330(3) ?
N3 C1 . 1.332(3) ?
N3 C2 . 1.364(3) ?
C7 C6 . 1.388(3) ?
C7 C2 . 1.416(3) ?
C2 C3 . 1.392(4) ?
C3 C4 . 1.371(4) ?
C3 H3 . 0.93 ?
C8 C9 . 1.363(3) ?
C8 C13 . 1.371(3) ?
C6 C5 . 1.366(3) ?
C6 H6 . 0.93 ?
C1 C14 . 1.506(4) ?
C4 C5 . 1.395(4) ?
C4 C18 . 1.439(4) ?
N4 C18 . 1.143(4) ?
C5 H5 . 0.93 ?
C13 C12 . 1.381(3) ?
C13 H13 . 0.93 ?
C14 C16 . 1.489(5) ?
C14 C17 . 1.497(5) ?
C14 C15 . 1.522(5) ?
C9 C10 . 1.380(4) ?
C9 H9 . 0.93 ?
C12 C11 . 1.364(5) ?
C12 H12 . 0.93 ?
C11 C10 . 1.361(5) ?
C11 H11 . 0.93 ?
C10 H10 . 0.93 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C7 . . 123.39(18) ?
N2 N1 C8 . . 114.55(18) ?
C7 N1 C8 . . 122.0(2) ?
C1 N2 N1 . . 115.5(2) ?
C1 N3 C2 . . 116.3(2) ?
N1 C7 C6 . . 123.6(2) ?
N1 C7 C2 . . 116.0(2) ?
C6 C7 C2 . . 120.4(2) ?
N3 C2 C3 . . 120.5(2) ?
N3 C2 C7 . . 121.4(2) ?
C3 C2 C7 . . 118.1(2) ?
C4 C3 C2 . . 120.8(2) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C9 C8 C13 . . 121.0(2) ?
C9 C8 N1 . . 119.9(2) ?
C13 C8 N1 . . 119.1(2) ?
C5 C6 C7 . . 120.2(2) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
N2 C1 N3 . . 127.4(2) ?
N2 C1 C14 . . 115.8(2) ?
N3 C1 C14 . . 116.8(2) ?
C3 C4 C5 . . 120.5(2) ?
C3 C4 C18 . . 119.8(2) ?
C5 C4 C18 . . 119.8(3) ?
C6 C5 C4 . . 120.0(2) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C8 C13 C12 . . 119.1(3) ?
C8 C13 H13 . . 120.5 ?
C12 C13 H13 . . 120.5 ?
N4 C18 C4 . . 179.1(3) ?
C16 C14 C17 . . 112.2(4) ?
C16 C14 C1 . . 112.9(2) ?
C17 C14 C1 . . 108.4(3) ?
C16 C14 C15 . . 108.6(3) ?
C17 C14 C15 . . 106.4(4) ?
C1 C14 C15 . . 107.9(3) ?
C8 C9 C10 . . 119.2(3) ?
C8 C9 H9 . . 120.4 ?
C10 C9 H9 . . 120.4 ?
C11 C12 C13 . . 120.2(3) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C10 C11 C12 . . 120.1(3) ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C11 C10 C9 . . 120.4(3) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?

