# 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 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_1Ph3tBuBT
_database_code_depnum_ccdc_archive 'CCDC 1048595'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;
#-------------------------------------------
# CHEMICAL DATA
_chemical_name_systematic        
;
3-tert-butyl-1,4-dihydro-1-phenyl-1,2,4-benzotriazin-4-yl
;
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H18 N3'
_chemical_formula_sum            'C17 H18 N3'
_chemical_formula_iupac          ?
_chemical_formula_weight         264.34

_chemical_melting_point          ?
#-------------------------------------------
# CRYSTAL DATA
#-------------------------------------------
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6624(13)
_cell_length_b                   9.8119(11)
_cell_length_c                   15.7422(18)
_cell_angle_alpha                90
_cell_angle_beta                 104.595(4)
_cell_angle_gamma                90
_cell_volume                     1444.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4995
_cell_measurement_theta_min      2.4690
_cell_measurement_theta_max      29.3549
_cell_measurement_temperature    296.(2)
#-------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.73
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564

_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.98

_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 scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            13831
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         29.38
_diffrn_reflns_theta_full        29.38
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.944
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17

#-------------------------------------------
#REFINEMENT DATA
#-------------------------------------------
_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             3762
_reflns_number_gt                2323
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1683
_refine_ls_goodness_of_fit_ref   0.860
_refine_ls_restrained_S_all      0.860
_refine_ls_number_reflns         3762
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[σ²(Fo²)+(0.1000P)²+0.3849P]
where P=(Fo²+2Fc²)/3
;

_atom_sites_solution_hydrogens   difmap
_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         0.192
_refine_diff_density_min         -0.345
_refine_ls_extinction_method     none

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 for Crystallography 1992, Vol C'
H H 0.0000 0.0000 'International Tables for Crystallography 1992, Vol C'
N N 0.0061 0.0033 'International Tables for Crystallography 1992, Vol C'

#-------------------------------------------
_computing_data_collection       
;
Bruker Instrument Service V3.0.28 (Bruker AXS Inc., 2013)
;
_computing_cell_refinement       'APEX2 v2013.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (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
N N2 0.38494(12) 0.35876(12) 0.19244(8) 0.0420(3) Uani d . . . 1 . .
N N1 0.52862(12) 0.33499(13) 0.22007(7) 0.0413(3) Uani d . . . 1 . .
N N3 0.37246(13) 0.35898(13) 0.34205(8) 0.0459(3) Uani d . . . 1 . .
C C7 0.60138(15) 0.32849(14) 0.30753(9) 0.0389(3) Uani d . . . 1 . .
C C2 0.51745(16) 0.34126(14) 0.36860(9) 0.0408(3) Uani d . . . 1 . .
C C8 0.59948(15) 0.32325(15) 0.15038(9) 0.0398(3) Uani d . . . 1 . .
C C1 0.31640(15) 0.36789(14) 0.25618(9) 0.0383(3) Uani d . . . 1 . .
C C6 0.74866(17) 0.31166(17) 0.33575(11) 0.0501(4) Uani d . . . 1 . .
C C3 0.5874(2) 0.33533(18) 0.45809(10) 0.0535(4) Uani d . . . 1 . .
C C14 0.15474(15) 0.38414(15) 0.22421(9) 0.0434(4) Uani d . . . 1 . .
C C9 0.64540(19) 0.19904(18) 0.12924(12) 0.0548(4) Uani d . . . 1 . .
C C4 0.7318(2) 0.31725(19) 0.48534(11) 0.0586(5) Uani d . . . 1 . .
C C5 0.8125(2) 0.30599(19) 0.42406(12) 0.0576(5) Uani d . . . 1 . .
C C11 0.72992(18) 0.3021(2) 0.01487(11) 0.0581(5) Uani d . . . 1 . .
C C17 0.0978(2) 0.4665(2) 0.29033(14) 0.0640(5) Uani d . . . 1 . .
C C16 0.1119(2) 0.4557(2) 0.13549(13) 0.0616(5) Uani d . . . 1 . .
C C10 0.7109(2) 0.18936(19) 0.06062(12) 0.0603(5) Uani d . . . 1 . .
C C13 0.6189(2) 0.4370(2) 0.10505(12) 0.0646(5) Uani d . . . 1 . .
C C15 0.0896(2) 0.2416(2) 0.21619(15) 0.0607(5) Uani d . . . 1 . .
C C12 0.6844(2) 0.4254(2) 0.03665(14) 0.0757(6) Uani d . . . 1 . .
H H1 0.527(2) 0.347(2) 0.4989(14) 0.072(6) Uiso d . . . 1 . .
H H2 0.776(2) 0.3125(18) 0.5466(14) 0.070(6) Uiso d . . . 1 . .
H H4 0.804(2) 0.3037(18) 0.2919(13) 0.063(5) Uiso d . . . 1 . .
H H3 0.911(2) 0.2935(19) 0.4427(13) 0.066(5) Uiso d . . . 1 . .
H H7 0.775(2) 0.2910(19) -0.0348(13) 0.074(6) Uiso d . . . 1 . .
H H5 0.635(2) 0.119(2) 0.1629(14) 0.080(6) Uiso d . . . 1 . .
H H6 0.743(2) 0.101(2) 0.0434(14) 0.085(6) Uiso d . . . 1 . .
H H9 0.593(2) 0.523(2) 0.1237(14) 0.090(7) Uiso d . . . 1 . .
H H8 0.703(3) 0.510(3) 0.0057(16) 0.108(8) Uiso d . . . 1 . .
H H18 0.111(2) 0.1988(19) 0.2759(14) 0.067(5) Uiso d . . . 1 . .
H H16 0.125(2) 0.185(2) 0.1715(14) 0.071(6) Uiso d . . . 1 . .
H H13 -0.007(3) 0.476(2) 0.2648(13) 0.080(6) Uiso d . . . 1 . .
H H17 -0.013(2) 0.250(2) 0.1954(13) 0.073(6) Uiso d . . . 1 . .
H H15 0.117(2) 0.420(2) 0.3471(14) 0.074(6) Uiso d . . . 1 . .
H H14 0.139(2) 0.563(3) 0.2955(15) 0.097(7) Uiso d . . . 1 . .
H H11 0.153(3) 0.548(3) 0.1382(16) 0.101(8) Uiso d . . . 1 . .
H H12 0.008(2) 0.469(2) 0.1181(13) 0.078(6) Uiso d . . . 1 . .
H H10 0.142(2) 0.404(2) 0.0880(14) 0.085(6) Uiso 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
N2 C1 . 1.3372(17) ?
N2 N1 . 1.3663(16) ?
N1 C7 . 1.3806(18) ?
N1 C8 . 1.4367(16) ?
N3 C1 . 1.3265(19) ?
N3 C2 . 1.3684(19) ?
C7 C6 . 1.390(2) ?
C7 C2 . 1.4109(19) ?
C2 C3 . 1.402(2) ?
C8 C13 . 1.363(2) ?
C8 C9 . 1.366(2) ?
C1 C14 . 1.524(2) ?
C6 C5 . 1.373(2) ?
C6 H4 . 0.977(19) ?
C3 C4 . 1.364(3) ?
C3 H1 . 0.98(2) ?
C14 C15 . 1.526(2) ?
C14 C17 . 1.526(2) ?
C14 C16 . 1.524(2) ?
C9 C10 . 1.386(2) ?
C9 H5 . 0.97(2) ?
C4 C5 . 1.390(3) ?
C4 H2 . 0.95(2) ?
C5 H3 . 0.93(2) ?
C11 C12 . 1.361(3) ?
C11 C10 . 1.357(3) ?
C11 H7 . 0.99(2) ?
C17 H13 . 0.99(2) ?
C17 H15 . 0.98(2) ?
C17 H14 . 1.02(3) ?
C16 H11 . 0.98(3) ?
C16 H12 . 0.98(2) ?
C16 H10 . 1.01(2) ?
C10 H6 . 0.98(2) ?
C13 C12 . 1.384(2) ?
C13 H9 . 0.95(2) ?
C15 H18 . 1.00(2) ?
C15 H16 . 1.02(2) ?
C15 H17 . 0.96(2) ?
C12 H8 . 1.00(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
C1 N2 N1 . . 115.35(11) ?
N2 N1 C7 . . 123.14(11) ?
N2 N1 C8 . . 114.34(11) ?
C7 N1 C8 . . 122.47(12) ?
C1 N3 C2 . . 116.32(11) ?
N1 C7 C6 . . 123.19(12) ?
N1 C7 C2 . . 116.09(13) ?
C6 C7 C2 . . 120.72(13) ?
N3 C2 C3 . . 120.63(13) ?
N3 C2 C7 . . 121.54(13) ?
C3 C2 C7 . . 117.83(14) ?
C13 C8 C9 . . 120.45(14) ?
C13 C8 N1 . . 119.28(13) ?
C9 C8 N1 . . 120.26(13) ?
N3 C1 N2 . . 127.44(13) ?
N3 C1 C14 . . 117.70(11) ?
N2 C1 C14 . . 114.80(12) ?
C5 C6 C7 . . 119.44(15) ?
C5 C6 H4 . . 121.7(11) ?
C7 C6 H4 . . 118.8(11) ?
C4 C3 C2 . . 121.16(15) ?
C4 C3 H1 . . 122.6(12) ?
C2 C3 H1 . . 116.2(12) ?
C1 C14 C15 . . 107.37(13) ?
C1 C14 C17 . . 110.25(13) ?
C15 C14 C17 . . 109.26(14) ?
C1 C14 C16 . . 111.71(12) ?
C15 C14 C16 . . 109.58(16) ?
C17 C14 C16 . . 108.65(16) ?
C8 C9 C10 . . 119.40(16) ?
C8 C9 H5 . . 120.4(12) ?
C10 C9 H5 . . 120.2(12) ?
C3 C4 C5 . . 120.05(16) ?
C3 C4 H2 . . 118.9(12) ?
C5 C4 H2 . . 121.0(12) ?
C6 C5 C4 . . 120.80(17) ?
C6 C5 H3 . . 119.1(12) ?
C4 C5 H3 . . 120.1(12) ?
C12 C11 C10 . . 119.69(15) ?
C12 C11 H7 . . 122.0(11) ?
C10 C11 H7 . . 118.3(11) ?
C14 C17 H13 . . 106.2(12) ?
C14 C17 H15 . . 111.1(12) ?
H13 C17 H15 . . 110.7(16) ?
C14 C17 H14 . . 110.3(13) ?
H13 C17 H14 . . 106.2(17) ?
H15 C17 H14 . . 112.0(18) ?
C14 C16 H11 . . 111.7(15) ?
C14 C16 H12 . . 109.9(12) ?
H11 C16 H12 . . 105.4(19) ?
C14 C16 H10 . . 112.6(13) ?
H11 C16 H10 . . 108.0(19) ?
H12 C16 H10 . . 109.0(16) ?
C11 C10 C9 . . 120.49(17) ?
C11 C10 H6 . . 118.7(12) ?
C9 C10 H6 . . 120.8(12) ?
C8 C13 C12 . . 119.37(17) ?
C8 C13 H9 . . 119.2(13) ?
C12 C13 H9 . . 121.3(13) ?
C14 C15 H18 . . 108.8(11) ?
C14 C15 H16 . . 110.9(11) ?
H18 C15 H16 . . 113.0(17) ?
C14 C15 H17 . . 108.4(12) ?
H18 C15 H17 . . 107.9(17) ?
H16 C15 H17 . . 107.7(16) ?
C11 C12 C13 . . 120.60(17) ?
C11 C12 H8 . . 120.4(14) ?
C13 C12 H8 . . 118.9(14) ?

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
C1 N2 N1 C7 . . . . -3.67(19) ?
C1 N2 N1 C8 . . . . 178.98(12) ?
N2 N1 C7 C6 . . . . -176.41(13) ?
C8 N1 C7 C6 . . . . 0.7(2) ?
N2 N1 C7 C2 . . . . 3.03(19) ?
C8 N1 C7 C2 . . . . -179.83(12) ?
C1 N3 C2 C3 . . . . 177.83(14) ?
C1 N3 C2 C7 . . . . -2.1(2) ?
N1 C7 C2 N3 . . . . 0.0(2) ?
C6 C7 C2 N3 . . . . 179.48(14) ?
N1 C7 C2 C3 . . . . -179.94(13) ?
C6 C7 C2 C3 . . . . -0.5(2) ?
N2 N1 C8 C13 . . . . 72.03(18) ?
C7 N1 C8 C13 . . . . -105.34(18) ?
N2 N1 C8 C9 . . . . -107.24(16) ?
C7 N1 C8 C9 . . . . 75.38(19) ?
C2 N3 C1 N2 . . . . 1.5(2) ?
C2 N3 C1 C14 . . . . 178.53(12) ?
N1 N2 C1 N3 . . . . 1.3(2) ?
N1 N2 C1 C14 . . . . -175.79(11) ?
N1 C7 C6 C5 . . . . -179.88(14) ?
C2 C7 C6 C5 . . . . 0.7(2) ?
N3 C2 C3 C4 . . . . 179.78(15) ?
C7 C2 C3 C4 . . . . -0.3(2) ?
N3 C1 C14 C15 . . . . -85.87(16) ?
N2 C1 C14 C15 . . . . 91.53(15) ?
N3 C1 C14 C17 . . . . 33.05(19) ?
N2 C1 C14 C17 . . . . -149.54(15) ?
N3 C1 C14 C16 . . . . 153.97(15) ?
N2 C1 C14 C16 . . . . -28.63(18) ?
C13 C8 C9 C10 . . . . -0.6(3) ?
N1 C8 C9 C10 . . . . 178.67(15) ?
C2 C3 C4 C5 . . . . 0.8(3) ?
C7 C6 C5 C4 . . . . -0.2(3) ?
C3 C4 C5 C6 . . . . -0.6(3) ?
C12 C11 C10 C9 . . . . 0.1(3) ?
C8 C9 C10 C11 . . . . 0.2(3) ?
C9 C8 C13 C12 . . . . 0.6(3) ?
N1 C8 C13 C12 . . . . -178.63(17) ?
C10 C11 C12 C13 . . . . 0.0(3) ?
C8 C13 C12 C11 . . . . -0.3(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_1Ph3tBu7CF3BT
_database_code_depnum_ccdc_archive 'CCDC 1048596'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;
#-------------------------------------------
# CHEMICAL DATA
_chemical_name_systematic        
;
3-tert-butyl-7-trifluoromethyl-1,4-dihydro-1-phenyl-1,2,4-benzotriazin-4-yl
;
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H17 F3 N3'
_chemical_formula_sum            'C18 H17 F3 N3'
_chemical_formula_iupac          ?
_chemical_formula_weight         332.34
_chemical_absolute_configuration ?

_chemical_melting_point          ?
#-------------------------------------------
# CRYSTAL DATA
#-------------------------------------------
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_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                   5.592(2)
_cell_length_b                   18.904(7)
_cell_length_c                   15.882(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.487(11)
_cell_angle_gamma                90
_cell_volume                     1677.3(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1622
_cell_measurement_theta_min      2.5082
_cell_measurement_theta_max      22.2728
_cell_measurement_temperature    296.(2)
#-------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            black-red
_exptl_crystal_size_max          0.780
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             692

_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.56
_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 scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            4642
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.35
_diffrn_reflns_theta_full        27.35
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.952
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20

#-------------------------------------------
#REFINEMENT DATA
#-------------------------------------------
_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             2871
_reflns_number_gt                1725
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.2069
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.059
_refine_ls_number_reflns         2871
_refine_ls_number_parameters     221
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[σ²(Fo²)+(0.1000P)²+0.4543P]
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         0.348
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 614 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   2.0(10)

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 for Crystallography 1992, Vol C'
H H 0.0000 0.0000 'International Tables for Crystallography 1992, Vol C'
N N 0.0061 0.0033 'International Tables for Crystallography 1992, Vol C'
F F 0.0171 0.0103 'International Tables for Crystallography 1992, Vol C'

#-------------------------------------------
_computing_data_collection       
;
Bruker Instrument Service V3.0.28 (Bruker AXS Inc., 2013)
;
_computing_cell_refinement       'APEX2 v2013.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (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
N N2 0.4499(9) 0.2707(2) 0.0587(3) 0.0566(12) Uani d . . . 1 . .
N N3 0.5458(9) 0.3241(2) 0.1926(3) 0.0607(14) Uani d . . . 1 . .
N N1 0.5976(9) 0.2161(2) 0.0803(3) 0.0553(12) Uani d . . . 1 . .
C C7 0.7237(10) 0.2119(3) 0.1569(3) 0.0484(13) Uani d . . . 1 . .
C C1 0.4346(10) 0.3215(3) 0.1169(3) 0.0505(14) Uani d . . . 1 . .
C C2 0.6923(11) 0.2681(3) 0.2129(3) 0.0542(15) Uani d . . . 1 . .
C C6 0.8813(10) 0.1555(3) 0.1770(3) 0.0520(15) Uani d . . . 1 . .
H H6 0.9028 0.1188 0.139 0.062 Uiso calc U . R 1 . .
C C5 1.0017(11) 0.1563(3) 0.2540(4) 0.0572(15) Uani d . . . 1 . .
C C18 1.1628(13) 0.0973(4) 0.2771(4) 0.0664(18) Uani d . . . 1 . .
C C3 0.8173(13) 0.2659(4) 0.2906(4) 0.075(2) Uani d . . . 1 . .
H H3 0.7969 0.3021 0.3293 0.09 Uiso calc U . R 1 . .
C C14 0.2864(11) 0.3850(3) 0.0891(4) 0.0553(14) Uani d . . . 1 . .
C C8 0.6083(10) 0.1615(3) 0.0164(3) 0.0461(14) Uani d . . . 1 . .
C C4 0.9709(13) 0.2108(3) 0.3112(4) 0.0734(19) Uani d . . . 1 . .
H H4 1.0537 0.2102 0.3633 0.088 Uiso calc U . R 1 . .
C C11 0.6061(12) 0.0627(3) -0.1094(4) 0.0589(15) Uani d . . . 1 . .
H H11 0.6032 0.0298 -0.1531 0.071 Uiso calc U . R 1 . .
C C12 0.4295(14) 0.0621(3) -0.0534(4) 0.0674(18) Uani d . . . 1 . .
H H12 0.3112 0.0275 -0.0574 0.081 Uiso calc U . R 1 . .
C C17 0.1642(14) 0.4185(4) 0.1641(5) 0.083(2) Uani d . . . 1 . .
H H17A 0.0714 0.3833 0.1915 0.124 Uiso calc U . R 1 . .
H H17B 0.0611 0.4561 0.1444 0.124 Uiso calc U . R 1 . .
H H17C 0.2837 0.437 0.2034 0.124 Uiso calc U . R 1 . .
C C16 0.4537(14) 0.4392(4) 0.0527(5) 0.084(2) Uani d . . . 1 . .
H H16A 0.5601 0.4571 0.0967 0.126 Uiso calc U . R 1 . .
H H16B 0.3616 0.4775 0.0283 0.126 Uiso calc U . R 1 . .
H H16C 0.5452 0.4173 0.0101 0.126 Uiso calc U . R 1 . .
C C13 0.4244(12) 0.1124(3) 0.0095(4) 0.0608(15) Uani d . . . 1 . .
H H13 0.3 0.1133 0.0465 0.073 Uiso calc U . R 1 . .
C C10 0.7875(13) 0.1108(4) -0.1025(4) 0.0717(19) Uani d . . . 1 . .
H H10 0.9108 0.1098 -0.14 0.086 Uiso calc U . R 1 A 4
C C9 0.7865(12) 0.1617(3) -0.0384(4) 0.0605(16) Uani d . . . 1 . .
H H9 0.9076 0.1954 -0.0336 0.073 Uiso calc U . R 1 . .
C C15 0.0939(14) 0.3653(4) 0.0227(5) 0.089(2) Uani d . . . 1 . .
H H15A 0.167 0.3435 -0.0244 0.133 Uiso calc U . R 1 . .
H H15B 0.0099 0.4072 0.0041 0.133 Uiso calc U . R 1 . .
H H15C -0.0166 0.3328 0.0463 0.133 Uiso calc U . R 1 . .
F F1 1.0599(12) 0.0450(3) 0.3132(6) 0.172(3) Uani d . . . 1 . .
F F3 1.2646(14) 0.0684(4) 0.2168(4) 0.170(3) Uani d . . . 1 . .
F F2 1.3308(15) 0.1123(4) 0.3330(5) 0.195(4) 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
N2 C1 . 1.338(7) ?
N2 N1 . 1.357(6) ?
N3 C1 . 1.331(7) ?
N3 C2 . 1.368(7) ?
N1 C7 . 1.382(7) ?
N1 C8 . 1.451(7) ?
C7 C2 . 1.401(7) ?
C7 C6 . 1.412(8) ?
C1 C14 . 1.513(8) ?
C2 C3 . 1.393(8) ?
C6 C5 . 1.371(8) ?
C6 H6 . 0.93 ?
C5 C4 . 1.389(8) ?
C5 C18 . 1.470(9) ?
C18 F3 . 1.258(8) ?
C18 F1 . 1.291(9) ?
C18 F2 . 1.296(9) ?
C3 C4 . 1.380(9) ?
C3 H3 . 0.93 ?
C14 C16 . 1.519(10) ?
C14 C15 . 1.521(10) ?
C14 C17 . 1.535(9) ?
C8 C9 . 1.350(8) ?
C8 C13 . 1.387(8) ?
C4 H4 . 0.93 ?
C11 C12 . 1.358(10) ?
C11 C10 . 1.364(9) ?
C11 H11 . 0.93 ?
C12 C13 . 1.380(8) ?
C12 H12 . 0.93 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C13 H13 . 0.93 ?
C10 C9 . 1.402(8) ?
C10 H10 . 0.93 ?
C9 H9 . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 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
C1 N2 N1 . . 115.4(5) ?
C1 N3 C2 . . 115.9(5) ?
N2 N1 C7 . . 123.2(4) ?
N2 N1 C8 . . 114.1(4) ?
C7 N1 C8 . . 122.7(4) ?
N1 C7 C2 . . 116.2(4) ?
N1 C7 C6 . . 122.1(5) ?
C2 C7 C6 . . 121.6(5) ?
N3 C1 N2 . . 127.5(5) ?
N3 C1 C14 . . 117.6(5) ?
N2 C1 C14 . . 114.8(5) ?
N3 C2 C3 . . 120.3(5) ?
N3 C2 C7 . . 121.8(5) ?
C3 C2 C7 . . 117.9(5) ?
C5 C6 C7 . . 118.1(5) ?
C5 C6 H6 . . 121.0 ?
C7 C6 H6 . . 121.0 ?
C6 C5 C4 . . 121.5(6) ?
C6 C5 C18 . . 119.1(5) ?
C4 C5 C18 . . 119.5(5) ?
F3 C18 F1 . . 103.4(8) ?
F3 C18 F2 . . 106.1(7) ?
F1 C18 F2 . . 100.7(7) ?
F3 C18 C5 . . 115.6(6) ?
F1 C18 C5 . . 114.3(7) ?
F2 C18 C5 . . 115.0(6) ?
C4 C3 C2 . . 121.1(6) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C1 C14 C16 . . 107.9(5) ?
C1 C14 C15 . . 111.7(5) ?
C16 C14 C15 . . 109.3(6) ?
C1 C14 C17 . . 111.0(5) ?
C16 C14 C17 . . 108.7(6) ?
C15 C14 C17 . . 108.3(6) ?
C9 C8 C13 . . 121.1(5) ?
C9 C8 N1 . . 120.2(5) ?
C13 C8 N1 . . 118.6(5) ?
C3 C4 C5 . . 119.9(6) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C12 C11 C10 . . 120.8(6) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C11 C12 C13 . . 120.5(6) ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
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 ?
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 ?
C12 C13 C8 . . 118.7(6) ?
C12 C13 H13 . . 120.7 ?
C8 C13 H13 . . 120.7 ?
C11 C10 C9 . . 119.4(6) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
C8 C9 C10 . . 119.5(6) ?
C8 C9 H9 . . 120.3 ?
C10 C9 H9 . . 120.3 ?
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 ?

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
C1 N2 N1 C7 . . . . 0.5(8) ?
C1 N2 N1 C8 . . . . 179.4(5) ?
N2 N1 C7 C2 . . . . -0.2(8) ?
C8 N1 C7 C2 . . . . -179.0(5) ?
N2 N1 C7 C6 . . . . -178.2(5) ?
C8 N1 C7 C6 . . . . 3.0(8) ?
C2 N3 C1 N2 . . . . 0.0(9) ?
C2 N3 C1 C14 . . . . -175.3(5) ?
N1 N2 C1 N3 . . . . -0.4(9) ?
N1 N2 C1 C14 . . . . 175.0(5) ?
C1 N3 C2 C3 . . . . 179.8(6) ?
C1 N3 C2 C7 . . . . 0.4(8) ?
N1 C7 C2 N3 . . . . -0.3(8) ?
C6 C7 C2 N3 . . . . 177.8(6) ?
N1 C7 C2 C3 . . . . -179.7(6) ?
C6 C7 C2 C3 . . . . -1.7(8) ?
N1 C7 C6 C5 . . . . 179.0(5) ?
C2 C7 C6 C5 . . . . 1.0(8) ?
C7 C6 C5 C4 . . . . 0.0(9) ?
C7 C6 C5 C18 . . . . 178.7(6) ?
C6 C5 C18 F3 . . . . 31.5(10) ?
C4 C5 C18 F3 . . . . -149.8(8) ?
C6 C5 C18 F1 . . . . -88.4(8) ?
C4 C5 C18 F1 . . . . 90.3(9) ?
C6 C5 C18 F2 . . . . 155.8(8) ?
C4 C5 C18 F2 . . . . -25.5(10) ?
N3 C2 C3 C4 . . . . -178.2(6) ?
C7 C2 C3 C4 . . . . 1.3(10) ?
N3 C1 C14 C16 . . . . 83.6(7) ?
N2 C1 C14 C16 . . . . -92.2(6) ?
N3 C1 C14 C15 . . . . -156.3(6) ?
N2 C1 C14 C15 . . . . 27.9(8) ?
N3 C1 C14 C17 . . . . -35.3(7) ?
N2 C1 C14 C17 . . . . 148.8(6) ?
N2 N1 C8 C9 . . . . 96.4(6) ?
C7 N1 C8 C9 . . . . -84.7(7) ?
N2 N1 C8 C13 . . . . -79.5(6) ?
C7 N1 C8 C13 . . . . 99.4(6) ?
C2 C3 C4 C5 . . . . -0.3(11) ?
C6 C5 C4 C3 . . . . -0.4(10) ?
C18 C5 C4 C3 . . . . -179.0(7) ?
C10 C11 C12 C13 . . . . 3.0(10) ?
C11 C12 C13 C8 . . . . -2.7(9) ?
C9 C8 C13 C12 . . . . 1.7(8) ?
N1 C8 C13 C12 . . . . 177.5(5) ?
C12 C11 C10 C9 . . . . -2.2(10) ?
C13 C8 C9 C10 . . . . -0.9(9) ?
N1 C8 C9 C10 . . . . -176.7(6) ?
C11 C10 C9 C8 . . . . 1.2(9) ?



