# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_c5583
_database_code_depnum_ccdc_archive 'CCDC 1915383'
loop_
_audit_author_name
_audit_author_address
'Gregory Leitus'
;Weizmann Institute of Science
Israel
;
_audit_update_record             
;
2019-06-23 deposited with the CCDC.	2019-07-04 downloaded from the CCDC.
;
# Crystallography: Gregory Leitus
# start Validation Reply Form
_vrf_PLAT027_c5583               
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      26.00 Degree
RESPONSE: The crystals formed by organic molecules (only light
elements are present - up to F) were short thin needles. Full data
could be only collected till resolution 1.7 A with Cu-radiation at 100 K to
maximize signal to noise. Structure was readily solved and refined.
;
_vrf_PLAT084_c5583               
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.41 Report
RESPONSE: See response on Alert level A
;
_vrf_PLAT340_c5583               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01388 Ang.  
RESPONSE: See response on Alert level A
;
_vrf_PLAT930_c5583               
;
PROBLEM: FCF-based   Twin Law ( 0 0 1)[ 0-1 5] Est.d BASF       0.34 Check 
RESPONSE: It is checked. BASF doesn't stabilize during refinement (possibly 
due to a low resolution), therefore, this twinning cannot be claimed or rejected.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1-Phenyl-3,7-bis(trifluoromethyl)-1,4-dihydro-1,2,4-benzotriazin-4-yl
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H8 F6 N3'
_chemical_formula_sum            'C15 H8 F6 N3'
_chemical_formula_weight         344.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8756(10)
_cell_length_b                   9.889(2)
_cell_length_c                   14.245(3)
_cell_angle_alpha                85.77(3)
_cell_angle_beta                 88.56(3)
_cell_angle_gamma                80.94(3)
_cell_volume                     676.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1484
_cell_measurement_theta_min      7.4640
_cell_measurement_theta_max      72.2650

_exptl_crystal_description       rods
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_F_000             346
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.437
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3974
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.111
_diffrn_reflns_theta_max         67.320
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2395
_reflns_number_gt                1782
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1144P)²+13.6661P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2395
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1545
_refine_ls_R_factor_gt           0.1359
_refine_ls_wR_factor_ref         0.4092
_refine_ls_wR_factor_gt          0.4010
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.1029(12) 0.0092(6) 0.1065(4) 0.0392(15) Uani 1 1 d . . . . .
F2 F 0.2789(14) -0.1137(6) 0.1495(5) 0.0519(18) Uani 1 1 d . . . . .
F3 F -0.0037(15) -0.0217(7) 0.2527(4) 0.0500(18) Uani 1 1 d . . . . .
F4 F 1.1635(14) 0.5916(6) 0.2581(4) 0.0454(16) Uani 1 1 d . . . . .
F5 F 0.7967(12) 0.7160(6) 0.2018(5) 0.0453(17) Uani 1 1 d . . . . .
F6 F 1.0949(13) 0.6114(6) 0.1103(4) 0.0400(15) Uani 1 1 d . . . . .
N1 N 0.6344(17) 0.3232(8) 0.3021(6) 0.0301(18) Uani 1 1 d . . . . .
N2 N 0.7920(17) 0.4267(8) 0.2903(6) 0.0309(18) Uani 1 1 d . . . . .
N3 N 0.7090(17) 0.4466(8) 0.1239(6) 0.0308(18) Uani 1 1 d . . . . .
C1 C 0.8087(19) 0.4787(10) 0.2023(7) 0.029(2) Uani 1 1 d . . . . .
C2 C 0.553(2) 0.3388(10) 0.1365(7) 0.030(2) Uani 1 1 d . . . . .
C3 C 0.5150(19) 0.2748(9) 0.2260(6) 0.026(2) Uani 1 1 d . . . . .
C4 C 0.3617(19) 0.1674(10) 0.2371(7) 0.030(2) Uani 1 1 d . . . . .
H4 H 0.3332 0.1244 0.2977 0.036 Uiso 1 1 calc R U . . .
C5 C 0.251(2) 0.1244(9) 0.1575(7) 0.031(2) Uani 1 1 d . . . . .
C6 C 0.282(2) 0.1890(11) 0.0696(8) 0.039(2) Uani 1 1 d . . . . .
H6 H 0.2006 0.1591 0.0164 0.046 Uiso 1 1 calc R U . . .
C7 C 0.431(2) 0.2967(11) 0.0586(7) 0.036(2) Uani 1 1 d . . . . .
H7 H 0.4497 0.3420 -0.0018 0.044 Uiso 1 1 calc R U . . .
C8 C 0.106(2) -0.0001(9) 0.1680(7) 0.030(2) Uani 1 1 d . . . . .
C9 C 0.968(2) 0.5993(10) 0.1923(7) 0.030(2) Uani 1 1 d . . . . .
C10 C 0.588(2) 0.2782(10) 0.3983(7) 0.029(2) Uani 1 1 d . . . . .
C13 C 0.504(2) 0.2051(12) 0.5855(7) 0.039(2) Uani 1 1 d . . . . .
H13 H 0.4756 0.1811 0.6504 0.046 Uiso 1 1 calc R U . A 1
C11 C 0.475(4) 0.375(2) 0.4564(13) 0.033(4) Uani 0.5 1 d . . P B 1
H11 H 0.4245 0.4677 0.4339 0.039 Uiso 0.5 1 calc R U P B 1
C12 C 0.436(5) 0.333(2) 0.5500(14) 0.039(5) Uani 0.5 1 d . . P B 1
H12 H 0.3553 0.3998 0.5911 0.047 Uiso 0.5 1 calc R U P B 1
C14 C 0.625(5) 0.102(2) 0.5217(14) 0.039(5) Uani 0.5 1 d . . P B 1
H14 H 0.6742 0.0086 0.5439 0.047 Uiso 0.5 1 calc R U P B 1
C15 C 0.667(4) 0.143(2) 0.4295(13) 0.032(4) Uani 0.5 1 d . . P B 1
H15 H 0.7495 0.0784 0.3870 0.039 Uiso 0.5 1 calc R U P B 1
C11A C 0.325(4) 0.308(2) 0.4395(14) 0.031(4) Uani 0.5 1 d . . P B 2
H11A H 0.1741 0.3536 0.4025 0.037 Uiso 0.5 1 calc R U P B 2
C12A C 0.281(4) 0.271(2) 0.5347(15) 0.036(5) Uani 0.5 1 d . . P B 2
H12A H 0.1023 0.2917 0.5632 0.044 Uiso 0.5 1 calc R U P B 2
C14A C 0.759(4) 0.188(2) 0.5504(14) 0.040(5) Uani 0.5 1 d . . P B 2
H14A H 0.9099 0.1517 0.5903 0.048 Uiso 0.5 1 calc R U P B 2
C15A C 0.810(5) 0.221(3) 0.4561(17) 0.049(6) Uani 0.5 1 d . . P B 2
H15A H 0.9933 0.2048 0.4310 0.059 Uiso 0.5 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C8 1.349(11) . ?
F2 C8 1.332(11) . ?
F3 C8 1.324(12) . ?
F4 C9 1.343(11) . ?
F5 C9 1.328(11) . ?
F6 C9 1.314(11) . ?
N1 N2 1.372(11) . ?
N1 C3 1.391(12) . ?
N1 C10 1.433(12) . ?
N2 C1 1.325(13) . ?
N3 C1 1.308(13) . ?
N3 C2 1.403(12) . ?
C1 C9 1.519(12) . ?
C2 C7 1.393(13) . ?
C2 C3 1.402(14) . ?
C3 C4 1.389(13) . ?
C4 C5 1.391(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(15) . ?
C5 C8 1.509(13) . ?
C6 C7 1.377(15) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C10 C11 1.35(2) . ?
C10 C15 1.37(2) . ?
C10 C11A 1.39(2) . ?
C10 C15A 1.40(3) . ?
C13 C14A 1.32(2) . ?
C13 C12 1.32(3) . ?
C13 C12A 1.37(2) . ?
C13 C14 1.46(2) . ?
C13 H13 0.9500 . ?
C11 C12 1.38(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 C15 1.37(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C11A C12A 1.40(3) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C14A C15A 1.38(3) . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C3 121.6(8) . . ?
N2 N1 C10 114.4(7) . . ?
C3 N1 C10 123.8(8) . . ?
C1 N2 N1 114.4(8) . . ?
C1 N3 C2 113.4(8) . . ?
N3 C1 N2 131.7(9) . . ?
N3 C1 C9 115.1(8) . . ?
N2 C1 C9 113.2(8) . . ?
C7 C2 C3 119.8(9) . . ?
C7 C2 N3 119.0(9) . . ?
C3 C2 N3 121.1(8) . . ?
C4 C3 N1 121.9(9) . . ?
C4 C3 C2 120.3(8) . . ?
N1 C3 C2 117.7(8) . . ?
C3 C4 C5 118.4(9) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 121.5(9) . . ?
C6 C5 C8 119.9(9) . . ?
C4 C5 C8 118.5(9) . . ?
C7 C6 C5 120.2(10) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 119.7(10) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
F3 C8 F2 107.5(8) . . ?
F3 C8 F1 106.3(8) . . ?
F2 C8 F1 105.5(7) . . ?
F3 C8 C5 114.1(8) . . ?
F2 C8 C5 111.3(8) . . ?
F1 C8 C5 111.7(8) . . ?
F6 C9 F5 107.1(8) . . ?
F6 C9 F4 106.6(8) . . ?
F5 C9 F4 106.6(8) . . ?
F6 C9 C1 113.4(8) . . ?
F5 C9 C1 110.2(8) . . ?
F4 C9 C1 112.6(8) . . ?
C11 C10 C15 122.3(14) . . ?
C11A C10 C15A 118.2(15) . . ?
C11 C10 N1 117.3(12) . . ?
C15 C10 N1 120.4(11) . . ?
C11A C10 N1 120.3(12) . . ?
C15A C10 N1 120.9(13) . . ?
C14A C13 C12A 122.4(15) . . ?
C12 C13 C14 117.7(14) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
C10 C11 C12 117.7(18) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
C13 C12 C11 124.0(18) . . ?
C13 C12 H12 118.0 . . ?
C11 C12 H12 118.0 . . ?
C15 C14 C13 118.5(18) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C10 119.8(17) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?
C10 C11A C12A 120.8(18) . . ?
C10 C11A H11A 119.6 . . ?
C12A C11A H11A 119.6 . . ?
C13 C12A C11A 117.7(17) . . ?
C13 C12A H12A 121.1 . . ?
C11A C12A H12A 121.1 . . ?
C13 C14A C15A 121.1(19) . . ?
C13 C14A H14A 119.5 . . ?
C15A C14A H14A 119.5 . . ?
C14A C15A C10 119(2) . . ?
C14A C15A H15A 120.4 . . ?
C10 C15A H15A 120.4 . . ?

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
C3 N1 N2 C1 2.7(13) . . . . ?
C10 N1 N2 C1 -172.8(8) . . . . ?
C2 N3 C1 N2 1.1(15) . . . . ?
C2 N3 C1 C9 -177.4(8) . . . . ?
N1 N2 C1 N3 -2.4(16) . . . . ?
N1 N2 C1 C9 176.2(8) . . . . ?
C1 N3 C2 C7 178.7(9) . . . . ?
C1 N3 C2 C3 -0.2(13) . . . . ?
N2 N1 C3 C4 178.1(8) . . . . ?
C10 N1 C3 C4 -6.8(14) . . . . ?
N2 N1 C3 C2 -2.2(13) . . . . ?
C10 N1 C3 C2 172.9(9) . . . . ?
C7 C2 C3 C4 1.6(14) . . . . ?
N3 C2 C3 C4 -179.4(8) . . . . ?
C7 C2 C3 N1 -178.1(9) . . . . ?
N3 C2 C3 N1 0.8(13) . . . . ?
N1 C3 C4 C5 -179.5(8) . . . . ?
C2 C3 C4 C5 0.8(13) . . . . ?
C3 C4 C5 C6 -2.4(14) . . . . ?
C3 C4 C5 C8 174.7(8) . . . . ?
C4 C5 C6 C7 1.6(16) . . . . ?
C8 C5 C6 C7 -175.5(9) . . . . ?
C5 C6 C7 C2 0.9(16) . . . . ?
C3 C2 C7 C6 -2.4(15) . . . . ?
N3 C2 C7 C6 178.6(10) . . . . ?
C6 C5 C8 F3 -155.7(9) . . . . ?
C4 C5 C8 F3 27.2(13) . . . . ?
C6 C5 C8 F2 82.4(12) . . . . ?
C4 C5 C8 F2 -94.7(10) . . . . ?
C6 C5 C8 F1 -35.2(13) . . . . ?
C4 C5 C8 F1 147.7(9) . . . . ?
N3 C1 C9 F6 -30.7(12) . . . . ?
N2 C1 C9 F6 150.5(9) . . . . ?
N3 C1 C9 F5 89.2(10) . . . . ?
N2 C1 C9 F5 -89.5(10) . . . . ?
N3 C1 C9 F4 -151.9(9) . . . . ?
N2 C1 C9 F4 29.3(12) . . . . ?
N2 N1 C10 C11 55.0(15) . . . . ?
C3 N1 C10 C11 -120.4(14) . . . . ?
N2 N1 C10 C15 -122.5(12) . . . . ?
C3 N1 C10 C15 62.1(15) . . . . ?
N2 N1 C10 C11A 109.3(13) . . . . ?
C3 N1 C10 C11A -66.1(14) . . . . ?
N2 N1 C10 C15A -61.9(17) . . . . ?
C3 N1 C10 C15A 122.7(16) . . . . ?
C15 C10 C11 C12 -1(3) . . . . ?
N1 C10 C11 C12 -178.4(15) . . . . ?
C14 C13 C12 C11 -1(3) . . . . ?
C10 C11 C12 C13 1(3) . . . . ?
C12 C13 C14 C15 1(3) . . . . ?
C13 C14 C15 C10 -2(3) . . . . ?
C11 C10 C15 C14 2(3) . . . . ?
N1 C10 C15 C14 178.9(16) . . . . ?
C15A C10 C11A C12A -5(3) . . . . ?
N1 C10 C11A C12A -176.4(15) . . . . ?
C14A C13 C12A C11A 7(3) . . . . ?
C10 C11A C12A C13 0(3) . . . . ?
C12A C13 C14A C15A -8(3) . . . . ?
C13 C14A C15A C10 2(4) . . . . ?
C11A C10 C15A C14A 4(3) . . . . ?
N1 C10 C15A C14A 175.4(17) . . . . ?

_refine_diff_density_max         0.805
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.139


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Cyclohexane'
_exptl_crystal_preparation       'Magnetic properties'
