# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_vbrjka4
_database_code_depnum_ccdc_archive 'CCDC 1979131'
loop_
_audit_author_name
_audit_author_address
'Dieter Schollmeyer'
;University of Mainz Department of Chemistry
Germany
;
_audit_update_record             
;
2020-01-21 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
N,N'-Diacetyl-N,N'-di(4-trifluoromethylphenyl)-hydrazine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 F6 N2 O2'
_chemical_formula_sum            'C18 H14 F6 N2 O2'
_chemical_formula_weight         404.31

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

_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+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.8529(9)
_cell_length_b                   12.6448(14)
_cell_length_c                   13.8015(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1894.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    5434
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      28.18

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_details      
; 158 frames, detector distance = 70 mm
;
_diffrn_reflns_number            5435
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.880
_diffrn_reflns_theta_max         28.242
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2298
_reflns_number_gt                1555
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     0.955
_reflns_Friedel_fraction_full    0.961

_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    SHELXT-2014
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0346P)²+1.1395P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_abs_structure_details 
;
 Flack x determined using 449 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2298
_refine_ls_number_parameters     155
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.167
_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
C1 C 0.5636(3) 0.3601(3) 0.1459(2) 0.0424(8) Uani 1 1 d . . . . .
C2 C 0.6457(4) 0.2768(3) 0.1517(3) 0.0516(10) Uani 1 1 d . . . . .
H2 H 0.695187 0.268004 0.207953 0.062 Uiso 1 1 calc R U . . .
C3 C 0.6557(4) 0.2064(3) 0.0754(3) 0.0555(10) Uani 1 1 d . . . . .
H3 H 0.712114 0.149141 0.079129 0.067 Uiso 1 1 calc R U . . .
C4 C 0.5837(3) 0.2194(3) -0.0059(3) 0.0498(9) Uani 1 1 d . . . . .
C5 C 0.5011(4) 0.3008(3) -0.0111(3) 0.0627(11) Uani 1 1 d . . . . .
H5 H 0.451401 0.309101 -0.067205 0.075 Uiso 1 1 calc R U . . .
C6 C 0.4897(4) 0.3707(3) 0.0650(3) 0.0599(11) Uani 1 1 d . . . . .
H6 H 0.430933 0.426239 0.061724 0.072 Uiso 1 1 calc R U . . .
N7 N 0.5550(3) 0.4344(2) 0.22403(19) 0.0441(7) Uani 1 1 d . . . . .
C8 C 0.6375(3) 0.5153(3) 0.2424(3) 0.0494(8) Uani 1 1 d . . . . .
C9 C 0.7440(4) 0.5245(3) 0.1733(3) 0.0635(12) Uani 1 1 d . . . . .
H9A H 0.712686 0.535548 0.107465 0.095 Uiso 1 1 calc R U . . .
H9B H 0.792814 0.459359 0.175308 0.095 Uiso 1 1 calc R U . . .
H9C H 0.795783 0.584563 0.192075 0.095 Uiso 1 1 calc R U . . .
O10 O 0.6225(3) 0.5754(2) 0.3098(2) 0.0598(8) Uani 1 1 d . . . . .
C11 C 0.5950(4) 0.1463(4) -0.0902(3) 0.0715(12) Uani 1 1 d D . . . .
F1 F 0.4965(6) 0.0987(8) -0.1148(6) 0.121(3) Uani 0.7 1 d D . P A 1
F2 F 0.6797(9) 0.0731(8) -0.0765(9) 0.118(4) Uani 0.7 1 d D . P A 1
F3 F 0.6322(9) 0.1982(7) -0.1696(5) 0.127(3) Uani 0.7 1 d D . P A 1
F1A F 0.5198(18) 0.0615(13) -0.0725(12) 0.113(6) Uani 0.3 1 d D . P A 2
F2A F 0.7013(16) 0.105(2) -0.105(2) 0.147(12) Uani 0.3 1 d D . P A 2
F3A F 0.551(3) 0.1796(16) -0.1706(11) 0.147(9) Uani 0.3 1 d D . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.381(5) . ?
C1 C2 1.382(5) . ?
C1 N7 1.433(4) . ?
C2 C3 1.383(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.367(5) . ?
C4 C11 1.492(6) . ?
C5 C6 1.378(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N7 C8 1.383(4) . ?
N7 N7 1.393(5) 3_655 ?
C8 O10 1.211(4) . ?
C8 C9 1.503(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 F1 1.272(7) . ?
C11 F3A 1.279(12) . ?
C11 F2A 1.284(15) . ?
C11 F2 1.317(8) . ?
C11 F3 1.340(7) . ?
C11 F1A 1.369(14) . ?

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
C6 C1 C2 119.7(3) . . ?
C6 C1 N7 120.5(3) . . ?
C2 C1 N7 119.8(3) . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 C11 118.7(4) . . ?
C3 C4 C11 121.0(3) . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 N7 N7 117.4(2) . 3_655 ?
C8 N7 C1 125.5(3) . . ?
N7 N7 C1 116.3(3) 3_655 . ?
O10 C8 N7 121.2(3) . . ?
O10 C8 C9 122.8(3) . . ?
N7 C8 C9 116.0(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F3A C11 F2A 109.6(16) . . ?
F1 C11 F2 107.0(8) . . ?
F1 C11 F3 105.4(6) . . ?
F2 C11 F3 104.6(8) . . ?
F3A C11 F1A 100.9(13) . . ?
F2A C11 F1A 104.0(16) . . ?
F1 C11 C4 115.6(5) . . ?
F3A C11 C4 116.2(9) . . ?
F2A C11 C4 116.8(13) . . ?
F2 C11 C4 112.3(6) . . ?
F3 C11 C4 111.0(5) . . ?
F1A C11 C4 107.3(8) . . ?

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
C6 C1 C2 C3 1.7(6) . . . . ?
N7 C1 C2 C3 -178.7(4) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C2 C3 C4 C11 178.4(4) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C11 C4 C5 C6 -179.0(4) . . . . ?
C4 C5 C6 C1 1.3(7) . . . . ?
C2 C1 C6 C5 -2.4(6) . . . . ?
N7 C1 C6 C5 178.1(4) . . . . ?
C6 C1 N7 C8 -103.0(4) . . . . ?
C2 C1 N7 C8 77.5(4) . . . . ?
C6 C1 N7 N7 66.6(4) . . . 3_655 ?
C2 C1 N7 N7 -112.9(4) . . . 3_655 ?
N7 N7 C8 O10 9.7(5) 3_655 . . . ?
C1 N7 C8 O10 179.3(3) . . . . ?
N7 N7 C8 C9 -169.3(3) 3_655 . . . ?
C1 N7 C8 C9 0.2(5) . . . . ?
C5 C4 C11 F1 -58.2(8) . . . . ?
C3 C4 C11 F1 122.5(7) . . . . ?
C5 C4 C11 F3A 17.5(17) . . . . ?
C3 C4 C11 F3A -161.8(16) . . . . ?
C5 C4 C11 F2A 149.4(17) . . . . ?
C3 C4 C11 F2A -29.9(18) . . . . ?
C5 C4 C11 F2 178.6(7) . . . . ?
C3 C4 C11 F2 -0.8(9) . . . . ?
C5 C4 C11 F3 61.8(7) . . . . ?
C3 C4 C11 F3 -117.5(6) . . . . ?
C5 C4 C11 F1A -94.4(10) . . . . ?
C3 C4 C11 F1A 86.2(10) . . . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.039

