# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_CB-CF3-Boc
_database_code_depnum_ccdc_archive 'CCDC 2049521'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2020-12-10 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT910_CB-CF3-Boc          
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 18 Note  
RESPONSE: Indeed the beamstop had been fixed too close to the sample
shading a bunch of low resolution data below theta_min 4 degrees. 
Despite a phi-scan at larger crystal-to-detector distance
the data scaling did not allow us to retrieve these missing low resolution
data.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
'di-tert-butyl 1-(trifluoromethyl)hydrazine-1,2-dicarboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H19 F3 N2 O4'
_chemical_formula_sum            'C11 H19 F3 N2 O4'
_chemical_formula_weight         300.28

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.7754(3)
_cell_length_b                   16.4149(5)
_cell_length_c                   9.7376(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.260(3)
_cell_angle_gamma                90
_cell_volume                     1526.88(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7056
_cell_measurement_theta_min      4.1590
_cell_measurement_theta_max      28.8830

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.83642
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku microsource mm003'
_diffrn_radiation_monochromator  'Rigaku MaxFlux double bounce layer optic'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'HPAD Dectris PILATUS3R 200K-A'
_diffrn_measurement_device       
;
 κ-geometry diffractometer
;
_diffrn_measurement_device_type  
;
Rigaku XtaLabPro AFC12 (Right) goniometer
;
_diffrn_reflns_number            15733
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.535
_diffrn_reflns_theta_max         26.731
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3226
_reflns_number_gt                2757
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 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)+(0.0405P)²+0.4357P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3213
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.50668(13) 0.37238(7) 0.67677(13) 0.0309(3) Uani 1 1 d . . . . .
F1 F 0.71123(9) 0.24811(6) 0.79046(9) 0.0558(3) Uani 1 1 d . . . . .
N1 N 0.53028(10) 0.29645(6) 0.61968(11) 0.0298(2) Uani 1 1 d . . . . .
O1 O 0.59972(10) 0.41116(6) 0.74515(12) 0.0493(3) Uani 1 1 d . . . . .
C2 C 0.31848(15) 0.46763(8) 0.68949(14) 0.0387(3) Uani 1 1 d . . . . .
F2 F 0.66892(10) 0.19168(6) 0.58963(11) 0.0581(3) Uani 1 1 d . . . . .
N2 N 0.42046(11) 0.24561(6) 0.56209(10) 0.0286(2) Uani 1 1 d . . . . .
H2N H 0.3874(16) 0.2527(9) 0.4768(18) 0.039(4) Uiso 1 1 d . . . . .
O2 O 0.37197(9) 0.39081(5) 0.63898(9) 0.0344(2) Uani 1 1 d . . . . .
C3 C 0.16306(19) 0.46017(12) 0.6303(2) 0.0659(5) Uani 1 1 d . . . . .
H3A H 0.146341 0.453757 0.528061 0.099 Uiso 1 1 calc R U . . .
H3B H 0.115567 0.509366 0.653070 0.099 Uiso 1 1 calc R U . . .
H3C H 0.126482 0.412551 0.671493 0.099 Uiso 1 1 calc R U . . .
F3 F 0.75946(9) 0.31039(6) 0.61470(13) 0.0652(3) Uani 1 1 d . . . . .
O3 O 0.37262(9) 0.21650(6) 0.77476(8) 0.0357(2) Uani 1 1 d . . . . .
C10 C 0.06062(16) 0.20175(11) 0.73223(19) 0.0546(4) Uani 1 1 d . . . . .
H10A H 0.134033 0.211978 0.816039 0.082 Uiso 1 1 calc R U . . .
H10B H -0.020513 0.176904 0.760097 0.082 Uiso 1 1 calc R U . . .
H10C H 0.032610 0.253357 0.683762 0.082 Uiso 1 1 calc R U . . .
C11 C 0.66671(14) 0.26220(8) 0.65422(15) 0.0377(3) Uani 1 1 d . . . . .
C4 C 0.3487(2) 0.46821(12) 0.84758(17) 0.0639(5) Uani 1 1 d . . . . .
H4A H 0.313132 0.417935 0.881558 0.096 Uiso 1 1 calc R U . . .
H4B H 0.302662 0.515236 0.880261 0.096 Uiso 1 1 calc R U . . .
H4C H 0.449999 0.471856 0.883890 0.096 Uiso 1 1 calc R U . . .
O4 O 0.22046(9) 0.18699(5) 0.56949(9) 0.0319(2) Uani 1 1 d . . . . .
C5 C 0.3793(2) 0.53889(10) 0.6256(2) 0.0667(5) Uani 1 1 d . . . . .
H5A H 0.479719 0.542854 0.666451 0.100 Uiso 1 1 calc R U . . .
H5B H 0.332607 0.589126 0.645008 0.100 Uiso 1 1 calc R U . . .
H5C H 0.365129 0.531102 0.523783 0.100 Uiso 1 1 calc R U . . .
C6 C 0.33834(12) 0.21619(7) 0.64792(11) 0.0264(2) Uani 1 1 d . . . . .
C7 C 0.11596(13) 0.14448(8) 0.63436(14) 0.0341(3) Uani 1 1 d . . . . .
C8 C 0.18147(16) 0.06824(9) 0.70731(17) 0.0482(4) Uani 1 1 d . . . . .
H8A H 0.225752 0.036955 0.642858 0.072 Uiso 1 1 calc R U . . .
H8B H 0.108893 0.035002 0.735663 0.072 Uiso 1 1 calc R U . . .
H8C H 0.252205 0.083364 0.790679 0.072 Uiso 1 1 calc R U . . .
C9 C 0.00237(16) 0.12363(10) 0.50725(17) 0.0498(4) Uani 1 1 d . . . . .
H9A H -0.034543 0.173885 0.458890 0.075 Uiso 1 1 calc R U . . .
H9B H -0.073393 0.094353 0.537685 0.075 Uiso 1 1 calc R U . . .
H9C H 0.041608 0.089161 0.443012 0.075 Uiso 1 1 calc R U . . .


_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 O1 1.1911(15) . ?
C1 O2 1.3248(15) . ?
C1 N1 1.4036(16) . ?
F1 C11 1.3258(16) . ?
N1 N2 1.3813(14) . ?
N1 C11 1.4203(16) . ?
C2 O2 1.4882(15) . ?
C2 C4 1.505(2) . ?
C2 C5 1.505(2) . ?
C2 C3 1.511(2) . ?
F2 C11 1.3197(17) . ?
N2 C6 1.3641(16) . ?
N2 H2N 0.833(16) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
F3 C11 1.3207(16) . ?
O3 C6 1.2092(14) . ?
C10 C7 1.5178(19) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
O4 C6 1.3294(14) . ?
O4 C7 1.4844(15) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 C8 1.5125(19) . ?
C7 C9 1.5161(19) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
O1 C1 O2 128.99(12) . . ?
O1 C1 N1 121.72(12) . . ?
O2 C1 N1 109.27(10) . . ?
N2 N1 C1 121.22(10) . . ?
N2 N1 C11 117.82(10) . . ?
C1 N1 C11 118.87(10) . . ?
O2 C2 C4 109.70(11) . . ?
O2 C2 C5 108.94(11) . . ?
C4 C2 C5 114.13(15) . . ?
O2 C2 C3 101.58(12) . . ?
C4 C2 C3 110.71(14) . . ?
C5 C2 C3 111.02(15) . . ?
C6 N2 N1 118.23(9) . . ?
C6 N2 H2N 120.4(11) . . ?
N1 N2 H2N 115.1(11) . . ?
C1 O2 C2 120.00(10) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F2 C11 F3 107.75(12) . . ?
F2 C11 F1 106.79(11) . . ?
F3 C11 F1 107.23(12) . . ?
F2 C11 N1 110.12(11) . . ?
F3 C11 N1 111.22(10) . . ?
F1 C11 N1 113.46(11) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 O4 C7 121.06(9) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 O4 127.36(11) . . ?
O3 C6 N2 123.56(11) . . ?
O4 C6 N2 109.07(9) . . ?
O4 C7 C8 109.14(10) . . ?
O4 C7 C9 102.10(10) . . ?
C8 C7 C9 111.12(12) . . ?
O4 C7 C10 110.20(11) . . ?
C8 C7 C10 112.92(13) . . ?
C9 C7 C10 110.83(12) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_TC138
_database_code_depnum_ccdc_archive 'CCDC 2049522'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2020-12-10 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
'(S)-1-oxo-1-(2-(trifluoromethyl)hydrazineyl)propan-2-aminium chloride'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H9 F3 N3 O 1+, Cl 1-'
_chemical_formula_sum            'C4 H9 Cl F3 N3 O'
_chemical_formula_weight         207.59

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'
Cl Cl 0.1484 0.1585 '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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   4.9770(3)
_cell_length_b                   7.7308(6)
_cell_length_c                   11.6315(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.771(7)
_cell_angle_gamma                90
_cell_volume                     447.50(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1440
_cell_measurement_theta_min      4.3960
_cell_measurement_theta_max      27.3340

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.436
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.36039
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku microsource mm003'
_diffrn_radiation_monochromator  'Rigaku MaxFlux double bounce layer optic'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'HPAD Dectris PILATUS3R 200K-A'
_diffrn_measurement_device       
;
 κ-geometry diffractometer
;
_diffrn_measurement_device_type  
;
Rigaku XtaLabPro AFC12 (Right) goniometer
;
_diffrn_reflns_number            5704
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.095
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             1759
_reflns_number_gt                1469
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_max     0.901
_reflns_Friedel_fraction_full    0.947

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_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)+(0.0528P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 558 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1753
_refine_ls_number_parameters     117
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.024
_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
O1 O 1.1500(4) 0.5606(5) 0.1073(2) 0.0474(6) Uani 1 1 d . . . . .
Cl1 Cl 0.30648(15) 0.04648(13) 0.13294(8) 0.0443(3) Uani 1 1 d . . . . .
N1 N 0.9019(7) 0.7302(4) 0.2191(3) 0.0465(8) Uani 1 1 d . . . . .
H1N H 0.998(10) 0.817(7) 0.205(4) 0.056 Uiso 1 1 d . U . . .
C1 C 0.7534(7) 0.4325(5) 0.1851(3) 0.0383(9) Uani 1 1 d . . . . .
H1 H 0.569536 0.477877 0.182955 0.046 Uiso 1 1 calc R U . . .
C2 C 0.9516(6) 0.5790(5) 0.1662(3) 0.0367(9) Uani 1 1 d . . . . .
N2 N 0.6661(7) 0.7580(5) 0.2796(3) 0.0480(9) Uani 1 1 d . . . . .
H2N H 0.565(10) 0.828(7) 0.244(4) 0.058 Uiso 1 1 d . U . . .
C3 C 0.7079(11) 0.8142(7) 0.3915(5) 0.0642(13) Uani 1 1 d . . . . .
F1 F 0.8289(9) 0.6962(5) 0.4552(3) 0.1003(12) Uani 1 1 d . . . . .
F2 F 0.4816(8) 0.8569(7) 0.4364(3) 0.1265(18) Uani 1 1 d . . . . .
F3 F 0.8698(8) 0.9537(5) 0.4019(3) 0.0985(12) Uani 1 1 d . . . . .
N3 N 0.7902(6) 0.3081(4) 0.0894(3) 0.0415(8) Uani 1 1 d . . . . .
H3N1 H 0.774716 0.363540 0.022571 0.050 Uiso 1 1 calc R U . . .
H3N2 H 0.665404 0.225932 0.093077 0.050 Uiso 1 1 calc R U . . .
H3N3 H 0.952506 0.260361 0.095174 0.050 Uiso 1 1 calc R U . . .
C4 C 0.8037(12) 0.3405(6) 0.2967(4) 0.0634(14) Uani 1 1 d . . . . .
H4A H 0.684333 0.243473 0.302268 0.095 Uiso 1 1 calc R U . . .
H4B H 0.772745 0.418507 0.359350 0.095 Uiso 1 1 calc R U . . .
H4C H 0.986375 0.300727 0.299893 0.095 Uiso 1 1 calc R U . . .


_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
O1 C2 1.218(4) . ?
N1 C2 1.346(5) . ?
N1 N2 1.393(5) . ?
N1 H1N 0.84(6) . ?
C1 N3 1.484(5) . ?
C1 C4 1.498(6) . ?
C1 C2 1.520(5) . ?
C1 H1 0.9800 . ?
N2 C3 1.385(6) . ?
N2 H2N 0.84(5) . ?
C3 F2 1.291(6) . ?
C3 F1 1.316(6) . ?
C3 F3 1.351(6) . ?
N3 H3N1 0.8900 . ?
N3 H3N2 0.8900 . ?
N3 H3N3 0.8900 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

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
C2 N1 N2 121.8(3) . . ?
C2 N1 H1N 120(3) . . ?
N2 N1 H1N 118(3) . . ?
N3 C1 C4 108.8(3) . . ?
N3 C1 C2 106.7(3) . . ?
C4 C1 C2 112.2(3) . . ?
N3 C1 H1 109.7 . . ?
C4 C1 H1 109.7 . . ?
C2 C1 H1 109.7 . . ?
O1 C2 N1 120.9(3) . . ?
O1 C2 C1 121.8(3) . . ?
N1 C2 C1 117.2(3) . . ?
C3 N2 N1 113.9(4) . . ?
C3 N2 H2N 110(3) . . ?
N1 N2 H2N 111(3) . . ?
F2 C3 F1 110.1(5) . . ?
F2 C3 F3 106.4(5) . . ?
F1 C3 F3 103.6(4) . . ?
F2 C3 N2 109.8(4) . . ?
F1 C3 N2 111.9(4) . . ?
F3 C3 N2 114.6(5) . . ?
C1 N3 H3N1 109.5 . . ?
C1 N3 H3N2 109.5 . . ?
H3N1 N3 H3N2 109.5 . . ?
C1 N3 H3N3 109.5 . . ?
H3N1 N3 H3N3 109.5 . . ?
H3N2 N3 H3N3 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C2 O1 175.0(3) . . . . ?
N2 N1 C2 C1 -6.1(5) . . . . ?
N3 C1 C2 O1 -21.3(4) . . . . ?
C4 C1 C2 O1 97.7(4) . . . . ?
N3 C1 C2 N1 159.9(3) . . . . ?
C4 C1 C2 N1 -81.1(4) . . . . ?
C2 N1 N2 C3 126.5(4) . . . . ?
N1 N2 C3 F2 172.2(4) . . . . ?
N1 N2 C3 F1 -65.1(6) . . . . ?
N1 N2 C3 F3 52.5(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N Cl1 0.84(6) 2.50(6) 3.331(4) 170(4) 1_665 yes
C1 H1 O1 0.98 2.34 3.278(4) 159.1 1_455 yes
N2 H2N Cl1 0.84(5) 2.48(6) 3.317(4) 175(4) 1_565 yes
N3 H3N1 Cl1 0.89 2.33 3.207(4) 169.6 2_655 yes
N3 H3N2 Cl1 0.89 2.31 3.190(3) 168.2 . yes
N3 H3N3 Cl1 0.89 2.45 3.304(3) 160.5 1_655 yes
C4 H4B F1 0.96 2.43 3.311(6) 152.0 . yes

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_TC139
_database_code_depnum_ccdc_archive 'CCDC 2049523'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2020-12-10 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_TC139               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Crystallization was poor and the crystal that was measured
on a powerful rotating anode working at the copper wavelength 
did not diffract intensively beyond atomic resolution and peaks 
looked smeared too. 
;
_vrf_PLAT089_TC139               
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       4.45 Note  
RESPONSE: compromise was done with the data resolution  cut-off
to retain useful information for structure solution and refinement.
;
_vrf_PLAT340_TC139               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02504 Ang.  
RESPONSE: consequence of weak data 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
'benzyl (S)-(1-oxo-1-(1-(trifluoromethyl)hydrazineyl)propan-2-yl)carbamate'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 F3 N3 O3, 0.33(H2 O)'
_chemical_formula_sum            'C12 H14.67 F3 N3 O3.33'
_chemical_formula_weight         311.27

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'
F F 0.0727 0.0534 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   5.128(3)
_cell_length_b                   27.296(13)
_cell_length_c                   15.794(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.556(12)
_cell_angle_gamma                90
_cell_volume                     2200.3(19)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3437
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      68.5

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.122
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_process_details   'Reqab-Rigaku (1998)'

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  'OSMIC CMF optics'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Rigaku Rapid2 curved large area IP'
_diffrn_measurement_device       
;
Crystal Goniometer chi-partial
;
_diffrn_measurement_device_type  
;
Rigaku MM007HF Spider
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            18721
_diffrn_reflns_av_unetI/netI     0.1336
_diffrn_reflns_av_R_equivalents  0.1440
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.811
_diffrn_reflns_theta_max         53.421
_diffrn_reflns_theta_full        53.421
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             5160
_reflns_number_gt                2471
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.974

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1227P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5157
_refine_ls_number_parameters     602
_refine_ls_number_restraints     196
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.0891
_refine_ls_wR_factor_ref         0.2454
_refine_ls_wR_factor_gt          0.2072
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_restrained_S_all      0.915
_refine_ls_shift/su_max          0.004
_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
C1A C 0.865(6) 0.5269(8) 1.0900(15) 0.141(6) Uani 1 1 d . . . . .
N2A N 0.952(2) 0.4767(5) 1.1051(7) 0.114(4) Uani 1 1 d . . . . .
N3A N 0.955(3) 0.4546(5) 1.1861(8) 0.115(4) Uani 1 1 d D . . . .
H3A1 H 1.084(15) 0.470(5) 1.215(7) 0.138 Uiso 1 1 d D U . . .
H3A2 H 0.796(9) 0.460(5) 1.201(9) 0.138 Uiso 1 1 d D U . . .
C4A C 1.049(3) 0.4502(5) 1.0387(11) 0.102(4) Uani 1 1 d . . . . .
O5A O 1.082(2) 0.4700(4) 0.9722(6) 0.132(4) Uani 1 1 d . . . . .
C6A C 1.131(3) 0.3972(5) 1.0620(7) 0.092(4) Uani 1 1 d . . . . .
H6A H 0.997201 0.381972 1.093523 0.110 Uiso 1 1 calc R U . . .
C7A C 1.393(3) 0.3948(6) 1.1147(10) 0.115(4) Uani 1 1 d . . . . .
H7AA H 1.437937 0.361210 1.126526 0.173 Uiso 1 1 calc R U . . .
H7AB H 1.381772 0.412030 1.167286 0.173 Uiso 1 1 calc R U . . .
H7AC H 1.524482 0.409689 1.083970 0.173 Uiso 1 1 calc R U . . .
N8A N 1.147(3) 0.3708(4) 0.9814(8) 0.103(3) Uani 1 1 d D . . . .
H8NA H 1.308(10) 0.365(5) 0.969(9) 0.124 Uiso 1 1 d D U . . .
C9A C 0.942(4) 0.3574(5) 0.9348(9) 0.097(4) Uani 1 1 d . . . . .
O10A O 0.714(2) 0.3648(4) 0.9509(6) 0.119(3) Uani 1 1 d . . . . .
O11A O 0.9982(19) 0.3330(3) 0.8635(6) 0.106(3) Uani 1 1 d . . . . .
C12A C 0.775(4) 0.3156(5) 0.8055(10) 0.129(5) Uani 1 1 d . U . . .
H12A H 0.616550 0.332305 0.818376 0.155 Uiso 1 1 calc R U . . .
H12B H 0.805094 0.323281 0.747311 0.155 Uiso 1 1 calc R U . . .
C13A C 0.740(3) 0.2626(5) 0.8141(9) 0.106(4) Uani 1 1 d . U . . .
C14A C 0.553(4) 0.2448(7) 0.8591(11) 0.146(6) Uani 1 1 d . U . . .
H14A H 0.445300 0.266811 0.884045 0.175 Uiso 1 1 calc R U . . .
C15A C 0.514(4) 0.1952(8) 0.8702(13) 0.160(7) Uani 1 1 d . U . . .
H15A H 0.387957 0.184195 0.904303 0.192 Uiso 1 1 calc R U . . .
C16A C 0.658(5) 0.1637(8) 0.8314(15) 0.161(7) Uani 1 1 d . U . . .
H16A H 0.622554 0.130445 0.835291 0.194 Uiso 1 1 calc R U . . .
C17A C 0.847(4) 0.1778(8) 0.7881(19) 0.181(8) Uani 1 1 d . U . . .
H17A H 0.956960 0.154875 0.766399 0.217 Uiso 1 1 calc R U . . .
C18A C 0.885(4) 0.2288(7) 0.7740(14) 0.160(6) Uani 1 1 d . U . . .
H18A H 1.006378 0.239121 0.737903 0.192 Uiso 1 1 calc R U . . .
F19A F 0.774(3) 0.5433(4) 1.1568(8) 0.197(5) Uani 1 1 d . . . . .
F20A F 0.703(3) 0.5321(4) 1.0237(9) 0.194(5) Uani 1 1 d . . . . .
F21A F 1.075(3) 0.5540(4) 1.0806(8) 0.186(5) Uani 1 1 d . . . . .
C1B C 0.187(4) 0.4448(7) 0.7448(13) 0.125(5) Uani 1 1 d . . . . .
N2B N 0.249(3) 0.4920(5) 0.7727(10) 0.116(4) Uani 1 1 d . . . . .
N3B N 0.456(4) 0.4998(6) 0.8371(12) 0.143(5) Uani 1 1 d D . . . .
H3B1 H 0.42(3) 0.497(7) 0.890(4) 0.172 Uiso 1 1 d D U . . .
H3B2 H 0.620(13) 0.493(7) 0.828(9) 0.172 Uiso 1 1 d D U . . .
C4B C 0.116(5) 0.5336(9) 0.7449(17) 0.144(7) Uani 1 1 d . . . . .
O5B O -0.068(4) 0.5263(5) 0.6890(11) 0.173(5) Uani 1 1 d . . . . .
C6B C 0.197(4) 0.5824(6) 0.7803(13) 0.142(6) Uani 1 1 d . . . . .
H6B H 0.388822 0.584484 0.789780 0.170 Uiso 1 1 calc R U . . .
C7B C 0.077(5) 0.5894(7) 0.8624(13) 0.181(9) Uani 1 1 d . . . . .
H7BA H 0.094118 0.623032 0.879674 0.272 Uiso 1 1 calc R U . . .
H7BB H 0.165252 0.568854 0.905496 0.272 Uiso 1 1 calc R U . . .
H7BC H -0.105089 0.580700 0.854557 0.272 Uiso 1 1 calc R U . . .
N8B N 0.093(3) 0.6210(5) 0.7195(12) 0.151(5) Uani 1 1 d D . . . .
H8NB H -0.073(13) 0.624(8) 0.700(12) 0.181 Uiso 1 1 d D U . . .
C9B C 0.237(5) 0.6392(6) 0.6606(10) 0.127(6) Uani 1 1 d . . . . .
O10B O 0.462(3) 0.6275(5) 0.6552(8) 0.163(5) Uani 1 1 d D . . . .
O11B O 0.103(2) 0.6738(4) 0.6143(8) 0.135(4) Uani 1 1 d . . . . .
C12B C 0.248(4) 0.6957(6) 0.5486(10) 0.140(5) Uani 1 1 d . U . . .
H12C H 0.312703 0.670440 0.512888 0.168 Uiso 1 1 calc R U . . .
H12D H 0.395149 0.714497 0.574203 0.168 Uiso 1 1 calc R U . . .
C13B C 0.062(4) 0.7277(7) 0.4983(11) 0.127(5) Uani 1 1 d . U . . .
C14B C -0.151(5) 0.7084(9) 0.4457(11) 0.150(6) Uani 1 1 d . U . . .
H14B H -0.174001 0.674615 0.444652 0.180 Uiso 1 1 calc R U . . .
C15B C -0.324(5) 0.7359(10) 0.3972(13) 0.166(7) Uani 1 1 d . U . . .
H15B H -0.462372 0.721096 0.364236 0.200 Uiso 1 1 calc R U . . .
C16B C -0.297(5) 0.7846(9) 0.3966(13) 0.164(6) Uani 1 1 d . U . . .
H16B H -0.413019 0.803476 0.361501 0.197 Uiso 1 1 calc R U . . .
C17B C -0.098(4) 0.8072(8) 0.4472(10) 0.144(6) Uani 1 1 d . U . . .
H17B H -0.083239 0.841159 0.448222 0.173 Uiso 1 1 calc R U . . .
C18B C 0.083(4) 0.7780(7) 0.4972(9) 0.135(5) Uani 1 1 d . U . . .
H18B H 0.219387 0.793043 0.530528 0.162 Uiso 1 1 calc R U . . .
F19B F 0.189(3) 0.4398(5) 0.6604(7) 0.183(4) Uani 1 1 d . . . . .
F20B F 0.339(3) 0.4126(4) 0.7797(7) 0.166(4) Uani 1 1 d . . . . .
F21B F -0.056(2) 0.4321(4) 0.7571(7) 0.158(4) Uani 1 1 d . . . . .
C1C C 0.378(6) 0.5643(8) 0.3590(14) 0.142(6) Uani 1 1 d . . . . .
N2C N 0.364(4) 0.5203(5) 0.4103(9) 0.148(5) Uani 1 1 d . . . . .
N3C N 0.268(4) 0.5244(5) 0.4931(10) 0.160(6) Uani 1 1 d D . . . .
H3C1 H 0.23(4) 0.504(4) 0.532(7) 0.192 Uiso 1 1 d D U . . .
H3C2 H 0.32(4) 0.554(3) 0.513(9) 0.192 Uiso 1 1 d D U . . .
C4C C 0.434(3) 0.4759(6) 0.3814(12) 0.116(5) Uani 1 1 d . . . . .
O5C O 0.495(2) 0.4726(3) 0.3096(6) 0.125(3) Uani 1 1 d . . . . .
C6C C 0.426(3) 0.4331(5) 0.4405(8) 0.104(4) Uani 1 1 d . . . . .
H6C H 0.260917 0.434595 0.466888 0.125 Uiso 1 1 calc R U . . .
C7C C 0.650(3) 0.4328(8) 0.5115(11) 0.138(5) Uani 1 1 d . . . . .
H7CA H 0.637784 0.461300 0.546610 0.207 Uiso 1 1 calc R U . . .
H7CB H 0.814532 0.433186 0.487135 0.207 Uiso 1 1 calc R U . . .
H7CC H 0.639179 0.403873 0.545458 0.207 Uiso 1 1 calc R U . . .
N8C N 0.424(3) 0.3874(4) 0.3884(8) 0.111(4) Uani 1 1 d D . . . .
H8NC H 0.574(15) 0.378(6) 0.370(9) 0.134 Uiso 1 1 d D U . . .
C9C C 0.197(5) 0.3676(6) 0.3548(9) 0.104(4) Uani 1 1 d . . . . .
O10C O -0.020(2) 0.3813(4) 0.3672(6) 0.122(3) Uani 1 1 d . . . . .
O11C O 0.254(2) 0.3296(4) 0.3065(6) 0.123(3) Uani 1 1 d . U . . .
C12C C 0.018(4) 0.3054(8) 0.2627(13) 0.158(6) Uani 1 1 d . U . . .
H12E H -0.078853 0.288855 0.304098 0.190 Uiso 1 1 calc R U . . .
H12F H -0.095590 0.329803 0.233747 0.190 Uiso 1 1 calc R U . . .
C13C C 0.101(3) 0.2699(4) 0.2011(7) 0.124(5) Uani 1 1 d G U . . .
C14C C -0.025(3) 0.2691(5) 0.1192(8) 0.169(7) Uani 1 1 d G U . . .
H14C H -0.162723 0.290516 0.104235 0.203 Uiso 1 1 calc R U . . .
C15C C 0.054(3) 0.2361(6) 0.0597(6) 0.183(8) Uani 1 1 d G U . . .
H15C H -0.030316 0.235535 0.004872 0.219 Uiso 1 1 calc R U . . .
C16C C 0.260(4) 0.2041(5) 0.0821(9) 0.194(9) Uani 1 1 d G U . . .
H16C H 0.313093 0.182012 0.042227 0.233 Uiso 1 1 calc R U . . .
C17C C 0.386(3) 0.2049(5) 0.1640(10) 0.209(9) Uani 1 1 d G U . . .
H17C H 0.524097 0.183469 0.178945 0.251 Uiso 1 1 calc R U . . .
C18C C 0.307(3) 0.2379(5) 0.2235(7) 0.171(7) Uani 1 1 d G U . . .
H18C H 0.391694 0.238450 0.278309 0.205 Uiso 1 1 calc R U . . .
F19C F 0.306(4) 0.6009(5) 0.3971(10) 0.246(8) Uani 1 1 d . . . . .
F20C F 0.232(4) 0.5615(5) 0.2866(10) 0.239(8) Uani 1 1 d . . . . .
F21C F 0.628(4) 0.5699(5) 0.3410(9) 0.205(6) Uani 1 1 d . . . . .
O1W O 0.755(5) 0.5757(7) 0.5477(10) 0.220(7) Uani 1 1 d D . . . .
H1W1 H 0.69(5) 0.599(2) 0.573(15) 0.330 Uiso 1 1 d D U . . .
H1W2 H 0.87(6) 0.564(12) 0.582(17) 0.330 Uiso 1 1 d D U . . .


_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
C1A F19A 1.275(18) . ?
C1A F20A 1.28(2) . ?
C1A F21A 1.32(2) . ?
C1A N2A 1.45(2) . ?
N2A C4A 1.405(18) . ?
N2A N3A 1.413(17) . ?
C4A O5A 1.207(16) . ?
C4A C6A 1.541(19) . ?
C6A N8A 1.471(17) . ?
C6A C7A 1.509(18) . ?
N8A C9A 1.277(19) . ?
C9A O10A 1.236(18) . ?
C9A O11A 1.363(16) . ?
O11A C12A 1.474(18) . ?
C12A C13A 1.47(2) . ?
C13A C14A 1.34(2) . ?
C13A C18A 1.38(2) . ?
C14A C15A 1.38(3) . ?
C15A C16A 1.32(3) . ?
C16A C17A 1.30(3) . ?
C17A C18A 1.42(3) . ?
C1B F20B 1.264(18) . ?
C1B F21B 1.33(2) . ?
C1B F19B 1.341(19) . ?
C1B N2B 1.39(2) . ?
N2B C4B 1.38(2) . ?
N2B N3B 1.41(2) . ?
C4B O5B 1.25(2) . ?
C4B C6B 1.49(3) . ?
C6B N8B 1.49(2) . ?
C6B C7B 1.50(2) . ?
N8B C9B 1.34(2) . ?
C9B O10B 1.20(2) . ?
C9B O11B 1.34(2) . ?
O11B C12B 1.460(18) . ?
C12B C13B 1.47(2) . ?
C13B C18B 1.38(2) . ?
C13B C14B 1.41(2) . ?
C14B C15B 1.34(3) . ?
C15B C16B 1.34(3) . ?
C16B C17B 1.38(3) . ?
C17B C18B 1.40(2) . ?
C1C F19C 1.24(2) . ?
C1C F20C 1.31(2) . ?
C1C F21C 1.35(3) . ?
C1C N2C 1.45(2) . ?
N2C C4C 1.357(18) . ?
N2C N3C 1.446(18) . ?
C4C O5C 1.209(17) . ?
C4C C6C 1.50(2) . ?
C6C N8C 1.495(18) . ?
C6C C7C 1.53(2) . ?
N8C C9C 1.34(2) . ?
C9C O10C 1.21(2) . ?
C9C O11C 1.336(18) . ?
O11C C12C 1.49(2) . ?
C12C C13C 1.47(2) . ?
C13C C14C 1.3900 . ?
C13C C18C 1.3900 . ?
C14C C15C 1.3900 . ?
C15C C16C 1.3900 . ?
C16C C17C 1.3900 . ?
C17C C18C 1.3900 . ?

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
F19A C1A F20A 112(2) . . ?
F19A C1A F21A 105.2(18) . . ?
F20A C1A F21A 108(2) . . ?
F19A C1A N2A 109.0(17) . . ?
F20A C1A N2A 113.8(17) . . ?
F21A C1A N2A 107.7(19) . . ?
C4A N2A N3A 118.8(13) . . ?
C4A N2A C1A 119.3(13) . . ?
N3A N2A C1A 121.8(12) . . ?
O5A C4A N2A 120.5(13) . . ?
O5A C4A C6A 124.8(13) . . ?
N2A C4A C6A 114.4(13) . . ?
N8A C6A C7A 109.8(11) . . ?
N8A C6A C4A 106.8(11) . . ?
C7A C6A C4A 112.3(12) . . ?
C9A N8A C6A 122.0(12) . . ?
O10A C9A N8A 125.2(14) . . ?
O10A C9A O11A 122.0(17) . . ?
N8A C9A O11A 112.8(16) . . ?
C9A O11A C12A 117.2(14) . . ?
C13A C12A O11A 110.8(12) . . ?
C14A C13A C18A 116.5(16) . . ?
C14A C13A C12A 120.4(15) . . ?
C18A C13A C12A 123.0(16) . . ?
C13A C14A C15A 122.9(17) . . ?
C16A C15A C14A 119(2) . . ?
C17A C16A C15A 122(2) . . ?
C16A C17A C18A 119(2) . . ?
C13A C18A C17A 120(2) . . ?
F20B C1B F21B 107.6(17) . . ?
F20B C1B F19B 107.5(15) . . ?
F21B C1B F19B 102.5(19) . . ?
F20B C1B N2B 113.2(19) . . ?
F21B C1B N2B 112.7(15) . . ?
F19B C1B N2B 112.7(16) . . ?
C4B N2B C1B 125(2) . . ?
C4B N2B N3B 114.8(18) . . ?
C1B N2B N3B 120.1(16) . . ?
O5B C4B N2B 114(2) . . ?
O5B C4B C6B 125(2) . . ?
N2B C4B C6B 120(2) . . ?
C4B C6B N8B 108.7(17) . . ?
C4B C6B C7B 108.4(16) . . ?
N8B C6B C7B 108.3(15) . . ?
C9B N8B C6B 121.3(16) . . ?
O10B C9B N8B 123.2(19) . . ?
O10B C9B O11B 126.2(16) . . ?
N8B C9B O11B 110.4(19) . . ?
C9B O11B C12B 114.0(14) . . ?
O11B C12B C13B 106.4(14) . . ?
C18B C13B C14B 115(2) . . ?
C18B C13B C12B 123.6(19) . . ?
C14B C13B C12B 121.5(19) . . ?
C15B C14B C13B 124(2) . . ?
C16B C15B C14B 120(3) . . ?
C15B C16B C17B 121(3) . . ?
C16B C17B C18B 119(2) . . ?
C13B C18B C17B 122(2) . . ?
F19C C1C F20C 107(2) . . ?
F19C C1C F21C 110(2) . . ?
F20C C1C F21C 107(2) . . ?
F19C C1C N2C 111.2(19) . . ?
F20C C1C N2C 113(2) . . ?
F21C C1C N2C 108.1(18) . . ?
C4C N2C N3C 119.9(14) . . ?
C4C N2C C1C 121.4(14) . . ?
N3C N2C C1C 118.6(14) . . ?
O5C C4C N2C 118.9(15) . . ?
O5C C4C C6C 123.5(13) . . ?
N2C C4C C6C 117.6(14) . . ?
N8C C6C C4C 107.8(11) . . ?
N8C C6C C7C 111.4(13) . . ?
C4C C6C C7C 113.5(14) . . ?
C9C N8C C6C 120.8(14) . . ?
O10C C9C O11C 126.0(18) . . ?
O10C C9C N8C 126.0(15) . . ?
O11C C9C N8C 108.0(18) . . ?
C9C O11C C12C 113.4(14) . . ?
C13C C12C O11C 109.0(14) . . ?
C14C C13C C18C 120.0 . . ?
C14C C13C C12C 119.3(13) . . ?
C18C C13C C12C 120.7(13) . . ?
C15C C14C C13C 120.0 . . ?
C14C C15C C16C 120.0 . . ?
C17C C16C C15C 120.0 . . ?
C16C C17C C18C 120.0 . . ?
C17C C18C C13C 120.0 . . ?

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
F19A C1A N2A C4A 177.0(16) . . . . ?
F20A C1A N2A C4A 51(3) . . . . ?
F21A C1A N2A C4A -69(2) . . . . ?
F19A C1A N2A N3A -6(3) . . . . ?
F20A C1A N2A N3A -132.4(17) . . . . ?
F21A C1A N2A N3A 107.4(16) . . . . ?
N3A N2A C4A O5A -170.3(14) . . . . ?
C1A N2A C4A O5A 6(2) . . . . ?
N3A N2A C4A C6A 4.2(17) . . . . ?
C1A N2A C4A C6A -179.0(16) . . . . ?
O5A C4A C6A N8A -23.3(19) . . . . ?
N2A C4A C6A N8A 162.5(12) . . . . ?
O5A C4A C6A C7A 97.1(17) . . . . ?
N2A C4A C6A C7A -77.2(15) . . . . ?
C7A C6A N8A C9A 163.2(13) . . . . ?
C4A C6A N8A C9A -74.8(15) . . . . ?
C6A N8A C9A O10A 0(2) . . . . ?
C6A N8A C9A O11A -179.3(10) . . . . ?
O10A C9A O11A C12A 0.1(18) . . . . ?
N8A C9A O11A C12A 179.6(11) . . . . ?
C9A O11A C12A C13A -104.4(15) . . . . ?
O11A C12A C13A C14A 101.5(19) . . . . ?
O11A C12A C13A C18A -81.9(19) . . . . ?
C18A C13A C14A C15A 4(3) . . . . ?
C12A C13A C14A C15A -179.2(17) . . . . ?
C13A C14A C15A C16A -3(3) . . . . ?
C14A C15A C16A C17A 5(4) . . . . ?
C15A C16A C17A C18A -7(4) . . . . ?
C14A C13A C18A C17A -6(3) . . . . ?
C12A C13A C18A C17A 178(2) . . . . ?
C16A C17A C18A C13A 7(4) . . . . ?
F20B C1B N2B C4B 179.8(15) . . . . ?
F21B C1B N2B C4B -58(2) . . . . ?
F19B C1B N2B C4B 58(2) . . . . ?
F20B C1B N2B N3B -3(2) . . . . ?
F21B C1B N2B N3B 119.3(17) . . . . ?
F19B C1B N2B N3B -125.3(17) . . . . ?
C1B N2B C4B O5B -2(3) . . . . ?
N3B N2B C4B O5B -179.0(17) . . . . ?
C1B N2B C4B C6B 179.0(16) . . . . ?
N3B N2B C4B C6B 2(2) . . . . ?
O5B C4B C6B N8B -20(3) . . . . ?
N2B C4B C6B N8B 159.5(15) . . . . ?
O5B C4B C6B C7B 98(2) . . . . ?
N2B C4B C6B C7B -83(2) . . . . ?
C4B C6B N8B C9B -94(2) . . . . ?
C7B C6B N8B C9B 148.5(19) . . . . ?
C6B N8B C9B O10B -4(3) . . . . ?
C6B N8B C9B O11B -179.2(16) . . . . ?
O10B C9B O11B C12B 4(3) . . . . ?
N8B C9B O11B C12B 179.7(15) . . . . ?
C9B O11B C12B C13B 173.1(15) . . . . ?
O11B C12B C13B C18B 112.4(17) . . . . ?
O11B C12B C13B C14B -68.4(19) . . . . ?
C18B C13B C14B C15B 0(3) . . . . ?
C12B C13B C14B C15B -178.8(17) . . . . ?
C13B C14B C15B C16B 1(3) . . . . ?
C14B C15B C16B C17B -2(3) . . . . ?
C15B C16B C17B C18B 3(3) . . . . ?
C14B C13B C18B C17B 0(2) . . . . ?
C12B C13B C18B C17B 179.2(14) . . . . ?
C16B C17B C18B C13B -1(2) . . . . ?
F19C C1C N2C C4C -180(2) . . . . ?
F20C C1C N2C C4C 59(3) . . . . ?
F21C C1C N2C C4C -59(3) . . . . ?
F19C C1C N2C N3C 1(3) . . . . ?
F20C C1C N2C N3C -119(2) . . . . ?
F21C C1C N2C N3C 122(2) . . . . ?
N3C N2C C4C O5C 174.6(17) . . . . ?
C1C N2C C4C O5C -4(3) . . . . ?
N3C N2C C4C C6C -4(3) . . . . ?
C1C N2C C4C C6C 176.9(19) . . . . ?
O5C C4C C6C N8C -17(2) . . . . ?
N2C C4C C6C N8C 162.0(15) . . . . ?
O5C C4C C6C C7C 106.9(18) . . . . ?
N2C C4C C6C C7C -74.1(19) . . . . ?
C4C C6C N8C C9C -88.8(15) . . . . ?
C7C C6C N8C C9C 146.0(13) . . . . ?
C6C N8C C9C O10C -6(2) . . . . ?
C6C N8C C9C O11C 175.4(11) . . . . ?
O10C C9C O11C C12C 3(2) . . . . ?
N8C C9C O11C C12C -177.8(13) . . . . ?
C9C O11C C12C C13C 170.6(14) . . . . ?
O11C C12C C13C C14C -133.3(13) . . . . ?
O11C C12C C13C C18C 45.7(19) . . . . ?
C18C C13C C14C C15C 0.0 . . . . ?
C12C C13C C14C C15C 179.0(13) . . . . ?
C13C C14C C15C C16C 0.0 . . . . ?
C14C C15C C16C C17C 0.0 . . . . ?
C15C C16C C17C C18C 0.0 . . . . ?
C16C C17C C18C C13C 0.0 . . . . ?
C14C C13C C18C C17C 0.0 . . . . ?
C12C C13C C18C C17C -179.0(13) . . . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.055

