# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_Cz-BzN
_audit_block_doi                 10.5517/ccdc.csd.cc2f9chm
_database_code_depnum_ccdc_archive 'CCDC 2243330'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-5d72m 2023
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2023-02-20 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
#2469_GuillotICMMO_T100K

_audit_creation_method           SHELXL-2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H8 F4 N2'
_chemical_formula_sum            'C19 H8 F4 N2'
_chemical_melting_point          ?


_exptl_crystal_description       block
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         340.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_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.
;

_cell_length_a                   7.1863(3)
_cell_length_b                   12.9975(5)
_cell_length_c                   15.4834(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1446.21(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    2064
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      29.48
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.130
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8772
_exptl_absorpt_correction_T_max  0.9461
_exptl_absorpt_process_details   'Bruker APEX2'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9978
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.631
_diffrn_reflns_theta_max         30.556
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2209
_reflns_number_gt                1521
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_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)+(0.0558P)²+0.4162P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         2209
_refine_ls_number_parameters     116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_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 0.000000 1.24729(15) 0.250000 0.0248(5) Uani 1 2 d S T P . .
C2 C 0.000000 1.13707(13) 0.250000 0.0186(4) Uani 1 2 d S T P . .
C3 C 0.0738(2) 1.08214(10) 0.31878(10) 0.0186(3) Uani 1 1 d . . . . .
C4 C 0.0786(2) 0.97605(10) 0.31745(9) 0.0165(3) Uani 1 1 d . . . . .
C5 C 0.000000 0.92012(13) 0.250000 0.0147(4) Uani 1 2 d S T P . .
C6 C 0.06040(19) 0.74931(10) 0.18163(9) 0.0153(3) Uani 1 1 d . . . . .
C7 C 0.1384(2) 0.77615(10) 0.10275(9) 0.0187(3) Uani 1 1 d . . . . .
H7 H 0.157832 0.846141 0.087550 0.022 Uiso 1 1 calc R U . . .
C8 C 0.1868(2) 0.69716(10) 0.04697(10) 0.0207(3) Uani 1 1 d . . . . .
H8 H 0.240229 0.713344 -0.007479 0.025 Uiso 1 1 calc R U . . .
C9 C 0.1584(2) 0.59388(11) 0.06935(10) 0.0205(3) Uani 1 1 d . . . . .
H9 H 0.189984 0.541292 0.029348 0.025 Uiso 1 1 calc R U . . .
C10 C 0.0849(2) 0.56745(10) 0.14890(10) 0.0177(3) Uani 1 1 d . . . . .
H10 H 0.067168 0.497289 0.164017 0.021 Uiso 1 1 calc R U . . .
C11 C 0.03720(18) 0.64578(9) 0.20662(9) 0.0150(3) Uani 1 1 d . . . . .
N1 N 0.000000 0.81261(11) 0.250000 0.0158(3) Uani 1 2 d S T P . .
N2 N 0.000000 1.33570(14) 0.250000 0.0361(5) Uani 1 2 d S T P . .
F1 F 0.16207(12) 0.92692(6) 0.38269(5) 0.0222(2) Uani 1 1 d . . . . .
F2 F 0.14549(12) 1.13211(6) 0.38629(6) 0.0256(2) Uani 1 1 d . . . . .


_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 N2 1.149(3) . ?
C1 C2 1.433(3) . ?
C2 C3 1.3875(17) . ?
C2 C3 1.3875(17) 3 ?
C3 F2 1.3341(16) . ?
C3 C4 1.3795(18) . ?
C4 F1 1.3371(15) . ?
C4 C5 1.3923(17) . ?
C5 N1 1.397(2) . ?
C6 C7 1.388(2) . ?
C6 N1 1.4092(16) . ?
C6 C11 1.4101(17) . ?
C7 C8 1.386(2) . ?
C8 C9 1.4014(19) . ?
C9 C10 1.383(2) . ?
C10 C11 1.3974(18) . ?
C11 C11 1.446(3) 3 ?

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 C1 C2 180.0 . . ?
C3 C2 C3 118.07(16) . 3 ?
C3 C2 C1 120.97(8) . . ?
C3 C2 C1 120.96(8) 3 . ?
F2 C3 C4 119.25(13) . . ?
F2 C3 C2 119.90(12) . . ?
C4 C3 C2 120.83(14) . . ?
F1 C4 C3 118.51(13) . . ?
F1 C4 C5 119.96(12) . . ?
C3 C4 C5 121.53(13) . . ?
C4 C5 C4 117.05(16) . 3 ?
C4 C5 N1 121.48(8) . . ?
C4 C5 N1 121.47(8) 3 . ?
C7 C6 N1 129.68(12) . . ?
C7 C6 C11 121.93(12) . . ?
N1 C6 C11 108.33(12) . . ?
C8 C7 C6 117.61(13) . . ?
C7 C8 C9 121.26(14) . . ?
C10 C9 C8 120.91(13) . . ?
C9 C10 C11 118.82(12) . . ?
C10 C11 C6 119.39(13) . . ?
C10 C11 C11 133.23(8) . 3 ?
C6 C11 C11 107.38(8) . 3 ?
C5 N1 C6 125.72(7) . . ?
C5 N1 C6 125.72(7) . 3 ?
C6 N1 C6 108.57(14) . 3 ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.061



####################################################################### 
# 
# 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_Pht-BzN
_audit_block_doi                 10.5517/ccdc.csd.cc2f9cjn
_database_code_depnum_ccdc_archive 'CCDC 2243331'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-5d72m 2023
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2023-02-20 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H8 F4 N2 S'
_chemical_formula_sum            'C19 H8 F4 N2 S'
_chemical_melting_point          ?


_exptl_crystal_description       block
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         372.33

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
_chemical_absolute_configuration .

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

_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.
;

_cell_length_a                   7.5813(2)
_cell_length_b                   12.9249(3)
_cell_length_c                   17.5802(4)
_cell_angle_alpha                109.8140(10)
_cell_angle_beta                 97.8320(10)
_cell_angle_gamma                98.0790(10)
_cell_volume                     1572.99(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9870
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      30.56
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.254
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8776
_exptl_absorpt_correction_T_max  0.9461
_exptl_absorpt_process_details   'Bruker APEX2'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34065
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.256
_diffrn_reflns_theta_max         30.634
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9425
_reflns_number_gt                7742
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_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)+(0.0417P)²+0.5844P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         9425
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_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
C7 C -0.25585(18) 0.34278(10) 0.13757(8) 0.0204(2) Uani 1 1 d . . . . .
C8 C -0.22455(17) 0.45850(10) 0.16495(8) 0.0186(2) Uani 1 1 d . . . . .
C9 C -0.11196(18) 0.28680(10) 0.13390(7) 0.0198(2) Uani 1 1 d . . . . .
C10 C 0.06369(18) 0.34994(10) 0.15741(7) 0.0187(2) Uani 1 1 d . . . . .
C11 C 0.09488(17) 0.46573(10) 0.18377(7) 0.0179(2) Uani 1 1 d . . . . .
C12 C -0.04903(17) 0.52205(9) 0.18768(7) 0.0165(2) Uani 1 1 d . . . . .
C13 C -0.00111(16) 0.69904(10) 0.30186(7) 0.0157(2) Uani 1 1 d . . . . .
C17 C -0.05455(16) 0.69339(9) 0.15847(7) 0.0157(2) Uani 1 1 d . . . . .
C18 C 0.06839(16) 0.81444(10) 0.33716(7) 0.0160(2) Uani 1 1 d . . . . .
C19 C 0.00863(16) 0.80886(10) 0.18121(7) 0.0161(2) Uani 1 1 d . . . . .
C22 C 0.07693(17) 0.87245(10) 0.42086(7) 0.0190(2) Uani 1 1 d . . . . .
H22 H 0.120454 0.951374 0.443948 0.023 Uiso 1 1 calc R U . . .
C25 C -0.15625(17) 0.63291(10) 0.07941(7) 0.0194(2) Uani 1 1 d . . . . .
H25 H -0.197848 0.554184 0.062522 0.023 Uiso 1 1 calc R U . . .
C26 C -0.04458(18) 0.70111(11) 0.43613(8) 0.0213(2) Uani 1 1 d . . . . .
H26 H -0.080978 0.661738 0.470070 0.026 Uiso 1 1 calc R U . . .
C27 C -0.13844(19) 0.80181(11) 0.04837(8) 0.0217(2) Uani 1 1 d . . . . .
H27 H -0.168389 0.838538 0.011257 0.026 Uiso 1 1 calc R U . . .
C29 C -0.19728(18) 0.68704(11) 0.02503(7) 0.0210(2) Uani 1 1 d . . . . .
H29 H -0.266502 0.644798 -0.028783 0.025 Uiso 1 1 calc R U . . .
C30 C -0.03493(18) 0.86249(10) 0.12688(8) 0.0194(2) Uani 1 1 d . . . . .
H30 H 0.006288 0.941210 0.143476 0.023 Uiso 1 1 calc R U . . .
C31 C 0.02256(17) 0.81596(11) 0.47045(7) 0.0210(2) Uani 1 1 d . . . . .
H31 H 0.031107 0.855521 0.527697 0.025 Uiso 1 1 calc R U . . .
C32 C -0.05879(17) 0.64340(10) 0.35218(7) 0.0194(2) Uani 1 1 d . . . . .
H32 H -0.108404 0.565145 0.328898 0.023 Uiso 1 1 calc R U . . .
C33 C -0.1446(2) 0.16647(11) 0.10733(8) 0.0243(3) Uani 1 1 d . . . . .
N2 N -0.1710(2) 0.07098(10) 0.08715(8) 0.0360(3) Uani 1 1 d . . . . .
N4 N -0.01190(14) 0.64113(8) 0.21619(6) 0.0167(2) Uani 1 1 d . . . . .
F5 F -0.36605(10) 0.50954(6) 0.17005(5) 0.02583(17) Uani 1 1 d . . . . .
F6 F -0.42607(11) 0.28451(7) 0.11494(6) 0.03000(19) Uani 1 1 d . . . . .
F7 F 0.26548(10) 0.52342(7) 0.20643(5) 0.02622(17) Uani 1 1 d . . . . .
F8 F 0.20472(11) 0.29841(7) 0.15429(5) 0.02512(17) Uani 1 1 d . . . . .
S2 S 0.15478(4) 0.88678(2) 0.27720(2) 0.01910(7) Uani 1 1 d . . . . .
C1 C 0.61530(16) 0.04414(10) 0.27626(7) 0.0158(2) Uani 1 1 d . . . . .
C2 C 0.64891(16) -0.05076(10) 0.29125(7) 0.0162(2) Uani 1 1 d . . . . .
C3 C 0.58185(17) -0.15736(10) 0.23309(8) 0.0187(2) Uani 1 1 d . . . . .
C4 C 0.48360(17) -0.17217(10) 0.15629(8) 0.0211(2) Uani 1 1 d . . . . .
C5 C 0.45492(18) -0.07778(11) 0.13954(7) 0.0220(3) Uani 1 1 d . . . . .
C6 C 0.51785(17) 0.02855(10) 0.19882(7) 0.0189(2) Uani 1 1 d . . . . .
C14 C 0.62578(16) 0.30950(10) 0.44824(8) 0.0186(2) Uani 1 1 d . . . . .
C15 C 0.89507(16) 0.32945(10) 0.36820(7) 0.0161(2) Uani 1 1 d . . . . .
C16 C 1.06763(17) 0.38708(10) 0.37155(7) 0.0187(2) Uani 1 1 d . . . . .
H16 H 1.097202 0.466626 0.396567 0.022 Uiso 1 1 calc R U . . .
C20 C 0.98381(17) 0.15428(10) 0.30258(7) 0.0186(2) Uani 1 1 d . . . . .
H20 H 0.956985 0.074556 0.279939 0.022 Uiso 1 1 calc R U . . .
C21 C 0.50536(17) 0.12131(11) 0.43647(8) 0.0197(2) Uani 1 1 d . . . . .
H21 H 0.483120 0.042496 0.407400 0.024 Uiso 1 1 calc R U . . .
C23 C 0.85267(16) 0.21222(10) 0.33415(7) 0.0155(2) Uani 1 1 d . . . . .
C24 C 1.15364(17) 0.21223(11) 0.30395(8) 0.0208(2) Uani 1 1 d . . . . .
H24 H 1.241320 0.171943 0.281111 0.025 Uiso 1 1 calc R U . . .
C28 C 0.60116(15) 0.19355(10) 0.40612(7) 0.0165(2) Uani 1 1 d . . . . .
C34 C 1.19618(17) 0.32856(11) 0.33845(7) 0.0206(2) Uani 1 1 d . . . . .
H34 H 1.312648 0.367892 0.339390 0.025 Uiso 1 1 calc R U . . .
C35 C 0.44214(18) 0.16409(12) 0.50917(8) 0.0244(3) Uani 1 1 d . . . . .
H35 H 0.376073 0.114171 0.529205 0.029 Uiso 1 1 calc R U . . .
C36 C 0.40476(19) -0.28215(12) 0.09611(9) 0.0286(3) Uani 1 1 d . . . . .
C37 C 0.56473(17) 0.35118(11) 0.52178(8) 0.0251(3) Uani 1 1 d . . . . .
H37 H 0.585288 0.429918 0.550873 0.030 Uiso 1 1 calc R U . . .
C38 C 0.47434(18) 0.27866(13) 0.55273(8) 0.0284(3) Uani 1 1 d . . . . .
H38 H 0.434676 0.307174 0.603445 0.034 Uiso 1 1 calc R U . . .
N1 N 0.3379(2) -0.36813(12) 0.04751(9) 0.0435(4) Uani 1 1 d . . . . .
N3 N 0.67816(14) 0.15527(8) 0.33460(6) 0.01647(19) Uani 1 1 d . . . . .
F1 F 0.74703(10) -0.03958(6) 0.36402(4) 0.02133(16) Uani 1 1 d . . . . .
F2 F 0.60941(11) -0.24639(6) 0.25172(5) 0.02631(17) Uani 1 1 d . . . . .
F3 F 0.36221(12) -0.08971(8) 0.06616(5) 0.0330(2) Uani 1 1 d . . . . .
F4 F 0.48333(12) 0.11703(7) 0.18110(5) 0.02688(17) Uani 1 1 d . . . . .
S1 S 0.72780(4) 0.40324(3) 0.40618(2) 0.02204(7) Uani 1 1 d . . . . .


_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
C7 F6 1.3321(14) . ?
C7 C8 1.3805(17) . ?
C7 C9 1.3882(18) . ?
C8 F5 1.3339(14) . ?
C8 C12 1.3894(17) . ?
C9 C10 1.3878(18) . ?
C9 C33 1.4373(17) . ?
C10 F8 1.3346(14) . ?
C10 C11 1.3824(17) . ?
C11 F7 1.3321(14) . ?
C11 C12 1.3909(17) . ?
C12 N4 1.4198(14) . ?
C13 C32 1.3925(17) . ?
C13 C18 1.3965(16) . ?
C13 N4 1.4214(15) . ?
C17 C25 1.3926(16) . ?
C17 C19 1.3996(16) . ?
C17 N4 1.4238(15) . ?
C18 C22 1.3943(16) . ?
C18 S2 1.7601(12) . ?
C19 C30 1.3890(17) . ?
C19 S2 1.7647(12) . ?
C22 C31 1.3812(18) . ?
C25 C29 1.3906(17) . ?
C26 C31 1.3869(18) . ?
C26 C32 1.3906(17) . ?
C27 C29 1.3853(18) . ?
C27 C30 1.3907(17) . ?
C33 N2 1.1418(17) . ?
C1 C2 1.3883(17) . ?
C1 C6 1.3921(16) . ?
C1 N3 1.4205(14) . ?
C2 F1 1.3401(13) . ?
C2 C3 1.3816(16) . ?
C3 F2 1.3340(14) . ?
C3 C4 1.3874(18) . ?
C4 C5 1.3867(19) . ?
C4 C36 1.4375(17) . ?
C5 F3 1.3302(14) . ?
C5 C6 1.3826(17) . ?
C6 F4 1.3330(14) . ?
C14 C37 1.3917(18) . ?
C14 C28 1.4001(16) . ?
C14 S1 1.7643(13) . ?
C15 C16 1.3947(17) . ?
C15 C23 1.3975(16) . ?
C15 S1 1.7614(12) . ?
C16 C34 1.3871(18) . ?
C20 C24 1.3884(17) . ?
C20 C23 1.3911(17) . ?
C21 C35 1.3897(18) . ?
C21 C28 1.3918(17) . ?
C23 N3 1.4232(15) . ?
C24 C34 1.3873(18) . ?
C28 N3 1.4233(15) . ?
C35 C38 1.385(2) . ?
C36 N1 1.1410(18) . ?
C37 C38 1.382(2) . ?

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
F6 C7 C8 119.50(12) . . ?
F6 C7 C9 119.80(11) . . ?
C8 C7 C9 120.69(12) . . ?
F5 C8 C7 119.01(11) . . ?
F5 C8 C12 119.81(10) . . ?
C7 C8 C12 121.17(11) . . ?
C10 C9 C7 118.36(11) . . ?
C10 C9 C33 120.96(12) . . ?
C7 C9 C33 120.67(12) . . ?
F8 C10 C11 119.39(11) . . ?
F8 C10 C9 119.70(11) . . ?
C11 C10 C9 120.91(11) . . ?
F7 C11 C10 119.10(11) . . ?
F7 C11 C12 120.04(11) . . ?
C10 C11 C12 120.85(11) . . ?
C8 C12 C11 118.00(11) . . ?
C8 C12 N4 122.66(11) . . ?
C11 C12 N4 119.32(11) . . ?
C32 C13 C18 118.63(11) . . ?
C32 C13 N4 121.53(10) . . ?
C18 C13 N4 119.83(11) . . ?
C25 C17 C19 118.68(11) . . ?
C25 C17 N4 122.01(10) . . ?
C19 C17 N4 119.31(10) . . ?
C22 C18 C13 120.34(11) . . ?
C22 C18 S2 119.43(9) . . ?
C13 C18 S2 120.18(9) . . ?
C30 C19 C17 120.50(11) . . ?
C30 C19 S2 119.07(9) . . ?
C17 C19 S2 120.34(9) . . ?
C31 C22 C18 120.47(11) . . ?
C29 C25 C17 120.41(11) . . ?
C31 C26 C32 120.21(12) . . ?
C29 C27 C30 119.07(12) . . ?
C27 C29 C25 120.81(11) . . ?
C19 C30 C27 120.49(11) . . ?
C22 C31 C26 119.56(11) . . ?
C26 C32 C13 120.74(11) . . ?
N2 C33 C9 179.14(16) . . ?
C12 N4 C13 116.69(10) . . ?
C12 N4 C17 118.31(9) . . ?
C13 N4 C17 120.68(9) . . ?
C18 S2 C19 99.57(6) . . ?
C2 C1 C6 117.56(10) . . ?
C2 C1 N3 123.69(10) . . ?
C6 C1 N3 118.73(11) . . ?
F1 C2 C3 118.77(11) . . ?
F1 C2 C1 119.65(10) . . ?
C3 C2 C1 121.58(11) . . ?
F2 C3 C2 119.54(11) . . ?
F2 C3 C4 120.02(11) . . ?
C2 C3 C4 120.43(11) . . ?
C5 C4 C3 118.47(11) . . ?
C5 C4 C36 119.89(12) . . ?
C3 C4 C36 121.57(13) . . ?
F3 C5 C6 119.53(12) . . ?
F3 C5 C4 119.63(11) . . ?
C6 C5 C4 120.82(11) . . ?
F4 C6 C5 119.04(11) . . ?
F4 C6 C1 119.90(11) . . ?
C5 C6 C1 121.07(12) . . ?
C37 C14 C28 120.31(12) . . ?
C37 C14 S1 119.79(10) . . ?
C28 C14 S1 119.86(9) . . ?
C16 C15 C23 120.24(11) . . ?
C16 C15 S1 120.54(9) . . ?
C23 C15 S1 119.22(9) . . ?
C34 C16 C15 120.17(11) . . ?
C24 C20 C23 120.41(11) . . ?
C35 C21 C28 120.21(12) . . ?
C20 C23 C15 119.08(11) . . ?
C20 C23 N3 121.77(10) . . ?
C15 C23 N3 119.12(11) . . ?
C34 C24 C20 120.46(12) . . ?
C21 C28 C14 118.81(11) . . ?
C21 C28 N3 123.11(11) . . ?
C14 C28 N3 118.07(11) . . ?
C16 C34 C24 119.60(11) . . ?
C38 C35 C21 120.75(13) . . ?
N1 C36 C4 177.89(18) . . ?
C38 C37 C14 120.39(12) . . ?
C37 C38 C35 119.41(12) . . ?
C1 N3 C23 117.29(9) . . ?
C1 N3 C28 120.38(10) . . ?
C23 N3 C28 119.24(9) . . ?
C15 S1 C14 98.14(6) . . ?

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.054



