# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2100108'
loop_
_audit_author_name
_audit_author_address
'Samuel Guieu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
2,5-bis(2-fluorophenyl)thiazolo[5,4-d]thiazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H4 F N S'
_chemical_formula_sum            'C8 H4 F N S'
_chemical_formula_weight         165.18

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      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                   8.820(4)
_cell_length_b                   5.152(2)
_cell_length_c                   14.649(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.24(2)
_cell_angle_gamma                90
_cell_volume                     665.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      2.310
_cell_measurement_theta_max      26.573

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   0.3442
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.419
_shelx_estimated_absorpt_T_min   0.679
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3625
_diffrn_reflns_av_unetI/netI     0.1332
_diffrn_reflns_av_R_equivalents  0.1834
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.310
_diffrn_reflns_theta_max         26.573
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.946
_reflns_number_total             1292
_reflns_number_gt                935
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.1806P)²+1.0533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1292
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1548
_refine_ls_R_factor_gt           0.1145
_refine_ls_wR_factor_ref         0.3303
_refine_ls_wR_factor_gt          0.3013
_refine_ls_goodness_of_fit_ref   1.282
_refine_ls_restrained_S_all      1.282
_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
S1 S 0.3312(2) 0.2291(3) 0.55099(11) 0.0214(7) Uani 1 1 d . . . . .
F1 F 0.1373(5) 0.6349(8) 0.5151(3) 0.0268(12) Uani 1 1 d . . . . .
N1 N 0.4707(7) 0.1777(10) 0.3961(4) 0.0204(14) Uani 1 1 d . . . . .
C1 C 0.1321(9) 0.9128(14) 0.2894(5) 0.0242(17) Uani 1 1 d . . . . .
H1 H 0.0786 1.0423 0.2555 0.029 Uiso 1 1 calc R U . . .
C2 C 0.0981(9) 0.8687(14) 0.3786(5) 0.0239(17) Uani 1 1 d . . . . .
H3 H 0.0241 0.9710 0.4080 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1732(9) 0.6732(13) 0.4252(5) 0.0198(16) Uani 1 1 d . . . . .
C4 C 0.2824(10) 0.5197(12) 0.3874(4) 0.0223(17) Uani 1 1 d . . . . .
C5 C 0.3643(9) 0.3126(12) 0.4363(4) 0.0203(16) Uani 1 1 d . . . . .
C6 C 0.4696(9) -0.0030(12) 0.5428(4) 0.0189(16) Uani 1 1 d . . . . .
C7 C 0.2465(10) 0.7661(13) 0.2474(5) 0.0264(18) Uani 1 1 d . . . . .
H4 H 0.2734 0.8018 0.1862 0.032 Uiso 1 1 calc R U . . .
C8 C 0.3191(9) 0.5704(13) 0.2958(4) 0.0239(17) Uani 1 1 d . . . . .
H2 H 0.3945 0.4691 0.2672 0.029 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
S1 C6 1.715(8) . ?
S1 C5 1.764(7) . ?
F1 C3 1.376(8) . ?
N1 C5 1.317(10) . ?
N1 C6 1.367(9) 3_656 ?
C1 C2 1.366(10) . ?
C1 C7 1.412(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(10) . ?
C2 H3 0.9500 . ?
C3 C4 1.372(11) . ?
C4 C8 1.411(9) . ?
C4 C5 1.467(10) . ?
C6 N1 1.366(9) 3_656 ?
C6 C6 1.376(14) 3_656 ?
C7 C8 1.382(10) . ?
C7 H4 0.9500 . ?
C8 H2 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
C6 S1 C5 88.3(3) . . ?
C5 N1 C6 108.8(6) . 3_656 ?
C2 C1 C7 120.0(7) . . ?
C2 C1 H1 120.0 . . ?
C7 C1 H1 120.0 . . ?
C1 C2 C3 118.9(7) . . ?
C1 C2 H3 120.6 . . ?
C3 C2 H3 120.6 . . ?
C4 C3 F1 118.8(6) . . ?
C4 C3 C2 123.7(7) . . ?
F1 C3 C2 117.5(6) . . ?
C3 C4 C8 117.0(6) . . ?
C3 C4 C5 124.3(6) . . ?
C8 C4 C5 118.6(7) . . ?
N1 C5 C4 120.9(6) . . ?
N1 C5 S1 115.6(5) . . ?
C4 C5 S1 123.6(6) . . ?
N1 C6 C6 117.3(9) 3_656 3_656 ?
N1 C6 S1 132.8(5) 3_656 . ?
C6 C6 S1 109.9(7) 3_656 . ?
C8 C7 C1 119.7(7) . . ?
C8 C7 H4 120.2 . . ?
C1 C7 H4 120.2 . . ?
C7 C8 C4 120.6(7) . . ?
C7 C8 H2 119.7 . . ?
C4 C8 H2 119.7 . . ?

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
C7 C1 C2 C3 -2.4(11) . . . . ?
C1 C2 C3 C4 0.6(11) . . . . ?
C1 C2 C3 F1 179.5(6) . . . . ?
F1 C3 C4 C8 -178.1(6) . . . . ?
C2 C3 C4 C8 0.8(11) . . . . ?
F1 C3 C4 C5 0.5(11) . . . . ?
C2 C3 C4 C5 179.4(7) . . . . ?
C6 N1 C5 C4 178.6(6) 3_656 . . . ?
C6 N1 C5 S1 -0.6(8) 3_656 . . . ?
C3 C4 C5 N1 -178.2(7) . . . . ?
C8 C4 C5 N1 0.4(11) . . . . ?
C3 C4 C5 S1 1.0(11) . . . . ?
C8 C4 C5 S1 179.6(5) . . . . ?
C6 S1 C5 N1 -0.3(6) . . . . ?
C6 S1 C5 C4 -179.5(6) . . . . ?
C5 S1 C6 N1 179.0(7) . . . 3_656 ?
C5 S1 C6 C6 1.0(7) . . . 3_656 ?
C2 C1 C7 C8 2.9(11) . . . . ?
C1 C7 C8 C4 -1.4(11) . . . . ?
C3 C4 C8 C7 -0.3(11) . . . . ?
C5 C4 C8 C7 -179.0(7) . . . . ?

_refine_diff_density_max         1.002
_refine_diff_density_min         -1.227
_refine_diff_density_rms         0.270

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2100109'
loop_
_audit_author_name
_audit_author_address
'Samuel Guieu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
2,5-bis(perfluorophenyl)thiazolo[5,4-d]thiazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 F10 N2 S2'
_chemical_formula_sum            'C16 F10 N2 S2'
_chemical_formula_weight         474.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   4.3379(7)
_cell_length_b                   16.178(2)
_cell_length_c                   10.9464(16)
_cell_angle_alpha                90
_cell_angle_beta                 101.031(5)
_cell_angle_gamma                90
_cell_volume                     754.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2469
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      29.64

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.089
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   0.5620
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.478
_shelx_estimated_absorpt_T_min   0.731
_shelx_estimated_absorpt_T_max   0.954
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11873
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.276
_diffrn_reflns_theta_max         30.542
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2298
_reflns_number_gt                1834
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0391P)²+0.2253P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2298
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
S01 S 0.17176(11) 0.95478(2) 0.35507(4) 0.02227(13) Uani 1 1 d . . . . .
F06 F -0.0498(3) 0.54282(6) 0.36493(10) 0.0293(3) Uani 1 1 d . . . . .
F08 F 0.6367(2) 0.73518(6) 0.58976(9) 0.0212(2) Uani 1 1 d . . . . .
F07 F 0.4598(3) 0.58096(6) 0.54501(9) 0.0273(2) Uani 1 1 d . . . . .
F04 F -0.2141(2) 0.82384(6) 0.27569(9) 0.0235(2) Uani 1 1 d . . . . .
F05 F -0.3836(2) 0.66699(6) 0.23343(9) 0.0263(2) Uani 1 1 d . . . . .
C02 C 0.3178(4) 0.87457(9) 0.45853(14) 0.0164(3) Uani 1 1 d . . . . .
C08 C 0.3799(4) 0.72232(10) 0.50212(14) 0.0166(3) Uani 1 1 d . . . . .
N01 N 0.5309(3) 0.89609(8) 0.55580(12) 0.0201(3) Uani 1 1 d . . . . .
C05 C -0.1316(4) 0.68438(10) 0.32074(14) 0.0194(3) Uani 1 1 d . . . . .
C03 C 0.2180(4) 0.78814(9) 0.43528(14) 0.0162(3) Uani 1 1 d . . . . .
C01 C 0.4168(4) 1.02146(10) 0.45013(14) 0.0176(3) Uani 1 1 d . . . . .
C06 C 0.0355(4) 0.62140(10) 0.38846(15) 0.0204(3) Uani 1 1 d . . . . .
C07 C 0.2912(4) 0.64088(9) 0.47939(15) 0.0191(3) Uani 1 1 d . . . . .
C04 C -0.0409(4) 0.76545(10) 0.34471(14) 0.0178(3) 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
S01 C01 1.7183(16) . ?
S01 C02 1.7588(15) . ?
F06 C06 1.3351(18) . ?
F08 C08 1.3402(18) . ?
F07 C07 1.3375(18) . ?
F04 C04 1.3457(18) . ?
F05 C05 1.3372(19) . ?
C02 N01 1.316(2) . ?
C02 C03 1.471(2) . ?
C08 C07 1.382(2) . ?
C08 C03 1.402(2) . ?
N01 C01 1.357(2) 3_676 ?
C05 C04 1.380(2) . ?
C05 C06 1.381(2) . ?
C03 C04 1.397(2) . ?
C01 C01 1.376(3) 3_676 ?
C06 C07 1.378(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
C01 S01 C02 88.19(8) . . ?
N01 C02 C03 121.95(14) . . ?
N01 C02 S01 115.87(12) . . ?
C03 C02 S01 122.14(12) . . ?
F08 C08 C07 116.19(14) . . ?
F08 C08 C03 121.36(14) . . ?
C07 C08 C03 122.41(15) . . ?
C02 N01 C01 108.64(13) . 3_676 ?
F05 C05 C04 120.02(15) . . ?
F05 C05 C06 120.11(15) . . ?
C04 C05 C06 119.86(15) . . ?
C04 C03 C08 115.15(14) . . ?
C04 C03 C02 122.83(14) . . ?
C08 C03 C02 122.02(15) . . ?
N01 C01 C01 117.82(18) 3_676 3_676 ?
N01 C01 S01 132.69(12) 3_676 . ?
C01 C01 S01 109.49(16) 3_676 . ?
F06 C06 C07 120.80(15) . . ?
F06 C06 C05 120.10(15) . . ?
C07 C06 C05 119.10(15) . . ?
F07 C07 C06 120.27(14) . . ?
F07 C07 C08 119.32(15) . . ?
C06 C07 C08 120.39(15) . . ?
F04 C04 C05 116.88(15) . . ?
F04 C04 C03 120.04(14) . . ?
C05 C04 C03 123.08(15) . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.079


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2100113'
loop_
_audit_author_name
_audit_author_address
'Samuel Guieu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
6-chloro-2-(2,6-dichlorophenyl)thiazolo[5,4-c]isoquinoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H7 Cl3 N2 S'
_chemical_formula_sum            'C16 H7 Cl3 N2 S'
_chemical_formula_weight         365.65

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'
S S 0.1246 0.1234 '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'

_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                   7.2602(4)
_cell_length_b                   15.8141(8)
_cell_length_c                   13.1144(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.323(2)
_cell_angle_gamma                90
_cell_volume                     1496.55(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8361
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      28.28

_exptl_crystal_description       flake
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   0.6228
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.747
_shelx_estimated_absorpt_T_min   0.807
_shelx_estimated_absorpt_T_max   0.964
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20157
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.576
_diffrn_reflns_theta_max         28.359
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3693
_reflns_number_gt                2769
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0273P)²+2.0285P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3693
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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
Cl1 Cl 0.07199(12) 0.55126(7) 0.27228(6) 0.0606(3) Uani 1 1 d . . . . .
Cl2 Cl 0.78398(11) 0.70584(6) 0.84393(6) 0.0511(2) Uani 1 1 d . . . . .
Cl3 Cl 0.17176(11) 0.56535(5) 0.97177(6) 0.0492(2) Uani 1 1 d . . . . .
S1 S 0.29242(11) 0.72482(5) 0.75526(6) 0.04172(19) Uani 1 1 d . . . . .
N1 N 0.3945(3) 0.56768(14) 0.75004(15) 0.0298(5) Uani 1 1 d . . . . .
C1 C 0.6543(5) 0.6358(2) 1.1179(2) 0.0453(7) Uani 1 1 d . . . . .
H1 H 0.712049 0.635733 1.186532 0.054 Uiso 1 1 calc R U . . .
C2 C 0.4775(4) 0.60432(19) 1.0976(2) 0.0411(7) Uani 1 1 d . . . . .
H8 H 0.413542 0.582822 1.151477 0.049 Uiso 1 1 calc R U . . .
C3 C 0.3942(4) 0.60446(17) 0.9975(2) 0.0332(6) Uani 1 1 d . . . . .
C4 C 0.4856(4) 0.63508(16) 0.91659(19) 0.0311(5) Uani 1 1 d . . . . .
C5 C 0.3966(4) 0.63358(16) 0.80934(19) 0.0313(5) Uani 1 1 d . . . . .
C6 C 0.3055(3) 0.58733(17) 0.65426(18) 0.0291(5) Uani 1 1 d . . . . .
C7 C 0.2805(3) 0.53080(17) 0.56993(18) 0.0293(5) Uani 1 1 d . . . . .
C8 C 0.3378(4) 0.44652(18) 0.5749(2) 0.0351(6) Uani 1 1 d . . . . .
H4 H 0.394244 0.423473 0.637623 0.042 Uiso 1 1 calc R U . . .
C9 C 0.3119(4) 0.3972(2) 0.4883(2) 0.0444(7) Uani 1 1 d . . . . .
H5 H 0.350772 0.339842 0.491459 0.053 Uiso 1 1 calc R U . . .
C10 C 0.2284(4) 0.4307(2) 0.3948(2) 0.0459(8) Uani 1 1 d . . . . .
H2 H 0.211921 0.395918 0.335421 0.055 Uiso 1 1 calc R U . . .
C11 C 0.2432(4) 0.66953(17) 0.6413(2) 0.0334(6) Uani 1 1 d . . . . .
N2 N 0.1571(3) 0.70367(16) 0.55409(18) 0.0414(6) Uani 1 1 d . . . . .
C13 C 0.1361(4) 0.6520(2) 0.4752(2) 0.0402(7) Uani 1 1 d . . . . .
H6 H 0.077753 0.673735 0.412271 0.048 Uiso 1 1 calc R U . . .
C14 C 0.1938(4) 0.56587(19) 0.47665(19) 0.0344(6) Uani 1 1 d . . . . .
C15 C 0.1716(4) 0.5122(2) 0.3896(2) 0.0397(7) Uani 1 1 d . . . . .
C16 C 0.6631(4) 0.66663(17) 0.9410(2) 0.0341(6) Uani 1 1 d . . . . .
C17 C 0.7503(4) 0.66755(19) 1.0407(2) 0.0403(6) Uani 1 1 d . . . . .
H7 H 0.872304 0.689322 1.055538 0.048 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
Cl1 C15 1.739(3) . ?
Cl2 C16 1.738(3) . ?
Cl3 C3 1.727(3) . ?
S1 C11 1.735(3) . ?
S1 C5 1.743(3) . ?
N1 C5 1.299(3) . ?
N1 C6 1.383(3) . ?
C1 C2 1.376(4) . ?
C1 C17 1.385(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(4) . ?
C2 H8 0.9500 . ?
C3 C4 1.399(4) . ?
C4 C16 1.386(4) . ?
C4 C5 1.482(3) . ?
C6 C11 1.381(4) . ?
C6 C7 1.418(3) . ?
C7 C8 1.396(4) . ?
C7 C14 1.425(4) . ?
C8 C9 1.373(4) . ?
C8 H4 0.9500 . ?
C9 C10 1.410(5) . ?
C9 H5 0.9500 . ?
C10 C15 1.354(5) . ?
C10 H2 0.9500 . ?
C11 N2 1.354(3) . ?
N2 C13 1.314(4) . ?
C13 C14 1.424(4) . ?
C13 H6 0.9500 . ?
C14 C15 1.417(4) . ?
C16 C17 1.389(4) . ?
C17 H7 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
C11 S1 C5 88.41(13) . . ?
C5 N1 C6 109.7(2) . . ?
C2 C1 C17 121.6(3) . . ?
C2 C1 H1 119.2 . . ?
C17 C1 H1 119.2 . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H8 120.5 . . ?
C3 C2 H8 120.5 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 Cl3 119.1(2) . . ?
C4 C3 Cl3 119.1(2) . . ?
C16 C4 C3 117.1(2) . . ?
C16 C4 C5 121.5(2) . . ?
C3 C4 C5 121.4(2) . . ?
N1 C5 C4 123.8(2) . . ?
N1 C5 S1 116.39(19) . . ?
C4 C5 S1 119.81(19) . . ?
C11 C6 N1 115.9(2) . . ?
C11 C6 C7 119.0(2) . . ?
N1 C6 C7 125.0(2) . . ?
C8 C7 C6 123.6(2) . . ?
C8 C7 C14 120.9(2) . . ?
C6 C7 C14 115.5(2) . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H4 120.3 . . ?
C7 C8 H4 120.3 . . ?
C8 C9 C10 120.9(3) . . ?
C8 C9 H5 119.6 . . ?
C10 C9 H5 119.6 . . ?
C15 C10 C9 120.1(3) . . ?
C15 C10 H2 120.0 . . ?
C9 C10 H2 120.0 . . ?
N2 C11 C6 126.5(3) . . ?
N2 C11 S1 124.0(2) . . ?
C6 C11 S1 109.57(19) . . ?
C13 N2 C11 114.8(2) . . ?
N2 C13 C14 125.2(3) . . ?
N2 C13 H6 117.4 . . ?
C14 C13 H6 117.4 . . ?
C15 C14 C13 123.7(3) . . ?
C15 C14 C7 117.3(3) . . ?
C13 C14 C7 119.0(2) . . ?
C10 C15 C14 121.5(3) . . ?
C10 C15 Cl1 118.5(2) . . ?
C14 C15 Cl1 120.0(3) . . ?
C4 C16 C17 122.5(3) . . ?
C4 C16 Cl2 119.4(2) . . ?
C17 C16 Cl2 118.1(2) . . ?
C1 C17 C16 118.1(3) . . ?
C1 C17 H7 121.0 . . ?
C16 C17 H7 121.0 . . ?

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
C17 C1 C2 C3 0.1(5) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 Cl3 -179.8(2) . . . . ?
C2 C3 C4 C16 -0.9(4) . . . . ?
Cl3 C3 C4 C16 179.4(2) . . . . ?
C2 C3 C4 C5 178.9(3) . . . . ?
Cl3 C3 C4 C5 -0.8(4) . . . . ?
C6 N1 C5 C4 -178.4(2) . . . . ?
C6 N1 C5 S1 -0.1(3) . . . . ?
C16 C4 C5 N1 97.0(3) . . . . ?
C3 C4 C5 N1 -82.9(3) . . . . ?
C16 C4 C5 S1 -81.2(3) . . . . ?
C3 C4 C5 S1 99.0(3) . . . . ?
C11 S1 C5 N1 -0.7(2) . . . . ?
C11 S1 C5 C4 177.7(2) . . . . ?
C5 N1 C6 C11 1.2(3) . . . . ?
C5 N1 C6 C7 178.9(2) . . . . ?
C11 C6 C7 C8 -179.9(2) . . . . ?
N1 C6 C7 C8 2.4(4) . . . . ?
C11 C6 C7 C14 1.1(3) . . . . ?
N1 C6 C7 C14 -176.6(2) . . . . ?
C6 C7 C8 C9 -178.3(3) . . . . ?
C14 C7 C8 C9 0.7(4) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C8 C9 C10 C15 -0.3(4) . . . . ?
N1 C6 C11 N2 178.2(3) . . . . ?
C7 C6 C11 N2 0.3(4) . . . . ?
N1 C6 C11 S1 -1.7(3) . . . . ?
C7 C6 C11 S1 -179.56(19) . . . . ?
C5 S1 C11 N2 -178.6(3) . . . . ?
C5 S1 C11 C6 1.2(2) . . . . ?
C6 C11 N2 C13 -1.3(4) . . . . ?
S1 C11 N2 C13 178.5(2) . . . . ?
C11 N2 C13 C14 0.8(4) . . . . ?
N2 C13 C14 C15 -179.0(3) . . . . ?
N2 C13 C14 C7 0.5(4) . . . . ?
C8 C7 C14 C15 -1.0(4) . . . . ?
C6 C7 C14 C15 178.0(2) . . . . ?
C8 C7 C14 C13 179.5(2) . . . . ?
C6 C7 C14 C13 -1.5(3) . . . . ?
C9 C10 C15 C14 0.0(4) . . . . ?
C9 C10 C15 Cl1 179.2(2) . . . . ?
C13 C14 C15 C10 -179.8(3) . . . . ?
C7 C14 C15 C10 0.7(4) . . . . ?
C13 C14 C15 Cl1 1.0(4) . . . . ?
C7 C14 C15 Cl1 -178.48(19) . . . . ?
C3 C4 C16 C17 0.8(4) . . . . ?
C5 C4 C16 C17 -179.0(3) . . . . ?
C3 C4 C16 Cl2 -179.9(2) . . . . ?
C5 C4 C16 Cl2 0.3(4) . . . . ?
C2 C1 C17 C16 -0.2(5) . . . . ?
C4 C16 C17 C1 -0.2(4) . . . . ?
Cl2 C16 C17 C1 -179.6(2) . . . . ?

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
C10 H2 Cl2 0.95 2.85 3.796(3) 172.1 3_666 yes
C10 H2 Cl2 0.95 2.85 3.796(3) 172.1 3_666 yes
C13 H6 Cl2 0.95 2.93 3.686(3) 137.9 4_475 yes
C17 H7 N2 0.95 2.67 3.576(4) 158.8 4_676 yes

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.111


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2100119'
loop_
_audit_author_name
_audit_author_address
'Samuel Guieu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 6,9-dichloro-2-(2,3,6-trichlorophenyl)thiazolo[5,4-c]isoquinoline
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H5 Cl5 N2 S'
_chemical_formula_sum            'C16 H5 Cl5 N2 S'
_chemical_formula_weight         434.53

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'
S S 0.1246 0.1234 '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'

_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                   12.0604(12)
_cell_length_b                   18.5095(16)
_cell_length_c                   7.5980(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.203(3)
_cell_angle_gamma                90
_cell_volume                     1611.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3219
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      21.71

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   0.6554
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.030
_shelx_estimated_absorpt_T_min   0.748
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28232
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_av_R_equivalents  0.0859
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.201
_diffrn_reflns_theta_max         28.423
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4018
_reflns_number_gt                2613
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0553P)²+4.8473P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4018
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1532
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
S1 S 0.89151(9) 0.21148(6) 0.68446(15) 0.0287(3) Uani 1 1 d . . . . .
Cl3 Cl 0.73865(9) -0.00257(6) 0.74582(15) 0.0300(3) Uani 1 1 d . . . . .
Cl2 Cl 0.53646(10) 0.04995(6) 0.22211(19) 0.0425(3) Uani 1 1 d . . . . .
Cl1 Cl 0.40553(10) 0.37658(6) 0.09711(18) 0.0396(3) Uani 1 1 d . . . . .
Cl5 Cl 1.11558(10) 0.13245(8) 0.63581(17) 0.0448(3) Uani 1 1 d . . . . .
Cl4 Cl 0.89165(13) -0.14062(6) 0.86775(18) 0.0474(4) Uani 1 1 d . . . . .
C02 C 0.5537(3) 0.2685(2) 0.2703(6) 0.0252(9) Uani 1 1 d . . . . .
N2 N 0.7313(3) 0.31064(19) 0.5013(5) 0.0279(8) Uani 1 1 d . . . . .
C08 C 0.6987(3) 0.1809(2) 0.4334(6) 0.0222(8) Uani 1 1 d . . . . .
C09 C 0.7611(3) 0.2402(2) 0.5281(6) 0.0253(9) Uani 1 1 d . . . . .
N1 N 0.7533(3) 0.11545(18) 0.4808(5) 0.0233(7) Uani 1 1 d . . . . .
C01 C 0.6312(4) 0.3228(2) 0.3738(6) 0.0294(10) Uani 1 1 d . . . . .
H01 H 0.6082 0.3718 0.3481 0.035 Uiso 1 1 calc R U . . .
C07 C 0.5867(3) 0.1940(2) 0.3002(6) 0.0227(8) Uani 1 1 d . . . . .
C06 C 0.5065(4) 0.1411(2) 0.1986(6) 0.0272(9) Uani 1 1 d . . . . .
C12 C 0.8815(4) -0.0016(2) 0.7437(6) 0.0274(9) Uani 1 1 d . . . . .
C05 C 0.3997(4) 0.1613(3) 0.0800(6) 0.0321(10) Uani 1 1 d . . . . .
H05 H 0.3460 0.1251 0.0179 0.038 Uiso 1 1 calc R U . . .
C10 C 0.8532(3) 0.1233(2) 0.6087(6) 0.0243(8) Uani 1 1 d . . . . .
C03 C 0.4441(4) 0.2861(2) 0.1416(6) 0.0278(9) Uani 1 1 d . . . . .
C11 C 0.9288(3) 0.0599(2) 0.6871(6) 0.0258(9) Uani 1 1 d . . . . .
C13 C 0.9507(4) -0.0628(3) 0.8044(6) 0.0347(11) Uani 1 1 d . . . . .
C14 C 1.0671(4) -0.0627(3) 0.8123(6) 0.0436(13) Uani 1 1 d . . . . .
H14 H 1.1135 -0.1046 0.8530 0.052 Uiso 1 1 calc R U . . .
C04 C 0.3677(4) 0.2345(3) 0.0481(6) 0.0323(10) Uani 1 1 d . . . . .
H04 H 0.2943 0.2476 -0.0369 0.039 Uiso 1 1 calc R U . . .
C16 C 1.0480(4) 0.0580(3) 0.7004(6) 0.0326(10) Uani 1 1 d . . . . .
C15 C 1.1153(4) -0.0027(3) 0.7617(7) 0.0416(12) Uani 1 1 d . . . . .
H15 H 1.1953 -0.0028 0.7687 0.050 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
S1 C09 1.732(4) . ?
S1 C10 1.744(4) . ?
Cl3 C12 1.728(4) . ?
Cl2 C06 1.723(4) . ?
Cl1 C03 1.743(4) . ?
Cl5 C16 1.747(5) . ?
Cl4 C13 1.740(5) . ?
C02 C03 1.415(6) . ?
C02 C01 1.430(6) . ?
C02 C07 1.432(5) . ?
N2 C01 1.310(6) . ?
N2 C09 1.351(5) . ?
C08 N1 1.373(5) . ?
C08 C09 1.396(6) . ?
C08 C07 1.433(6) . ?
N1 C10 1.299(5) . ?
C01 H01 0.9500 . ?
C07 C06 1.423(6) . ?
C06 C05 1.373(6) . ?
C12 C13 1.396(6) . ?
C12 C11 1.400(6) . ?
C05 C04 1.408(6) . ?
C05 H05 0.9500 . ?
C10 C11 1.491(6) . ?
C03 C04 1.363(6) . ?
C11 C16 1.410(6) . ?
C13 C14 1.387(7) . ?
C14 C15 1.362(8) . ?
C14 H14 0.9500 . ?
C04 H04 0.9500 . ?
C16 C15 1.380(7) . ?
C15 H15 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
C09 S1 C10 88.32(19) . . ?
C03 C02 C01 121.8(4) . . ?
C03 C02 C07 119.0(4) . . ?
C01 C02 C07 119.2(4) . . ?
C01 N2 C09 114.7(4) . . ?
N1 C08 C09 114.9(4) . . ?
N1 C08 C07 127.1(4) . . ?
C09 C08 C07 118.0(4) . . ?
N2 C09 C08 127.2(4) . . ?
N2 C09 S1 122.8(3) . . ?
C08 C09 S1 109.9(3) . . ?
C10 N1 C08 110.8(3) . . ?
N2 C01 C02 125.4(4) . . ?
N2 C01 H01 117.3 . . ?
C02 C01 H01 117.3 . . ?
C06 C07 C08 126.7(4) . . ?
C06 C07 C02 118.0(4) . . ?
C08 C07 C02 115.4(4) . . ?
C05 C06 C07 120.4(4) . . ?
C05 C06 Cl2 117.3(3) . . ?
C07 C06 Cl2 122.2(3) . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 Cl3 118.9(4) . . ?
C11 C12 Cl3 120.9(3) . . ?
C06 C05 C04 121.7(4) . . ?
C06 C05 H05 119.1 . . ?
C04 C05 H05 119.1 . . ?
N1 C10 C11 121.3(4) . . ?
N1 C10 S1 116.1(3) . . ?
C11 C10 S1 122.6(3) . . ?
C04 C03 C02 122.1(4) . . ?
C04 C03 Cl1 118.5(3) . . ?
C02 C03 Cl1 119.4(3) . . ?
C12 C11 C16 117.5(4) . . ?
C12 C11 C10 120.4(4) . . ?
C16 C11 C10 122.0(4) . . ?
C14 C13 C12 120.4(5) . . ?
C14 C13 Cl4 119.0(4) . . ?
C12 C13 Cl4 120.6(4) . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C03 C04 C05 118.7(4) . . ?
C03 C04 H04 120.7 . . ?
C05 C04 H04 120.7 . . ?
C15 C16 C11 121.6(5) . . ?
C15 C16 Cl5 117.4(4) . . ?
C11 C16 Cl5 121.0(4) . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?

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
C01 N2 C09 C08 1.4(6) . . . . ?
C01 N2 C09 S1 178.0(3) . . . . ?
N1 C08 C09 N2 175.9(4) . . . . ?
C07 C08 C09 N2 -4.4(6) . . . . ?
N1 C08 C09 S1 -1.0(4) . . . . ?
C07 C08 C09 S1 178.7(3) . . . . ?
C10 S1 C09 N2 -176.3(4) . . . . ?
C10 S1 C09 C08 0.8(3) . . . . ?
C09 C08 N1 C10 0.7(5) . . . . ?
C07 C08 N1 C10 -179.0(4) . . . . ?
C09 N2 C01 C02 1.9(6) . . . . ?
C03 C02 C01 N2 176.6(4) . . . . ?
C07 C02 C01 N2 -2.1(6) . . . . ?
N1 C08 C07 C06 4.1(7) . . . . ?
C09 C08 C07 C06 -175.6(4) . . . . ?
N1 C08 C07 C02 -176.5(4) . . . . ?
C09 C08 C07 C02 3.8(5) . . . . ?
C03 C02 C07 C06 -0.3(6) . . . . ?
C01 C02 C07 C06 178.4(4) . . . . ?
C03 C02 C07 C08 -179.7(3) . . . . ?
C01 C02 C07 C08 -1.0(5) . . . . ?
C08 C07 C06 C05 177.5(4) . . . . ?
C02 C07 C06 C05 -1.9(6) . . . . ?
C08 C07 C06 Cl2 -0.9(6) . . . . ?
C02 C07 C06 Cl2 179.8(3) . . . . ?
C07 C06 C05 C04 2.9(7) . . . . ?
Cl2 C06 C05 C04 -178.7(3) . . . . ?
C08 N1 C10 C11 178.8(3) . . . . ?
C08 N1 C10 S1 -0.1(4) . . . . ?
C09 S1 C10 N1 -0.4(3) . . . . ?
C09 S1 C10 C11 -179.3(4) . . . . ?
C01 C02 C03 C04 -177.2(4) . . . . ?
C07 C02 C03 C04 1.5(6) . . . . ?
C01 C02 C03 Cl1 3.9(5) . . . . ?
C07 C02 C03 Cl1 -177.4(3) . . . . ?
C13 C12 C11 C16 -2.2(6) . . . . ?
Cl3 C12 C11 C16 176.1(3) . . . . ?
C13 C12 C11 C10 175.3(4) . . . . ?
Cl3 C12 C11 C10 -6.4(5) . . . . ?
N1 C10 C11 C12 -47.7(6) . . . . ?
S1 C10 C11 C12 131.1(4) . . . . ?
N1 C10 C11 C16 129.7(4) . . . . ?
S1 C10 C11 C16 -51.4(5) . . . . ?
C11 C12 C13 C14 1.2(6) . . . . ?
Cl3 C12 C13 C14 -177.2(3) . . . . ?
C11 C12 C13 Cl4 -177.8(3) . . . . ?
Cl3 C12 C13 Cl4 3.9(5) . . . . ?
C12 C13 C14 C15 0.4(7) . . . . ?
Cl4 C13 C14 C15 179.4(4) . . . . ?
C02 C03 C04 C05 -0.5(6) . . . . ?
Cl1 C03 C04 C05 178.4(3) . . . . ?
C06 C05 C04 C03 -1.7(7) . . . . ?
C12 C11 C16 C15 1.9(6) . . . . ?
C10 C11 C16 C15 -175.6(4) . . . . ?
C12 C11 C16 Cl5 -179.2(3) . . . . ?
C10 C11 C16 Cl5 3.3(6) . . . . ?
C13 C14 C15 C16 -0.7(7) . . . . ?
C11 C16 C15 C14 -0.4(7) . . . . ?
Cl5 C16 C15 C14 -179.3(4) . . . . ?

_refine_diff_density_max         2.344
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.109

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2100112'
loop_
_audit_author_name
_audit_author_address
'Samuel Guieu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 6,7,9-trifluoro-2-(2,3,5,6-tetrafluorophenyl)thiazolo[5,4-c]isoquinoline
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H3 F7 N2 S'
_chemical_formula_sum            'C16 H3 F7 N2 S'
_chemical_formula_weight         388.26

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   16.53(3)
_cell_length_b                   3.794(6)
_cell_length_c                   21.65(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.57(4)
_cell_angle_gamma                90
_cell_volume                     1351(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      2.477
_cell_measurement_theta_max      28.861

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.909
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   0.4546
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.331
_shelx_estimated_absorpt_T_min   0.778
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71076
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17784
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.477
_diffrn_reflns_theta_max         28.861
_diffrn_reflns_theta_full        25.243
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3516
_reflns_number_gt                2749
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.1117P)²+0.6997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3516
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1779
_refine_ls_wR_factor_gt          0.1604
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
S1 S 0.58203(3) 0.23153(15) 0.33147(3) 0.02244(19) Uani 1 1 d . . . . .
F1 F 0.15419(10) 0.7540(5) 0.43980(8) 0.0372(4) Uani 1 1 d . . . . .
F2 F 0.30507(8) 0.8446(4) 0.26811(6) 0.0234(3) Uani 1 1 d . . . . .
F3 F 0.27906(10) 0.4312(5) 0.50551(7) 0.0378(4) Uani 1 1 d . . . . .
F4 F 0.68543(9) 0.1624(4) 0.24404(7) 0.0333(4) Uani 1 1 d . . . . .
F5 F 0.50838(11) 0.7693(5) 0.04995(7) 0.0393(4) Uani 1 1 d . . . . .
F6 F 0.44679(9) 0.7409(4) 0.15636(7) 0.0290(4) Uani 1 1 d . . . . .
F7 F 0.74716(10) 0.2134(5) 0.13646(9) 0.0438(5) Uani 1 1 d . . . . .
N1 N 0.45544(11) 0.5293(5) 0.27270(8) 0.0191(4) Uani 1 1 d . . . . .
N2 N 0.49427(13) 0.2131(5) 0.43097(10) 0.0242(4) Uani 1 1 d . . . . .
C1 C 0.22239(15) 0.6905(7) 0.41312(12) 0.0254(5) Uani 1 1 d . . . . .
C2 C 0.28610(15) 0.5281(7) 0.44642(10) 0.0261(5) Uani 1 1 d . . . . .
C3 C 0.35833(14) 0.4562(6) 0.41991(10) 0.0213(5) Uani 1 1 d . . . . .
C4 C 0.36404(13) 0.5581(6) 0.35757(10) 0.0182(4) Uani 1 1 d . . . . .
C5 C 0.43759(13) 0.4721(6) 0.33232(10) 0.0178(4) Uani 1 1 d . . . . .
C6 C 0.52855(13) 0.4167(6) 0.26545(10) 0.0200(4) Uani 1 1 d . . . . .
C7 C 0.56311(13) 0.4457(6) 0.20595(10) 0.0209(5) Uani 1 1 d . . . . .
C8 C 0.64021(15) 0.3193(6) 0.19702(12) 0.0258(5) Uani 1 1 d . . . . .
C9 C 0.67234(15) 0.3426(7) 0.14106(13) 0.0303(6) Uani 1 1 d . . . . .
C10 C 0.62944(17) 0.4914(7) 0.09025(13) 0.0339(6) Uani 1 1 d . . . . .
H1 H 0.6512 0.5061 0.0523 0.041 Uiso 1 1 calc R U . . .
C11 C 0.22696(15) 0.7968(6) 0.35174(11) 0.0235(5) Uani 1 1 d . . . . .
H3 H 0.1833 0.9076 0.3293 0.028 Uiso 1 1 calc R U . . .
C12 C 0.29751(15) 0.7326(6) 0.32592(10) 0.0194(5) Uani 1 1 d . . . . .
C13 C 0.49853(14) 0.3073(6) 0.37083(10) 0.0202(5) Uani 1 1 d . . . . .
C14 C 0.42580(16) 0.2829(6) 0.45389(11) 0.0243(5) Uani 1 1 d . . . . .
H2 H 0.4205 0.2162 0.4946 0.029 Uiso 1 1 calc R U . . .
C15 C 0.55296(16) 0.6182(7) 0.09766(11) 0.0288(5) Uani 1 1 d . . . . .
C16 C 0.52027(14) 0.5998(6) 0.15373(11) 0.0235(5) 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
S1 C13 1.715(3) . ?
S1 C6 1.753(3) . ?
F1 C1 1.337(3) . ?
F2 C12 1.339(3) . ?
F3 C2 1.347(3) . ?
F4 C8 1.342(3) . ?
F5 C15 1.338(3) . ?
F6 C16 1.333(3) . ?
F7 C9 1.343(3) . ?
N1 C6 1.305(3) . ?
N1 C5 1.369(3) . ?
N2 C14 1.306(4) . ?
N2 C13 1.358(4) . ?
C1 C2 1.364(4) . ?
C1 C11 1.398(4) . ?
C2 C3 1.401(4) . ?
C3 C4 1.416(4) . ?
C3 C14 1.435(4) . ?
C4 C12 1.404(3) . ?
C4 C5 1.418(4) . ?
C5 C13 1.392(3) . ?
C6 C7 1.463(4) . ?
C7 C8 1.392(4) . ?
C7 C16 1.402(4) . ?
C8 C9 1.372(4) . ?
C9 C10 1.371(4) . ?
C10 C15 1.376(4) . ?
C10 H1 0.9300 . ?
C11 C12 1.363(4) . ?
C11 H3 0.9300 . ?
C14 H2 0.9300 . ?
C15 C16 1.377(4) . ?

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
C13 S1 C6 88.38(15) . . ?
C6 N1 C5 110.37(18) . . ?
C14 N2 C13 116.0(2) . . ?
F1 C1 C2 119.5(2) . . ?
F1 C1 C11 119.0(2) . . ?
C2 C1 C11 121.5(2) . . ?
F3 C2 C1 119.5(2) . . ?
F3 C2 C3 119.4(2) . . ?
C1 C2 C3 121.1(2) . . ?
C2 C3 C4 118.4(2) . . ?
C2 C3 C14 122.0(2) . . ?
C4 C3 C14 119.6(2) . . ?
C12 C4 C3 118.2(2) . . ?
C12 C4 C5 125.5(2) . . ?
C3 C4 C5 116.3(2) . . ?
N1 C5 C13 115.2(2) . . ?
N1 C5 C4 126.73(19) . . ?
C13 C5 C4 118.0(2) . . ?
N1 C6 C7 121.7(2) . . ?
N1 C6 S1 115.63(18) . . ?
C7 C6 S1 122.63(19) . . ?
C8 C7 C16 115.4(2) . . ?
C8 C7 C6 122.5(2) . . ?
C16 C7 C6 122.1(2) . . ?
F4 C8 C9 117.6(2) . . ?
F4 C8 C7 119.8(2) . . ?
C9 C8 C7 122.6(2) . . ?
F7 C9 C10 119.9(3) . . ?
F7 C9 C8 118.7(2) . . ?
C10 C9 C8 121.4(3) . . ?
C9 C10 C15 117.4(2) . . ?
C9 C10 H1 121.3 . . ?
C15 C10 H1 121.3 . . ?
C12 C11 C1 117.8(2) . . ?
C12 C11 H3 121.1 . . ?
C1 C11 H3 121.1 . . ?
F2 C12 C11 119.2(2) . . ?
F2 C12 C4 117.8(2) . . ?
C11 C12 C4 123.0(2) . . ?
N2 C13 C5 126.2(2) . . ?
N2 C13 S1 123.45(19) . . ?
C5 C13 S1 110.4(2) . . ?
N2 C14 C3 123.9(2) . . ?
N2 C14 H2 118.1 . . ?
C3 C14 H2 118.1 . . ?
F5 C15 C10 120.2(2) . . ?
F5 C15 C16 117.9(3) . . ?
C10 C15 C16 121.9(2) . . ?
F6 C16 C15 117.0(2) . . ?
F6 C16 C7 121.6(2) . . ?
C15 C16 C7 121.4(2) . . ?

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
F1 C1 C2 F3 0.6(4) . . . . ?
C11 C1 C2 F3 179.8(2) . . . . ?
F1 C1 C2 C3 179.7(2) . . . . ?
C11 C1 C2 C3 -1.1(4) . . . . ?
F3 C2 C3 C4 179.49(19) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
F3 C2 C3 C14 -0.3(3) . . . . ?
C1 C2 C3 C14 -179.4(2) . . . . ?
C2 C3 C4 C12 1.3(3) . . . . ?
C14 C3 C4 C12 -178.9(2) . . . . ?
C2 C3 C4 C5 -178.54(19) . . . . ?
C14 C3 C4 C5 1.2(3) . . . . ?
C6 N1 C5 C13 -0.9(3) . . . . ?
C6 N1 C5 C4 -179.8(2) . . . . ?
C12 C4 C5 N1 -3.0(4) . . . . ?
C3 C4 C5 N1 176.85(19) . . . . ?
C12 C4 C5 C13 178.1(2) . . . . ?
C3 C4 C5 C13 -2.0(3) . . . . ?
C5 N1 C6 C7 -179.97(19) . . . . ?
C5 N1 C6 S1 -0.2(2) . . . . ?
C13 S1 C6 N1 0.93(18) . . . . ?
C13 S1 C6 C7 -179.31(19) . . . . ?
N1 C6 C7 C8 -178.4(2) . . . . ?
S1 C6 C7 C8 1.8(3) . . . . ?
N1 C6 C7 C16 0.9(3) . . . . ?
S1 C6 C7 C16 -178.88(17) . . . . ?
C16 C7 C8 F4 -179.0(2) . . . . ?
C6 C7 C8 F4 0.3(3) . . . . ?
C16 C7 C8 C9 -0.1(3) . . . . ?
C6 C7 C8 C9 179.2(2) . . . . ?
F4 C8 C9 F7 -1.0(4) . . . . ?
C7 C8 C9 F7 -179.9(2) . . . . ?
F4 C8 C9 C10 178.5(2) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
F7 C9 C10 C15 179.7(2) . . . . ?
C8 C9 C10 C15 0.3(4) . . . . ?
F1 C1 C11 C12 179.2(2) . . . . ?
C2 C1 C11 C12 0.1(4) . . . . ?
C1 C11 C12 F2 -177.17(19) . . . . ?
C1 C11 C12 C4 1.7(3) . . . . ?
C3 C4 C12 F2 176.51(18) . . . . ?
C5 C4 C12 F2 -3.7(3) . . . . ?
C3 C4 C12 C11 -2.4(3) . . . . ?
C5 C4 C12 C11 177.4(2) . . . . ?
C14 N2 C13 C5 0.7(3) . . . . ?
C14 N2 C13 S1 -178.66(17) . . . . ?
N1 C5 C13 N2 -177.8(2) . . . . ?
C4 C5 C13 N2 1.2(3) . . . . ?
N1 C5 C13 S1 1.6(2) . . . . ?
C4 C5 C13 S1 -179.41(16) . . . . ?
C6 S1 C13 N2 178.1(2) . . . . ?
C6 S1 C13 C5 -1.34(17) . . . . ?
C13 N2 C14 C3 -1.6(3) . . . . ?
C2 C3 C14 N2 -179.6(2) . . . . ?
C4 C3 C14 N2 0.7(3) . . . . ?
C9 C10 C15 F5 179.4(2) . . . . ?
C9 C10 C15 C16 0.4(4) . . . . ?
F5 C15 C16 F6 -1.2(3) . . . . ?
C10 C15 C16 F6 177.9(2) . . . . ?
F5 C15 C16 C7 -180.0(2) . . . . ?
C10 C15 C16 C7 -0.9(4) . . . . ?
C8 C7 C16 F6 -178.0(2) . . . . ?
C6 C7 C16 F6 2.7(3) . . . . ?
C8 C7 C16 C15 0.8(3) . . . . ?
C6 C7 C16 C15 -178.6(2) . . . . ?

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
C10 H1 F1 0.93 2.60 3.459(6) 153.0 4_675
C11 H3 F6 0.93 2.54 3.319(5) 141.6 2
C14 H2 N2 0.93 2.61 3.295(5) 131.4 3_656
C10 H1 F1 0.93 2.60 3.459(6) 153.0 4_675
C11 H3 F6 0.93 2.54 3.319(5) 141.6 2
C14 H2 N2 0.93 2.61 3.295(5) 131.4 3_656

_refine_diff_density_max         1.062
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.120

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2100114'
loop_
_audit_author_name
_audit_author_address
'Samuel Guieu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
2-(2-fluoro-6-(trifluoromethyl)phenyl)-6-(trifluoromethyl)thiazolo[5,4-c]isoquinoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H7 F7 N2 S1'
_chemical_formula_sum            'C36 H14 F14 N4 S2'
_chemical_formula_weight         832.63

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      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                   8.139(2)
_cell_length_b                   37.120(6)
_cell_length_c                   10.902(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.83(2)
_cell_angle_gamma                90
_cell_volume                     3276.7(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1776
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      24.13

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   0.6624
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.279
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.989
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            65242
_diffrn_reflns_av_unetI/netI     0.1306
_diffrn_reflns_av_R_equivalents  0.1666
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -53
_diffrn_reflns_limit_k_max       53
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.097
_diffrn_reflns_theta_max         30.614
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10047
_reflns_number_gt                4970
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0515P)²+0.6428P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10047
_refine_ls_number_parameters     505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1741
_refine_ls_wR_factor_gt          0.1372
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
S01A S -0.00247(13) 0.53738(2) 0.36657(8) 0.0375(2) Uani 1 1 d . . . . .
S01B S 0.74274(11) 0.71296(2) 0.93118(7) 0.0300(2) Uani 1 1 d . . . . .
F5A F 0.2140(3) 0.68792(7) -0.1225(2) 0.0698(8) Uani 1 1 d . . . . .
F6A F 0.0626(2) 0.64097(6) -0.14259(17) 0.0490(6) Uani 1 1 d . . . . .
F2A F 0.3940(2) 0.55878(6) 0.76550(19) 0.0508(6) Uani 1 1 d . . . . .
F3A F 0.3260(3) 0.54782(9) 0.5747(2) 0.0818(9) Uani 1 1 d . . . . .
F4A F 0.2944(3) 0.60050(7) 0.6463(2) 0.0663(8) Uani 1 1 d . . . . .
F1A F -0.3081(2) 0.55318(6) 0.55680(19) 0.0521(6) Uani 1 1 d . . . . .
F7A F 0.3182(2) 0.63595(7) -0.07949(19) 0.0539(6) Uani 1 1 d . . . . .
F5B F 0.5092(3) 0.52059(5) 1.2093(2) 0.0542(6) Uani 1 1 d . . . . .
F7B F 0.7054(3) 0.53608(5) 1.1041(2) 0.0472(5) Uani 1 1 d . . . . .
F1B F 0.9945(2) 0.76923(5) 1.0539(2) 0.0456(5) Uani 1 1 d . . . . .
F4B F 0.3716(2) 0.76121(5) 1.00797(18) 0.0417(5) Uani 1 1 d . . . . .
F2B F 0.3752(2) 0.76458(6) 1.20527(19) 0.0431(5) Uani 1 1 d . . . . .
F3B F 0.3017(2) 0.81031(6) 1.0930(2) 0.0531(6) Uani 1 1 d . . . . .
F6B F 0.4548(3) 0.54415(5) 1.02981(19) 0.0462(6) Uani 1 1 d . . . . .
N01A N 0.0170(3) 0.60326(6) 0.4465(2) 0.0257(6) Uani 1 1 d . . . . .
N01B N 0.6483(3) 0.71325(7) 1.1527(2) 0.0259(6) Uani 1 1 d . . . . .
N02B N 0.7058(3) 0.63958(7) 0.9408(2) 0.0288(6) Uani 1 1 d . . . . .
C04A C 0.1495(5) 0.69427(9) 0.1129(3) 0.0394(9) Uani 1 1 d . . . . .
H04A H 0.176463 0.714541 0.065728 0.047 Uiso 1 1 calc R U . . .
C05A C 0.1142(5) 0.69918(9) 0.2352(3) 0.0448(10) Uani 1 1 d . . . . .
H05A H 0.114794 0.722750 0.269254 0.054 Uiso 1 1 calc R U . . .
C06A C 0.0789(4) 0.67028(9) 0.3055(3) 0.0366(8) Uani 1 1 d . . . . .
H06A H 0.057224 0.673727 0.388740 0.044 Uiso 1 1 calc R U . . .
C07A C 0.0745(4) 0.63550(8) 0.2549(3) 0.0269(7) Uani 1 1 d . . . . .
C08A C 0.0420(4) 0.60388(8) 0.3225(3) 0.0238(7) Uani 1 1 d . . . . .
C10A C -0.0053(4) 0.57025(8) 0.4805(3) 0.0248(7) Uani 1 1 d . . . . .
C11A C -0.0245(4) 0.55882(8) 0.6093(3) 0.0232(6) Uani 1 1 d . . . . .
C12A C -0.1783(4) 0.54974(9) 0.6428(3) 0.0296(7) Uani 1 1 d . . . . .
C13A C -0.2048(4) 0.53733(9) 0.7585(3) 0.0338(8) Uani 1 1 d . . . . .
H13A H -0.312982 0.531629 0.777833 0.041 Uiso 1 1 calc R U . . .
C14A C -0.0706(4) 0.53340(9) 0.8452(3) 0.0333(8) Uani 1 1 d . . . . .
H14A H -0.085418 0.524509 0.925058 0.040 Uiso 1 1 calc R U . . .
C18A C 0.1842(4) 0.65655(10) -0.0698(3) 0.0383(9) Uani 1 1 d . . . . .
C03A C 0.1456(4) 0.66074(9) 0.0608(3) 0.0302(7) Uani 1 1 d . . . . .
C09A C 0.0377(4) 0.57099(8) 0.2642(3) 0.0289(7) Uani 1 1 d . . . . .
N02A N 0.0657(4) 0.56517(7) 0.1444(2) 0.0375(7) Uani 1 1 d . . . . .
C01A C 0.0995(4) 0.59438(9) 0.0832(3) 0.0322(8) Uani 1 1 d . . . . .
H01A H 0.120674 0.591382 -0.000249 0.039 Uiso 1 1 calc R U . . .
C02A C 0.1070(4) 0.62995(8) 0.1311(3) 0.0265(7) Uani 1 1 d . . . . .
C15A C 0.0862(4) 0.54242(8) 0.8159(3) 0.0298(7) Uani 1 1 d . . . . .
H15A H 0.178327 0.539664 0.876060 0.036 Uiso 1 1 calc R U . . .
C16A C 0.1097(4) 0.55536(8) 0.7002(3) 0.0257(7) Uani 1 1 d . . . . .
C17A C 0.2801(4) 0.56514(11) 0.6715(3) 0.0400(9) Uani 1 1 d . . . . .
C14B C 0.7711(4) 0.84629(8) 1.1468(3) 0.0315(8) Uani 1 1 d . . . . .
H14B H 0.790801 0.870607 1.171239 0.038 Uiso 1 1 calc R U . . .
C13B C 0.8987(4) 0.82542(8) 1.1138(3) 0.0295(7) Uani 1 1 d . . . . .
H13B H 1.006332 0.835203 1.112074 0.035 Uiso 1 1 calc R U . . .
C12B C 0.8666(4) 0.78981(9) 1.0832(3) 0.0288(7) Uani 1 1 d . . . . .
C11B C 0.7129(4) 0.77357(8) 1.0843(3) 0.0248(7) Uani 1 1 d . . . . .
C10B C 0.6966(4) 0.73423(8) 1.0660(3) 0.0259(7) Uani 1 1 d . . . . .
C08B C 0.6475(4) 0.67795(8) 1.1130(3) 0.0245(7) Uani 1 1 d . . . . .
C07B C 0.6009(4) 0.64794(8) 1.1827(3) 0.0268(7) Uani 1 1 d . . . . .
C02B C 0.6080(4) 0.61383(8) 1.1254(3) 0.0243(7) Uani 1 1 d . . . . .
C03B C 0.5563(4) 0.58296(8) 1.1915(3) 0.0281(7) Uani 1 1 d . . . . .
C04B C 0.5034(4) 0.58696(9) 1.3056(3) 0.0354(8) Uani 1 1 d . . . . .
H04B H 0.470050 0.566345 1.348416 0.042 Uiso 1 1 calc R U . . .
C18B C 0.5560(4) 0.54633(9) 1.1344(3) 0.0335(8) Uani 1 1 d . . . . .
C01B C 0.6637(4) 0.61186(8) 1.0055(3) 0.0277(7) Uani 1 1 d . . . . .
H01B H 0.670951 0.588646 0.969723 0.033 Uiso 1 1 calc R U . . .
C09B C 0.6956(4) 0.67225(8) 0.9967(3) 0.0250(7) Uani 1 1 d . . . . .
C15B C 0.6132(4) 0.83190(8) 1.1446(3) 0.0287(7) Uani 1 1 d . . . . .
H15B H 0.524775 0.846643 1.165436 0.034 Uiso 1 1 calc R U . . .
C16B C 0.5839(4) 0.79637(8) 1.1123(3) 0.0261(7) Uani 1 1 d . . . . .
C17B C 0.4092(4) 0.78294(10) 1.1049(3) 0.0364(8) Uani 1 1 d . . . . .
C06B C 0.5460(4) 0.65087(9) 1.3009(3) 0.0340(8) Uani 1 1 d . . . . .
H06B H 0.542800 0.673795 1.339330 0.041 Uiso 1 1 calc R U . . .
C05B C 0.4976(5) 0.62089(9) 1.3605(3) 0.0400(9) Uani 1 1 d . . . . .
H05B H 0.459635 0.623140 1.439754 0.048 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
S01A C09A 1.727(3) . ?
S01A C10A 1.743(3) . ?
S01B C09B 1.731(3) . ?
S01B C10B 1.742(3) . ?
F5A C18A 1.332(4) . ?
F6A C18A 1.335(4) . ?
F2A C17A 1.331(4) . ?
F3A C17A 1.321(4) . ?
F4A C17A 1.349(4) . ?
F1A C12A 1.345(3) . ?
F7A C18A 1.345(4) . ?
F5B C18B 1.337(4) . ?
F7B C18B 1.347(4) . ?
F1B C12B 1.355(4) . ?
F4B C17B 1.339(4) . ?
F2B C17B 1.342(4) . ?
F3B C17B 1.339(4) . ?
F6B C18B 1.339(4) . ?
N01A C10A 1.298(4) . ?
N01A C08A 1.387(4) . ?
N01B C10B 1.316(4) . ?
N01B C08B 1.380(4) . ?
N02B C01B 1.312(4) . ?
N02B C09B 1.364(4) . ?
C04A C03A 1.367(5) . ?
C04A C05A 1.404(5) . ?
C05A C06A 1.366(5) . ?
C06A C07A 1.403(4) . ?
C07A C02A 1.416(4) . ?
C07A C08A 1.425(4) . ?
C08A C09A 1.375(4) . ?
C10A C11A 1.491(4) . ?
C11A C12A 1.381(4) . ?
C11A C16A 1.404(4) . ?
C12A C13A 1.380(4) . ?
C13A C14A 1.378(5) . ?
C14A C15A 1.388(5) . ?
C18A C03A 1.497(5) . ?
C03A C02A 1.429(4) . ?
C09A N02A 1.365(4) . ?
N02A C01A 1.317(4) . ?
C01A C02A 1.419(4) . ?
C15A C16A 1.382(4) . ?
C16A C17A 1.497(5) . ?
C14B C13B 1.373(5) . ?
C14B C15B 1.390(5) . ?
C13B C12B 1.382(4) . ?
C12B C11B 1.390(4) . ?
C11B C16B 1.406(4) . ?
C11B C10B 1.478(4) . ?
C08B C09B 1.380(4) . ?
C08B C07B 1.422(4) . ?
C07B C06B 1.411(4) . ?
C07B C02B 1.416(4) . ?
C02B C01B 1.429(4) . ?
C02B C03B 1.439(4) . ?
C03B C04B 1.365(4) . ?
C03B C18B 1.496(4) . ?
C04B C05B 1.397(5) . ?
C15B C16B 1.380(4) . ?
C16B C17B 1.501(5) . ?
C06B C05B 1.367(4) . ?

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
C09A S01A C10A 88.39(15) . . ?
C09B S01B C10B 88.38(15) . . ?
C10A N01A C08A 109.4(2) . . ?
C10B N01B C08B 109.2(3) . . ?
C01B N02B C09B 115.2(3) . . ?
C03A C04A C05A 121.0(3) . . ?
C06A C05A C04A 120.4(3) . . ?
C05A C06A C07A 120.0(3) . . ?
C06A C07A C02A 120.6(3) . . ?
C06A C07A C08A 123.6(3) . . ?
C02A C07A C08A 115.8(3) . . ?
C09A C08A N01A 115.9(3) . . ?
C09A C08A C07A 119.3(3) . . ?
N01A C08A C07A 124.8(3) . . ?
N01A C10A C11A 124.7(3) . . ?
N01A C10A S01A 116.4(2) . . ?
C11A C10A S01A 118.8(2) . . ?
C12A C11A C16A 116.9(3) . . ?
C12A C11A C10A 120.2(3) . . ?
C16A C11A C10A 122.8(3) . . ?
F1A C12A C13A 119.0(3) . . ?
F1A C12A C11A 117.4(3) . . ?
C13A C12A C11A 123.6(3) . . ?
C14A C13A C12A 118.4(3) . . ?
C13A C14A C15A 120.0(3) . . ?
F5A C18A F6A 106.2(3) . . ?
F5A C18A F7A 106.2(3) . . ?
F6A C18A F7A 105.4(3) . . ?
F5A C18A C03A 112.6(3) . . ?
F6A C18A C03A 113.3(3) . . ?
F7A C18A C03A 112.6(3) . . ?
C04A C03A C02A 120.1(3) . . ?
C04A C03A C18A 119.5(3) . . ?
C02A C03A C18A 120.4(3) . . ?
N02A C09A C08A 125.7(3) . . ?
N02A C09A S01A 124.4(2) . . ?
C08A C09A S01A 109.9(2) . . ?
C01A N02A C09A 114.7(3) . . ?
N02A C01A C02A 125.7(3) . . ?
C07A C02A C01A 118.7(3) . . ?
C07A C02A C03A 117.9(3) . . ?
C01A C02A C03A 123.4(3) . . ?
C16A C15A C14A 120.7(3) . . ?
C15A C16A C11A 120.4(3) . . ?
C15A C16A C17A 119.5(3) . . ?
C11A C16A C17A 120.1(3) . . ?
F3A C17A F2A 107.3(3) . . ?
F3A C17A F4A 105.9(3) . . ?
F2A C17A F4A 105.2(3) . . ?
F3A C17A C16A 113.1(3) . . ?
F2A C17A C16A 112.5(3) . . ?
F4A C17A C16A 112.3(3) . . ?
C13B C14B C15B 120.1(3) . . ?
C14B C13B C12B 118.3(3) . . ?
F1B C12B C13B 117.7(3) . . ?
F1B C12B C11B 118.1(3) . . ?
C13B C12B C11B 124.1(3) . . ?
C12B C11B C16B 115.7(3) . . ?
C12B C11B C10B 119.7(3) . . ?
C16B C11B C10B 124.5(3) . . ?
N01B C10B C11B 121.1(3) . . ?
N01B C10B S01B 116.3(2) . . ?
C11B C10B S01B 122.5(2) . . ?
N01B C08B C09B 116.2(3) . . ?
N01B C08B C07B 124.7(3) . . ?
C09B C08B C07B 119.1(3) . . ?
C06B C07B C02B 120.2(3) . . ?
C06B C07B C08B 123.7(3) . . ?
C02B C07B C08B 116.1(3) . . ?
C07B C02B C01B 118.7(3) . . ?
C07B C02B C03B 117.7(3) . . ?
C01B C02B C03B 123.6(3) . . ?
C04B C03B C02B 120.3(3) . . ?
C04B C03B C18B 119.4(3) . . ?
C02B C03B C18B 120.2(3) . . ?
C03B C04B C05B 121.1(3) . . ?
F5B C18B F6B 106.8(3) . . ?
F5B C18B F7B 105.6(3) . . ?
F6B C18B F7B 105.5(3) . . ?
F5B C18B C03B 112.5(3) . . ?
F6B C18B C03B 112.6(3) . . ?
F7B C18B C03B 113.3(3) . . ?
N02B C01B C02B 125.2(3) . . ?
N02B C09B C08B 125.6(3) . . ?
N02B C09B S01B 124.4(2) . . ?
C08B C09B S01B 109.9(2) . . ?
C16B C15B C14B 120.5(3) . . ?
C15B C16B C11B 121.2(3) . . ?
C15B C16B C17B 118.0(3) . . ?
C11B C16B C17B 120.8(3) . . ?
F3B C17B F4B 106.6(3) . . ?
F3B C17B F2B 106.1(3) . . ?
F4B C17B F2B 106.7(3) . . ?
F3B C17B C16B 111.1(3) . . ?
F4B C17B C16B 112.5(3) . . ?
F2B C17B C16B 113.4(3) . . ?
C05B C06B C07B 120.3(3) . . ?
C06B C05B C04B 120.4(3) . . ?

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.083


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2100117'
loop_
_audit_author_name
_audit_author_address
'Samuel Guieu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
2,5-bis(2-chloro-6-methylphenyl)thiazolo[5,4-d]thiazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 Cl2 N2 S2'
_chemical_formula_sum            'C9 H6 Cl N S'
_chemical_formula_weight         195.66

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'
S S 0.1246 0.1234 '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'

_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'

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

_cell_length_a                   12.5438(9)
_cell_length_b                   14.9504(11)
_cell_length_c                   9.2980(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1743.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5841
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      26.29

_exptl_crystal_description       flake
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   0.6339
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.613
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.970
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20890
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.049
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_full        25.242
_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             1794
_reflns_number_gt                1413
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1373P)²+6.9505P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1794
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0870
_refine_ls_wR_factor_ref         0.2688
_refine_ls_wR_factor_gt          0.2478
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
Cl1 Cl 0.84362(12) 0.50796(12) 0.66513(19) 0.0634(6) Uani 1 1 d . . . . .
S1 S 0.63765(13) 0.54005(12) 0.4044(3) 0.0773(8) Uani 1 1 d . . . . .
N1 N 0.5762(3) 0.4038(3) 0.5507(5) 0.0451(11) Uani 1 1 d . . . . .
N2 C 0.6753(4) 0.2835(3) 0.2810(5) 0.0375(11) Uani 1 1 d . . . . .
H2A H 0.701714 0.265606 0.186125 0.056 Uiso 1 1 calc R U . . .
H2B H 0.622613 0.331410 0.270035 0.056 Uiso 1 1 calc R U . . .
H2C H 0.641854 0.231959 0.328165 0.056 Uiso 1 1 calc R U . . .
C1 C 0.9581(5) 0.3058(4) 0.4444(7) 0.0546(15) Uani 1 1 d . . . . .
H1 H 1.024733 0.276102 0.435943 0.065 Uiso 1 1 calc R U . . .
C2 C 0.8718(5) 0.2768(3) 0.3649(7) 0.0504(15) Uani 1 1 d . . . . .
H2 H 0.880375 0.227752 0.300948 0.060 Uiso 1 1 calc R U . . .
C3 C 0.7719(4) 0.3182(3) 0.3764(6) 0.0415(12) Uani 1 1 d . . . . .
C4 C 0.7617(3) 0.3903(3) 0.4706(5) 0.0314(10) Uani 1 1 d . . . . .
C5 C 0.6572(3) 0.4369(3) 0.4843(5) 0.0319(10) Uani 1 1 d . . . . .
C6 C 0.5079(4) 0.5379(3) 0.4627(6) 0.0395(11) Uani 1 1 d . . . . .
C7 C 0.9479(4) 0.3770(4) 0.5349(6) 0.0481(13) Uani 1 1 d . . . . .
H3 H 1.007343 0.397247 0.589134 0.058 Uiso 1 1 calc R U . . .
C8 C 0.8509(4) 0.4193(3) 0.5472(6) 0.0377(11) 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
Cl1 C8 1.722(5) . ?
S1 C6 1.715(5) . ?
S1 C5 1.729(5) . ?
N1 C5 1.289(6) . ?
N1 C6 1.374(6) 5_666 ?
N2 C3 1.589(7) . ?
N2 H2A 0.9800 . ?
N2 H2B 0.9800 . ?
N2 H2C 0.9800 . ?
C1 C7 1.363(9) . ?
C1 C2 1.380(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.402(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(7) . ?
C4 C8 1.395(7) . ?
C4 C5 1.490(6) . ?
C6 C6 1.345(9) 5_666 ?
C7 C8 1.376(7) . ?
C7 H3 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
C6 S1 C5 89.0(2) . . ?
C5 N1 C6 108.6(4) . 5_666 ?
C3 N2 H2A 109.5 . . ?
C3 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C3 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C7 C1 C2 120.2(5) . . ?
C7 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C1 C2 C3 121.4(5) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 118.1(5) . . ?
C4 C3 N2 122.2(4) . . ?
C2 C3 N2 119.7(5) . . ?
C3 C4 C8 119.1(4) . . ?
C3 C4 C5 119.7(4) . . ?
C8 C4 C5 121.1(4) . . ?
N1 C5 C4 123.7(4) . . ?
N1 C5 S1 115.9(3) . . ?
C4 C5 S1 120.4(3) . . ?
C6 C6 N1 117.9(6) 5_666 5_666 ?
C6 C6 S1 108.6(5) 5_666 . ?
N1 C6 S1 133.5(4) 5_666 . ?
C1 C7 C8 119.6(6) . . ?
C1 C7 H3 120.2 . . ?
C8 C7 H3 120.2 . . ?
C7 C8 C4 121.6(5) . . ?
C7 C8 Cl1 117.0(4) . . ?
C4 C8 Cl1 121.4(3) . . ?

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
C7 C1 C2 C3 -1.1(9) . . . . ?
C1 C2 C3 C4 0.3(8) . . . . ?
C1 C2 C3 N2 179.1(5) . . . . ?
C2 C3 C4 C8 1.1(7) . . . . ?
N2 C3 C4 C8 -177.6(4) . . . . ?
C2 C3 C4 C5 179.1(4) . . . . ?
N2 C3 C4 C5 0.3(7) . . . . ?
C6 N1 C5 C4 -177.3(5) 5_666 . . . ?
C6 N1 C5 S1 0.8(6) 5_666 . . . ?
C3 C4 C5 N1 74.0(7) . . . . ?
C8 C4 C5 N1 -108.1(6) . . . . ?
C3 C4 C5 S1 -104.0(5) . . . . ?
C8 C4 C5 S1 73.9(6) . . . . ?
C6 S1 C5 N1 -1.1(5) . . . . ?
C6 S1 C5 C4 177.1(4) . . . . ?
C5 S1 C6 C6 1.0(6) . . . 5_666 ?
C5 S1 C6 N1 180.0(6) . . . 5_666 ?
C2 C1 C7 C8 0.4(9) . . . . ?
C1 C7 C8 C4 1.0(8) . . . . ?
C1 C7 C8 Cl1 179.3(4) . . . . ?
C3 C4 C8 C7 -1.8(7) . . . . ?
C5 C4 C8 C7 -179.7(5) . . . . ?
C3 C4 C8 Cl1 -180.0(4) . . . . ?
C5 C4 C8 Cl1 2.1(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
C2 H2 S1 0.95 2.98 3.561(5) 121.2 6_755 yes
C2 H2 S1 0.95 2.98 3.561(5) 121.2 6_755 yes

_refine_diff_density_max         1.109
_refine_diff_density_min         -0.939
_refine_diff_density_rms         0.113


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 2100116'
loop_
_audit_author_name
_audit_author_address
'Samuel Guieu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
2-(2-chloro-6-methylphenyl)-6-methylthiazolo[5,4-c]isoquinoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Cl N2 S'
_chemical_formula_sum            'C18 H13 Cl N2 S'
_chemical_formula_weight         324.81

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'
S S 0.1246 0.1234 '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'

_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                   7.3032(8)
_cell_length_b                   15.9713(16)
_cell_length_c                   13.2331(16)
_cell_angle_alpha                90
_cell_angle_beta                 97.530(4)
_cell_angle_gamma                90
_cell_volume                     1530.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8730
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   0.5908
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.383
_shelx_estimated_absorpt_T_min   0.803
_shelx_estimated_absorpt_T_max   0.862
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15522
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.551
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3780
_reflns_number_gt                3155
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0593P)²+0.9062P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3780
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
Cl1 Cl 0.79490(8) 0.70374(4) 0.84413(4) 0.05425(19) Uani 1 1 d . . . . .
S1 S 0.30542(8) 0.72303(3) 0.75449(4) 0.04284(16) Uani 1 1 d . . . . .
N1 N 0.4042(2) 0.56692(9) 0.75319(11) 0.0302(3) Uani 1 1 d . . . . .
N2 N 0.1660(2) 0.69975(12) 0.55382(14) 0.0422(4) Uani 1 1 d . . . . .
C1 C 0.0851(4) 0.5408(2) 0.28980(16) 0.0588(7) Uani 1 1 d . . . . .
H1 H 0.088133 0.496968 0.238181 0.088 Uiso 1 1 calc R U . . .
H12 H 0.153516 0.589849 0.270818 0.088 Uiso 1 1 calc R U . . .
H11 H -0.043338 0.556538 0.294109 0.088 Uiso 1 1 calc R U . . .
C2 C 0.1730(3) 0.50825(16) 0.39214(15) 0.0422(5) Uani 1 1 d . . . . .
C3 C 0.1996(2) 0.56143(13) 0.47973(14) 0.0341(4) Uani 1 1 d . . . . .
C4 C 0.2876(2) 0.52871(12) 0.57334(13) 0.0301(4) Uani 1 1 d . . . . .
C5 C 0.3151(2) 0.58544(11) 0.65676(13) 0.0287(3) Uani 1 1 d . . . . .
C6 C 0.4092(3) 0.63284(11) 0.81079(14) 0.0323(4) Uani 1 1 d . . . . .
C7 C 0.4984(3) 0.63575(11) 0.91836(14) 0.0327(4) Uani 1 1 d . . . . .
C8 C 0.4052(3) 0.60606(12) 0.99754(15) 0.0365(4) Uani 1 1 d . . . . .
C9 C 0.4940(3) 0.61093(14) 1.09693(16) 0.0449(5) Uani 1 1 d . . . . .
H3 H 0.433017 0.590637 1.151180 0.054 Uiso 1 1 calc R U . . .
C10 C 0.6691(3) 0.64469(14) 1.11852(16) 0.0477(5) Uani 1 1 d . . . . .
H2 H 0.725725 0.647900 1.187256 0.057 Uiso 1 1 calc R U . . .
C11 C 0.2089(3) 0.56923(14) 0.97561(17) 0.0446(5) Uani 1 1 d . . . . .
H5 H 0.169255 0.549446 1.039407 0.067 Uiso 1 1 calc R U . . .
H4 H 0.209065 0.522292 0.927933 0.067 Uiso 1 1 calc R U . . .
H6 H 0.123551 0.612559 0.945561 0.067 Uiso 1 1 calc R U . . .
C12 C 0.6756(3) 0.66830(12) 0.94191(14) 0.0360(4) Uani 1 1 d . . . . .
C13 C 0.7624(3) 0.67373(14) 1.04161(16) 0.0437(5) Uani 1 1 d . . . . .
H7 H 0.882846 0.696827 1.056322 0.052 Uiso 1 1 calc R U . . .
C14 C 0.2530(3) 0.66707(12) 0.64205(14) 0.0345(4) Uani 1 1 d . . . . .
C15 C 0.2318(3) 0.42728(16) 0.40228(16) 0.0466(5) Uani 1 1 d . . . . .
H8 H 0.213621 0.391461 0.344519 0.056 Uiso 1 1 calc R U . . .
C16 C 0.3185(3) 0.39497(14) 0.49537(17) 0.0448(5) Uani 1 1 d . . . . .
H10 H 0.357878 0.338241 0.499293 0.054 Uiso 1 1 calc R U . . .
C17 C 0.3466(3) 0.44473(12) 0.58050(15) 0.0358(4) Uani 1 1 d . . . . .
H9 H 0.405045 0.422858 0.643332 0.043 Uiso 1 1 calc R U . . .
C18 C 0.1432(3) 0.64664(14) 0.47689(16) 0.0422(5) Uani 1 1 d . . . . .
H13 H 0.083469 0.667265 0.413696 0.051 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
Cl1 C12 1.746(2) . ?
S1 C14 1.735(2) . ?
S1 C6 1.7484(19) . ?
N1 C6 1.297(2) . ?
N1 C5 1.386(2) . ?
N2 C18 1.319(3) . ?
N2 C14 1.358(2) . ?
C1 C2 1.512(3) . ?
C1 H1 0.9800 . ?
C1 H12 0.9800 . ?
C1 H11 0.9800 . ?
C2 C15 1.364(3) . ?
C2 C3 1.430(3) . ?
C3 C4 1.418(2) . ?
C3 C18 1.421(3) . ?
C4 C17 1.408(3) . ?
C4 C5 1.422(2) . ?
C5 C14 1.386(3) . ?
C6 C7 1.486(2) . ?
C7 C12 1.392(3) . ?
C7 C8 1.404(3) . ?
C8 C9 1.390(3) . ?
C8 C11 1.542(3) . ?
C9 C10 1.383(3) . ?
C9 H3 0.9500 . ?
C10 C13 1.378(3) . ?
C10 H2 0.9500 . ?
C11 H5 0.9800 . ?
C11 H4 0.9800 . ?
C11 H6 0.9800 . ?
C12 C13 1.389(3) . ?
C13 H7 0.9500 . ?
C15 C16 1.407(3) . ?
C15 H8 0.9500 . ?
C16 C17 1.372(3) . ?
C16 H10 0.9500 . ?
C17 H9 0.9500 . ?
C18 H13 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
C14 S1 C6 88.60(9) . . ?
C6 N1 C5 109.96(15) . . ?
C18 N2 C14 114.45(18) . . ?
C2 C1 H1 109.5 . . ?
C2 C1 H12 109.5 . . ?
H1 C1 H12 109.5 . . ?
C2 C1 H11 109.5 . . ?
H1 C1 H11 109.5 . . ?
H12 C1 H11 109.5 . . ?
C15 C2 C3 118.42(19) . . ?
C15 C2 C1 120.3(2) . . ?
C3 C2 C1 121.2(2) . . ?
C4 C3 C18 118.20(17) . . ?
C4 C3 C2 119.16(19) . . ?
C18 C3 C2 122.64(18) . . ?
C17 C4 C3 120.62(17) . . ?
C17 C4 C5 122.94(17) . . ?
C3 C4 C5 116.43(17) . . ?
C14 C5 N1 115.83(16) . . ?
C14 C5 C4 118.68(16) . . ?
N1 C5 C4 125.47(16) . . ?
N1 C6 C7 124.27(16) . . ?
N1 C6 S1 116.17(14) . . ?
C7 C6 S1 119.56(13) . . ?
C12 C7 C8 119.09(17) . . ?
C12 C7 C6 120.26(17) . . ?
C8 C7 C6 120.65(17) . . ?
C9 C8 C7 118.40(19) . . ?
C9 C8 C11 120.41(19) . . ?
C7 C8 C11 121.19(18) . . ?
C10 C9 C8 121.4(2) . . ?
C10 C9 H3 119.3 . . ?
C8 C9 H3 119.3 . . ?
C13 C10 C9 120.8(2) . . ?
C13 C10 H2 119.6 . . ?
C9 C10 H2 119.6 . . ?
C8 C11 H5 109.5 . . ?
C8 C11 H4 109.5 . . ?
H5 C11 H4 109.5 . . ?
C8 C11 H6 109.5 . . ?
H5 C11 H6 109.5 . . ?
H4 C11 H6 109.5 . . ?
C13 C12 C7 122.08(19) . . ?
C13 C12 Cl1 118.27(16) . . ?
C7 C12 Cl1 119.65(15) . . ?
C10 C13 C12 118.2(2) . . ?
C10 C13 H7 120.9 . . ?
C12 C13 H7 120.9 . . ?
N2 C14 C5 126.16(18) . . ?
N2 C14 S1 124.41(15) . . ?
C5 C14 S1 109.43(13) . . ?
C2 C15 C16 122.25(19) . . ?
C2 C15 H8 118.9 . . ?
C16 C15 H8 118.9 . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H10 119.7 . . ?
C15 C16 H10 119.7 . . ?
C16 C17 C4 119.00(19) . . ?
C16 C17 H9 120.5 . . ?
C4 C17 H9 120.5 . . ?
N2 C18 C3 126.07(18) . . ?
N2 C18 H13 117.0 . . ?
C3 C18 H13 117.0 . . ?

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
C15 C2 C3 C4 0.7(3) . . . . ?
C1 C2 C3 C4 -178.19(17) . . . . ?
C15 C2 C3 C18 180.00(19) . . . . ?
C1 C2 C3 C18 1.1(3) . . . . ?
C18 C3 C4 C17 -179.91(17) . . . . ?
C2 C3 C4 C17 -0.5(3) . . . . ?
C18 C3 C4 C5 -1.3(2) . . . . ?
C2 C3 C4 C5 178.10(16) . . . . ?
C6 N1 C5 C14 0.2(2) . . . . ?
C6 N1 C5 C4 178.70(17) . . . . ?
C17 C4 C5 C14 179.63(17) . . . . ?
C3 C4 C5 C14 1.0(2) . . . . ?
C17 C4 C5 N1 1.2(3) . . . . ?
C3 C4 C5 N1 -177.40(16) . . . . ?
C5 N1 C6 C7 -178.58(17) . . . . ?
C5 N1 C6 S1 0.5(2) . . . . ?
C14 S1 C6 N1 -0.85(16) . . . . ?
C14 S1 C6 C7 178.29(16) . . . . ?
N1 C6 C7 C12 98.4(2) . . . . ?
S1 C6 C7 C12 -80.6(2) . . . . ?
N1 C6 C7 C8 -81.8(2) . . . . ?
S1 C6 C7 C8 99.17(19) . . . . ?
C12 C7 C8 C9 0.4(3) . . . . ?
C6 C7 C8 C9 -179.39(18) . . . . ?
C12 C7 C8 C11 -179.87(18) . . . . ?
C6 C7 C8 C11 0.3(3) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C11 C8 C9 C10 -179.2(2) . . . . ?
C8 C9 C10 C13 -0.8(3) . . . . ?
C8 C7 C12 C13 -1.1(3) . . . . ?
C6 C7 C12 C13 178.67(18) . . . . ?
C8 C7 C12 Cl1 178.86(14) . . . . ?
C6 C7 C12 Cl1 -1.3(2) . . . . ?
C9 C10 C13 C12 0.1(3) . . . . ?
C7 C12 C13 C10 0.9(3) . . . . ?
Cl1 C12 C13 C10 -179.14(17) . . . . ?
C18 N2 C14 C5 -0.6(3) . . . . ?
C18 N2 C14 S1 178.63(16) . . . . ?
N1 C5 C14 N2 178.52(18) . . . . ?
C4 C5 C14 N2 -0.1(3) . . . . ?
N1 C5 C14 S1 -0.8(2) . . . . ?
C4 C5 C14 S1 -179.42(13) . . . . ?
C6 S1 C14 N2 -178.49(18) . . . . ?
C6 S1 C14 C5 0.89(15) . . . . ?
C3 C2 C15 C16 -0.5(3) . . . . ?
C1 C2 C15 C16 178.36(19) . . . . ?
C2 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C4 -0.1(3) . . . . ?
C3 C4 C17 C16 0.2(3) . . . . ?
C5 C4 C17 C16 -178.31(18) . . . . ?
C14 N2 C18 C3 0.4(3) . . . . ?
C4 C3 C18 N2 0.6(3) . . . . ?
C2 C3 C18 N2 -178.7(2) . . . . ?

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
C13 H7 N2 0.95 2.65 3.559(3) 160.4 4_676 yes
C13 H7 N2 0.95 2.65 3.559(3) 160.4 4_676 yes

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.069


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 2100115'
loop_
_audit_author_name
_audit_author_address
'Samuel Guieu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
2,5-bis(2,6-difluorophenyl)thiazolo[5,4-d]thiazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H6 F4 N2 S2'
_chemical_formula_sum            'C16 H6 F4 N2 S2'
_chemical_formula_weight         366.35

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'

_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                   3.8831(2)
_cell_length_b                   11.9865(7)
_cell_length_c                   15.5339(9)
_cell_angle_alpha                83.534(2)
_cell_angle_beta                 83.375(3)
_cell_angle_gamma                84.296(3)
_cell_volume                     710.89(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9860
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      30.57

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   0.6406
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.421
_shelx_estimated_absorpt_T_min   0.729
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27838
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.716
_diffrn_reflns_theta_max         30.591
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4382
_reflns_number_gt                4064
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0424P)²+0.2350P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4382
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0806
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
S1B S 0.18228(7) 0.15322(2) 0.45499(2) 0.01952(7) Uani 1 1 d . . . . .
F1B F 0.3260(2) 0.35202(6) 0.49399(5) 0.03237(16) Uani 1 1 d . . . . .
F2B F -0.3069(2) 0.17157(6) 0.74046(4) 0.02937(15) Uani 1 1 d . . . . .
N1B N 0.1110(2) -0.05853(7) 0.39826(5) 0.01961(16) Uani 1 1 d . . . . .
C01B C 0.0750(2) 0.01667(8) 0.45876(6) 0.01750(17) Uani 1 1 d . . . . .
C02B C 0.0130(2) 0.15324(8) 0.56579(6) 0.01736(17) Uani 1 1 d . . . . .
C03B C 0.0147(3) 0.25260(8) 0.61316(6) 0.01860(18) Uani 1 1 d . . . . .
C08B C -0.1391(3) 0.25871(9) 0.69928(7) 0.02103(19) Uani 1 1 d . . . . .
C04B C 0.1702(3) 0.35040(9) 0.57702(7) 0.02243(19) Uani 1 1 d . . . . .
C05B C 0.1817(3) 0.44465(9) 0.61966(8) 0.0271(2) Uani 1 1 d . . . . .
H05B H 0.2914 0.5083 0.5913 0.033 Uiso 1 1 calc R U . . .
C06B C 0.0294(3) 0.44420(10) 0.70473(8) 0.0277(2) Uani 1 1 d . . . . .
H06B H 0.0358 0.5078 0.7357 0.033 Uiso 1 1 calc R U . . .
C07B C -0.1325(3) 0.35116(10) 0.74478(7) 0.0255(2) Uani 1 1 d . . . . .
H07B H -0.2382 0.3508 0.8031 0.031 Uiso 1 1 calc R U . . .
S1A S 0.19264(7) 0.34849(2) 0.95575(2) 0.01983(7) Uani 1 1 d . . . . .
F1A F 0.5051(2) 0.14354(6) 0.99356(5) 0.03824(19) Uani 1 1 d . . . . .
F2A F 0.4604(2) 0.34673(7) 1.23925(5) 0.03723(19) Uani 1 1 d . . . . .
N1A N -0.1646(2) 0.55645(7) 0.89956(5) 0.01990(16) Uani 1 1 d . . . . .
C03A C 0.4611(3) 0.25277(8) 1.11228(6) 0.01887(18) Uani 1 1 d . . . . .
C01A C -0.0061(3) 0.48309(8) 0.95944(6) 0.01792(17) Uani 1 1 d . . . . .
C02A C 0.2782(2) 0.34994(8) 1.06526(6) 0.01772(17) Uani 1 1 d . . . . .
C08A C 0.5426(3) 0.25313(9) 1.19825(7) 0.0226(2) Uani 1 1 d . . . . .
C07A C 0.7070(3) 0.16170(10) 1.24409(7) 0.0268(2) Uani 1 1 d . . . . .
H07A H 0.7558 0.1663 1.3021 0.032 Uiso 1 1 calc R U . . .
C06A C 0.8006(3) 0.06310(10) 1.20500(8) 0.0298(2) Uani 1 1 d . . . . .
H06A H 0.9116 -0.0004 1.2364 0.036 Uiso 1 1 calc R U . . .
C05A C 0.7319(4) 0.05742(10) 1.12003(9) 0.0314(2) Uani 1 1 d . . . . .
H05A H 0.7961 -0.0094 1.0923 0.038 Uiso 1 1 calc R U . . .
C04A C 0.5678(3) 0.15118(9) 1.07673(7) 0.0250(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
S1B C01B 1.7217(10) . ?
S1B C02B 1.7702(10) . ?
F1B C04B 1.3589(13) . ?
F2B C08B 1.3466(13) . ?
N1B C02B 1.3177(13) 2_556 ?
N1B C01B 1.3604(12) . ?
C01B C01B 1.3781(18) 2_556 ?
C02B N1B 1.3177(13) 2_556 ?
C02B C03B 1.4697(13) . ?
C03B C04B 1.4028(14) . ?
C03B C08B 1.4074(14) . ?
C08B C07B 1.3837(14) . ?
C04B C05B 1.3794(15) . ?
C05B C06B 1.3837(17) . ?
C05B H05B 0.9500 . ?
C06B C07B 1.3851(17) . ?
C06B H06B 0.9500 . ?
C07B H07B 0.9500 . ?
S1A C01A 1.7219(10) . ?
S1A C02A 1.7727(10) . ?
F1A C04A 1.3567(13) . ?
F2A C08A 1.3449(13) . ?
N1A C02A 1.3176(13) 2_567 ?
N1A C01A 1.3629(12) . ?
C03A C04A 1.3993(15) . ?
C03A C08A 1.4082(14) . ?
C03A C02A 1.4690(14) . ?
C01A C01A 1.3739(18) 2_567 ?
C02A N1A 1.3176(13) 2_567 ?
C08A C07A 1.3805(15) . ?
C07A C06A 1.3867(17) . ?
C07A H07A 0.9500 . ?
C06A C05A 1.3867(18) . ?
C06A H06A 0.9500 . ?
C05A C04A 1.3812(16) . ?
C05A H05A 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
C01B S1B C02B 88.56(4) . . ?
C02B N1B C01B 108.99(8) 2_556 . ?
N1B C01B C01B 118.09(11) . 2_556 ?
N1B C01B S1B 132.75(7) . . ?
C01B C01B S1B 109.16(10) 2_556 . ?
N1B C02B C03B 123.25(9) 2_556 . ?
N1B C02B S1B 115.21(7) 2_556 . ?
C03B C02B S1B 121.54(7) . . ?
C04B C03B C08B 113.50(9) . . ?
C04B C03B C02B 123.30(9) . . ?
C08B C03B C02B 123.20(9) . . ?
F2B C08B C07B 117.18(9) . . ?
F2B C08B C03B 119.35(9) . . ?
C07B C08B C03B 123.46(10) . . ?
F1B C04B C05B 117.32(10) . . ?
F1B C04B C03B 117.61(9) . . ?
C05B C04B C03B 125.06(10) . . ?
C04B C05B C06B 118.33(11) . . ?
C04B C05B H05B 120.8 . . ?
C06B C05B H05B 120.8 . . ?
C05B C06B C07B 120.10(10) . . ?
C05B C06B H06B 120.0 . . ?
C07B C06B H06B 120.0 . . ?
C08B C07B C06B 119.54(10) . . ?
C08B C07B H07B 120.2 . . ?
C06B C07B H07B 120.2 . . ?
C01A S1A C02A 88.48(5) . . ?
C02A N1A C01A 109.11(8) 2_567 . ?
C04A C03A C08A 113.62(9) . . ?
C04A C03A C02A 123.59(9) . . ?
C08A C03A C02A 122.79(9) . . ?
N1A C01A C01A 117.95(11) . 2_567 ?
N1A C01A S1A 132.65(7) . . ?
C01A C01A S1A 109.40(10) 2_567 . ?
N1A C02A C03A 123.29(9) 2_567 . ?
N1A C02A S1A 115.06(7) 2_567 . ?
C03A C02A S1A 121.65(7) . . ?
F2A C08A C07A 116.96(10) . . ?
F2A C08A C03A 119.50(9) . . ?
C07A C08A C03A 123.54(10) . . ?
C08A C07A C06A 119.61(10) . . ?
C08A C07A H07A 120.2 . . ?
C06A C07A H07A 120.2 . . ?
C07A C06A C05A 119.86(11) . . ?
C07A C06A H06A 120.1 . . ?
C05A C06A H06A 120.1 . . ?
C04A C05A C06A 118.42(11) . . ?
C04A C05A H05A 120.8 . . ?
C06A C05A H05A 120.8 . . ?
F1A C04A C05A 117.22(10) . . ?
F1A C04A C03A 117.83(9) . . ?
C05A C04A C03A 124.94(10) . . ?

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
C02B N1B C01B C01B -0.11(15) 2_556 . . 2_556 ?
C02B N1B C01B S1B 179.83(8) 2_556 . . . ?
C02B S1B C01B N1B 179.92(10) . . . . ?
C02B S1B C01B C01B -0.14(10) . . . 2_556 ?
C01B S1B C02B N1B 0.22(8) . . . 2_556 ?
C01B S1B C02B C03B 179.98(8) . . . . ?
N1B C02B C03B C04B 175.02(10) 2_556 . . . ?
S1B C02B C03B C04B -4.72(14) . . . . ?
N1B C02B C03B C08B -4.87(15) 2_556 . . . ?
S1B C02B C03B C08B 175.39(8) . . . . ?
C04B C03B C08B F2B 177.90(9) . . . . ?
C02B C03B C08B F2B -2.20(15) . . . . ?
C04B C03B C08B C07B -1.19(15) . . . . ?
C02B C03B C08B C07B 178.70(10) . . . . ?
C08B C03B C04B F1B 179.88(9) . . . . ?
C02B C03B C04B F1B -0.02(15) . . . . ?
C08B C03B C04B C05B 0.87(16) . . . . ?
C02B C03B C04B C05B -179.03(10) . . . . ?
F1B C04B C05B C06B -179.02(10) . . . . ?
C03B C04B C05B C06B -0.01(18) . . . . ?
C04B C05B C06B C07B -0.62(17) . . . . ?
F2B C08B C07B C06B -178.45(10) . . . . ?
C03B C08B C07B C06B 0.66(16) . . . . ?
C05B C06B C07B C08B 0.31(17) . . . . ?
C02A N1A C01A C01A 0.19(15) 2_567 . . 2_567 ?
C02A N1A C01A S1A 179.72(8) 2_567 . . . ?
C02A S1A C01A N1A -179.87(10) . . . . ?
C02A S1A C01A C01A -0.32(10) . . . 2_567 ?
C04A C03A C02A N1A 176.87(10) . . . 2_567 ?
C08A C03A C02A N1A -2.52(15) . . . 2_567 ?
C04A C03A C02A S1A -2.81(14) . . . . ?
C08A C03A C02A S1A 177.81(8) . . . . ?
C01A S1A C02A N1A 0.24(8) . . . 2_567 ?
C01A S1A C02A C03A 179.94(8) . . . . ?
C04A C03A C08A F2A 178.61(10) . . . . ?
C02A C03A C08A F2A -1.95(16) . . . . ?
C04A C03A C08A C07A -1.00(16) . . . . ?
C02A C03A C08A C07A 178.44(10) . . . . ?
F2A C08A C07A C06A -179.51(11) . . . . ?
C03A C08A C07A C06A 0.11(18) . . . . ?
C08A C07A C06A C05A 0.68(18) . . . . ?
C07A C06A C05A C04A -0.49(19) . . . . ?
C06A C05A C04A F1A 179.70(11) . . . . ?
C06A C05A C04A C03A -0.5(2) . . . . ?
C08A C03A C04A F1A -179.01(10) . . . . ?
C02A C03A C04A F1A 1.56(16) . . . . ?
C08A C03A C04A C05A 1.22(17) . . . . ?
C02A C03A C04A C05A -178.21(11) . . . . ?

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC9
_database_code_depnum_ccdc_archive 'CCDC 2100110'
loop_
_audit_author_name
_audit_author_address
'Samuel Guieu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
6,7,8,9-tetrafluoro-2-(perfluorophenyl)thiazolo[5,4-c]isoquinoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H F9 N2 S'
_chemical_formula_sum            'C16 H F9 N2 S'
_chemical_formula_weight         424.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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                   13.3364(18)
_cell_length_b                   5.0810(7)
_cell_length_c                   21.565(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.017(5)
_cell_angle_gamma                90
_cell_volume                     1417.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2842
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      24.93

_exptl_crystal_description       flake
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   0.6478
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.344
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.983
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21657
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.574
_diffrn_reflns_theta_max         28.335
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3526
_reflns_number_gt                2491
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1400P)²+3.4167P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3526
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0844
_refine_ls_wR_factor_ref         0.2635
_refine_ls_wR_factor_gt          0.2396
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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
S01 S 0.64353(10) 0.1201(2) 0.95603(6) 0.0321(4) Uani 1 1 d . . . . .
F13 F 1.0441(2) 0.6052(5) 0.87760(13) 0.0331(7) Uani 1 1 d . . . . .
F15 F 0.8490(2) -0.1263(5) 0.78426(12) 0.0315(7) Uani 1 1 d . . . . .
F12 F 0.9251(2) 0.6687(5) 0.95825(13) 0.0295(6) Uani 1 1 d . . . . .
2 N 0.7671(3) 0.5058(7) 1.00528(17) 0.0219(7) Uani 1 1 d . . . . .
F05 F 0.8118(2) 1.1859(6) 1.19318(13) 0.0314(6) Uani 1 1 d . . . . .
F16 F 0.7240(2) -0.0712(6) 0.86261(14) 0.0383(7) Uani 1 1 d . . . . .
C08 C 0.6947(3) 0.4828(8) 1.03936(19) 0.0196(8) Uani 1 1 d . . . . .
F04 F 0.6619(2) 1.0720(6) 1.25200(14) 0.0380(7) Uani 1 1 d . . . . .
F06 F 0.8330(2) 0.9162(5) 1.09046(12) 0.0272(6) Uani 1 1 d . . . . .
C01 C 0.5394(3) 0.3793(8) 1.1016(2) 0.0238(9) Uani 1 1 d . . . . .
H01 H 0.487168 0.342718 1.123500 0.029 Uiso 1 1 calc R U . . .
F14 F 1.0111(2) 0.2074(6) 0.79142(12) 0.0322(6) Uani 1 1 d . . . . .
C10 C 0.7514(3) 0.3265(8) 0.9594(2) 0.0216(8) Uani 1 1 d . . . . .
C06 C 0.7579(3) 0.8489(8) 1.11807(19) 0.0207(8) Uani 1 1 d . . . . .
F03 F 0.5253(2) 0.6759(6) 1.20748(15) 0.0408(8) Uani 1 1 d . . . . .
C09 C 0.6145(3) 0.2627(8) 1.01588(19) 0.0190(8) Uiso 1 1 d . . . . .
C12 C 0.9022(3) 0.4670(9) 0.9167(2) 0.0236(9) Uani 1 1 d . . . . .
C07 C 0.6888(3) 0.6422(8) 1.09354(19) 0.0215(8) Uani 1 1 d . . . . .
C04 C 0.6681(4) 0.9274(9) 1.2010(2) 0.0265(9) Uani 1 1 d . . . . .
1 N 0.5427(3) 0.2320(9) 1.0498(2) 0.0370(10) Uani 1 1 d . . . . .
C05 C 0.7474(3) 0.9897(9) 1.1706(2) 0.0236(9) Uani 1 1 d . . . . .
C15 C 0.8669(4) 0.0694(8) 0.8275(2) 0.0247(9) Uani 1 1 d . . . . .
C14 C 0.9494(3) 0.2351(9) 0.83052(19) 0.0245(9) Uani 1 1 d . . . . .
C11 C 0.8183(3) 0.3002(8) 0.9152(2) 0.0220(8) Uani 1 1 d . . . . .
C02 C 0.6096(3) 0.5836(8) 1.1246(2) 0.0236(9) Uani 1 1 d . . . . .
C03 C 0.6009(3) 0.7304(9) 1.1786(2) 0.0275(10) Uani 1 1 d . . . . .
C13 C 0.9664(3) 0.4373(8) 0.8753(2) 0.0233(9) Uani 1 1 d . . . . .
C16 C 0.8032(3) 0.1019(8) 0.8686(2) 0.0225(9) 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
S01 C09 1.607(4) . ?
S01 C10 1.768(4) . ?
F13 C13 1.334(5) . ?
F15 C15 1.345(5) . ?
F12 C12 1.347(5) . ?
2 C10 1.324(6) . ?
2 C08 1.353(5) . ?
F05 C05 1.329(5) . ?
F16 C16 1.356(5) . ?
C08 C07 1.439(6) . ?
C08 C09 1.546(6) . ?
F04 C04 1.341(5) . ?
F06 C06 1.329(5) . ?
C01 1 1.355(6) . ?
C01 C02 1.405(6) . ?
F14 C14 1.321(5) . ?
C10 C11 1.460(6) . ?
C06 C05 1.374(6) . ?
C06 C07 1.413(6) . ?
F03 C03 1.337(5) . ?
C09 1 1.346(6) . ?
C12 C13 1.386(6) . ?
C12 C11 1.399(6) . ?
C07 C02 1.413(6) . ?
C04 C03 1.353(7) . ?
C04 C05 1.410(6) . ?
C15 C14 1.374(6) . ?
C15 C16 1.377(6) . ?
C14 C13 1.390(6) . ?
C11 C16 1.403(6) . ?
C02 C03 1.411(6) . ?

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
C09 S01 C10 93.0(2) . . ?
C10 2 C08 110.0(3) . . ?
2 C08 C07 125.4(4) . . ?
2 C08 C09 114.4(3) . . ?
C07 C08 C09 120.2(4) . . ?
1 C01 C02 123.2(4) . . ?
2 C10 C11 122.7(4) . . ?
2 C10 S01 114.7(3) . . ?
C11 C10 S01 122.6(3) . . ?
F06 C06 C05 118.2(4) . . ?
F06 C06 C07 121.2(4) . . ?
C05 C06 C07 120.6(4) . . ?
1 C09 C08 115.6(4) . . ?
1 C09 S01 136.5(4) . . ?
C08 C09 S01 107.9(3) . . ?
F12 C12 C13 115.9(4) . . ?
F12 C12 C11 121.8(4) . . ?
C13 C12 C11 122.4(4) . . ?
C06 C07 C02 118.3(4) . . ?
C06 C07 C08 124.3(4) . . ?
C02 C07 C08 117.4(4) . . ?
F04 C04 C03 122.1(4) . . ?
F04 C04 C05 117.5(4) . . ?
C03 C04 C05 120.4(4) . . ?
C09 1 C01 123.6(4) . . ?
F05 C05 C06 120.5(4) . . ?
F05 C05 C04 119.2(4) . . ?
C06 C05 C04 120.3(4) . . ?
F15 C15 C14 119.4(4) . . ?
F15 C15 C16 120.1(4) . . ?
C14 C15 C16 120.5(4) . . ?
F14 C14 C15 121.4(4) . . ?
F14 C14 C13 120.0(4) . . ?
C15 C14 C13 118.6(4) . . ?
C12 C11 C16 115.2(4) . . ?
C12 C11 C10 122.8(4) . . ?
C16 C11 C10 122.0(4) . . ?
C01 C02 C03 120.1(4) . . ?
C01 C02 C07 120.0(4) . . ?
C03 C02 C07 120.0(4) . . ?
F03 C03 C04 119.7(4) . . ?
F03 C03 C02 119.8(4) . . ?
C04 C03 C02 120.5(4) . . ?
F13 C13 C12 120.1(4) . . ?
F13 C13 C14 119.6(4) . . ?
C12 C13 C14 120.4(4) . . ?
F16 C16 C15 116.6(4) . . ?
F16 C16 C11 120.5(4) . . ?
C15 C16 C11 122.9(4) . . ?

_refine_diff_density_max         2.532
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.143


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC10
_database_code_depnum_ccdc_archive 'CCDC 2100111'
loop_
_audit_author_name
_audit_author_address
'Samuel Guieu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
2,5-bis(2,6-dibromophenyl)thiazolo[5,4-d]thiazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H6 Br4 N2 S2'
_chemical_formula_sum            'C8 H3 Br2 N S'
_chemical_formula_weight         304.99

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

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

_cell_length_a                   12.4146(11)
_cell_length_b                   14.9366(11)
_cell_length_c                   9.6752(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1794.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1144
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      21.62

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.258
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   0.2977
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    9.206
_shelx_estimated_absorpt_T_min   0.260
_shelx_estimated_absorpt_T_max   0.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9696
_diffrn_reflns_av_unetI/netI     0.0854
_diffrn_reflns_av_R_equivalents  0.0954
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.133
_diffrn_reflns_theta_max         26.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1843
_reflns_number_gt                1187
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0225P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1843
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
Br1 Br 0.66002(5) 0.27992(4) 0.73308(6) 0.0355(2) Uani 1 1 d . . . . .
Br2 Br 0.84611(5) 0.51422(4) 0.33198(6) 0.02826(19) Uani 1 1 d . . . . .
S1 S 0.63433(13) 0.53374(9) 0.61101(17) 0.0328(4) Uani 1 1 d . . . . .
N1 N 0.5786(4) 0.4061(3) 0.4412(4) 0.0210(11) Uani 1 1 d . . . . .
C1 C 0.9606(5) 0.3003(4) 0.5537(6) 0.0290(15) Uani 1 1 d . . . . .
H1 H 1.027268 0.269321 0.560687 0.035 Uiso 1 1 calc R U . . .
C2 C 0.8738(5) 0.2731(3) 0.6332(6) 0.0240(14) Uani 1 1 d . . . . .
H3 H 0.880929 0.224730 0.696217 0.029 Uiso 1 1 calc R U . . .
C3 C 0.7761(4) 0.3178(3) 0.6194(5) 0.0207(13) Uani 1 1 d . . . . .
C4 C 0.7637(4) 0.3895(3) 0.5293(5) 0.0165(12) Uani 1 1 d . . . . .
C5 C 0.6575(5) 0.4353(3) 0.5170(5) 0.0195(13) Uani 1 1 d . . . . .
C6 C 0.5064(5) 0.5359(3) 0.5436(5) 0.0188(13) Uani 1 1 d . . . . .
C7 C 0.8543(5) 0.4159(3) 0.4543(5) 0.0190(13) Uani 1 1 d . . . . .
C8 C 0.9513(5) 0.3713(3) 0.4652(5) 0.0216(13) Uani 1 1 d . . . . .
H2 H 1.011340 0.389915 0.411512 0.026 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
Br1 C3 1.899(5) . ?
Br2 C7 1.889(5) . ?
S1 C6 1.717(6) . ?
S1 C5 1.752(5) . ?
N1 C5 1.299(7) . ?
N1 C6 1.372(6) 5_666 ?
C1 C8 1.369(7) . ?
C1 C2 1.385(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(7) . ?
C2 H3 0.9500 . ?
C3 C4 1.390(7) . ?
C4 C7 1.394(7) . ?
C4 C5 1.491(7) . ?
C6 C6 1.374(9) 5_666 ?
C7 C8 1.380(7) . ?
C8 H2 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
C6 S1 C5 88.3(3) . . ?
C5 N1 C6 107.9(4) . 5_666 ?
C8 C1 C2 120.6(5) . . ?
C8 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C2 C3 119.0(5) . . ?
C1 C2 H3 120.5 . . ?
C3 C2 H3 120.5 . . ?
C4 C3 C2 121.7(5) . . ?
C4 C3 Br1 120.6(4) . . ?
C2 C3 Br1 117.6(4) . . ?
C3 C4 C7 117.1(5) . . ?
C3 C4 C5 120.1(5) . . ?
C7 C4 C5 122.8(4) . . ?
N1 C5 C4 123.9(4) . . ?
N1 C5 S1 116.8(4) . . ?
C4 C5 S1 119.3(4) . . ?
N1 C6 C6 118.0(6) 5_666 5_666 ?
N1 C6 S1 133.0(4) 5_666 . ?
C6 C6 S1 109.0(5) 5_666 . ?
C8 C7 C4 121.8(5) . . ?
C8 C7 Br2 118.0(4) . . ?
C4 C7 Br2 120.2(4) . . ?
C1 C8 C7 119.7(5) . . ?
C1 C8 H2 120.1 . . ?
C7 C8 H2 120.1 . . ?

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
C8 C1 C2 C3 1.5(8) . . . . ?
C1 C2 C3 C4 -0.8(8) . . . . ?
C1 C2 C3 Br1 -178.8(4) . . . . ?
C2 C3 C4 C7 -1.0(7) . . . . ?
Br1 C3 C4 C7 176.9(4) . . . . ?
C2 C3 C4 C5 179.7(5) . . . . ?
Br1 C3 C4 C5 -2.3(6) . . . . ?
C6 N1 C5 C4 179.2(5) 5_666 . . . ?
C6 N1 C5 S1 0.1(6) 5_666 . . . ?
C3 C4 C5 N1 -81.9(7) . . . . ?
C7 C4 C5 N1 98.8(6) . . . . ?
C3 C4 C5 S1 97.2(5) . . . . ?
C7 C4 C5 S1 -82.1(6) . . . . ?
C6 S1 C5 N1 0.4(4) . . . . ?
C6 S1 C5 C4 -178.7(4) . . . . ?
C5 S1 C6 N1 -179.4(5) . . . 5_666 ?
C5 S1 C6 C6 -0.8(5) . . . 5_666 ?
C3 C4 C7 C8 2.1(7) . . . . ?
C5 C4 C7 C8 -178.7(4) . . . . ?
C3 C4 C7 Br2 -178.7(3) . . . . ?
C5 C4 C7 Br2 0.5(7) . . . . ?
C2 C1 C8 C7 -0.5(8) . . . . ?
C4 C7 C8 C1 -1.4(8) . . . . ?
Br2 C7 C8 C1 179.4(4) . . . . ?

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
C2 H3 S1 0.95 2.98 3.584(5) 123.1 6_755 yes
C2 H3 S1 0.95 2.98 3.584(5) 123.1 6_755 yes

_refine_diff_density_max         0.809
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.149


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC11
_database_code_depnum_ccdc_archive 'CCDC 2100118'
loop_
_audit_author_name
_audit_author_address
'Samuel Guieu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
2,5-bis(2-fluoro-6-(trifluoromethyl)phenyl)thiazolo[5,4-d]thiazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H3 F4 N S'
_chemical_formula_sum            'C9 H3 F4 N S'
_chemical_formula_weight         233.18

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.760(9)
_cell_length_b                   9.903(11)
_cell_length_c                   11.438(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.58(3)
_cell_angle_gamma                90
_cell_volume                     876.2(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4122
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      32.36

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   0.6864
_exptl_transmission_factor_max   0.7465
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.394
_shelx_estimated_absorpt_T_min   0.858
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6864
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14168
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.724
_diffrn_reflns_theta_max         33.311
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3381
_reflns_number_gt                2800
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0463P)²+0.2871P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3381
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0926
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
S1 S 0.59656(4) 0.57519(3) 0.65857(2) 0.02427(9) Uani 1 1 d . . . . .
F1 F 0.69709(10) 0.33915(9) 0.84226(7) 0.03163(19) Uani 1 1 d . . . . .
F2 F -0.01432(11) 0.54157(11) 0.82985(8) 0.0374(2) Uani 1 1 d . . . . .
F3 F 0.15898(12) 0.59013(10) 0.70107(9) 0.0409(2) Uani 1 1 d . . . . .
F4 F 0.01899(12) 0.40482(10) 0.68957(8) 0.0404(2) Uani 1 1 d . . . . .
N1 N 0.38017(13) 0.38768(10) 0.58518(8) 0.02021(19) Uani 1 1 d . . . . .
C1 C 0.34046(19) 0.31545(14) 1.02178(10) 0.0278(3) Uani 1 1 d . . . . .
H1 H 0.314979 0.281991 1.096306 0.033 Uiso 1 1 calc R U . . .
C2 C 0.50586(18) 0.30555(13) 0.98736(10) 0.0256(2) Uani 1 1 d . . . . .
H2 H 0.596334 0.267815 1.037948 0.031 Uiso 1 1 calc R U . . .
C3 C 0.53643(15) 0.35199(12) 0.87734(10) 0.0209(2) Uani 1 1 d . . . . .
C4 C 0.41113(15) 0.40794(11) 0.79912(9) 0.01694(19) Uani 1 1 d . . . . .
C5 C 0.45241(14) 0.44545(11) 0.67958(9) 0.01735(19) Uani 1 1 d . . . . .
C6 C 0.44175(14) 0.44851(12) 0.48992(9) 0.0182(2) Uani 1 1 d . . . . .
C7 C 0.21097(17) 0.37395(14) 0.94831(10) 0.0245(2) Uani 1 1 d . . . . .
H3 H 0.097472 0.381667 0.973179 0.029 Uiso 1 1 calc R U . . .
C8 C 0.24607(15) 0.42144(11) 0.83843(9) 0.0185(2) Uani 1 1 d . . . . .
C9 C 0.10329(16) 0.48916(13) 0.76446(10) 0.0234(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
S1 C6 1.717(2) 3_666 ?
S1 C5 1.7328(18) . ?
F1 C3 1.346(2) . ?
F2 C9 1.3308(17) . ?
F3 C9 1.3275(18) . ?
F4 C9 1.3303(18) . ?
N1 C5 1.3080(18) . ?
N1 C6 1.3644(18) . ?
C1 C2 1.376(2) . ?
C1 C7 1.384(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.378(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.3834(19) . ?
C4 C8 1.397(2) . ?
C4 C5 1.476(2) . ?
C6 C6 1.370(2) 3_666 ?
C7 C8 1.389(2) . ?
C7 H3 0.9500 . ?
C8 C9 1.498(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
C6 S1 C5 88.46(6) 3_666 . ?
C5 N1 C6 108.17(12) . . ?
C2 C1 C7 120.31(13) . . ?
C2 C1 H1 119.8 . . ?
C7 C1 H1 119.8 . . ?
C1 C2 C3 118.04(12) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
F1 C3 C2 118.15(11) . . ?
F1 C3 C4 117.71(12) . . ?
C2 C3 C4 124.12(13) . . ?
C3 C4 C8 116.44(12) . . ?
C3 C4 C5 120.42(12) . . ?
C8 C4 C5 123.10(10) . . ?
N1 C5 C4 122.96(12) . . ?
N1 C5 S1 116.66(10) . . ?
C4 C5 S1 120.35(8) . . ?
N1 C6 C6 117.56(13) . 3_666 ?
N1 C6 S1 133.29(10) . 3_666 ?
C6 C6 S1 109.15(11) 3_666 3_666 ?
C1 C7 C8 120.37(13) . . ?
C1 C7 H3 119.8 . . ?
C8 C7 H3 119.8 . . ?
C7 C8 C4 120.65(11) . . ?
C7 C8 C9 118.23(12) . . ?
C4 C8 C9 121.12(12) . . ?
F3 C9 F4 106.62(13) . . ?
F3 C9 F2 106.32(13) . . ?
F4 C9 F2 106.42(13) . . ?
F3 C9 C8 112.79(12) . . ?
F4 C9 C8 112.72(13) . . ?
F2 C9 C8 111.51(12) . . ?

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
C7 C1 C2 C3 -1.72(19) . . . . ?
C1 C2 C3 F1 -178.27(11) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
F1 C3 C4 C8 -179.29(10) . . . . ?
C2 C3 C4 C8 2.49(18) . . . . ?
F1 C3 C4 C5 2.95(16) . . . . ?
C2 C3 C4 C5 -175.28(11) . . . . ?
C6 N1 C5 C4 177.90(10) . . . . ?
C6 N1 C5 S1 0.16(13) . . . . ?
C3 C4 C5 N1 115.90(15) . . . . ?
C8 C4 C5 N1 -61.72(17) . . . . ?
C3 C4 C5 S1 -66.44(15) . . . . ?
C8 C4 C5 S1 115.94(13) . . . . ?
C6 S1 C5 N1 0.03(10) 3_666 . . . ?
C6 S1 C5 C4 -177.77(10) 3_666 . . . ?
C5 N1 C6 C6 -0.34(18) . . . 3_666 ?
C5 N1 C6 S1 -179.86(10) . . . 3_666 ?
C2 C1 C7 C8 1.0(2) . . . . ?
C1 C7 C8 C4 1.61(19) . . . . ?
C1 C7 C8 C9 -177.44(12) . . . . ?
C3 C4 C8 C7 -3.22(16) . . . . ?
C5 C4 C8 C7 174.49(11) . . . . ?
C3 C4 C8 C9 175.81(11) . . . . ?
C5 C4 C8 C9 -6.49(17) . . . . ?
C7 C8 C9 F3 144.57(12) . . . . ?
C4 C8 C9 F3 -34.48(16) . . . . ?
C7 C8 C9 F4 -94.63(14) . . . . ?
C4 C8 C9 F4 86.33(15) . . . . ?
C7 C8 C9 F2 25.01(16) . . . . ?
C4 C8 C9 F2 -154.04(11) . . . . ?

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
C2 H2 F4 0.95 2.54 3.108(3) 118.5 4_666 yes
C2 H2 F4 0.95 2.54 3.108(3) 118.5 4_666 yes

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.061


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
