#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:17:51 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273382 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/12/7061228.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7061228
loop_
_publ_author_name
'Costa, Letícia D.'
'Guieu, Samuel'
'Faustino, Maria do Amparo F.'
'Tomé, Augusto C.'
_publ_section_title
;
 Straightforward synthesis of thiazolo[5,4-c]isoquinolines from
 dithiooxamide and 2-halobenzaldehydes
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3602
_journal_page_last               3615
_journal_paper_doi               10.1039/D1NJ05536D
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C16 H F9 N2 S'
_chemical_formula_sum            'C16 H F9 N2 S'
_chemical_formula_weight         424.25
_chemical_name_systematic
6,7,8,9-tetrafluoro-2-(perfluorophenyl)thiazolo[5,4-c]isoquinoline
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-29 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.017(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3364(18)
_cell_length_b                   5.0810(7)
_cell_length_c                   21.565(3)
_cell_measurement_reflns_used    2842
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.93
_cell_measurement_theta_min      2.78
_cell_volume                     1417.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            21657
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.335
_diffrn_reflns_theta_min         1.574
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_description       flake
_exptl_crystal_F_000             832
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.6478
_refine_diff_density_max         2.532
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0844
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1400P)²+3.4167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2396
_refine_ls_wR_factor_ref         0.2635
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2491
_reflns_number_total             3526
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj05536d2.cif
_cod_data_source_block           shelx_CCDC9
_cod_depositor_comments
'Adding full bibliography for 7061219--7061230.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7061228
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.875
_shelx_estimated_absorpt_t_max   0.983
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'
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 . . . . .
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'
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) . . ?
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) . ?
