#------------------------------------------------------------------------------
#$Date: 2019-11-24 16:45:52 +0100 (dom 24 de nov de 2019) $
#$Revision: 238895 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/55/1555560.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_1555560
loop_
_publ_author_name
'Castanheiro, Thomas'
'Suffert, Jean'
'Gulea, Mihaela'
'Donnard, Morgan'
_publ_section_title
;
 Aerobic Copper-Mediated Domino Three-Component Approach to
 2-Aminobenzothiazole Derivatives.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2588
_journal_page_last               2591
_journal_paper_doi               10.1021/acs.orglett.6b00967
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C14 H8 F2 N2 O S'
_chemical_formula_sum            'C14 H8 F2 N2 O S'
_chemical_formula_weight         290.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                88.575(2)
_cell_angle_beta                 86.523(2)
_cell_angle_gamma                88.004(2)
_cell_formula_units_Z            2
_cell_length_a                   5.7370(5)
_cell_length_b                   7.6865(7)
_cell_length_c                   13.5874(12)
_cell_measurement_reflns_used    4604
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.02
_cell_measurement_theta_min      2.65
_cell_volume                     597.55(9)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Superflip (Palatinus and Chapuis,2007)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_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  0.0225
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8751
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.024
_diffrn_reflns_theta_min         2.652
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_description       prism
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0443
_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)+(0.0532P)²+0.3829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1143
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2668
_reflns_number_total             3143
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b00967_si_001.cif
_cod_data_source_block           jstc151001
_cod_database_code               1555560
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.3831(3) 0.2843(2) 0.23535(12) 0.0190(3) Uani 1 1 d . .
C2 C 0.4147(3) 0.2712(2) 0.33657(13) 0.0237(4) Uani 1 1 d . .
H2 H 0.5548 0.2207 0.3601 0.028 Uiso 1 1 calc R U
C3 C 0.2387(3) 0.3332(2) 0.40171(13) 0.0263(4) Uani 1 1 d . .
H3 H 0.2588 0.3255 0.4706 0.032 Uiso 1 1 calc R U
C4 C 0.0302(3) 0.4074(2) 0.36756(14) 0.0266(4) Uani 1 1 d . .
H4 H -0.0895 0.4474 0.4138 0.032 Uiso 1 1 calc R U
C5 C -0.0033(3) 0.4231(2) 0.26767(14) 0.0240(4) Uani 1 1 d . .
H5 H -0.1433 0.4744 0.2445 0.029 Uiso 1 1 calc R U
C6 C 0.1749(3) 0.3612(2) 0.20209(12) 0.0187(3) Uani 1 1 d . .
C7 C 0.4605(3) 0.2601(2) 0.07583(12) 0.0183(3) Uani 1 1 d . .
C8 C 0.5286(3) 0.2525(2) -0.10351(12) 0.0195(3) Uani 1 1 d . .
C9 C 0.6908(3) 0.1912(2) -0.18723(12) 0.0181(3) Uani 1 1 d . .
C10 C 0.6178(3) 0.2255(2) -0.28263(13) 0.0237(4) Uani 1 1 d . .
H10 H 0.4734 0.2861 -0.2920 0.028 Uiso 1 1 calc R U
C11 C 0.7570(3) 0.1707(3) -0.36237(13) 0.0270(4) Uani 1 1 d . .
C12 C 0.9700(3) 0.0835(2) -0.35411(14) 0.0272(4) Uani 1 1 d . .
H12 H 1.0625 0.0486 -0.4110 0.033 Uiso 1 1 calc R U
C13 C 1.0445(3) 0.0487(2) -0.26051(13) 0.0241(4) Uani 1 1 d . .
H13 H 1.1896 -0.0115 -0.2518 0.029 Uiso 1 1 calc R U
C14 C 0.9053(3) 0.1026(2) -0.17995(12) 0.0201(3) Uani 1 1 d . .
N1 N 0.5427(3) 0.22582(19) 0.16120(11) 0.0205(3) Uani 1 1 d . .
N2 N 0.5894(3) 0.21179(19) -0.00965(11) 0.0207(3) Uani 1 1 d . .
O1 O 0.3472(2) 0.33423(18) -0.11874(9) 0.0275(3) Uani 1 1 d . .
F1 F 0.6809(2) 0.20235(19) -0.45429(9) 0.0445(4) Uani 1 1 d . .
F2 F 0.98547(19) 0.06362(15) -0.08952(8) 0.0274(3) Uani 1 1 d . .
S1 S 0.18412(7) 0.36338(6) 0.07355(3) 0.02066(13) Uani 1 1 d . .
H2N H 0.715(4) 0.163(3) 0.0007(18) 0.039(7) Uiso 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
N1 C1 C2 125.39(15)
N1 C1 C6 115.01(15)
C2 C1 C6 119.59(15)
C3 C2 C1 118.84(16)
C3 C2 H2 120.6
C1 C2 H2 120.6
C2 C3 C4 120.99(17)
C2 C3 H3 119.5
C4 C3 H3 119.5
C5 C4 C3 120.98(17)
C5 C4 H4 119.5
C3 C4 H4 119.5
C4 C5 C6 117.94(16)
C4 C5 H5 121.0
C6 C5 H5 121.0
C5 C6 C1 121.65(16)
C5 C6 S1 128.46(13)
C1 C6 S1 109.89(12)
N1 C7 N2 119.87(15)
N1 C7 S1 117.72(13)
N2 C7 S1 122.40(12)
O1 C8 N2 121.25(16)
O1 C8 C9 121.08(15)
N2 C8 C9 117.66(14)
C14 C9 C10 116.74(15)
C14 C9 C8 126.73(15)
C10 C9 C8 116.53(15)
C11 C10 C9 119.36(16)
C11 C10 H10 120.3
C9 C10 H10 120.3
F1 C11 C10 118.45(17)
F1 C11 C12 118.23(17)
C10 C11 C12 123.32(16)
C11 C12 C13 118.03(17)
C11 C12 H12 121.0
C13 C12 H12 121.0
C14 C13 C12 119.04(17)
C14 C13 H13 120.5
C12 C13 H13 120.5
F2 C14 C13 116.71(15)
F2 C14 C9 119.77(15)
C13 C14 C9 123.52(15)
C7 N1 C1 109.57(14)
C8 N2 C7 124.95(15)
C8 N2 H2N 121.3(18)
C7 N2 H2N 113.5(18)
C6 S1 C7 87.80(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.392(2)
C1 C2 1.399(2)
C1 C6 1.408(2)
C2 C3 1.382(3)
C2 H2 0.9500
C3 C4 1.407(3)
C3 H3 0.9500
C4 C5 1.384(3)
C4 H4 0.9500
C5 C6 1.393(2)
C5 H5 0.9500
C6 S1 1.7438(17)
C7 N1 1.296(2)
C7 N2 1.390(2)
C7 S1 1.7499(16)
C8 O1 1.223(2)
C8 N2 1.368(2)
C8 C9 1.500(2)
C9 C14 1.393(2)
C9 C10 1.402(2)
C10 C11 1.372(3)
C10 H10 0.9500
C11 F1 1.361(2)
C11 C12 1.382(3)
C12 C13 1.383(2)
C12 H12 0.9500
C13 C14 1.379(2)
C13 H13 0.9500
C14 F2 1.3609(18)
N2 H2N 0.82(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
N1 C1 C2 C3 -179.09(17)
C6 C1 C2 C3 0.6(3)
C1 C2 C3 C4 0.3(3)
C2 C3 C4 C5 -1.0(3)
C3 C4 C5 C6 0.7(3)
C4 C5 C6 C1 0.2(3)
C4 C5 C6 S1 -179.73(13)
N1 C1 C6 C5 178.84(15)
C2 C1 C6 C5 -0.9(3)
N1 C1 C6 S1 -1.21(19)
C2 C1 C6 S1 179.09(13)
O1 C8 C9 C14 177.67(17)
N2 C8 C9 C14 -3.1(3)
O1 C8 C9 C10 -2.9(2)
N2 C8 C9 C10 176.30(15)
C14 C9 C10 C11 0.4(3)
C8 C9 C10 C11 -179.11(16)
C9 C10 C11 F1 178.79(15)
C9 C10 C11 C12 -0.7(3)
F1 C11 C12 C13 -178.80(16)
C10 C11 C12 C13 0.7(3)
C11 C12 C13 C14 -0.3(3)
C12 C13 C14 F2 179.35(15)
C12 C13 C14 C9 0.1(3)
C10 C9 C14 F2 -179.33(14)
C8 C9 C14 F2 0.1(3)
C10 C9 C14 C13 -0.1(3)
C8 C9 C14 C13 179.35(16)
N2 C7 N1 C1 -179.37(15)
S1 C7 N1 C1 -0.58(19)
C2 C1 N1 C7 -179.17(16)
C6 C1 N1 C7 1.2(2)
O1 C8 N2 C7 -1.5(3)
C9 C8 N2 C7 179.24(15)
N1 C7 N2 C8 -174.84(15)
S1 C7 N2 C8 6.4(2)
C5 C6 S1 C7 -179.36(17)
C1 C6 S1 C7 0.70(13)
N1 C7 S1 C6 -0.08(14)
N2 C7 S1 C6 178.68(15)
