#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151750.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_7151750
loop_
_publ_author_name
'Ponce González, Julia'
'Edgar, Mark'
'Elsegood, Mark R. J.'
'Weaver, George W.'
_publ_section_title
;
 Synthesis of fluorinated fused benzofurans and benzothiophenes:
 Smiles-type rearrangement and cyclisation of perfluoro(het)aryl ethers
 and sulfides.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2294
_journal_page_last               2305
_journal_paper_doi               10.1039/c0ob00790k
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C11 H4 F3 N S'
_chemical_formula_sum            'C11 H4 F3 N S'
_chemical_formula_weight         239.21
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'all non-H atoms found by direct methods'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.979(2)
_cell_angle_beta                 97.143(2)
_cell_angle_gamma                113.863(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2230(8)
_cell_length_b                   7.9584(9)
_cell_length_c                   9.1866(10)
_cell_measurement_reflns_used    2860
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.93
_cell_measurement_theta_min      2.32
_cell_volume                     462.01(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7449
_diffrn_reflns_theta_full        27.08
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         2.32
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS v2007/5, Sheldrick, G.M., (2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0467P)²+0.1159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0881
_reflns_number_gt                3172
_reflns_number_total             3593
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c0ob00790k.txt
_cod_data_source_block           8
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151750
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.30418(5) 0.25106(5) 0.92937(4) 0.02511(10) Uani 1 1 d . . .
C2 C 0.28484(19) 0.20442(19) 1.10501(15) 0.0215(3) Uani 1 1 d . . .
C3 C 0.2995(2) 0.32815(19) 1.23902(16) 0.0246(3) Uani 1 1 d . . .
F3 F 0.33273(13) 0.50808(11) 1.24488(10) 0.0348(2) Uani 1 1 d . . .
C4 C 0.2781(2) 0.2600(2) 1.36502(16) 0.0267(3) Uani 1 1 d . . .
F4 F 0.28771(14) 0.37427(13) 1.49616(10) 0.0375(2) Uani 1 1 d . . .
N5 N 0.24641(18) 0.08544(17) 1.36810(13) 0.0273(3) Uani 1 1 d . . .
C6 C 0.2334(2) -0.02883(19) 1.24080(16) 0.0237(3) Uani 1 1 d . . .
F6 F 0.20183(14) -0.20500(12) 1.24751(10) 0.0336(2) Uani 1 1 d . . .
C7 C 0.24900(19) 0.01659(18) 1.10301(15) 0.0204(3) Uani 1 1 d . . .
C8 C 0.23457(19) -0.09414(18) 0.95362(15) 0.0208(3) Uani 1 1 d . . .
C9 C 0.1961(2) -0.28496(19) 0.90387(16) 0.0250(3) Uani 1 1 d . . .
H9 H 0.1770 -0.3623 0.9730 0.030 Uiso 1 1 calc R . .
C10 C 0.1863(2) -0.3598(2) 0.75254(17) 0.0304(3) Uani 1 1 d . . .
H10 H 0.1596 -0.4895 0.7179 0.036 Uiso 1 1 calc R . .
C11 C 0.2149(2) -0.2477(2) 0.65055(17) 0.0317(3) Uani 1 1 d . . .
H11 H 0.2082 -0.3020 0.5474 0.038 Uiso 1 1 calc R . .
C12 C 0.2529(2) -0.0589(2) 0.69643(16) 0.0287(3) Uani 1 1 d . . .
H12 H 0.2725 0.0173 0.6265 0.034 Uiso 1 1 calc R . .
C13 C 0.26171(19) 0.01646(19) 0.84829(15) 0.0227(3) 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C13 90.90(6) . . ?
C3 C2 C7 119.57(12) . . ?
C3 C2 S1 127.54(11) . . ?
C7 C2 S1 112.89(10) . . ?
F3 C3 C4 121.26(12) . . ?
F3 C3 C2 121.16(13) . . ?
C4 C3 C2 117.58(13) . . ?
N5 C4 F4 115.98(13) . . ?
N5 C4 C3 124.65(13) . . ?
F4 C4 C3 119.37(13) . . ?
C6 N5 C4 116.84(12) . . ?
N5 C6 F6 115.49(12) . . ?
N5 C6 C7 125.83(12) . . ?
F6 C6 C7 118.68(12) . . ?
C6 C7 C2 115.52(12) . . ?
C6 C7 C8 132.09(12) . . ?
C2 C7 C8 112.39(11) . . ?
C9 C8 C13 119.03(12) . . ?
C9 C8 C7 130.08(12) . . ?
C13 C8 C7 110.89(11) . . ?
C10 C9 C8 119.14(13) . . ?
C9 C10 C11 120.91(14) . . ?
C12 C11 C10 121.21(13) . . ?
C11 C12 C13 118.03(13) . . ?
C12 C13 C8 121.68(13) . . ?
C12 C13 S1 125.39(11) . . ?
C8 C13 S1 112.93(10) . . ?
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 C2 1.7329(14) . ?
S1 C13 1.7564(14) . ?
C2 C3 1.3849(19) . ?
C2 C7 1.4060(17) . ?
C3 F3 1.3417(15) . ?
C3 C4 1.369(2) . ?
C4 N5 1.3197(19) . ?
C4 F4 1.3396(16) . ?
N5 C6 1.3047(18) . ?
C6 F6 1.3413(15) . ?
C6 C7 1.3866(18) . ?
C7 C8 1.4492(18) . ?
C8 C9 1.3981(18) . ?
C8 C13 1.4077(18) . ?
C9 C10 1.385(2) . ?
C10 C11 1.391(2) . ?
C11 C12 1.381(2) . ?
C12 C13 1.3923(19) . ?
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
C13 S1 C2 C3 -179.08(13) . . . . ?
C13 S1 C2 C7 0.52(10) . . . . ?
C7 C2 C3 F3 -179.72(11) . . . . ?
S1 C2 C3 F3 -0.14(19) . . . . ?
C7 C2 C3 C4 0.06(19) . . . . ?
S1 C2 C3 C4 179.64(10) . . . . ?
F3 C3 C4 N5 -179.59(12) . . . . ?
C2 C3 C4 N5 0.6(2) . . . . ?
F3 C3 C4 F4 0.92(19) . . . . ?
C2 C3 C4 F4 -178.86(11) . . . . ?
F4 C4 N5 C6 178.98(12) . . . . ?
C3 C4 N5 C6 -0.5(2) . . . . ?
C4 N5 C6 F6 179.80(11) . . . . ?
C4 N5 C6 C7 -0.3(2) . . . . ?
N5 C6 C7 C2 0.9(2) . . . . ?
F6 C6 C7 C2 -179.18(11) . . . . ?
N5 C6 C7 C8 -178.81(13) . . . . ?
F6 C6 C7 C8 1.1(2) . . . . ?
C3 C2 C7 C6 -0.76(18) . . . . ?
S1 C2 C7 C6 179.60(9) . . . . ?
C3 C2 C7 C8 179.04(11) . . . . ?
S1 C2 C7 C8 -0.60(14) . . . . ?
C6 C7 C8 C9 1.3(2) . . . . ?
C2 C7 C8 C9 -178.46(13) . . . . ?
C6 C7 C8 C13 -179.89(13) . . . . ?
C2 C7 C8 C13 0.36(15) . . . . ?
C13 C8 C9 C10 0.16(19) . . . . ?
C7 C8 C9 C10 178.90(13) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C12 C13 C8 0.5(2) . . . . ?
C11 C12 C13 S1 -179.01(10) . . . . ?
C9 C8 C13 C12 -0.54(19) . . . . ?
C7 C8 C13 C12 -179.51(11) . . . . ?
C9 C8 C13 S1 179.00(10) . . . . ?
C7 C8 C13 S1 0.03(14) . . . . ?
C2 S1 C13 C12 179.21(12) . . . . ?
C2 S1 C13 C8 -0.31(10) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653472
2 PubChem 12580092
