#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:44:49 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/61/7156109.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_7156109
loop_
_publ_author_name
'Jardim, Guilherme A. M.'
'Oliveira, Willian X. C.'
'de Freitas, Rossimiriam P.'
'Menna-Barreto, Rubem F S'
'Silva, Thaissa L.'
'Goulart, Marilia O. F.'
'da Silva Júnior, Eufrânio N'
_publ_section_title
;
 Direct sequential C-H iodination/organoyl-thiolation for the benzenoid
 A-ring modification of quinonoid deactivated systems: a new protocol for
 potent trypanocidal quinones.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1686
_journal_page_last               1691
_journal_paper_doi               10.1039/c8ob00196k
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C12 H4 F6 O2 S2'
_chemical_formula_sum            'C12 H4 F6 O2 S2'
_chemical_formula_weight         358.27
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-11-17 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.9490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.67670(10)
_cell_length_b                   19.3071(3)
_cell_length_c                   14.5648(2)
_cell_measurement_reflns_used    6243
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      66.4230
_cell_measurement_theta_min      3.8090
_cell_volume                     1302.47(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SuperFlip (Palatinus & Chapius, 2007)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11706
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.544
_diffrn_reflns_theta_max         66.544
_diffrn_reflns_theta_min         3.825
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.489
_exptl_absorpt_correction_T_max  0.808
_exptl_absorpt_correction_T_min  0.366
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_description       Needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0518P)²+0.2550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0937
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1984
_reflns_number_total             2307
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ob00196k2.cif
_cod_data_source_block           shelx_CCDC5
_cod_depositor_comments
'Adding full bibliography for 7156104--7156114.cif.'
_cod_database_code               7156109
_shelx_shelxl_version_number     2014/7
_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'
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
S2 S 0.65654(12) 0.47099(3) 0.24868(3) 0.03108(17) Uani 1 1 d . .
S1 S -0.01470(12) 0.21013(3) 0.05288(4) 0.03067(17) Uani 1 1 d . .
F6 F 0.3701(3) 0.46015(7) 0.39394(10) 0.0426(3) Uani 1 1 d . .
F3 F -0.3204(3) 0.19605(7) 0.19332(10) 0.0409(3) Uani 1 1 d . .
F4 F 0.7489(3) 0.39767(8) 0.40175(10) 0.0490(4) Uani 1 1 d . .
F2 F 0.0837(3) 0.14282(7) 0.21321(10) 0.0436(3) Uani 1 1 d . .
F1 F -0.2592(3) 0.10652(7) 0.11132(11) 0.0502(4) Uani 1 1 d . .
F5 F 0.7863(3) 0.50840(8) 0.41416(9) 0.0469(4) Uani 1 1 d . .
O1 O 0.2034(4) 0.26605(9) -0.08126(10) 0.0392(4) Uani 1 1 d . .
O2 O 0.7727(4) 0.47951(9) 0.08210(11) 0.0437(4) Uani 1 1 d . .
C8 C 0.1658(4) 0.28235(10) 0.10962(14) 0.0241(4) Uani 1 1 d . .
C4A C 0.4834(4) 0.38249(10) 0.10332(13) 0.0231(4) Uani 1 1 d . .
C8A C 0.3332(4) 0.32522(10) 0.05991(13) 0.0223(4) Uani 1 1 d . .
C5 C 0.4682(4) 0.39794(10) 0.19673(13) 0.0242(4) Uani 1 1 d . .
C9 C -0.1298(5) 0.16275(11) 0.14849(16) 0.0325(5) Uani 1 1 d . .
C10 C 0.6337(5) 0.45727(11) 0.37008(15) 0.0317(5) Uani 1 1 d . .
C7 C 0.1545(5) 0.29864(11) 0.20235(14) 0.0287(5) Uani 1 1 d . .
H8 H 0.0455 0.2709 0.2366 0.034 Uiso 1 1 calc R U
C6 C 0.2999(5) 0.35447(11) 0.24455(14) 0.0291(5) Uani 1 1 d . .
H7 H 0.2862 0.3636 0.3065 0.035 Uiso 1 1 calc R U
C4 C 0.6624(5) 0.42579(11) 0.04941(15) 0.0286(4) Uani 1 1 d . .
C2 C 0.5622(5) 0.34995(12) -0.08488(15) 0.0345(5) Uani 1 1 d . .
H2 H 0.5949 0.3371 -0.1441 0.041 Uiso 1 1 calc R U
C1 C 0.3555(5) 0.31009(11) -0.03880(14) 0.0272(4) Uani 1 1 d . .
C3 C 0.7030(5) 0.40362(12) -0.04432(15) 0.0344(5) Uani 1 1 d . .
H3 H 0.8308 0.4279 -0.0759 0.041 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C5 S2 C10 101.99(10)
C8 S1 C9 102.24(10)
C7 C8 C8A 117.64(18)
C7 C8 S1 123.30(16)
C8A C8 S1 119.05(15)
C5 C4A C8A 120.78(17)
C5 C4A C4 120.08(18)
C8A C4A C4 119.13(17)
C8 C8A C4A 120.53(17)
C8 C8A C1 120.09(18)
C4A C8A C1 119.37(17)
C6 C5 C4A 117.51(18)
C6 C5 S2 122.95(15)
C4A C5 S2 119.54(15)
F1 C9 F2 107.99(17)
F1 C9 F3 107.19(18)
F2 C9 F3 106.15(18)
F1 C9 S1 105.55(15)
F2 C9 S1 114.66(16)
F3 C9 S1 114.91(15)
F4 C10 F6 107.01(19)
F4 C10 F5 108.14(18)
F6 C10 F5 107.35(17)
F4 C10 S2 113.06(15)
F6 C10 S2 115.65(16)
F5 C10 S2 105.27(15)
C6 C7 C8 121.85(19)
C6 C7 H8 119.1
C8 C7 H8 119.1
C7 C6 C5 121.68(19)
C7 C6 H7 119.2
C5 C6 H7 119.2
O2 C4 C3 120.44(19)
O2 C4 C4A 120.66(19)
C3 C4 C4A 118.90(18)
C3 C2 C1 121.7(2)
C3 C2 H2 119.2
C1 C2 H2 119.2
O1 C1 C2 120.52(19)
O1 C1 C8A 120.89(19)
C2 C1 C8A 118.58(18)
C2 C3 C4 121.6(2)
C2 C3 H3 119.2
C4 C3 H3 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S2 C5 1.776(2)
S2 C10 1.806(2)
S1 C8 1.774(2)
S1 C9 1.809(2)
F6 C10 1.327(3)
F3 C9 1.340(3)
F4 C10 1.326(3)
F2 C9 1.331(3)
F1 C9 1.322(3)
F5 C10 1.330(3)
O1 C1 1.221(3)
O2 C4 1.225(3)
C8 C7 1.395(3)
C8 C8A 1.407(3)
C4A C5 1.404(3)
C4A C8A 1.412(3)
C4A C4 1.483(3)
C8A C1 1.485(3)
C5 C6 1.400(3)
C7 C6 1.373(3)
C7 H8 0.9300
C6 H7 0.9300
C4 C3 1.468(3)
C2 C3 1.322(3)
C2 C1 1.468(3)
C2 H2 0.9300
C3 H3 0.9300
