#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:44:49 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/61/7156108.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_7156108
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         'C16 H9 Br O2 S'
_chemical_formula_sum            'C16 H9 Br O2 S'
_chemical_formula_weight         345.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                89.939(5)
_cell_angle_beta                 74.827(5)
_cell_angle_gamma                68.477(6)
_cell_formula_units_Z            2
_cell_length_a                   7.8595(5)
_cell_length_b                   7.9836(5)
_cell_length_c                   12.2941(7)
_cell_measurement_reflns_used    4147
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      25.9000
_cell_measurement_theta_min      3.3370
_cell_volume                     688.73(8)
_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      250(2)
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18417
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.547
_diffrn_reflns_theta_min         2.758
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.132
_exptl_absorpt_correction_T_max  0.796
_exptl_absorpt_correction_T_min  0.459
_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            'Dark Orange'
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_description       Plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0426
_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)+(0.0245P)²+0.2982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2223
_reflns_number_total             3541
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ob00196k2.cif
_cod_data_source_block           shelx_CCDC4
_cod_depositor_comments
'Adding full bibliography for 7156104--7156114.cif.'
_cod_database_code               7156108
_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, -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
Br1 Br 0.26937(5) 0.26559(5) 0.09408(3) 0.07821(16) Uani 1 1 d . .
S1 S 1.06230(9) 0.24278(9) -0.23629(6) 0.04502(18) Uani 1 1 d . .
O2 O 1.4177(3) 0.2141(2) -0.34983(16) 0.0492(5) Uani 1 1 d . .
O1 O 1.7667(3) -0.5010(3) -0.44031(18) 0.0602(5) Uani 1 1 d . .
C12 C 0.5023(4) 0.2614(3) -0.0039(2) 0.0449(7) Uani 1 1 d . .
C13 C 0.6580(4) 0.2198(4) 0.0366(2) 0.0532(7) Uani 1 1 d . .
H13 H 0.6490 0.1956 0.1123 0.064 Uiso 1 1 calc R U
C7 C 1.1801(4) -0.2932(4) -0.2987(2) 0.0450(7) Uani 1 1 d . .
H7 H 1.1106 -0.3688 -0.2876 0.054 Uiso 1 1 calc R U
C4A C 1.3816(3) -0.0659(3) -0.33551(18) 0.0301(5) Uani 1 1 d . .
C3 C 1.7011(4) -0.0390(4) -0.4129(2) 0.0444(6) Uani 1 1 d . .
H3 H 1.7739 0.0336 -0.4260 0.053 Uiso 1 1 calc R U
C5 C 1.1843(3) 0.0073(3) -0.28174(19) 0.0320(5) Uani 1 1 d . .
C8A C 1.4743(3) -0.2543(3) -0.36609(19) 0.0331(5) Uani 1 1 d . .
C4 C 1.4935(3) 0.0491(3) -0.36357(19) 0.0351(6) Uani 1 1 d . .
C8 C 1.3737(4) -0.3664(3) -0.3484(2) 0.0411(6) Uani 1 1 d . .
H8 H 1.4368 -0.4915 -0.3701 0.049 Uiso 1 1 calc R U
C1 C 1.6842(4) -0.3376(4) -0.4177(2) 0.0408(6) Uani 1 1 d . .
C14 C 0.8276(4) 0.2137(4) -0.0347(2) 0.0487(7) Uani 1 1 d . .
H14 H 0.9347 0.1862 -0.0073 0.058 Uiso 1 1 calc R U
C2 C 1.7893(4) -0.2158(4) -0.4396(2) 0.0459(7) Uani 1 1 d . .
H2 H 1.9217 -0.2649 -0.4732 0.055 Uiso 1 1 calc R U
C6 C 1.0866(3) -0.1100(3) -0.2650(2) 0.0395(6) Uani 1 1 d . .
H6 H 0.9546 -0.0631 -0.2300 0.047 Uiso 1 1 calc R U
C10 C 0.6822(4) 0.2932(4) -0.1850(2) 0.0444(6) Uani 1 1 d . .
H10 H 0.6900 0.3196 -0.2602 0.053 Uiso 1 1 calc R U
C9 C 0.8420(3) 0.2476(3) -0.1463(2) 0.0382(6) Uani 1 1 d . .
C11 C 0.5107(4) 0.2999(4) -0.1135(2) 0.0484(7) Uani 1 1 d . .
H11 H 0.4020 0.3304 -0.1396 0.058 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 0.0033 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 S1 C9 101.19(11)
C11 C12 C13 121.6(3)
C11 C12 Br1 119.3(2)
C13 C12 Br1 119.2(2)
C12 C13 C14 119.3(3)
C12 C13 H13 120.4
C14 C13 H13 120.4
C8 C7 C6 120.7(2)
C8 C7 H7 119.6
C6 C7 H7 119.6
C5 C4A C8A 119.2(2)
C5 C4A C4 121.9(2)
C8A C4A C4 118.9(2)
C2 C3 C4 122.7(2)
C2 C3 H3 118.7
C4 C3 H3 118.7
C6 C5 C4A 118.3(2)
C6 C5 S1 120.79(18)
C4A C5 S1 120.96(17)
C8 C8A C4A 121.1(2)
C8 C8A C1 118.2(2)
C4A C8A C1 120.7(2)
O2 C4 C3 119.8(2)
O2 C4 C4A 121.7(2)
C3 C4 C4A 118.5(2)
C7 C8 C8A 119.4(2)
C7 C8 H8 120.3
C8A C8 H8 120.3
O1 C1 C2 121.1(2)
O1 C1 C8A 121.2(2)
C2 C1 C8A 117.7(2)
C13 C14 C9 120.6(3)
C13 C14 H14 119.7
C9 C14 H14 119.7
C3 C2 C1 121.3(2)
C3 C2 H2 119.3
C1 C2 H2 119.3
C7 C6 C5 121.3(2)
C7 C6 H6 119.3
C5 C6 H6 119.3
C9 C10 C11 120.4(3)
C9 C10 H10 119.8
C11 C10 H10 119.8
C14 C9 C10 119.3(2)
C14 C9 S1 119.7(2)
C10 C9 S1 120.9(2)
C12 C11 C10 118.9(3)
C12 C11 H11 120.6
C10 C11 H11 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C12 1.898(3)
S1 C5 1.779(2)
S1 C9 1.781(3)
O2 C4 1.221(3)
O1 C1 1.219(3)
C12 C11 1.371(4)
C12 C13 1.370(4)
C13 C14 1.374(4)
C13 H13 0.9400
C7 C8 1.375(4)
C7 C6 1.380(3)
C7 H7 0.9400
C4A C5 1.408(3)
C4A C8A 1.410(3)
C4A C4 1.473(3)
C3 C2 1.321(4)
C3 C4 1.472(3)
C3 H3 0.9400
C5 C6 1.397(3)
C8A C8 1.379(3)
C8A C1 1.488(3)
C8 H8 0.9400
C1 C2 1.474(4)
C14 C9 1.381(4)
C14 H14 0.9400
C2 H2 0.9400
C6 H6 0.9400
C10 C9 1.384(4)
C10 C11 1.385(4)
C10 H10 0.9400
C11 H11 0.9400
