#------------------------------------------------------------------------------
#$Date: 2017-02-04 04:25:52 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191387 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/51/1545136.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_1545136
loop_
_publ_author_name
'Li, Minghao'
'Petersen, Jeffrey L.'
'Hoover, Jessica M.'
_publ_section_title
;
 Silver-Mediated Oxidative Decarboxylative Trifluoromethylthiolation of
 Coumarin-3-carboxylic Acids.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              638
_journal_page_last               641
_journal_paper_doi               10.1021/acs.orglett.6b03806
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C11 H6 Br F3 O3 S'
_chemical_formula_weight         355.13
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9189(5)
_cell_length_b                   13.9189(5)
_cell_length_c                   12.9169(5)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      32.5300
_cell_measurement_theta_min      3.1543
_cell_volume                     2502.47(16)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS D8 Venture fixed chi'
_diffrn_measurement_method       'omega scan, PHOTON 100 CMOS'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26231
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.27
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.489
_exptl_absorpt_correction_T_max  0.52
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.885
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelopiped
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.517
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.301
_refine_ls_abs_structure_details
;
Flack x determined using 1341 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0261
_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)+(0.0298P)²+0.5417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0609
_reflns_number_gt                3384
_reflns_number_total             3645
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b03806_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1545136.cif.'
_cod_original_cell_volume        2502.5(2)
_cod_database_code               1545136
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
Br Br1 -0.08405(2) 0.79658(2) 0.13110(2) 0.02378(8) Uani d . . 1
S S1 0.37367(5) 0.44732(5) 0.17470(6) 0.02328(16) Uani d . . 1
F F1 0.33095(15) 0.48305(17) 0.36833(18) 0.0438(5) Uani d . . 1
F F2 0.46011(13) 0.40289(15) 0.34159(17) 0.0380(5) Uani d . . 1
F F3 0.32252(18) 0.33402(18) 0.32811(19) 0.0542(7) Uani d . . 1
O O1 0.09268(12) 0.40354(12) 0.12048(13) 0.0153(3) Uani d . . 1
O O2 0.21497(14) 0.30264(14) 0.12445(17) 0.0240(4) Uani d . . 1
O O3 -0.09256(13) 0.41998(14) 0.10024(13) 0.0174(4) Uani d . . 1
C C1 -0.04382(18) 0.50319(19) 0.11123(18) 0.0148(5) Uani d . . 1
C C2 -0.08413(18) 0.5947(2) 0.11291(18) 0.0162(5) Uani d . . 1
H H2 -0.1516 0.6028 0.1057 0.019 Uiso calc U R 1
C C3 -0.02447(18) 0.67450(19) 0.1253(2) 0.0170(5) Uani d . . 1
C C4 0.07354(18) 0.66758(19) 0.13510(19) 0.0155(5) Uani d . . 1
H H4 0.1124 0.7233 0.142 0.019 Uiso calc U R 1
C C5 0.11464(17) 0.57487(18) 0.13452(18) 0.0137(4) Uani d . . 1
C C6 0.21525(18) 0.5588(2) 0.15285(19) 0.0156(5) Uani d . . 1
H H6 0.2571 0.6118 0.1635 0.019 Uiso calc U R 1
C C7 0.25043(18) 0.4683(2) 0.1550(2) 0.0168(5) Uani d . . 1
C C8 0.18916(18) 0.38468(18) 0.1331(2) 0.0175(5) Uani d . . 1
C C9 0.05634(17) 0.49487(18) 0.12230(19) 0.0140(4) Uani d . . 1
C C10 -0.19530(19) 0.4277(2) 0.0915(2) 0.0234(6) Uani d . . 1
H H10A -0.2213 0.4573 0.1544 0.035 Uiso calc U R 1
H H10B -0.2231 0.3635 0.0828 0.035 Uiso calc U R 1
H H10C -0.2116 0.4675 0.0315 0.035 Uiso calc U R 1
C C11 0.3701(2) 0.4154(2) 0.3089(3) 0.0291(7) Uani d . . 1
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'
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'
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
C7 S1 C11 98.90(13)
C9 O1 C8 122.4(2)
C1 O3 C10 116.4(2)
O3 C1 C2 125.7(2)
O3 C1 C9 116.0(2)
C2 C1 C9 118.3(2)
C1 C2 C3 119.3(2)
C4 C3 C2 123.1(2)
C4 C3 Br1 119.6(2)
C2 C3 Br1 117.27(18)
C3 C4 C5 117.8(2)
C9 C5 C4 119.8(2)
C9 C5 C6 117.6(2)
C4 C5 C6 122.4(2)
C7 C6 C5 120.1(2)
C6 C7 C8 121.6(2)
C6 C7 S1 120.8(2)
C8 C7 S1 117.5(2)
O2 C8 O1 117.5(2)
O2 C8 C7 126.6(2)
O1 C8 C7 115.9(2)
O1 C9 C5 122.1(2)
O1 C9 C1 116.2(2)
C5 C9 C1 121.7(2)
F1 C11 F2 107.1(3)
F1 C11 F3 106.9(3)
F2 C11 F3 107.3(3)
F1 C11 S1 113.2(2)
F2 C11 S1 108.2(2)
F3 C11 S1 113.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.892(3)
S1 C7 1.759(3)
S1 C11 1.791(3)
F1 C11 1.332(4)
F2 C11 1.333(3)
F3 C11 1.335(4)
O1 C9 1.368(3)
O1 C8 1.378(3)
O2 C8 1.202(3)
O3 C1 1.350(3)
O3 C10 1.438(3)
C1 C2 1.392(4)
C1 C9 1.406(3)
C2 C3 1.396(4)
C3 C4 1.373(3)
C4 C5 1.412(3)
C5 C9 1.387(3)
C5 C6 1.438(3)
C6 C7 1.351(4)
C7 C8 1.471(4)
