#------------------------------------------------------------------------------
#$Date: 2019-11-24 01:46:31 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236093 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/38/1553847.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_1553847
loop_
_publ_author_name
'Zhang, Yunxiao'
'Wu, Dongping'
'Weng, Zhiqiang'
_publ_section_title
;
 Synthesis of 1,2,2-trifluorovinyl sulphides and selenides from
 trifluorovinylation of organic thiocyanates and selenocyanates
;
_journal_issue                   11
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2226
_journal_paper_doi               10.1039/C7QO00595D
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C8 H6 Br F3 O S'
_chemical_formula_weight         287.10
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-06-09 deposited with the CCDC.
2017-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.906(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.993(7)
_cell_length_b                   3.9406(12)
_cell_length_c                   12.147(4)
_cell_measurement_temperature    296(2)
_cell_volume                     999.5(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0642
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3253
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    4.328
_exptl_crystal_density_diffrn    1.908
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0768P)²+1.0967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                1426
_reflns_number_total             1736
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00595d2.cif
_cod_data_source_block           P21_c
_cod_original_cell_volume        999.5(5)
_cod_database_code               1553847
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
Br1 Br 0.06037(3) 0.70622(15) 0.68534(5) 0.0457(3) Uani 1 1 d
S1 S 0.28104(7) 0.3049(4) 0.38142(10) 0.0335(4) Uani 1 1 d
C7 C 0.1898(2) 0.6083(14) 0.6434(5) 0.0310(11) Uani 1 1 d
C6 C 0.1273(2) 0.5674(13) 0.5995(4) 0.0309(11) Uani 1 1 d
C8 C 0.2389(3) 0.5184(14) 0.5815(4) 0.0321(12) Uani 1 1 d
F3 F 0.35100(18) 0.0487(11) 0.5566(3) 0.0614(10) Uani 1 1 d
F2 F 0.38664(17) 0.0679(12) 0.2853(3) 0.0609(10) Uani 1 1 d
C4 C 0.1605(3) 0.3462(15) 0.4352(5) 0.0389(13) Uani 1 1 d
C3 C 0.2243(2) 0.3894(12) 0.4768(4) 0.0267(11) Uani 1 1 d
C5 C 0.1122(3) 0.4343(17) 0.4973(5) 0.0418(14) Uani 1 1 d
C2 C 0.3448(2) 0.0959(13) 0.4587(4) 0.0265(10) Uani 1 1 d
C1 C 0.3949(2) -0.0349(13) 0.3855(4) 0.0277(11) Uani 1 1 d
F1 F 0.43827(19) -0.2174(10) 0.4262(3) 0.0576(10) Uani 1 1 d
O1 O 0.4657(3) -0.1286(14) 0.1620(4) 0.0421(12) Uani 1 1 d
H1A H 0.452(3) -0.150(16) 0.118(5) 0.016(19) Uiso 1 1 d
H1B H 0.490(4) 0.01(3) 0.151(7) 0.08(3) Uiso 1 1 d
H4 H 0.151(3) 0.263(11) 0.366(5) 0.021(13) Uiso 1 1 d
H7 H 0.199(3) 0.705(14) 0.707(5) 0.033(16) Uiso 1 1 d
H8 H 0.279(3) 0.540(14) 0.613(5) 0.033(14) Uiso 1 1 d
H5 H 0.073(4) 0.41(2) 0.469(6) 0.06(2) 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'
Br Br -0.2901 2.4595 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 S1 C3 105.3(2)
C6 C7 C8 119.7(5)
C5 C6 C7 121.6(5)
C5 C6 Br1 119.7(4)
C7 C6 Br1 118.7(4)
C3 C8 C7 119.4(5)
C5 C4 C3 120.5(5)
C8 C3 C4 119.7(5)
C8 C3 S1 124.9(4)
C4 C3 S1 115.1(4)
C6 C5 C4 119.2(5)
F3 C2 C1 120.8(4)
F3 C2 S1 127.0(4)
C1 C2 S1 112.2(3)
F1 C1 F2 126.4(5)
F1 C1 C2 119.3(4)
F2 C1 C2 114.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C6 1.913(5)
S1 C2 1.759(5)
S1 C3 1.776(5)
C7 C6 1.374(7)
C7 C8 1.383(7)
C6 C5 1.355(8)
C8 C3 1.374(7)
F3 C2 1.197(5)
F2 C1 1.278(6)
C4 C5 1.368(8)
C4 C3 1.393(8)
C2 C1 1.535(7)
C1 F1 1.224(6)
