#------------------------------------------------------------------------------
#$Date: 2017-03-04 04:01:26 +0200 (Sat, 04 Mar 2017) $
#$Revision: 192965 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/54/4345409.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_4345409
loop_
_publ_author_name
'Egalahewa, Sathsara'
'Albayer, Mohammad'
'Aprile, Antonino'
'Dutton, Jason L.'
_publ_section_title
;
 Diverse Reactions of Thiophenes, Selenophenes, and Tellurophenes with
 Strongly Oxidizing I(III) PhI(L)2 Reagents.
;
_journal_issue                   3
_journal_name_full               'Inorganic chemistry'
_journal_page_first              1282
_journal_page_last               1288
_journal_paper_doi               10.1021/acs.inorgchem.6b02386
_journal_volume                  56
_journal_year                    2017
_chemical_formula_sum            'C11 H8 F3 I O3 S2'
_chemical_formula_weight         436.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   '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
_cell_angle_alpha                90.00
_cell_angle_beta                 113.66(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.392(3)
_cell_length_b                   10.379(2)
_cell_length_c                   12.365(3)
_cell_measurement_reflns_used    7051
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      76.2700
_cell_measurement_theta_min      3.8790
_cell_volume                     1456.7(7)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    SHELXP
_computing_publication_material  SHELXP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8916
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         5.78
_exptl_absorpt_coefficient_mu    20.331
_exptl_absorpt_correction_T_max  0.1393
_exptl_absorpt_correction_T_min  0.0592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.989
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.100
_refine_diff_density_min         -1.042
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2390
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0356
_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
'calc w=1/[σ²(Fo²)+(0.0691P)²+1.0025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                2340
_reflns_number_total             2390
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic6b02386_si_002.cif
_cod_data_source_block           13
_cod_original_cell_volume        1456.7(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4345409
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.354579(19) 1.01921(2) -0.230077(18) 0.02565(15) Uani 1 1 d . C .
S2 S 0.32352(8) 1.07592(8) 0.08824(8) 0.0285(2) Uani 1 1 d . . .
O3 O 0.3982(3) 0.9709(3) 0.1531(4) 0.0413(8) Uani 1 1 d . . .
C4 C 0.3623(3) 0.9607(4) -0.3888(3) 0.0265(7) Uani 1 1 d . . .
O5 O 0.3229(3) 1.1836(3) 0.1600(3) 0.0447(7) Uani 1 1 d . . .
O6 O 0.3337(3) 1.1074(4) -0.0205(3) 0.0496(8) Uani 1 1 d . . .
C7 C 0.1754(5) 1.0096(5) 0.0426(5) 0.0445(11) Uani 1 1 d . . .
C8 C 0.3851(4) 0.8305(4) -0.4027(4) 0.0337(8) Uani 1 1 d . . .
H8A H 0.3981 0.7694 -0.3415 0.040 Uiso 1 1 calc R . .
F9 F 0.1613(3) 0.9061(4) -0.0230(3) 0.0722(10) Uani 1 1 d . . .
C10 C 0.3430(3) 1.0526(4) -0.4813(3) 0.0263(7) Uani 1 1 d . . .
H10A H 0.3283 1.1408 -0.4717 0.032 Uiso 1 1 calc R . .
C11 C 0.3466(5) 1.0084(5) -0.5829(5) 0.0411(11) Uani 1 1 d . . .
H11A H 0.3342 1.0670 -0.6458 0.049 Uiso 1 1 calc R . .
C12 C 0.1728(4) 1.0117(4) -0.2928(4) 0.0324(9) Uani 1 1 d D . .
F13 F 0.1535(4) 0.9793(5) 0.1352(4) 0.0785(13) Uani 1 1 d . . .
C14 C 0.3676(5) 0.8813(5) -0.5968(4) 0.0457(11) Uani 1 1 d . . .
H14A H 0.3681 0.8532 -0.6697 0.055 Uiso 1 1 calc R . .
C15 C 0.3877(5) 0.7952(5) -0.5092(4) 0.0487(11) Uani 1 1 d . . .
H15A H 0.4040 0.7081 -0.5211 0.058 Uiso 1 1 calc R . .
F17 F 0.0962(3) 1.0946(5) -0.0201(4) 0.0802(12) Uani 1 1 d . . .
C18 C -0.0308(5) 1.0624(8) -0.3655(5) 0.0625(15) Uani 1 1 d D . .
H18 H -0.1007 1.1128 -0.3930 0.075 Uiso 1 1 calc R A 1
C20 C -0.0218(5) 0.9352(7) -0.3558(5) 0.0578(13) Uani 1 1 d D C .
H20 H -0.0919 0.8858 -0.3774 0.069 Uiso 1 1 calc R B 1
S1 S 0.1060(3) 0.8585(5) -0.3077(4) 0.0503(11) Uani 0.493(7) 1 d P C 1
C3 C 0.0858(8) 1.1059(14) -0.3261(19) 0.095(13) Uani 0.493(7) 1 d PD C 1
H3A H 0.1044 1.1950 -0.3223 0.114 Uiso 0.493(7) 1 calc PR C 1
S3 S 0.0928(3) 1.1535(5) -0.3284(5) 0.0534(11) Uani 0.507(7) 1 d P C 2
C3B C 0.0976(8) 0.9080(12) -0.3171(19) 0.062(6) Uani 0.507(7) 1 d PD C 2
H3BA H 0.1260 0.8220 -0.3079 0.074 Uiso 0.507(7) 1 calc PR C 2
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'
I I -0.3257 6.8362 '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
C12 I1 C4 95.20(17)
O5 S2 O6 115.3(2)
O5 S2 O3 114.0(2)
O6 S2 O3 114.4(2)
O5 S2 C7 103.4(2)
O6 S2 C7 104.6(2)
O3 S2 C7 103.2(2)
C8 C4 C10 121.3(3)
C8 C4 I1 118.7(3)
C10 C4 I1 119.9(3)
F9 C7 F17 107.5(5)
F9 C7 F13 108.6(4)
F17 C7 F13 107.9(5)
F9 C7 S2 111.5(4)
F17 C7 S2 110.4(4)
F13 C7 S2 110.8(4)
C15 C8 C4 117.1(4)
C11 C10 C4 117.2(4)
C10 C11 C14 121.4(5)
C3B C12 C3 96.3(8)
C3B C12 S3 110.0(6)
C3 C12 S3 13.8(5)
C3B C12 S1 13.0(5)
C3 C12 S1 109.1(6)
S3 C12 S1 122.9(3)
C3B C12 I1 130.7(5)
C3 C12 I1 133.0(6)
S3 C12 I1 119.3(3)
S1 C12 I1 117.8(3)
C15 C14 C11 121.4(5)
C14 C15 C8 121.5(4)
C20 C18 C3 104.5(7)
C20 C18 S3 119.7(5)
C3 C18 S3 15.2(5)
C18 C20 C3B 105.8(7)
C18 C20 S1 123.0(5)
C3B C20 S1 17.3(4)
C20 S1 C12 86.9(3)
C12 C3 C18 116.4(10)
C18 S3 C12 87.6(4)
C12 C3B C20 116.8(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C12 2.069(5)
I1 C4 2.094(4)
S2 O5 1.429(3)
S2 O6 1.437(3)
S2 O3 1.447(3)
S2 C7 1.824(5)
C4 C8 1.405(5)
C4 C10 1.433(5)
C7 F9 1.315(7)
C7 F17 1.316(7)
C7 F13 1.317(7)
C8 C15 1.379(6)
C10 C11 1.354(7)
C11 C14 1.369(7)
C12 C3B 1.375(10)
C12 C3 1.390(10)
C12 S3 1.730(5)
C12 S1 1.767(6)
C14 C15 1.349(7)
C18 C20 1.327(11)
C18 C3 1.402(10)
C18 S3 1.699(8)
C20 C3B 1.389(9)
C20 S1 1.655(7)
