#------------------------------------------------------------------------------
#$Date: 2017-03-04 04:01:26 +0200 (Sat, 04 Mar 2017) $
#$Revision: 192965 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/54/4345407.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_4345407
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            'C10.75 H7.75 F3 I O3 S Se'
_chemical_formula_weight         479.84
_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                 114.16(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.544(3)
_cell_length_b                   10.340(2)
_cell_length_c                   12.411(3)
_cell_measurement_reflns_used    6221
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      77.278
_cell_measurement_theta_min      3.8170
_cell_volume                     1468.8(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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0740
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11618
_diffrn_reflns_theta_full        70.04
_diffrn_reflns_theta_max         70.04
_diffrn_reflns_theta_min         3.86
_exptl_absorpt_coefficient_mu    21.663
_exptl_absorpt_correction_T_max  0.1395
_exptl_absorpt_correction_T_min  0.0872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    2.170
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             905
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         4.146
_refine_diff_density_min         -2.203
_refine_diff_density_rms         0.320
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2798
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0690
_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)+(0.1396P)²+10.8210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1880
_refine_ls_wR_factor_ref         0.1923
_reflns_number_gt                2585
_reflns_number_total             2798
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic6b02386_si_002.cif
_cod_data_source_block           10
_cod_original_cell_volume        1468.8(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4345407
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 0.64466(4) 0.52231(5) 0.73092(4) 0.0159(3) Uani 1 1 d . C .
S1 S 0.32349(17) 0.42858(18) 0.58767(18) 0.0180(4) Uani 1 1 d . . .
O3 O 0.3996(6) 0.5316(6) 0.6552(7) 0.0287(15) Uani 1 1 d . . .
O2 O 0.3164(6) 0.3208(6) 0.6556(6) 0.0329(15) Uani 1 1 d . . .
C4 C 0.6582(6) 0.5611(6) 0.9910(5) 0.0080(12) Uiso 1 1 d D . .
H4A H 0.6718 0.6507 0.9850 0.010 Uiso 1 1 calc R . .
C101 C 0.1786(9) 0.5011(12) 0.5370(10) 0.034(2) Uani 1 1 d . . .
C7 C 0.6385(7) 0.4672(7) 0.8937(7) 0.0163(16) Uani 1 1 d D . .
C10 C 0.8238(9) 0.5260(9) 0.7939(9) 0.028(2) Uani 1 1 d D . .
C17 C 0.6117(8) 0.3333(8) 0.9037(9) 0.0268(19) Uani 1 1 d . . .
H17A H 0.5967 0.2733 0.8412 0.032 Uiso 1 1 calc R . .
C18 C 0.6326(9) 0.3862(12) 1.0978(10) 0.038(2) Uani 1 1 d . . .
H18A H 0.6323 0.3565 1.1701 0.045 Uiso 1 1 calc R . .
C19 C 0.6549(10) 0.5069(11) 1.0879(8) 0.034(2) Uani 1 1 d D . .
H19A H 0.6700 0.5612 1.1543 0.041 Uiso 1 1 calc R . .
C22 C 0.6094(10) 0.2988(10) 1.0062(10) 0.040(2) Uani 1 1 d . . .
H22A H 0.5912 0.2118 1.0167 0.048 Uiso 1 1 calc R . .
O1 O 0.3357(7) 0.3953(8) 0.4804(6) 0.0364(16) Uani 1 1 d . . .
F3 F 0.1541(7) 0.5307(11) 0.6282(8) 0.073(3) Uani 1 1 d . . .
C36 C 1.0404(10) 0.5732(13) 0.8718(11) 0.044(3) Uani 1 1 d . . .
H36 H 1.1175 0.6068 0.8993 0.053 Uiso 1 1 calc R A 1
F2 F 0.1707(7) 0.6065(8) 0.4732(8) 0.063(2) Uani 1 1 d . . .
F1 F 0.0987(6) 0.4225(10) 0.4694(8) 0.064(2) Uani 1 1 d . . .
C31 C 1.0176(9) 0.4452(13) 0.8574(12) 0.047(3) Uani 1 1 d D C .
H31 H 1.0751 0.3795 0.8741 0.056 Uiso 1 1 calc R B 1
Se1 Se 0.91215(11) 0.67726(14) 0.83457(14) 0.0339(4) Uani 0.75 1 d P C 1
C1A C 0.8973(9) 0.4233(12) 0.8144(15) 0.034(3) Uani 0.75 1 d PD C 1
H1A H 0.8673 0.3377 0.7995 0.041 Uiso 0.75 1 calc PR C 1
Se2 Se 0.8973(6) 0.3498(11) 0.8126(8) 0.072(2) Uani 0.25 1 d P 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'
Se Se -0.7943 1.1372 '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
C10 I1 C7 95.9(4)
O2 S1 O1 114.6(5)
O2 S1 O3 114.8(4)
O1 S1 O3 114.6(5)
O2 S1 C101 103.4(5)
O1 S1 C101 104.3(5)
O3 S1 C101 103.0(5)
C19 C4 C7 113.5(7)
C19 C4 H4A 123.3
C7 C4 H4A 123.3
F1 C101 F3 108.1(11)
F1 C101 F2 106.2(10)
F3 C101 F2 109.5(11)
F1 C101 S1 111.3(8)
F3 C101 S1 110.3(8)
F2 C101 S1 111.3(8)
C17 C7 C4 121.5(7)
C17 C7 I1 116.1(6)
C4 C7 I1 122.4(5)
C1A C10 Se1 108.8(8)
C1A C10 Se2 13.6(6)
Se1 C10 Se2 122.4(6)
C1A C10 I1 127.5(8)
Se1 C10 I1 123.7(4)
Se2 C10 I1 113.9(5)
C22 C17 C7 115.9(8)
C22 C17 H17A 122.1
C7 C17 H17A 122.1
C19 C18 C22 122.1(10)
C19 C18 H18A 119.0
C22 C18 H18A 119.0
C18 C19 C4 125.0(10)
C18 C19 H19A 117.5
C4 C19 H19A 117.5
C17 C22 C18 122.0(9)
C17 C22 H22A 119.0
C18 C22 H22A 119.0
C31 C36 Se1 115.2(8)
C31 C36 H36 122.4
Se1 C36 H36 122.4
C36 C31 C1A 110.3(11)
C36 C31 Se2 136.5(10)
C1A C31 Se2 26.3(5)
C36 C31 H31 124.9
C1A C31 H31 124.9
Se2 C31 H31 98.6
C36 Se1 C10 86.5(5)
C10 C1A C31 119.2(12)
C10 C1A H1A 120.4
C31 C1A H1A 120.4
C31 Se2 C10 79.4(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C10 2.056(10)
I1 C7 2.130(8)
S1 O2 1.422(7)
S1 O1 1.443(7)
S1 O3 1.447(7)
S1 C101 1.824(10)
C4 C19 1.344(9)
C4 C7 1.490(7)
C4 H4A 0.9500
C101 F1 1.296(14)
C101 F3 1.324(15)
C101 F2 1.328(14)
C7 C17 1.442(11)
C10 C1A 1.360(9)
C10 Se1 1.863(10)
C10 Se2 2.011(12)
C17 C22 1.332(15)
C17 H17A 0.9500
C18 C19 1.296(16)
C18 C22 1.387(17)
C18 H18A 0.9500
C19 H19A 0.9500
C22 H22A 0.9500
C36 C31 1.35(2)
C36 Se1 1.830(12)
C36 H36 0.9500
C31 C1A 1.398(9)
C31 Se2 1.695(15)
C31 H31 0.9500
C1A H1A 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 S1 C101 F1 -63.1(10)
O1 S1 C101 F1 57.0(10)
O3 S1 C101 F1 177.0(9)
O2 S1 C101 F3 56.9(10)
O1 S1 C101 F3 177.1(9)
O3 S1 C101 F3 -62.9(10)
O2 S1 C101 F2 178.6(8)
O1 S1 C101 F2 -61.2(9)
O3 S1 C101 F2 58.8(9)
C19 C4 C7 C17 3.5(12)
C19 C4 C7 I1 -177.7(7)
C10 I1 C7 C17 -102.7(7)
C10 I1 C7 C4 78.4(7)
C7 I1 C10 C1A 78.1(12)
C7 I1 C10 Se1 -101.1(6)
C7 I1 C10 Se2 77.3(5)
C4 C7 C17 C22 -2.0(13)
I1 C7 C17 C22 179.2(8)
C22 C18 C19 C4 -0.1(18)
C7 C4 C19 C18 -2.5(15)
C7 C17 C22 C18 -0.8(16)
C19 C18 C22 C17 1.9(18)
Se1 C36 C31 C1A 1.0(16)
Se1 C36 C31 Se2 0(2)
C31 C36 Se1 C10 -1.2(10)
C1A C10 Se1 C36 1.1(10)
Se2 C10 Se1 C36 2.1(7)
I1 C10 Se1 C36 -179.6(7)
Se1 C10 C1A C31 -0.9(18)
Se2 C10 C1A C31 -177(5)
I1 C10 C1A C31 179.8(10)
C36 C31 C1A C10 0(2)
Se2 C31 C1A C10 178(3)
C36 C31 Se2 C10 1.4(16)
C1A C31 Se2 C10 -1.1(18)
C1A C10 Se2 C31 2(4)
Se1 C10 Se2 C31 -2.1(8)
I1 C10 Se2 C31 179.5(7)
