#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:19:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178778 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/32/4103239.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_4103239
loop_
_publ_author_name
'Scott A. Snyder'
'Daniel S. Treitler'
'Alexandria P. Brucks'
_publ_section_title
;
 Simple Reagents for Direct Halonium-Induced Polyene Cyclizations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14303
_journal_page_last               14314
_journal_paper_doi               10.1021/ja106813s
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C8 H20 Cl7 I2 S2 Sb'
_chemical_formula_weight         804.06
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                119.1030(10)
_cell_angle_beta                 90.4650(10)
_cell_angle_gamma                91.2360(10)
_cell_formula_units_Z            4
_cell_length_a                   11.3702(8)
_cell_length_b                   15.5446(10)
_cell_length_c                   15.5823(10)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      32.30
_cell_measurement_theta_min      2.36
_cell_volume                     2405.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38835
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    4.656
_exptl_absorpt_correction_T_max  0.4012
_exptl_absorpt_correction_T_min  0.2640
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            ORANGE
_exptl_crystal_density_diffrn    2.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         4.461
_refine_diff_density_min         -3.206
_refine_diff_density_rms         0.189
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         14595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0556
_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)+(0.0700P)²+13.3141P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1600
_reflns_number_gt                11210
_reflns_number_total             14595
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja106813s_si_006.cif
_cod_data_source_block           abis10
_cod_database_code               4103239
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Sb1 Sb 1.0000 1.0000 1.0000 0.03080(12) Uani 1 2 d S
Sb2 Sb 1.0000 0.5000 0.5000 0.03141(13) Uani 1 2 d S
Sb3 Sb 0.5000 1.5000 1.0000 0.03880(15) Uani 1 2 d S
Sb4 Sb 0.5000 1.0000 0.5000 0.03689(14) Uani 1 2 d S
Cl11 Cl 0.82081(17) 1.08204(15) 1.05981(15) 0.0475(4) Uani 1 1 d .
Cl12 Cl 1.10607(18) 1.13365(14) 1.12884(14) 0.0469(4) Uani 1 1 d .
Cl13 Cl 0.97954(18) 0.92457(15) 1.09988(15) 0.0462(4) Uani 1 1 d .
Cl21 Cl 1.0962(2) 0.36562(16) 0.37348(16) 0.0602(6) Uani 1 1 d .
Cl22 Cl 0.8153(2) 0.4277(2) 0.42701(19) 0.0621(6) Uani 1 1 d .
Cl23 Cl 1.00754(19) 0.58328(14) 0.40688(14) 0.0447(4) Uani 1 1 d .
Cl31 Cl 0.6262(3) 1.6278(2) 1.1141(2) 0.0756(8) Uani 1 1 d .
Cl32 Cl 0.5240(2) 1.40915(19) 1.0838(2) 0.0605(6) Uani 1 1 d .
Cl33 Cl 0.3365(3) 1.5765(2) 1.0974(3) 0.0859(10) Uani 1 1 d .
Cl41 Cl 0.3864(2) 0.86886(18) 0.37545(18) 0.0620(6) Uani 1 1 d .
Cl42 Cl 0.6731(2) 0.93387(19) 0.4113(2) 0.0635(6) Uani 1 1 d .
Cl43 Cl 0.47710(19) 1.09228(15) 0.41652(16) 0.0495(4) Uani 1 1 d .
I11 I 1.03129(5) 0.43792(4) -0.14524(3) 0.04280(12) Uani 1 1 d .
I12 I 0.97236(4) 0.15448(3) -0.41286(3) 0.03896(11) Uani 1 1 d .
I21 I 0.53724(5) 0.64718(4) 0.56820(4) 0.05204(14) Uani 1 1 d .
I22 I 0.53861(5) 0.92344(5) 0.85158(4) 0.04953(14) Uani 1 1 d .
Cl1 Cl 1.0499(2) 0.23112(13) -0.21968(11) 0.0457(4) Uani 1 1 d .
Cl2 Cl 0.5197(3) 0.72288(15) 0.77232(14) 0.0633(7) Uani 1 1 d .
S11 S 1.02947(18) 0.62160(14) -0.06270(13) 0.0430(4) Uani 1 1 d .
S12 S 0.91553(18) 0.08698(13) -0.58974(14) 0.0416(4) Uani 1 1 d .
S21 S 0.5515(2) 0.56325(17) 0.38402(18) 0.0551(5) Uani 1 1 d .
S22 S 0.5701(3) 1.1016(2) 0.9214(2) 0.0749(9) Uani 1 1 d .
C11 C 1.2109(8) 0.6412(9) -0.1660(7) 0.064(3) Uani 1 1 d .
H11A H 1.2374 0.6568 -0.2167 0.096 Uiso 1 1 calc R
H11B H 1.2317 0.5737 -0.1842 0.096 Uiso 1 1 calc R
H11C H 1.2491 0.6872 -0.1030 0.096 Uiso 1 1 calc R
C12 C 1.0789(8) 0.6506(7) -0.1568(6) 0.0490(18) Uani 1 1 d .
H12A H 1.0399 0.6048 -0.2206 0.059 Uiso 1 1 calc R
H12B H 1.0574 0.7185 -0.1390 0.059 Uiso 1 1 calc R
C13 C 0.8745(8) 0.6515(6) -0.0528(6) 0.0513(19) Uani 1 1 d .
H13A H 0.8368 0.6271 -0.0113 0.062 Uiso 1 1 calc R
H13B H 0.8690 0.7241 -0.0179 0.062 Uiso 1 1 calc R
C14 C 0.8061(8) 0.6121(7) -0.1454(7) 0.055(2) Uani 1 1 d .
H14A H 0.7244 0.6325 -0.1312 0.082 Uiso 1 1 calc R
H14B H 0.8082 0.5400 -0.1802 0.082 Uiso 1 1 calc R
H14C H 0.8402 0.6375 -0.1866 0.082 Uiso 1 1 calc R
C15 C 1.1455(9) 0.0773(9) -0.6384(8) 0.067(3) Uani 1 1 d .
H15A H 1.2108 0.1031 -0.6607 0.100 Uiso 1 1 calc R
H15B H 1.1307 0.0075 -0.6858 0.100 Uiso 1 1 calc R
H15C H 1.1657 0.0843 -0.5740 0.100 Uiso 1 1 calc R
C16 C 1.0381(8) 0.1332(6) -0.6306(6) 0.0474(17) Uani 1 1 d .
H16A H 1.0183 0.1270 -0.6954 0.057 Uiso 1 1 calc R
H16B H 1.0531 0.2039 -0.5834 0.057 Uiso 1 1 calc R
C17 C 0.8014(8) 0.1701(6) -0.5808(6) 0.0494(18) Uani 1 1 d .
H17A H 0.7337 0.1613 -0.5459 0.059 Uiso 1 1 calc R
H17B H 0.8317 0.2389 -0.5417 0.059 Uiso 1 1 calc R
C18 C 0.7603(12) 0.1523(10) -0.6808(8) 0.082(4) Uani 1 1 d .
H18A H 0.6986 0.1985 -0.6729 0.124 Uiso 1 1 calc R
H18B H 0.7289 0.0846 -0.7192 0.124 Uiso 1 1 calc R
H18C H 0.8267 0.1623 -0.7149 0.124 Uiso 1 1 calc R
C21 C 0.7274(11) 0.6826(11) 0.3832(15) 0.110(6) Uani 1 1 d .
H21A H 0.7525 0.7345 0.3683 0.165 Uiso 1 1 calc R
H21B H 0.7734 0.6237 0.3448 0.165 Uiso 1 1 calc R
H21C H 0.7401 0.7056 0.4534 0.165 Uiso 1 1 calc R
C22 C 0.6027(15) 0.6586(11) 0.3579(12) 0.099(4) Uani 1 1 d .
H22A H 0.5899 0.6364 0.2872 0.119 Uiso 1 1 calc R
H22B H 0.5566 0.7184 0.3958 0.119 Uiso 1 1 calc R
C23 C 0.3933(12) 0.5415(10) 0.3393(10) 0.086(4) Uani 1 1 d .
H23A H 0.3925 0.5069 0.2666 0.103 Uiso 1 1 calc R
H23B H 0.3552 0.4966 0.3597 0.103 Uiso 1 1 calc R
C24 C 0.3260(10) 0.6236(10) 0.3712(9) 0.078(3) Uani 1 1 d .
H24A H 0.2459 0.6036 0.3438 0.117 Uiso 1 1 calc R
H24B H 0.3606 0.6678 0.3494 0.117 Uiso 1 1 calc R
H24C H 0.3236 0.6578 0.4431 0.117 Uiso 1 1 calc R
C25 C 0.7464(11) 1.1861(9) 0.8661(8) 0.077(3) Uani 1 1 d .
H25A H 0.8128 1.1799 0.8239 0.116 Uiso 1 1 calc R
H25B H 0.7735 1.2194 0.9349 0.116 Uiso 1 1 calc R
H25C H 0.6853 1.2247 0.8572 0.116 Uiso 1 1 calc R
C26 C 0.7006(10) 1.0928(9) 0.8410(8) 0.069(3) Uani 1 1 d .
H26A H 0.7627 1.0536 0.8493 0.083 Uiso 1 1 calc R
H26B H 0.6748 1.0586 0.7711 0.083 Uiso 1 1 calc R
C27 C 0.4581(11) 1.1306(10) 0.8617(10) 0.083(3) Uani 1 1 d .
H27A H 0.4788 1.1926 0.8615 0.099 Uiso 1 1 calc R
H27B H 0.4479 1.0774 0.7928 0.099 Uiso 1 1 calc R
C28 C 0.3511(11) 1.1413(9) 0.9142(13) 0.103(6) Uani 1 1 d .
H28A H 0.2870 1.1571 0.8822 0.154 Uiso 1 1 calc R
H28B H 0.3618 1.1945 0.9821 0.154 Uiso 1 1 calc R
H28C H 0.3314 1.0795 0.9142 0.154 Uiso 1 1 calc R
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
Cl12 Sb1 Cl12 179.999(1) 2_777 .
Cl12 Sb1 Cl13 89.90(7) 2_777 2_777
Cl12 Sb1 Cl13 90.10(7) . 2_777
Cl12 Sb1 Cl13 90.10(7) 2_777 .
Cl12 Sb1 Cl13 89.90(7) . .
Cl13 Sb1 Cl13 180.000(1) 2_777 .
Cl12 Sb1 Cl11 89.58(7) 2_777 .
Cl12 Sb1 Cl11 90.42(7) . .
Cl13 Sb1 Cl11 89.77(7) 2_777 .
Cl13 Sb1 Cl11 90.23(7) . .
Cl12 Sb1 Cl11 90.42(7) 2_777 2_777
Cl12 Sb1 Cl11 89.58(7) . 2_777
Cl13 Sb1 Cl11 90.23(7) 2_777 2_777
Cl13 Sb1 Cl11 89.77(7) . 2_777
Cl11 Sb1 Cl11 180.00(11) . 2_777
Cl21 Sb2 Cl21 179.998(1) . 2_766
Cl21 Sb2 Cl22 90.34(10) . .
Cl21 Sb2 Cl22 89.66(10) 2_766 .
Cl21 Sb2 Cl22 89.66(10) . 2_766
Cl21 Sb2 Cl22 90.34(10) 2_766 2_766
Cl22 Sb2 Cl22 179.999(1) . 2_766
Cl21 Sb2 Cl23 89.95(7) . .
Cl21 Sb2 Cl23 90.05(7) 2_766 .
Cl22 Sb2 Cl23 90.24(7) . .
Cl22 Sb2 Cl23 89.76(7) 2_766 .
Cl21 Sb2 Cl23 90.05(7) . 2_766
Cl21 Sb2 Cl23 89.95(7) 2_766 2_766
Cl22 Sb2 Cl23 89.76(7) . 2_766
Cl22 Sb2 Cl23 90.24(7) 2_766 2_766
Cl23 Sb2 Cl23 179.999(1) . 2_766
Cl33 Sb3 Cl33 179.999(2) . 2_687
Cl33 Sb3 Cl31 90.50(13) . .
Cl33 Sb3 Cl31 89.50(14) 2_687 .
Cl33 Sb3 Cl31 89.50(14) . 2_687
Cl33 Sb3 Cl31 90.50(13) 2_687 2_687
Cl31 Sb3 Cl31 179.999(1) . 2_687
Cl33 Sb3 Cl32 89.61(10) . .
Cl33 Sb3 Cl32 90.39(10) 2_687 .
Cl31 Sb3 Cl32 91.23(9) . .
Cl31 Sb3 Cl32 88.77(9) 2_687 .
Cl33 Sb3 Cl32 90.39(10) . 2_687
Cl33 Sb3 Cl32 89.61(10) 2_687 2_687
Cl31 Sb3 Cl32 88.77(9) . 2_687
Cl31 Sb3 Cl32 91.23(9) 2_687 2_687
Cl32 Sb3 Cl32 180.00(8) . 2_687
Cl41 Sb4 Cl41 180.0 2_676 .
Cl41 Sb4 Cl42 89.67(10) 2_676 .
Cl41 Sb4 Cl42 90.33(10) . .
Cl41 Sb4 Cl42 90.33(10) 2_676 2_676
Cl41 Sb4 Cl42 89.67(10) . 2_676
Cl42 Sb4 Cl42 180.000(1) . 2_676
Cl41 Sb4 Cl43 90.12(8) 2_676 .
Cl41 Sb4 Cl43 89.88(8) . .
Cl42 Sb4 Cl43 89.23(8) . .
Cl42 Sb4 Cl43 90.77(8) 2_676 .
Cl41 Sb4 Cl43 89.88(8) 2_676 2_676
Cl41 Sb4 Cl43 90.12(8) . 2_676
Cl42 Sb4 Cl43 90.77(8) . 2_676
Cl42 Sb4 Cl43 89.23(8) 2_676 2_676
Cl43 Sb4 Cl43 179.999(1) . 2_676
S12 I12 Cl1 176.35(7) . .
S21 I21 Cl2 174.51(7) . .
S22 I22 Cl2 176.10(11) . .
I22 Cl2 I21 105.24(7) . .
C13 S11 C12 102.5(4) . .
C13 S11 I11 105.1(3) . .
C12 S11 I11 104.0(3) . .
C17 S12 C16 101.3(4) . .
C17 S12 I12 101.0(3) . .
C16 S12 I12 100.3(3) . .
C22 S21 C23 103.1(7) . .
C22 S21 I21 104.9(5) . .
C23 S21 I21 103.9(4) . .
C27 S22 C26 100.1(6) . .
C27 S22 I22 101.8(5) . .
C26 S22 I22 95.5(4) . .
C11 C12 S11 109.5(7) . .
C14 C13 S11 116.6(6) . .
C15 C16 S12 110.5(7) . .
C18 C17 S12 111.9(7) . .
C21 C22 S21 111.4(12) . .
C24 C23 S21 116.5(10) . .
C25 C26 S22 110.9(8) . .
C28 C27 S22 107.8(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sb1 Cl12 2.3656(18) 2_777
Sb1 Cl12 2.3657(18) .
Sb1 Cl13 2.3707(17) 2_777
Sb1 Cl13 2.3707(17) .
Sb1 Cl11 2.3734(18) .
Sb1 Cl11 2.3734(19) 2_777
Sb2 Cl21 2.361(2) .
Sb2 Cl21 2.361(2) 2_766
Sb2 Cl22 2.363(2) .
Sb2 Cl22 2.363(2) 2_766
Sb2 Cl23 2.3691(16) .
Sb2 Cl23 2.3691(16) 2_766
Sb3 Cl33 2.358(2) .
Sb3 Cl33 2.358(2) 2_687
Sb3 Cl31 2.359(3) .
Sb3 Cl31 2.359(3) 2_687
Sb3 Cl32 2.3624(19) .
Sb3 Cl32 2.3625(19) 2_687
Sb4 Cl41 2.364(2) 2_676
Sb4 Cl41 2.364(2) .
Sb4 Cl42 2.364(2) .
Sb4 Cl42 2.364(2) 2_676
Sb4 Cl43 2.3757(18) .
Sb4 Cl43 2.3757(18) 2_676
I11 S11 2.498(2) .
I12 S12 2.4987(19) .
I12 Cl1 2.7713(17) .
I21 S21 2.518(3) .
I21 Cl2 2.814(2) .
I22 S22 2.450(3) .
I22 Cl2 2.741(2) .
S11 C13 1.821(9) .
S11 C12 1.821(8) .
S12 C17 1.810(9) .
S12 C16 1.811(8) .
S21 C22 1.804(15) .
S21 C23 1.887(14) .
S22 C27 1.761(13) .
S22 C26 1.915(11) .
C11 C12 1.512(12) .
C13 C14 1.471(13) .
C15 C16 1.486(13) .
C17 C18 1.511(13) .
C21 C22 1.460(19) .
C23 C24 1.375(18) .
C25 C26 1.393(17) .
C27 C28 1.439(16) .
