#------------------------------------------------------------------------------
#$Date: 2015-08-05 22:57:45 +0300 (Wed, 05 Aug 2015) $
#$Revision: 152908 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/06/1520660.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_1520660
loop_
_publ_author_name
'Sproul, Kyle C.'
'Chalifoux, Wesley A.'
_publ_section_title
;
 Highly Regio- and Diastereoselective Formation of Tetrasubstituted
 (Z)-1,2-Dihaloalkenes from the Halogenation of Trimethylsilyl Alkynes
 with ICl.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3334
_journal_page_last               3337
_journal_paper_doi               10.1021/acs.orglett.5b01558
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C16 H10 Cl2 I2'
_chemical_formula_weight         526.94
_chemical_name_common            5
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.0806(4)
_cell_length_b                   15.5457(6)
_cell_length_c                   23.2185(9)
_cell_measurement_reflns_used    9679
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.41
_cell_volume                     3277.6(2)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            57466
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         1.754
_exptl_absorpt_coefficient_mu    4.151
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.136
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.244
_refine_diff_density_max         2.092
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       0.00003(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         4777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0209P)²+8.2819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0617
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4490
_reflns_number_total             4777
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b01558_si_002.cif
_cod_data_source_block           ks003_0m
_cod_depositor_comments
'Adding full bibliography for 1520659--1520660.cif.'
_cod_database_code               1520660
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.273
_shelx_estimated_absorpt_t_max   0.431
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.3386(3) 0.64071(15) 0.35848(10) 0.0135(4) Uani 1 1 d . .
C2 C 0.4108(3) 0.56107(15) 0.35118(10) 0.0144(4) Uani 1 1 d . .
C3 C 0.3405(3) 0.48453(17) 0.36592(11) 0.0188(5) Uani 1 1 d . .
H3 H 0.3888 0.4312 0.3593 0.023 Uiso 1 1 calc R U
C4 C 0.2003(3) 0.48522(17) 0.39018(12) 0.0209(5) Uani 1 1 d . .
H4 H 0.1530 0.4328 0.4000 0.025 Uiso 1 1 calc R U
C5 C 0.1304(3) 0.56320(17) 0.39981(11) 0.0192(5) Uani 1 1 d . .
H5 H 0.0356 0.5641 0.4171 0.023 Uiso 1 1 calc R U
C6 C 0.1982(3) 0.64069(16) 0.38425(10) 0.0151(4) Uani 1 1 d . .
C7 C 0.4074(3) 0.72243(15) 0.33827(10) 0.0126(4) Uani 1 1 d . .
C8 C 0.3377(3) 0.77163(16) 0.29575(10) 0.0147(4) Uani 1 1 d . .
H8 H 0.2450 0.7538 0.2810 0.018 Uiso 1 1 calc R U
C9 C 0.4029(3) 0.84614(16) 0.27501(10) 0.0163(4) Uani 1 1 d . .
H9 H 0.3550 0.8791 0.2461 0.020 Uiso 1 1 calc R U
C10 C 0.5389(3) 0.87266(16) 0.29662(11) 0.0179(5) Uani 1 1 d . .
H10 H 0.5842 0.9233 0.2821 0.021 Uiso 1 1 calc R U
C11 C 0.6078(3) 0.82493(16) 0.33933(11) 0.0177(4) Uani 1 1 d . .
H11 H 0.6996 0.8436 0.3545 0.021 Uiso 1 1 calc R U
C12 C 0.5432(3) 0.75001(16) 0.35993(10) 0.0152(4) Uani 1 1 d . .
H12 H 0.5915 0.7173 0.3889 0.018 Uiso 1 1 calc R U
C13 C 0.5629(3) 0.55646(15) 0.32777(10) 0.0170(5) Uani 1 1 d . .
C14 C 0.6831(3) 0.53228(17) 0.35577(12) 0.0208(5) Uani 1 1 d . .
H14 H 0.7737 0.5303 0.3353 0.025 Uiso 1 1 calc R U
C15 C 0.1214(3) 0.72256(17) 0.39674(10) 0.0170(4) Uani 1 1 d . .
C16 C 0.1517(3) 0.77933(17) 0.43796(11) 0.0180(5) Uani 1 1 d . .
H16 H 0.0926 0.8295 0.4411 0.022 Uiso 1 1 calc R U
Cl1 Cl 0.58270(8) 0.58411(4) 0.25485(3) 0.02305(13) Uani 1 1 d . .
Cl2 Cl -0.03198(7) 0.74323(5) 0.35277(3) 0.02474(13) Uani 1 1 d . .
I1 I 0.68273(2) 0.49823(2) 0.44288(2) 0.02361(5) Uani 1 1 d . .
I2 I 0.32391(2) 0.76179(2) 0.49557(2) 0.02070(5) Uani 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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 118.1(2)
C6 C1 C7 120.9(2)
C2 C1 C7 121.0(2)
C3 C2 C1 120.4(2)
C3 C2 C13 118.4(2)
C1 C2 C13 121.2(2)
C4 C3 C2 120.8(2)
C4 C3 H3 119.6
C2 C3 H3 119.6
C5 C4 C3 119.4(2)
C5 C4 H4 120.3
C3 C4 H4 120.3
C4 C5 C6 120.6(2)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C1 120.5(2)
C5 C6 C15 118.8(2)
C1 C6 C15 120.7(2)
C8 C7 C12 119.0(2)
C8 C7 C1 119.9(2)
C12 C7 C1 121.1(2)
C9 C8 C7 120.5(2)
C9 C8 H8 119.7
C7 C8 H8 119.7
C8 C9 C10 120.0(2)
C8 C9 H9 120.0
C10 C9 H9 120.0
C11 C10 C9 119.9(2)
C11 C10 H10 120.1
C9 C10 H10 120.1
C12 C11 C10 120.2(2)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C7 120.4(2)
C11 C12 H12 119.8
C7 C12 H12 119.8
C14 C13 C2 126.9(2)
C14 C13 Cl1 117.2(2)
C2 C13 Cl1 115.87(18)
C13 C14 I1 123.02(19)
C13 C14 H14 118.5
I1 C14 H14 118.5
C16 C15 C6 127.9(2)
C16 C15 Cl2 117.4(2)
C6 C15 Cl2 114.66(18)
C15 C16 I2 122.16(19)
C15 C16 H16 118.9
I2 C16 H16 118.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.408(3)
C1 C2 1.411(3)
C1 C7 1.491(3)
C2 C3 1.393(3)
C2 C13 1.485(3)
C3 C4 1.392(4)
C3 H3 0.9500
C4 C5 1.387(4)
C4 H4 0.9500
C5 C6 1.401(3)
C5 H5 0.9500
C6 C15 1.480(3)
C7 C8 1.400(3)
C7 C12 1.399(3)
C8 C9 1.387(3)
C8 H8 0.9500
C9 C10 1.395(3)
C9 H9 0.9500
C10 C11 1.388(4)
C10 H10 0.9500
C11 C12 1.389(3)
C11 H11 0.9500
C12 H12 0.9500
C13 C14 1.325(4)
C13 Cl1 1.756(3)
C14 I1 2.091(3)
C14 H14 0.9500
C15 C16 1.331(4)
C15 Cl2 1.756(2)
C16 I2 2.076(3)
C16 H16 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
C6 C1 C2 C3 3.9(3)
C7 C1 C2 C3 -174.7(2)
C6 C1 C2 C13 -176.1(2)
C7 C1 C2 C13 5.3(3)
C1 C2 C3 C4 -2.6(4)
C13 C2 C3 C4 177.4(2)
C2 C3 C4 C5 -0.1(4)
C3 C4 C5 C6 1.4(4)
C4 C5 C6 C1 0.1(4)
C4 C5 C6 C15 -178.4(2)
C2 C1 C6 C5 -2.7(3)
C7 C1 C6 C5 175.9(2)
C2 C1 C6 C15 175.7(2)
C7 C1 C6 C15 -5.6(3)
C6 C1 C7 C8 -60.7(3)
C2 C1 C7 C8 117.9(3)
C6 C1 C7 C12 121.1(2)
C2 C1 C7 C12 -60.3(3)
C12 C7 C8 C9 0.6(3)
C1 C7 C8 C9 -177.6(2)
C7 C8 C9 C10 -0.1(4)
C8 C9 C10 C11 -0.8(4)
C9 C10 C11 C12 1.1(4)
C10 C11 C12 C7 -0.7(4)
C8 C7 C12 C11 -0.2(3)
C1 C7 C12 C11 178.0(2)
C3 C2 C13 C14 -67.5(3)
C1 C2 C13 C14 112.5(3)
C3 C2 C13 Cl1 111.1(2)
C1 C2 C13 Cl1 -68.9(3)
C2 C13 C14 I1 -2.1(4)
Cl1 C13 C14 I1 179.30(13)
C5 C6 C15 C16 105.1(3)
C1 C6 C15 C16 -73.3(3)
C5 C6 C15 Cl2 -72.3(3)
C1 C6 C15 Cl2 109.3(2)
C6 C15 C16 I2 0.2(4)
Cl2 C15 C16 I2 177.49(12)
