#------------------------------------------------------------------------------
#$Date: 2019-11-25 08:40:09 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240546 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/98/4129898.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_4129898
loop_
_publ_author_name
'Carrera, Elisa I.'
'Lanterna, Anabel E.'
'Lough, Alan J.'
'Scaiano, Juan C.'
'Seferos, Dwight S.'
_publ_section_title
;
 A Mechanistic Study of Halogen Addition and Photoelimination from
 π-Conjugated Tellurophenes.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2678
_journal_page_last               2689
_journal_paper_doi               10.1021/jacs.5b11649
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C24 H28 Br2 Te'
_chemical_formula_sum            'C24 H28 Br2 Te'
_chemical_formula_weight         603.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.781(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.066(3)
_cell_length_b                   9.7784(9)
_cell_length_c                   7.1871(7)
_cell_measurement_reflns_used    6278
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.17
_cell_volume                     2323.6(4)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14409
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_min         2.172
_diffrn_source
'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    4.726
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.802
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0193
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0409P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0543
_refine_ls_wR_factor_ref         0.0586
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2311
_reflns_number_total             2685
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b11649_si_005.cif
_cod_data_source_block           d15104
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4129898
_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   0.579
_shelx_estimated_absorpt_t_max   0.765
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Te1 Te 1.0000 0.16717(2) 0.2500 0.01529(7) Uani 1 2 d S T P
Br1 Br 1.04480(2) 0.17856(2) 0.56165(3) 0.02364(8) Uani 1 1 d . . .
C1 C 0.98154(6) 0.44983(19) 0.3018(3) 0.0190(4) Uani 1 1 d . . .
H1 H 0.9695 0.5342 0.3358 0.023 Uiso 1 1 calc R U .
C2 C 0.96382(7) 0.33055(18) 0.3512(3) 0.0168(4) Uani 1 1 d . . .
C3 C 0.92688(6) 0.30627(19) 0.4528(3) 0.0176(4) Uani 1 1 d . . .
C4 C 0.90967(7) 0.17646(19) 0.4687(3) 0.0238(5) Uani 1 1 d . . .
H4A H 0.9222 0.1011 0.4095 0.029 Uiso 1 1 calc R U .
C5 C 0.87465(7) 0.1549(2) 0.5690(3) 0.0258(5) Uani 1 1 d . . .
H5A H 0.8637 0.0652 0.5760 0.031 Uiso 1 1 calc R U .
C6 C 0.85515(7) 0.2619(2) 0.6596(3) 0.0218(4) Uani 1 1 d . . .
C7 C 0.87257(7) 0.3922(2) 0.6422(3) 0.0227(5) Uani 1 1 d . . .
H7A H 0.8600 0.4674 0.7018 0.027 Uiso 1 1 calc R U .
C8 C 0.90698(6) 0.4150(2) 0.5425(3) 0.0195(4) Uani 1 1 d . . .
H8A H 0.9175 0.5051 0.5338 0.023 Uiso 1 1 calc R U .
C9 C 0.81780(7) 0.2415(2) 0.7793(3) 0.0296(5) Uani 1 1 d . . .
C10 C 0.83059(10) 0.2553(3) 0.9851(4) 0.0490(8) Uani 1 1 d . . .
H10A H 0.8516 0.1876 1.0146 0.073 Uiso 1 1 calc R U .
H10B H 0.8071 0.2396 1.0641 0.073 Uiso 1 1 calc R U .
H10C H 0.8412 0.3474 1.0077 0.073 Uiso 1 1 calc R U .
C11 C 0.79866(8) 0.1009(3) 0.7525(4) 0.0382(6) Uani 1 1 d . . .
H11A H 0.8180 0.0301 0.7910 0.057 Uiso 1 1 calc R U .
H11B H 0.7914 0.0881 0.6210 0.057 Uiso 1 1 calc R U .
H11C H 0.7743 0.0942 0.8281 0.057 Uiso 1 1 calc R U .
C12 C 0.78581(10) 0.3498(3) 0.7322(6) 0.0680(11) Uani 1 1 d . . .
H12A H 0.7792 0.3459 0.5989 0.102 Uiso 1 1 calc R U .
H12B H 0.7964 0.4407 0.7635 0.102 Uiso 1 1 calc R U .
H12C H 0.7614 0.3320 0.8039 0.102 Uiso 1 1 calc R U .
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'
Te Te -0.5308 1.6751 '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
C2 Te1 C2 82.80(11) . 2_755
C2 Te1 Br1 86.98(6) . 2_755
C2 Te1 Br1 89.44(6) 2_755 2_755
C2 Te1 Br1 89.44(6) . .
C2 Te1 Br1 86.98(6) 2_755 .
Br1 Te1 Br1 175.220(10) 2_755 .
C2 C1 C1 120.58(12) . 2_755
C2 C1 H1 119.7 . .
C1 C1 H1 119.7 2_755 .
C1 C2 C3 129.99(17) . .
C1 C2 Te1 108.02(15) . .
C3 C2 Te1 121.98(13) . .
C4 C3 C8 117.0(2) . .
C4 C3 C2 122.45(18) . .
C8 C3 C2 120.52(17) . .
C5 C4 C3 121.63(19) . .
C5 C4 H4A 119.2 . .
C3 C4 H4A 119.2 . .
C4 C5 C6 121.48(19) . .
C4 C5 H5A 119.3 . .
C6 C5 H5A 119.3 . .
C5 C6 C7 116.5(2) . .
C5 C6 C9 123.15(19) . .
C7 C6 C9 120.30(19) . .
C8 C7 C6 122.61(19) . .
C8 C7 H7A 118.7 . .
C6 C7 H7A 118.7 . .
C7 C8 C3 120.76(19) . .
C7 C8 H8A 119.6 . .
C3 C8 H8A 119.6 . .
C11 C9 C6 112.59(18) . .
C11 C9 C12 108.1(2) . .
C6 C9 C12 110.3(2) . .
C11 C9 C10 108.0(2) . .
C6 C9 C10 108.4(2) . .
C12 C9 C10 109.4(2) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Te1 C2 2.1297(19) .
Te1 C2 2.1298(19) 2_755
Te1 Br1 2.6708(3) 2_755
Te1 Br1 2.6709(3) .
C1 C2 1.355(3) .
C1 C1 1.438(4) 2_755
C1 H1 0.9500 .
C2 C3 1.451(3) .
C3 C4 1.396(3) .
C3 C8 1.411(3) .
C4 C5 1.388(3) .
C4 H4A 0.9500 .
C5 C6 1.396(3) .
C5 H5A 0.9500 .
C6 C7 1.404(3) .
C6 C9 1.528(3) .
C7 C8 1.371(3) .
C7 H7A 0.9500 .
C8 H8A 0.9500 .
C9 C11 1.525(3) .
C9 C12 1.531(4) .
C9 C10 1.539(4) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
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
_geom_torsion_site_symmetry_1
C1 C1 C2 C3 -179.4(2) 2_755
C1 C1 C2 Te1 0.1(3) 2_755
C1 C2 C3 C4 170.4(2) .
Te1 C2 C3 C4 -9.1(3) .
C1 C2 C3 C8 -10.4(3) .
Te1 C2 C3 C8 170.16(14) .
C8 C3 C4 C5 -0.3(3) .
C2 C3 C4 C5 179.0(2) .
C3 C4 C5 C6 -0.4(4) .
C4 C5 C6 C7 0.7(3) .
C4 C5 C6 C9 -176.8(2) .
C5 C6 C7 C8 -0.2(3) .
C9 C6 C7 C8 177.4(2) .
C6 C7 C8 C3 -0.5(3) .
C4 C3 C8 C7 0.8(3) .
C2 C3 C8 C7 -178.56(19) .
C5 C6 C9 C11 -13.4(3) .
C7 C6 C9 C11 169.2(2) .
C5 C6 C9 C12 -134.3(3) .
C7 C6 C9 C12 48.3(3) .
C5 C6 C9 C10 106.0(3) .
C7 C6 C9 C10 -71.4(3) .
