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#$Date: 2019-11-25 08:39:52 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240545 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/98/4129897.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_4129897
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 O2 Te'
_chemical_formula_sum            'C24 H28 Br2 O2 Te'
_chemical_formula_weight         635.88
_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                 100.070(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   34.193(3)
_cell_length_b                   10.0162(8)
_cell_length_c                   6.9968(6)
_cell_measurement_reflns_used    4935
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      2.42
_cell_volume                     2359.4(3)
_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 0.999
_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  0.0315
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13172
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.595
_diffrn_reflns_theta_min         2.121
_diffrn_source
'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    4.665
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_description       needle
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0220
_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)+(0.0176P)²+2.4190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0439
_refine_ls_wR_factor_ref         0.0471
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2278
_reflns_number_total             2726
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b11649_si_004.cif
_cod_data_source_block           d15123
_cod_original_cell_volume        2359.4(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4129897
_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   0.487
_shelx_estimated_absorpt_t_max   0.835
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 0.16744(2) 0.2500 0.01487(6) Uani 1 2 d S T P
Br1 Br 0.95696(2) 0.17880(2) -0.10635(3) 0.02218(7) Uani 1 1 d . . .
O1 O 0.81957(6) 0.21747(19) 0.5776(3) 0.0331(5) Uani 1 1 d . . .
C1 C 0.98139(7) 0.4431(2) 0.2860(3) 0.0169(5) Uani 1 1 d . . .
H1 H 0.9692 0.5254 0.3089 0.020 Uiso 1 1 calc R U .
C2 C 0.96383(7) 0.3268(2) 0.3208(3) 0.0154(5) Uani 1 1 d . . .
C3 C 0.92673(7) 0.2999(2) 0.3884(3) 0.0167(5) Uani 1 1 d . . .
C4 C 0.90519(7) 0.4034(2) 0.4568(3) 0.0211(5) Uani 1 1 d . . .
H4A H 0.9150 0.4922 0.4582 0.025 Uiso 1 1 calc R U .
C5 C 0.86993(8) 0.3790(2) 0.5222(4) 0.0239(5) Uani 1 1 d . . .
H5A H 0.8558 0.4510 0.5666 0.029 Uiso 1 1 calc R U .
C6 C 0.85503(7) 0.2496(2) 0.5233(4) 0.0235(5) Uani 1 1 d . . .
C7 C 0.87588(8) 0.1462(2) 0.4559(4) 0.0266(6) Uani 1 1 d . . .
H7A H 0.8659 0.0576 0.4545 0.032 Uiso 1 1 calc R U .
C8 C 0.91127(8) 0.1712(2) 0.3902(4) 0.0228(5) Uani 1 1 d . . .
H8A H 0.9252 0.0989 0.3455 0.027 Uiso 1 1 calc R U .
C9 C 0.81076(8) 0.2547(2) 0.7700(4) 0.0249(6) Uani 1 1 d . . .
C10 C 0.78896(8) 0.3879(3) 0.7529(4) 0.0321(6) Uani 1 1 d . . .
H10A H 0.7802 0.4083 0.8758 0.048 Uiso 1 1 calc R U .
H10B H 0.7658 0.3828 0.6486 0.048 Uiso 1 1 calc R U .
H10C H 0.8068 0.4584 0.7232 0.048 Uiso 1 1 calc R U .
C11 C 0.84788(8) 0.2573(3) 0.9219(4) 0.0304(6) Uani 1 1 d . . .
H11A H 0.8407 0.2721 1.0499 0.046 Uiso 1 1 calc R U .
H11B H 0.8652 0.3296 0.8930 0.046 Uiso 1 1 calc R U .
H11C H 0.8618 0.1718 0.9215 0.046 Uiso 1 1 calc R U .
C12 C 0.78261(9) 0.1441(3) 0.8114(5) 0.0412(8) Uani 1 1 d . . .
H12A H 0.7755 0.1583 0.9398 0.062 Uiso 1 1 calc R U .
H12B H 0.7957 0.0573 0.8086 0.062 Uiso 1 1 calc R U .
H12C H 0.7585 0.1459 0.7124 0.062 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'
O O 0.0106 0.0060 '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 82.94(12) 2_755 .
C2 Te1 Br1 89.91(6) 2_755 .
C2 Te1 Br1 86.42(6) . .
C2 Te1 Br1 86.42(6) 2_755 2_755
C2 Te1 Br1 89.92(6) . 2_755
Br1 Te1 Br1 175.108(12) . 2_755
C6 O1 C9 121.64(19) . .
C2 C1 C1 120.50(13) . 2_755
C2 C1 H1 119.8 . .
C1 C1 H1 119.8 2_755 .
C1 C2 C3 131.16(19) . .
C1 C2 Te1 108.03(15) . .
C3 C2 Te1 120.79(15) . .
C8 C3 C4 117.2(2) . .
C8 C3 C2 121.9(2) . .
C4 C3 C2 120.9(2) . .
C5 C4 C3 121.5(2) . .
C5 C4 H4A 119.3 . .
C3 C4 H4A 119.3 . .
C4 C5 C6 120.4(2) . .
C4 C5 H5A 119.8 . .
C6 C5 H5A 119.8 . .
O1 C6 C7 116.9(2) . .
O1 C6 C5 124.2(2) . .
C7 C6 C5 118.9(2) . .
C6 C7 C8 120.5(2) . .
C6 C7 H7A 119.8 . .
C8 C7 H7A 119.8 . .
C7 C8 C3 121.5(2) . .
C7 C8 H8A 119.2 . .
C3 C8 H8A 119.2 . .
O1 C9 C11 111.5(2) . .
O1 C9 C10 108.9(2) . .
C11 C9 C10 112.4(2) . .
O1 C9 C12 103.0(2) . .
C11 C9 C12 111.1(2) . .
C10 C9 C12 109.5(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 2.130(2) 2_755
Te1 C2 2.130(2) .
Te1 Br1 2.6669(3) .
Te1 Br1 2.6669(3) 2_755
O1 C6 1.371(3) .
O1 C9 1.478(3) .
C1 C2 1.352(3) .
C1 C1 1.448(4) 2_755
C1 H1 0.9500 .
C2 C3 1.455(3) .
C3 C8 1.394(3) .
C3 C4 1.404(3) .
C4 C5 1.384(3) .
C4 H4A 0.9500 .
C5 C6 1.394(3) .
C5 H5A 0.9500 .
C6 C7 1.386(3) .
C7 C8 1.391(3) .
C7 H7A 0.9500 .
C8 H8A 0.9500 .
C9 C11 1.506(4) .
C9 C10 1.523(3) .
C9 C12 1.527(3) .
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 -178.6(3) 2_755
C1 C1 C2 Te1 -0.4(3) 2_755
C1 C2 C3 C8 171.2(2) .
Te1 C2 C3 C8 -6.9(3) .
C1 C2 C3 C4 -9.5(4) .
Te1 C2 C3 C4 172.44(18) .
C8 C3 C4 C5 -0.4(4) .
C2 C3 C4 C5 -179.7(2) .
C3 C4 C5 C6 0.6(4) .
C9 O1 C6 C7 127.3(2) .
C9 O1 C6 C5 -56.3(4) .
C4 C5 C6 O1 -177.1(2) .
C4 C5 C6 C7 -0.7(4) .
O1 C6 C7 C8 177.3(2) .
C5 C6 C7 C8 0.7(4) .
C6 C7 C8 C3 -0.5(4) .
C4 C3 C8 C7 0.3(4) .
C2 C3 C8 C7 179.7(2) .
C6 O1 C9 C11 -31.2(3) .
C6 O1 C9 C10 93.3(3) .
C6 O1 C9 C12 -150.4(2) .
