#------------------------------------------------------------------------------
#$Date: 2015-12-06 09:46:18 +0200 (Sun, 06 Dec 2015) $
#$Revision: 170809 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/17/4031736.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_4031736
loop_
_publ_author_name
'Gluyas, Josef B. G.'
'Manici, Valentina'
'Gückel, Simon'
'Vincent, Kevin B.'
'Yufit, Dmitry S.'
'Howard, Judith A. K.'
'Skelton, Brian W.'
'Beeby, Andrew'
'Kaupp, Martin'
'Low, Paul J.'
_publ_section_title
;
 Cross-Conjugated Systems Based On An (E)-Hexa-3-en-1,5-diyne-3,4-diyl
 Skeleton: Spectroscopic and Spectroelectrochemical Investigations.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11501
_journal_page_last               11512
_journal_paper_doi               10.1021/acs.joc.5b02240
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C24 H26 Br2 Si2'
_chemical_formula_sum            'C24 H26 Br2 Si2'
_chemical_formula_weight         530.45
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-28
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                114.280(2)
_cell_angle_beta                 94.306(2)
_cell_angle_gamma                95.903(2)
_cell_formula_units_Z            1
_cell_length_a                   7.5780(5)
_cell_length_b                   9.1129(6)
_cell_length_c                   9.9879(7)
_cell_measurement_reflns_used    2325
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.25
_cell_volume                     620.13(7)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8019
_diffrn_reflns_theta_full        29.49
_diffrn_reflns_theta_max         29.49
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           10.0
_diffrn_source_power             0.3
_diffrn_source_target            Mo
_diffrn_source_type              'sealed X-ray tube'
_diffrn_source_voltage           30.0
_exptl_absorpt_coefficient_mu    3.372
_exptl_absorpt_correction_T_max  0.9559
_exptl_absorpt_correction_T_min  0.2019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.0470 before and 0.0250 after correction.
The Ratio of minimum to maximum transmission is 0.2112.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.160
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0363
_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)+(0.0350P)²+0.4500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0887
_reflns_number_gt                2589
_reflns_number_total             3449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02240_si_002.cif
_cod_data_source_block           9_13srv145
_cod_depositor_comments
'Adding full bibliography for 4031734--4031737.cif.'
_cod_database_code               4031736
_olex2_refinement_description
;
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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
Br1 Br 1.29237(4) 0.83854(4) 0.46576(4) 0.03491(11) Uani 1 1 d
Si1 Si 0.28932(11) 0.20850(9) -0.03162(8) 0.02622(17) Uani 1 1 d
C1 C 0.5386(3) 0.4944(3) 0.4388(3) 0.0209(5) Uani 1 1 d
C2 C 0.4506(3) 0.3959(3) 0.2913(3) 0.0217(5) Uani 1 1 d
C3 C 0.3885(3) 0.3210(3) 0.1637(3) 0.0237(5) Uani 1 1 d
C4 C 0.2404(5) -0.0108(4) -0.0713(4) 0.0364(7) Uani 1 1 d
C5 C 0.0795(5) 0.2897(4) -0.0552(4) 0.0422(8) Uani 1 1 d
C6 C 0.4496(6) 0.2416(5) -0.1502(4) 0.0504(9) Uani 1 1 d
C7 C 0.7193(3) 0.5816(3) 0.4461(3) 0.0205(5) Uani 1 1 d
C8 C 0.7728(3) 0.7447(3) 0.5426(3) 0.0224(5) Uani 1 1 d
C9 C 0.9421(3) 0.8222(3) 0.5471(3) 0.0230(5) Uani 1 1 d
C10 C 1.0582(3) 0.7351(3) 0.4552(3) 0.0233(5) Uani 1 1 d
C11 C 1.0076(4) 0.5745(3) 0.3565(3) 0.0248(5) Uani 1 1 d
C12 C 0.8383(3) 0.4994(3) 0.3515(3) 0.0232(5) Uani 1 1 d
H4A H 0.342(5) -0.052(4) -0.072(4) 0.046(10) Uiso 1 1 d
H4B H 0.164(6) -0.065(5) -0.157(5) 0.066(13) Uiso 1 1 d
H4C H 0.177(6) -0.024(5) 0.006(5) 0.070(13) Uiso 1 1 d
H5A H 0.025(5) 0.233(5) -0.152(5) 0.059(12) Uiso 1 1 d
H5B H 0.113(5) 0.394(5) -0.037(4) 0.062(12) Uiso 1 1 d
H5C H -0.011(5) 0.282(5) 0.024(4) 0.060(12) Uiso 1 1 d
H6A H 0.557(5) 0.214(4) -0.139(4) 0.039(10) Uiso 1 1 d
H6B H 0.402(6) 0.185(6) -0.245(6) 0.084(15) Uiso 1 1 d
H6C H 0.494(6) 0.365(6) -0.122(5) 0.088(15) Uiso 1 1 d
H8 H 0.697(4) 0.801(4) 0.603(3) 0.032(8) Uiso 1 1 d
H9 H 0.978(4) 0.937(4) 0.614(3) 0.031(8) Uiso 1 1 d
H11 H 1.084(4) 0.516(4) 0.290(4) 0.036(9) Uiso 1 1 d
H12 H 0.798(4) 0.389(4) 0.287(3) 0.030(8) Uiso 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
C3 Si1 C4 107.99(14) .
C3 Si1 C5 107.54(14) .
C3 Si1 C6 108.78(17) .
C5 Si1 C4 110.65(17) .
C6 Si1 C4 111.24(19) .
C6 Si1 C5 110.5(2) .
C1 C1 C2 122.0(3) 2_666
C1 C1 C7 123.5(3) 2_666
C2 C1 C7 114.5(2) .
C3 C2 C1 174.1(3) .
C2 C3 Si1 178.8(2) .
Si1 C4 H4A 110(2) .
Si1 C4 H4B 110(3) .
Si1 C4 H4C 110(2) .
H4A C4 H4B 113(3) .
H4A C4 H4C 108(3) .
H4B C4 H4C 106(3) .
Si1 C5 H5A 109(2) .
Si1 C5 H5B 106(3) .
Si1 C5 H5C 111(2) .
H5A C5 H5B 110(3) .
H5A C5 H5C 111(3) .
H5B C5 H5C 110(3) .
Si1 C6 H6A 116(2) .
Si1 C6 H6B 109(3) .
Si1 C6 H6C 114(3) .
H6A C6 H6B 108(4) .
H6A C6 H6C 96(3) .
H6B C6 H6C 114(4) .
C8 C7 C1 122.1(2) .
C8 C7 C12 118.4(2) .
C12 C7 C1 119.5(2) .
C7 C8 H8 120(2) .
C9 C8 C7 120.7(2) .
C9 C8 H8 119(2) .
C8 C9 H9 119.9(18) .
C10 C9 C8 119.1(2) .
C10 C9 H9 120.9(18) .
C9 C10 Br1 119.3(2) .
C11 C10 Br1 119.27(19) .
C11 C10 C9 121.5(2) .
C10 C11 H11 122(2) .
C12 C11 C10 118.9(2) .
C12 C11 H11 119(2) .
C7 C12 H12 116.6(18) .
C11 C12 C7 121.4(2) .
C11 C12 H12 122.0(18) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C10 1.896(2) .
Si1 C3 1.844(3) .
Si1 C4 1.861(3) .
Si1 C5 1.860(3) .
Si1 C6 1.845(4) .
C1 C1 1.365(5) 2_666
C1 C2 1.436(3) .
C1 C7 1.492(3) .
C2 C3 1.200(4) .
C4 H4A 0.89(4) .
C4 H4B 0.91(4) .
C4 H4C 0.98(4) .
C5 H5A 0.93(4) .
C5 H5B 0.90(4) .
C5 H5C 1.10(4) .
C6 H6A 0.89(4) .
C6 H6B 0.90(5) .
C6 H6C 1.05(5) .
C7 C8 1.394(3) .
C7 C12 1.397(3) .
C8 C9 1.388(4) .
C8 H8 0.91(3) .
C9 C10 1.383(4) .
C9 H9 0.98(3) .
C10 C11 1.379(4) .
C11 C12 1.378(4) .
C11 H11 0.95(3) .
C12 H12 0.95(3) .
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
C2 C1 C7 C8 135.1(2)
C2 C1 C7 C12 -43.4(3)
