#------------------------------------------------------------------------------
#$Date: 2015-09-25 16:14:04 +0300 (Fri, 25 Sep 2015) $
#$Revision: 158308 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/78/7117848.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_7117848
loop_
_publ_author_name
'Philipp Biegger'
'Manuel Schaffroth'
'Kerstin Brodner'
'Olena Tverskoy'
'Frank Rominger'
'Uwe H. F. Bunz'
_publ_section_title
;
 Bisalkynylated 3,6-diiminocyclohexa-1,4-diene-1,4-diamine
;
_journal_name_full               Chem.Commun.
_journal_page_first              14844
_journal_paper_doi               10.1039/C5cc05427C
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C28 H42 N4 S2 Si2'
_chemical_formula_weight         554.95
_chemical_name_common            '1 in manuscript'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-06-23 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.3033(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5203(3)
_cell_length_b                   15.4125(6)
_cell_length_c                   11.7589(5)
_cell_measurement_reflns_used    6688
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.20
_cell_volume                     1523.86(10)
_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      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14317
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.449
_diffrn_reflns_theta_min         2.197
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.9585
_exptl_absorpt_correction_T_min  0.8692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       plate
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0380P)²+1.1862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                2623
_reflns_number_total             3094
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc05427c2.cif
_cod_data_source_block           mas16
_cod_database_code               7117848
_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   0.965
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.76719(6) 0.34254(3) 0.39729(4) 0.01829(14) Uani 1 1 d . . . . .
C1 C 0.6348(2) 0.16327(11) 0.43802(15) 0.0193(4) Uani 1 1 d . . . . .
C2 C 0.6899(2) 0.23232(12) 0.41698(16) 0.0220(4) Uani 1 1 d . . . . .
C11 C 0.5686(2) 0.08310(11) 0.46650(15) 0.0168(4) Uani 1 1 d . . . . .
C12 C 0.4040(2) 0.07197(11) 0.46705(15) 0.0166(4) Uani 1 1 d . . . . .
N13 N 0.29250(18) 0.13428(10) 0.43861(14) 0.0218(3) Uani 1 1 d . . . . .
S1 S 0.12552(5) 0.09156(3) 0.45336(4) 0.02465(14) Uani 1 1 d . . . . .
N14 N 0.17745(18) -0.00485(10) 0.49604(13) 0.0208(3) Uani 1 1 d . . . . .
C15 C 0.3375(2) -0.00880(11) 0.50051(14) 0.0165(4) Uani 1 1 d . . . . .
C21 C 0.8738(2) 0.34452(12) 0.26870(16) 0.0234(4) Uani 1 1 d . . . . .
H21 H 0.7914 0.3569 0.1999 0.028 Uiso 1 1 calc R U . . .
C22 C 0.9948(3) 0.41919(14) 0.27728(18) 0.0324(5) Uani 1 1 d . . . . .
H22A H 0.9428 0.4735 0.2934 0.049 Uiso 1 1 calc R U . . .
H22B H 1.0831 0.4072 0.3397 0.049 Uiso 1 1 calc R U . . .
H22C H 1.0355 0.4245 0.2043 0.049 Uiso 1 1 calc R U . . .
C23 C 0.9542(3) 0.25945(14) 0.2435(2) 0.0371(5) Uani 1 1 d . . . . .
H23A H 0.8767 0.2120 0.2381 0.056 Uiso 1 1 calc R U . . .
H23B H 0.9949 0.2646 0.1705 0.056 Uiso 1 1 calc R U . . .
H23C H 1.0425 0.2473 0.3059 0.056 Uiso 1 1 calc R U . . .
C24 C 0.5893(2) 0.41768(13) 0.37402(18) 0.0292(5) Uani 1 1 d . . . . .
H24 H 0.5436 0.4179 0.4472 0.035 Uiso 1 1 calc R U . . .
C25 C 0.6368(3) 0.51135(14) 0.3521(3) 0.0492(7) Uani 1 1 d . . . . .
H25A H 0.7211 0.5300 0.4141 0.074 Uiso 1 1 calc R U . . .
H25B H 0.6756 0.5146 0.2782 0.074 Uiso 1 1 calc R U . . .
H25C H 0.5442 0.5493 0.3500 0.074 Uiso 1 1 calc R U . . .
C26 C 0.4581(3) 0.38669(17) 0.2788(2) 0.0474(6) Uani 1 1 d . . . . .
H26A H 0.4295 0.3268 0.2944 0.071 Uiso 1 1 calc R U . . .
H26B H 0.3646 0.4241 0.2764 0.071 Uiso 1 1 calc R U . . .
H26C H 0.4961 0.3893 0.2045 0.071 Uiso 1 1 calc R U . . .
C27 C 0.9014(2) 0.36959(12) 0.53608(16) 0.0244(4) Uani 1 1 d . . . . .
H27 H 0.9471 0.4284 0.5268 0.029 Uiso 1 1 calc R U . . .
C28 C 1.0409(3) 0.30609(16) 0.5635(2) 0.0396(5) Uani 1 1 d . . . . .
H28A H 1.0989 0.3035 0.4980 0.059 Uiso 1 1 calc R U . . .
H28B H 1.1127 0.3259 0.6321 0.059 Uiso 1 1 calc R U . . .
H28C H 1.0004 0.2483 0.5777 0.059 Uiso 1 1 calc R U . . .
C29 C 0.8101(3) 0.37421(17) 0.63764(19) 0.0433(6) Uani 1 1 d . . . . .
H29A H 0.7211 0.4149 0.6195 0.065 Uiso 1 1 calc R U . . .
H29B H 0.7691 0.3165 0.6520 0.065 Uiso 1 1 calc R U . . .
H29C H 0.8814 0.3942 0.7065 0.065 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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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 Si1 C27 105.88(8) . .
C2 Si1 C21 110.03(8) . .
C27 Si1 C21 112.83(9) . .
C2 Si1 C24 106.67(9) . .
C27 Si1 C24 110.50(9) . .
C21 Si1 C24 110.65(9) . .
C2 C1 C11 178.0(2) . .
C1 C2 Si1 174.38(17) . .
C12 C11 C15 114.70(15) . 3_656
C12 C11 C1 122.58(16) . .
C15 C11 C1 122.70(16) 3_656 .
N13 C12 C11 124.72(16) . .
N13 C12 C15 112.77(15) . .
C11 C12 C15 122.50(16) . .
C12 N13 S1 106.35(12) . .
N13 S1 N14 102.08(8) . .
C15 N14 S1 106.12(12) . .
N14 C15 C11 124.52(16) . 3_656
N14 C15 C12 112.68(15) . .
C11 C15 C12 122.80(16) 3_656 .
C23 C21 C22 109.74(17) . .
C23 C21 Si1 115.46(14) . .
C22 C21 Si1 111.35(13) . .
C23 C21 H21 106.6 . .
C22 C21 H21 106.6 . .
Si1 C21 H21 106.6 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C21 C23 H23A 109.5 . .
C21 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C21 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C26 C24 C25 110.7(2) . .
C26 C24 Si1 112.91(15) . .
C25 C24 Si1 111.94(15) . .
C26 C24 H24 107.0 . .
C25 C24 H24 107.0 . .
Si1 C24 H24 107.0 . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C24 C26 H26A 109.5 . .
C24 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C24 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C29 C27 C28 109.94(18) . .
C29 C27 Si1 111.91(15) . .
C28 C27 Si1 112.49(14) . .
C29 C27 H27 107.4 . .
C28 C27 H27 107.4 . .
Si1 C27 H27 107.4 . .
C27 C28 H28A 109.5 . .
C27 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C27 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
C27 C29 H29A 109.5 . .
C27 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C27 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C2 1.8501(18) .
Si1 C27 1.8819(19) .
Si1 C21 1.8857(19) .
Si1 C24 1.892(2) .
C1 C2 1.205(3) .
C1 C11 1.421(2) .
C11 C12 1.414(2) .
C11 C15 1.415(2) 3_656
C12 N13 1.354(2) .
C12 C15 1.448(2) .
N13 S1 1.6024(15) .
S1 N14 1.6074(16) .
N14 C15 1.358(2) .
C15 C11 1.415(2) 3_656
C21 C23 1.530(3) .
C21 C22 1.537(3) .
C21 H21 1.0000 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 C26 1.525(3) .
C24 C25 1.532(3) .
C24 H24 1.0000 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 C29 1.529(3) .
C27 C28 1.533(3) .
C27 H27 1.0000 .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C15 C11 C12 N13 179.98(16) 3_656 . . .
C1 C11 C12 N13 1.6(3) . . . .
C15 C11 C12 C15 0.9(3) 3_656 . . .
C1 C11 C12 C15 -177.49(16) . . . .
C11 C12 N13 S1 -179.50(14) . . . .
C15 C12 N13 S1 -0.34(18) . . . .
C12 N13 S1 N14 0.42(14) . . . .
N13 S1 N14 C15 -0.36(14) . . . .
S1 N14 C15 C11 -179.55(14) . . . 3_656
S1 N14 C15 C12 0.20(18) . . . .
N13 C12 C15 N14 0.1(2) . . . .
C11 C12 C15 N14 179.28(16) . . . .
N13 C12 C15 C11 179.85(16) . . . 3_656
C11 C12 C15 C11 -1.0(3) . . . 3_656
C2 Si1 C21 C23 -30.59(18) . . . .
C27 Si1 C21 C23 87.41(17) . . . .
C24 Si1 C21 C23 -148.21(15) . . . .
C2 Si1 C21 C22 -156.59(14) . . . .
C27 Si1 C21 C22 -38.59(17) . . . .
C24 Si1 C21 C22 85.78(16) . . . .
C2 Si1 C24 C26 -52.19(18) . . . .
C27 Si1 C24 C26 -166.83(16) . . . .
C21 Si1 C24 C26 67.48(18) . . . .
C2 Si1 C24 C25 -177.95(17) . . . .
C27 Si1 C24 C25 67.41(19) . . . .
C21 Si1 C24 C25 -58.28(19) . . . .
C2 Si1 C27 C29 -63.83(17) . . . .
C21 Si1 C27 C29 175.76(15) . . . .
C24 Si1 C27 C29 51.31(17) . . . .
C2 Si1 C27 C28 60.52(16) . . . .
C21 Si1 C27 C28 -59.88(16) . . . .
C24 Si1 C27 C28 175.66(14) . . . .
