#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/25/4082590.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_4082590
loop_
_publ_author_name
'Kämpfe, Alexander'
'Kroke, Edwin'
'Wagler, Jörg'
_publ_section_title
;
 Silicon Compounds of 1,1-Bis(pyrrol-2-yl)ethenes: Molecular Structures
 and Chemical and Spectroscopic Properties
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              112
_journal_paper_doi               10.1021/om400868w
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C20 H30 N2 Si, 0.5(C6 H14)'
_chemical_formula_sum            'C23 H37 N2 Si'
_chemical_formula_weight         369.64
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.998(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8979(7)
_cell_length_b                   8.5767(3)
_cell_length_c                   20.6662(11)
_cell_measurement_reflns_used    27288
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.58
_cell_volume                     2218.24(19)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'ORTEP32 (Farugia)'
_computing_publication_material  'CIFTAB (Sheldrick)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe IPDS-2T'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23756
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   XShape
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0445P)²+0.4812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                3616
_reflns_number_total             4839
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400868w_si_002.cif
_cod_data_source_block           compound4a
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4082590
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Si1 Si 0.43639(3) 0.26339(5) 0.26858(2) 0.02566(11) Uani 1 1 d .
N1 N 0.53014(9) 0.40879(14) 0.26389(6) 0.0258(3) Uani 1 1 d .
N2 N 0.33105(9) 0.31626(14) 0.20113(6) 0.0245(3) Uani 1 1 d .
C1 C 0.61726(11) 0.46108(18) 0.31339(7) 0.0286(3) Uani 1 1 d .
C2 C 0.66785(11) 0.57839(18) 0.28773(8) 0.0305(3) Uani 1 1 d .
C3 C 0.61184(11) 0.60107(18) 0.22000(8) 0.0305(3) Uani 1 1 d .
C4 C 0.52909(11) 0.49474(17) 0.20576(7) 0.0266(3) Uani 1 1 d .
C5 C 0.45005(11) 0.46251(18) 0.14300(7) 0.0280(3) Uani 1 1 d .
C6 C 0.34454(11) 0.40234(17) 0.14587(7) 0.0259(3) Uani 1 1 d .
C7 C 0.24612(11) 0.41805(17) 0.10142(7) 0.0281(3) Uani 1 1 d .
C8 C 0.16982(11) 0.33957(17) 0.12972(7) 0.0280(3) Uani 1 1 d .
C9 C 0.22282(10) 0.27763(17) 0.18961(7) 0.0265(3) Uani 1 1 d .
C10 C 0.64686(12) 0.3935(2) 0.38221(8) 0.0354(4) Uani 1 1 d .
H10A H 0.7207 0.4220 0.4039 0.053 Uiso 1 1 calc R
H10B H 0.6405 0.2797 0.3795 0.053 Uiso 1 1 calc R
H10C H 0.5988 0.4345 0.4083 0.053 Uiso 1 1 calc R
C11 C 0.76451(12) 0.6678(2) 0.32500(9) 0.0372(4) Uani 1 1 d .
H11A H 0.7996 0.7161 0.2923 0.045 Uiso 1 1 calc R
H11B H 0.8159 0.5938 0.3523 0.045 Uiso 1 1 calc R
C12 C 0.73924(14) 0.7946(2) 0.37030(11) 0.0533(5) Uani 1 1 d .
H12A H 0.6930 0.8732 0.3433 0.080 Uiso 1 1 calc R
H12B H 0.8058 0.8439 0.3947 0.080 Uiso 1 1 calc R
H12C H 0.7026 0.7485 0.4021 0.080 Uiso 1 1 calc R
C13 C 0.63817(14) 0.7235(2) 0.17477(9) 0.0443(4) Uani 1 1 d .
H13A H 0.6835 0.6782 0.1478 0.066 Uiso 1 1 calc R
H13B H 0.6762 0.8095 0.2016 0.066 Uiso 1 1 calc R
H13C H 0.5720 0.7629 0.1454 0.066 Uiso 1 1 calc R
C14 C 0.47359(13) 0.4883(2) 0.08385(8) 0.0379(4) Uani 1 1 d .
H14A H 0.5418 0.5278 0.0825 0.045 Uiso 1 1 calc R
H14B H 0.4219 0.4671 0.0435 0.045 Uiso 1 1 calc R
C15 C 0.21997(13) 0.5060(2) 0.03667(8) 0.0382(4) Uani 1 1 d .
H15A H 0.2669 0.5971 0.0402 0.057 Uiso 1 1 calc R
H15B H 0.1453 0.5405 0.0269 0.057 Uiso 1 1 calc R
H15C H 0.2306 0.4379 0.0007 0.057 Uiso 1 1 calc R
C16 C 0.05210(11) 0.3234(2) 0.09773(8) 0.0348(4) Uani 1 1 d .
H16A H 0.0233 0.4262 0.0802 0.042 Uiso 1 1 calc R
H16B H 0.0145 0.2910 0.1320 0.042 Uiso 1 1 calc R
C17 C 0.02939(13) 0.2049(2) 0.04100(9) 0.0423(4) Uani 1 1 d .
H17A H 0.0654 0.2373 0.0065 0.064 Uiso 1 1 calc R
H17B H -0.0478 0.1990 0.0218 0.064 Uiso 1 1 calc R
H17C H 0.0560 0.1023 0.0583 0.064 Uiso 1 1 calc R
C18 C 0.17936(12) 0.1819(2) 0.23740(8) 0.0349(4) Uani 1 1 d .
H18A H 0.1064 0.1489 0.2160 0.052 Uiso 1 1 calc R
H18B H 0.1787 0.2442 0.2770 0.052 Uiso 1 1 calc R
H18C H 0.2245 0.0897 0.2505 0.052 Uiso 1 1 calc R
C19 C 0.48877(13) 0.0681(2) 0.25597(9) 0.0399(4) Uani 1 1 d .
H19A H 0.5089 0.0655 0.2132 0.060 Uiso 1 1 calc R
H19B H 0.4336 -0.0105 0.2559 0.060 Uiso 1 1 calc R
H19C H 0.5516 0.0457 0.2922 0.060 Uiso 1 1 calc R
C20 C 0.39537(12) 0.2744(2) 0.34825(8) 0.0379(4) Uani 1 1 d .
H20A H 0.4583 0.2623 0.3855 0.057 Uiso 1 1 calc R
H20B H 0.3441 0.1910 0.3499 0.057 Uiso 1 1 calc R
H20C H 0.3619 0.3758 0.3516 0.057 Uiso 1 1 calc R
C21 C 0.31556(16) -0.0278(3) 0.07895(11) 0.0578(5) Uani 1 1 d .
H21A H 0.2589 -0.0639 0.0413 0.087 Uiso 1 1 calc R
H21B H 0.2850 0.0425 0.1068 0.087 Uiso 1 1 calc R
H21C H 0.3482 -0.1175 0.1055 0.087 Uiso 1 1 calc R
C22 C 0.39987(15) 0.0583(2) 0.05296(10) 0.0491(5) Uani 1 1 d .
H22A H 0.3657 0.1473 0.0254 0.059 Uiso 1 1 calc R
H22B H 0.4538 0.1011 0.0913 0.059 Uiso 1 1 calc R
C23 C 0.45607(14) -0.0418(2) 0.01181(9) 0.0418(4) Uani 1 1 d .
H23A H 0.4025 -0.0808 -0.0276 0.050 Uiso 1 1 calc R
H23B H 0.4874 -0.1334 0.0387 0.050 Uiso 1 1 calc R
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'
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
N2 Si1 N1 100.60(6) . .
N2 Si1 C19 111.20(7) . .
N1 Si1 C19 110.84(7) . .
N2 Si1 C20 111.14(7) . .
N1 Si1 C20 111.21(7) . .
C19 Si1 C20 111.40(8) . .
C1 N1 C4 107.27(12) . .
C1 N1 Si1 129.04(10) . .
C4 N1 Si1 123.69(10) . .
C9 N2 C6 107.50(11) . .
C9 N2 Si1 128.58(10) . .
C6 N2 Si1 123.85(9) . .
C2 C1 N1 108.99(13) . .
C2 C1 C10 127.92(13) . .
N1 C1 C10 123.09(13) . .
C1 C2 C3 107.70(13) . .
C1 C2 C11 125.94(14) . .
C3 C2 C11 126.36(14) . .
C4 C3 C2 107.54(13) . .
C4 C3 C13 127.60(14) . .
C2 C3 C13 124.82(14) . .
C3 C4 N1 108.47(12) . .
C3 C4 C5 130.40(13) . .
N1 C4 C5 121.11(13) . .
C14 C5 C4 120.63(13) . .
C14 C5 C6 120.56(14) . .
C4 C5 C6 118.81(12) . .
C7 C6 N2 108.49(12) . .
C7 C6 C5 130.50(13) . .
N2 C6 C5 120.99(12) . .
C6 C7 C8 107.15(13) . .
C6 C7 C15 127.85(13) . .
C8 C7 C15 124.95(13) . .
C9 C8 C7 108.07(12) . .
C9 C8 C16 126.19(14) . .
C7 C8 C16 125.71(14) . .
C8 C9 N2 108.78(12) . .
C8 C9 C18 128.77(13) . .
N2 C9 C18 122.45(13) . .
C1 C10 H10A 109.5 . .
C1 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C1 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C2 C11 C12 113.86(13) . .
C2 C11 H11A 108.8 . .
C12 C11 H11A 108.8 . .
C2 C11 H11B 108.8 . .
C12 C11 H11B 108.8 . .
H11A C11 H11B 107.7 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C3 C13 H13A 109.5 . .
C3 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C3 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C5 C14 H14A 120.0 . .
C5 C14 H14B 120.0 . .
H14A C14 H14B 120.0 . .
C7 C15 H15A 109.5 . .
C7 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C7 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C8 C16 C17 112.57(13) . .
C8 C16 H16A 109.1 . .
C17 C16 H16A 109.1 . .
C8 C16 H16B 109.1 . .
C17 C16 H16B 109.1 . .
H16A C16 H16B 107.8 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C9 C18 H18A 109.5 . .
C9 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C9 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
Si1 C19 H19A 109.5 . .
Si1 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
Si1 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
Si1 C20 H20A 109.5 . .
Si1 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
Si1 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C22 C21 H21A 109.5 . .
C22 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C22 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C23 C22 C21 113.90(17) . .
C23 C22 H22A 108.8 . .
C21 C22 H22A 108.8 . .
C23 C22 H22B 108.8 . .
C21 C22 H22B 108.8 . .
H22A C22 H22B 107.7 . .
C22 C23 C23 114.14(19) . 3_655
C22 C23 H23A 108.7 . .
C23 C23 H23A 108.7 3_655 .
C22 C23 H23B 108.7 . .
C23 C23 H23B 108.7 3_655 .
H23A C23 H23B 107.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 N2 1.7544(12) .
Si1 N1 1.7559(12) .
Si1 C19 1.8482(17) .
Si1 C20 1.8497(16) .
N1 C1 1.3978(18) .
N1 C4 1.4068(18) .
N2 C9 1.3980(17) .
N2 C6 1.4056(18) .
C1 C2 1.374(2) .
C1 C10 1.497(2) .
C2 C3 1.425(2) .
C2 C11 1.507(2) .
C3 C4 1.380(2) .
C3 C13 1.499(2) .
C4 C5 1.469(2) .
C5 C14 1.347(2) .
C5 C6 1.4700(19) .
C6 C7 1.3817(19) .
C7 C8 1.429(2) .
C7 C15 1.502(2) .
C8 C9 1.368(2) .
C8 C16 1.5087(19) .
C9 C18 1.494(2) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C12 1.521(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9500 .
C14 H14B 0.9500 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C17 1.526(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 C22 1.516(3) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 C23 1.512(2) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C23 1.518(3) 3_655
C23 H23A 0.9900 .
C23 H23B 0.9900 .
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_4
N2 Si1 N1 C1 159.16(12) .
C19 Si1 N1 C1 -83.13(14) .
C20 Si1 N1 C1 41.38(14) .
N2 Si1 N1 C4 -21.38(12) .
C19 Si1 N1 C4 96.32(12) .
C20 Si1 N1 C4 -139.17(12) .
N1 Si1 N2 C9 -158.88(12) .
C19 Si1 N2 C9 83.68(14) .
C20 Si1 N2 C9 -41.04(15) .
N1 Si1 N2 C6 24.56(12) .
C19 Si1 N2 C6 -92.88(13) .
C20 Si1 N2 C6 142.40(12) .
C4 N1 C1 C2 1.32(16) .
Si1 N1 C1 C2 -179.15(10) .
C4 N1 C1 C10 -178.08(13) .
Si1 N1 C1 C10 1.4(2) .
N1 C1 C2 C3 -0.27(17) .
C10 C1 C2 C3 179.10(15) .
N1 C1 C2 C11 179.13(14) .
C10 C1 C2 C11 -1.5(3) .
C1 C2 C3 C4 -0.92(17) .
C11 C2 C3 C4 179.69(14) .
C1 C2 C3 C13 177.09(15) .
C11 C2 C3 C13 -2.3(3) .
C2 C3 C4 N1 1.74(16) .
C13 C3 C4 N1 -176.19(15) .
C2 C3 C4 C5 -176.86(15) .
C13 C3 C4 C5 5.2(3) .
C1 N1 C4 C3 -1.90(16) .
Si1 N1 C4 C3 178.55(10) .
C1 N1 C4 C5 176.85(13) .
Si1 N1 C4 C5 -2.70(19) .
C3 C4 C5 C14 28.1(3) .
N1 C4 C5 C14 -150.31(15) .
C3 C4 C5 C6 -151.54(15) .
N1 C4 C5 C6 30.0(2) .
C9 N2 C6 C7 0.68(16) .
Si1 N2 C6 C7 177.86(10) .
C9 N2 C6 C5 179.24(13) .
Si1 N2 C6 C5 -3.57(19) .
C14 C5 C6 C7 -28.2(3) .
C4 C5 C6 C7 151.47(15) .
C14 C5 C6 N2 153.59(15) .
C4 C5 C6 N2 -26.7(2) .
N2 C6 C7 C8 -0.12(16) .
C5 C6 C7 C8 -178.51(15) .
N2 C6 C7 C15 177.31(14) .
C5 C6 C7 C15 -1.1(3) .
C6 C7 C8 C9 -0.49(17) .
C15 C7 C8 C9 -178.02(14) .
C6 C7 C8 C16 -178.52(14) .
C15 C7 C8 C16 4.0(2) .
C7 C8 C9 N2 0.92(16) .
C16 C8 C9 N2 178.94(14) .
C7 C8 C9 C18 -178.33(15) .
C16 C8 C9 C18 -0.3(3) .
C6 N2 C9 C8 -0.99(16) .
Si1 N2 C9 C8 -178.00(10) .
C6 N2 C9 C18 178.32(13) .
Si1 N2 C9 C18 1.3(2) .
C1 C2 C11 C12 -78.8(2) .
C3 C2 C11 C12 100.5(2) .
C9 C8 C16 C17 -103.26(19) .
C7 C8 C16 C17 74.4(2) .
C21 C22 C23 C23 -177.46(19) 3_655
