#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:49:12 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178583 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/94/4069407.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_4069407
loop_
_publ_author_name
'Walker, Randon H.'
'Miller, Karla A.'
'Scott, Sara L.'
'Cygan, Zuzanna T.'
'Bartolin, Jeffrey M.'
'Kampf, Jeff W.'
'Banaszak Holl, Mark M.'
_publ_section_title
;
 Silylene- and Germylene-Mediated C−H Activation: Reaction with
 Alkanes, Ethers, and Amines
;
_journal_issue                   9
_journal_name_full               Organometallics
_journal_page_first              2744
_journal_paper_doi               10.1021/om900182z
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C16 H32 I N3 Si'
_chemical_formula_sum            'C16 H32 I N3 Si'
_chemical_formula_weight         421.44
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.403(1)
_cell_angle_beta                 95.239(1)
_cell_angle_gamma                118.010(1)
_cell_formula_units_Z            2
_cell_length_a                   9.4165(4)
_cell_length_b                   9.5587(4)
_cell_length_c                   12.2601(5)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      33.22
_cell_measurement_theta_min      2.95
_cell_volume                     955.12(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART-APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            42226
_diffrn_reflns_theta_full        33.22
_diffrn_reflns_theta_max         33.22
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    1.739
_exptl_absorpt_correction_T_max  0.7010
_exptl_absorpt_correction_T_min  0.5977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  Blessing, R. Acta Cryst. (1995) A51 33-38.
  Sheldrick, G.  SADABS (Version 2007/4) Bruker AXS area
  detector absorption and other corrections, University of
  Gottingen, Germany 2007.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.445
_refine_diff_density_min         -0.957
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         7220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0198
_refine_ls_R_factor_gt           0.0193
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0219P)²+0.4949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0494
_reflns_number_gt                7053
_reflns_number_total             7220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900182z_si_002.cif
_cod_data_source_block           rwa_-_Compound_(13)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        955.11(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4069407
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
_atom_site_refinement_flags
Si1 Si 0.00793(4) 0.30709(4) 0.24859(2) 0.01074(5) Uani 1 1 d .
I1 I 0.044995(9) 0.586677(8) 0.314955(6) 0.01564(3) Uani 1 1 d .
N1 N -0.19404(11) 0.17132(11) 0.19687(7) 0.01251(15) Uani 1 1 d .
N2 N 0.07040(11) 0.30101(11) 0.12141(7) 0.01235(15) Uani 1 1 d .
N3 N 0.17010(12) 0.14683(12) 0.32721(8) 0.01394(16) Uani 1 1 d .
C1 C -0.34478(13) 0.11905(13) 0.24673(9) 0.01416(18) Uani 1 1 d .
C2 C -0.45323(15) -0.06347(15) 0.21135(11) 0.0215(2) Uani 1 1 d .
H2A H -0.4867 -0.0897 0.1304 0.032 Uiso 1 1 calc R
H2B H -0.5501 -0.0994 0.2475 0.032 Uiso 1 1 calc R
H2C H -0.3922 -0.1180 0.2335 0.032 Uiso 1 1 calc R
C3 C -0.43554(15) 0.20702(17) 0.20847(11) 0.0208(2) Uani 1 1 d .
H3A H -0.3657 0.3233 0.2328 0.031 Uiso 1 1 calc R
H3B H -0.5356 0.1712 0.2410 0.031 Uiso 1 1 calc R
H3C H -0.4633 0.1829 0.1271 0.031 Uiso 1 1 calc R
C4 C -0.30132(15) 0.15822(15) 0.37350(10) 0.0181(2) Uani 1 1 d .
H4A H -0.2512 0.0955 0.3990 0.027 Uiso 1 1 calc R
H4B H -0.4005 0.1310 0.4059 0.027 Uiso 1 1 calc R
H4C H -0.2244 0.2733 0.3969 0.027 Uiso 1 1 calc R
C5 C -0.21042(13) 0.14048(14) 0.07946(9) 0.01504(18) Uani 1 1 d .
H5A H -0.3130 0.0757 0.0327 0.018 Uiso 1 1 calc R
C6 C -0.06975(13) 0.20990(13) 0.03936(9) 0.01459(18) Uani 1 1 d .
H6A H -0.0649 0.1986 -0.0380 0.018 Uiso 1 1 calc R
C7 C 0.23024(13) 0.39286(13) 0.08593(9) 0.01392(17) Uani 1 1 d .
C8 C 0.22847(15) 0.52329(16) 0.02436(11) 0.0209(2) Uani 1 1 d .
H8A H 0.1411 0.4729 -0.0403 0.031 Uiso 1 1 calc R
H8B H 0.3336 0.5824 -0.0006 0.031 Uiso 1 1 calc R
H8C H 0.2096 0.5980 0.0746 0.031 Uiso 1 1 calc R
C9 C 0.26531(16) 0.27757(17) 0.01089(11) 0.0228(2) Uani 1 1 d .
H9A H 0.2552 0.1892 0.0490 0.034 Uiso 1 1 calc R
H9B H 0.3762 0.3358 -0.0058 0.034 Uiso 1 1 calc R
H9C H 0.1870 0.2339 -0.0586 0.034 Uiso 1 1 calc R
C10 C 0.36212(14) 0.47109(14) 0.18957(10) 0.01627(19) Uani 1 1 d .
H10A H 0.3423 0.5473 0.2373 0.024 Uiso 1 1 calc R
H10B H 0.4694 0.5284 0.1672 0.024 Uiso 1 1 calc R
H10C H 0.3591 0.3877 0.2306 0.024 Uiso 1 1 calc R
C11 C 0.10386(13) 0.25157(13) 0.36903(9) 0.01299(17) Uani 1 1 d .
H11A H 0.0132 0.1858 0.4087 0.016 Uiso 1 1 calc R
C12 C 0.23084(14) 0.39547(13) 0.45580(9) 0.01444(18) Uani 1 1 d .
H12A H 0.3207 0.4672 0.4192 0.017 Uiso 1 1 calc R
H12B H 0.1797 0.4575 0.4869 0.017 Uiso 1 1 calc R
C13 C 0.30038(14) 0.34265(15) 0.55000(9) 0.01605(19) Uani 1 1 d .
H13A H 0.2141 0.2834 0.5935 0.019 Uiso 1 1 calc R
H13B H 0.3892 0.4384 0.6005 0.019 Uiso 1 1 calc R
C14 C 0.36621(14) 0.23468(15) 0.50228(10) 0.01738(19) Uani 1 1 d .
H14A H 0.4595 0.2969 0.4649 0.021 Uiso 1 1 calc R
H14B H 0.4049 0.1946 0.5631 0.021 Uiso 1 1 calc R
C15 C 0.23205(14) 0.09364(14) 0.41938(9) 0.01608(19) Uani 1 1 d .
H15A H 0.2748 0.0232 0.3890 0.019 Uiso 1 1 calc R
H15B H 0.1412 0.0297 0.4582 0.019 Uiso 1 1 calc R
C16 C 0.04740(15) 0.00327(14) 0.25002(10) 0.0184(2) Uani 1 1 d .
H16A H 0.0944 -0.0656 0.2276 0.028 Uiso 1 1 calc R
H16B H 0.0118 0.0352 0.1841 0.028 Uiso 1 1 calc R
H16C H -0.0463 -0.0561 0.2866 0.028 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'
I I -0.4742 1.8119 '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
N2 Si1 N1 94.14(4)
N2 Si1 C11 119.13(5)
N1 Si1 C11 115.15(5)
N2 Si1 I1 109.58(3)
N1 Si1 I1 111.01(3)
C11 Si1 I1 107.33(3)
C5 N1 C1 117.96(9)
C5 N1 Si1 107.70(7)
C1 N1 Si1 132.40(7)
C6 N2 C7 118.96(9)
C6 N2 Si1 108.11(7)
C7 N2 Si1 131.86(7)
C16 N3 C15 107.80(9)
C16 N3 C11 112.10(9)
C15 N3 C11 110.94(9)
N1 C1 C4 109.80(9)
N1 C1 C3 109.81(9)
C4 C1 C3 109.02(10)
N1 C1 C2 109.24(9)
C4 C1 C2 108.64(9)
C3 C1 C2 110.32(10)
C6 C5 N1 114.78(10)
C5 C6 N2 114.60(9)
N2 C7 C9 109.31(9)
N2 C7 C10 108.50(9)
C9 C7 C10 108.87(10)
N2 C7 C8 109.59(9)
C9 C7 C8 110.73(10)
C10 C7 C8 109.79(10)
N3 C11 C12 111.34(9)
N3 C11 Si1 110.94(7)
C12 C11 Si1 114.64(7)
C13 C12 C11 111.89(9)
C12 C13 C14 109.76(9)
C15 C14 C13 109.38(9)
N3 C15 C14 111.97(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Si1 N2 1.7205(10)
Si1 N1 1.7266(10)
Si1 C11 1.9130(11)
Si1 I1 2.5521(3)
N1 C5 1.4160(14)
N1 C1 1.4827(14)
N2 C6 1.4123(14)
N2 C7 1.4796(14)
N3 C16 1.4612(15)
N3 C15 1.4703(14)
N3 C11 1.4781(14)
C1 C4 1.5276(16)
C1 C3 1.5321(16)
C1 C2 1.5335(17)
C5 C6 1.3427(15)
C7 C9 1.5300(17)
C7 C10 1.5309(16)
C7 C8 1.5335(17)
C11 C12 1.5330(15)
C12 C13 1.5232(16)
C13 C14 1.5245(17)
C14 C15 1.5187(16)
