#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:13:37 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179236 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/56/4315608.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_4315608
loop_
_publ_author_name
'Soumya Sarkar'
'Kevin P. McGowan'
'Jeffrey A. Culver'
'Adam R. Carlson'
'Jürgen Koller'
'Andrew J. Peloquin'
'Melanie K. Veige'
'Khalil A. Abboud'
'Adam S. Veige'
_publ_section_title
;
 NCN Trianionic Pincer Ligand Precursors: Synthesis of Bimetallic,
 Chelating Diamide, and Pincer Group IV Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5143
_journal_page_last               5156
_journal_paper_doi               10.1021/ic100232s
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C19 H30 N Si'
_chemical_formula_weight         300.53
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2010-01-28 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.947(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.3735(2)
_cell_length_b                   8.7733(5)
_cell_length_c                   24.6156(14)
_cell_measurement_reflns_used    83
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     3747.0(3)
_computing_cell_refinement
'Bruker SMART v5.624 & SAINT 6.36a (Bruker 1998'
_computing_data_collection       'Bruker SMART v5.624 (Bruker 1998)'
_computing_data_reduction        'Bruker SHELXTL v6.12 (Bruker 2000)'
_computing_molecular_graphics    'Bruker SHELXTL v6.12'
_computing_publication_material  'Bruker SHELXTL v6.12'
_computing_structure_refinement  'Bruker SHELXTL v6.12'
_computing_structure_solution    'Bruker SHELXTL v6.12'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'SMART CCD area detector'
_diffrn_measurement_method       'ω 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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11752
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9733
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL  v6.12 (Bruker 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.065
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0414
_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)+(0.0512P)²+2.6807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                3473
_reflns_number_total             4227
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic100232s_si_001_05.cif
_cod_data_source_block           kv07
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        3747.0(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4315608
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.14976(2) 0.47534(5) 0.364437(16) 0.02938(12) Uani 1 1 d . . .
N1 N 0.13985(6) 0.66526(13) 0.34597(4) 0.0258(2) Uani 1 1 d . . .
C1 C 0.05804(11) 0.3664(2) 0.35295(9) 0.0540(5) Uani 1 1 d . . .
H1A H 0.0179 0.4126 0.3741 0.081 Uiso 1 1 calc R . .
H1B H 0.0661 0.2605 0.3645 0.081 Uiso 1 1 calc R . .
H1C H 0.0420 0.3690 0.3142 0.081 Uiso 1 1 calc R . .
C2 C 0.22194(12) 0.3790(2) 0.32269(8) 0.0553(5) Uani 1 1 d . . .
H2A H 0.2715 0.4320 0.3273 0.083 Uiso 1 1 calc R . .
H2B H 0.2041 0.3814 0.2843 0.083 Uiso 1 1 calc R . .
H2C H 0.2282 0.2729 0.3346 0.083 Uiso 1 1 calc R . .
C3 C 0.18239(11) 0.46796(19) 0.43745(7) 0.0451(4) Uani 1 1 d . . .
H3A H 0.2305 0.5254 0.4430 0.068 Uiso 1 1 calc R . .
H3B H 0.1910 0.3617 0.4484 0.068 Uiso 1 1 calc R . .
H3C H 0.1428 0.5129 0.4595 0.068 Uiso 1 1 calc R . .
C4 C 0.14394(8) 0.79054(15) 0.38385(5) 0.0254(3) Uani 1 1 d . . .
C5 C 0.07729(8) 0.83894(16) 0.40908(5) 0.0284(3) Uani 1 1 d . . .
C6 C 0.08274(10) 0.96368(17) 0.44438(6) 0.0360(3) Uani 1 1 d . . .
H6A H 0.0380 0.9975 0.4615 0.043 Uiso 1 1 calc R . .
C7 C 0.15175(10) 1.03873(18) 0.45494(6) 0.0396(4) Uani 1 1 d . . .
H7A H 0.1543 1.1233 0.4791 0.048 Uiso 1 1 calc R . .
C8 C 0.21705(9) 0.99017(17) 0.43023(6) 0.0360(3) Uani 1 1 d . . .
H8A H 0.2643 1.0425 0.4375 0.043 Uiso 1 1 calc R . .
C9 C 0.21489(8) 0.86601(16) 0.39489(6) 0.0294(3) Uani 1 1 d . . .
C10 C 0.00029(8) 0.75757(17) 0.40115(6) 0.0328(3) Uani 1 1 d . . .
H10A H 0.0045 0.6822 0.3710 0.039 Uiso 1 1 calc R . .
C11 C -0.01796(10) 0.6697(2) 0.45263(7) 0.0441(4) Uani 1 1 d . . .
H11A H 0.0246 0.6001 0.4625 0.066 Uiso 1 1 calc R . .
H11B H -0.0655 0.6110 0.4459 0.066 Uiso 1 1 calc R . .
H11C H -0.0247 0.7417 0.4825 0.066 Uiso 1 1 calc R . .
C12 C -0.06589(10) 0.8665(2) 0.38540(8) 0.0490(4) Uani 1 1 d . . .
H12A H -0.0539 0.9224 0.3524 0.074 Uiso 1 1 calc R . .
H12B H -0.0727 0.9388 0.4151 0.074 Uiso 1 1 calc R . .
H12C H -0.1135 0.8080 0.3786 0.074 Uiso 1 1 calc R . .
C13 C 0.28953(9) 0.81410(18) 0.37104(6) 0.0355(3) Uani 1 1 d . . .
H13A H 0.2778 0.7232 0.3475 0.043 Uiso 1 1 calc R . .
C14 C 0.32342(10) 0.9382(2) 0.33564(7) 0.0477(4) Uani 1 1 d . . .
H14A H 0.2851 0.9683 0.3070 0.072 Uiso 1 1 calc R . .
H14B H 0.3694 0.8989 0.3190 0.072 Uiso 1 1 calc R . .
H14C H 0.3374 1.0269 0.3582 0.072 Uiso 1 1 calc R . .
C15 C 0.34958(10) 0.7664(2) 0.41606(8) 0.0469(4) Uani 1 1 d . . .
H15A H 0.3277 0.6870 0.4386 0.070 Uiso 1 1 calc R . .
H15B H 0.3636 0.8550 0.4387 0.070 Uiso 1 1 calc R . .
H15C H 0.3956 0.7269 0.3995 0.070 Uiso 1 1 calc R . .
C16 C 0.13785(9) 0.71128(18) 0.28817(6) 0.0325(3) Uani 1 1 d . . .
H16A H 0.1421 0.6186 0.2656 0.039 Uiso 1 1 calc R . .
H16B H 0.1835 0.7755 0.2822 0.039 Uiso 1 1 calc R . .
C17 C 0.06642(9) 0.79788(17) 0.26869(6) 0.0320(3) Uani 1 1 d . . .
C18 C 0.06558(11) 0.95697(19) 0.26858(7) 0.0432(4) Uani 1 1 d . . .
H18A H 0.1101 1.0119 0.2813 0.052 Uiso 1 1 calc R . .
C19 C 0.0000 1.0350(3) 0.2500 0.0506(7) Uani 1 2 d S . .
H19A H 0.0000 1.1432 0.2500 0.061 Uiso 1 2 calc SR . .
C20 C 0.0000 0.7211(2) 0.2500 0.0300(4) Uani 1 2 d S . .
H20A H 0.0000 0.6128 0.2500 0.036 Uiso 1 2 calc SR . .
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
_geom_angle_publ_flag
N1 Si1 C3 107.97(7) . . ?
N1 Si1 C2 110.60(8) . . ?
C3 Si1 C2 109.69(9) . . ?
N1 Si1 C1 112.32(7) . . ?
C3 Si1 C1 110.13(9) . . ?
C2 Si1 C1 106.11(10) . . ?
C4 N1 C16 114.37(11) . . ?
C4 N1 Si1 124.24(9) . . ?
C16 N1 Si1 120.82(9) . . ?
Si1 C1 H1A 109.5 . . ?
Si1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Si1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Si1 C2 H2A 109.5 . . ?
Si1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Si1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
Si1 C3 H3A 109.5 . . ?
Si1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Si1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C9 120.21(13) . . ?
C5 C4 N1 120.10(12) . . ?
C9 C4 N1 119.68(12) . . ?
C6 C5 C4 118.67(13) . . ?
C6 C5 C10 118.59(13) . . ?
C4 C5 C10 122.70(12) . . ?
C7 C6 C5 121.39(14) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C6 C7 C8 119.65(14) . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 H7A 120.2 . . ?
C7 C8 C9 121.31(14) . . ?
C7 C8 H8A 119.3 . . ?
C9 C8 H8A 119.3 . . ?
C8 C9 C4 118.78(14) . . ?
C8 C9 C13 118.63(13) . . ?
C4 C9 C13 122.56(13) . . ?
C5 C10 C12 112.61(13) . . ?
C5 C10 C11 110.41(12) . . ?
C12 C10 C11 109.85(14) . . ?
C5 C10 H10A 107.9 . . ?
C12 C10 H10A 107.9 . . ?
C11 C10 H10A 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 C14 111.55(13) . . ?
C9 C13 C15 111.29(13) . . ?
C14 C13 C15 109.67(13) . . ?
C9 C13 H13A 108.1 . . ?
C14 C13 H13A 108.1 . . ?
C15 C13 H13A 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 114.90(12) . . ?
N1 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
N1 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C20 C17 C18 118.31(15) . . ?
C20 C17 C16 120.93(14) . . ?
C18 C17 C16 120.76(14) . . ?
C19 C18 C17 120.17(16) . . ?
C19 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C18 C19 C18 120.8(2) 2 . ?
C18 C19 H19A 119.6 2 . ?
C18 C19 H19A 119.6 . . ?
C17 C20 C17 122.20(19) 2 . ?
C17 C20 H20A 118.9 2 . ?
C17 C20 H20A 118.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 N1 1.7333(12) . ?
Si1 C3 1.8577(17) . ?
Si1 C2 1.8643(18) . ?
Si1 C1 1.8671(18) . ?
N1 C4 1.4407(17) . ?
N1 C16 1.4776(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.407(2) . ?
C4 C9 1.4134(19) . ?
C5 C6 1.398(2) . ?
C5 C10 1.520(2) . ?
C6 C7 1.381(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.382(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.393(2) . ?
C8 H8A 0.9500 . ?
C9 C13 1.520(2) . ?
C10 C12 1.529(2) . ?
C10 C11 1.530(2) . ?
C10 H10A 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.531(2) . ?
C13 C15 1.541(2) . ?
C13 H13A 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.512(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C20 1.3937(17) . ?
C17 C18 1.396(2) . ?
C18 C19 1.386(2) . ?
C18 H18A 0.9500 . ?
C19 C18 1.386(2) 2 ?
C19 H19A 0.9500 . ?
C20 C17 1.3937(17) 2 ?
C20 H20A 0.9500 . ?
