#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:44:03 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178791 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/45/4104562.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_4104562
loop_
_publ_author_name
'Kenji Mochida'
'Masaki Shimizu'
'Tamejiro Hiyama'
_publ_contact_author             'Masaki Shimizu'
_publ_contact_author_email       m.shimizu@hs2.ecs.kyoto-u.ac.jp
_publ_contact_author_fax         +81-75-383-2445
_publ_contact_author_phone       +81-75-383-2444
_publ_section_title
;
 Palladium-Catalyzed Intramolecular Coupling of 2-[(2-Pyrrolyl)silyl]aryl
 Triflates through 1,2-Silicon Migration
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8350
_journal_page_last               8351
_journal_paper_doi               10.1021/ja901622b
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C22 H24 N2 Si'
_chemical_formula_weight         344.52
_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
_audit_update_record
;
2009-02-26 # Formatted by publCIF
;
_cell_angle_alpha                85.742(2)
_cell_angle_beta                 89.861(2)
_cell_angle_gamma                89.268(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8753(7)
_cell_length_b                   9.9812(9)
_cell_length_c                   12.5882(11)
_cell_measurement_reflns_used    2129
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      25.55
_cell_measurement_theta_min      2.52
_cell_volume                     986.68(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0145
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5412
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.9754
_exptl_absorpt_correction_T_min  0.9401
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0599
_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)+(0.1256P)²+0.1147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1836
_refine_ls_wR_factor_ref         0.1960
_reflns_number_gt                2795
_reflns_number_total             3614
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja901622b_5h.cif
_cod_data_source_block           5h
_cod_database_code               4104562
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 0.10732(8) 0.65953(6) 0.76971(5) 0.0580(3) Uani 1 1 d .
C10 C 0.0013(3) 0.9181(2) 0.78290(17) 0.0502(5) Uani 1 1 d .
N1 N 0.1511(2) 1.0085(2) 0.60983(15) 0.0575(5) Uani 1 1 d .
C1 C 0.1733(3) 0.7864(2) 0.66497(18) 0.0578(6) Uani 1 1 d .
C16 C -0.0143(3) 0.7912(2) 0.84000(18) 0.0533(5) Uani 1 1 d .
C9 C 0.1074(3) 0.9098(2) 0.68754(17) 0.0524(5) Uani 1 1 d .
C11 C -0.0831(3) 1.0298(3) 0.8184(2) 0.0614(6) Uani 1 1 d .
H11 H -0.0726 1.1133 0.7812 0.074 Uiso 1 1 calc R
C13 C -0.1987(3) 0.8945(3) 0.96487(19) 0.0620(6) Uani 1 1 d .
C7 C 0.2444(3) 0.9460(3) 0.53275(18) 0.0611(6) Uani 1 1 d .
C15 C -0.1134(3) 0.7812(3) 0.93071(18) 0.0605(6) Uani 1 1 d .
H15 H -0.1239 0.6986 0.9695 0.073 Uiso 1 1 calc R
C12 C -0.1819(3) 1.0163(3) 0.9086(2) 0.0659(7) Uani 1 1 d .
H12 H -0.2384 1.0912 0.9318 0.079 Uiso 1 1 calc R
C2 C 0.2608(3) 0.8092(3) 0.56462(19) 0.0616(6) Uani 1 1 d .
C6 C 0.3111(3) 1.0015(3) 0.4371(2) 0.0754(8) Uani 1 1 d .
H6 H 0.2993 1.0928 0.4175 0.090 Uiso 1 1 calc R
C17 C -0.0354(4) 0.5279(3) 0.7211(2) 0.0752(7) Uani 1 1 d .
H17 H 0.0349 0.4733 0.6762 0.090 Uiso 1 1 calc R
C8 C 0.1196(3) 1.1514(3) 0.6080(2) 0.0718(7) Uani 1 1 d .
H8A H -0.0003 1.1690 0.6028 0.108 Uiso 1 1 calc R
H8B H 0.1761 1.1956 0.5478 0.108 Uiso 1 1 calc R
H8C H 0.1621 1.1846 0.6724 0.108 Uiso 1 1 calc R
C14 C -0.3030(4) 0.8815(3) 1.0597(2) 0.0786(8) Uani 1 1 d .
C3 C 0.3484(3) 0.7258(3) 0.4981(2) 0.0776(8) Uani 1 1 d .
H3 H 0.3625 0.6345 0.5174 0.093 Uiso 1 1 calc R
C20 C 0.2863(4) 0.5814(3) 0.8529(2) 0.0774(8) Uani 1 1 d .
H20 H 0.2365 0.5301 0.9144 0.093 Uiso 1 1 calc R
C4 C 0.4134(4) 0.7816(4) 0.4032(2) 0.0888(10) Uani 1 1 d .
H4 H 0.4715 0.7271 0.3582 0.107 Uiso 1 1 calc R
C5 C 0.3935(4) 0.9186(4) 0.3736(2) 0.0903(11) Uani 1 1 d .
H5 H 0.4378 0.9534 0.3090 0.108 Uiso 1 1 calc R
N2 N -0.3821(4) 0.8707(4) 1.1342(2) 0.1093(10) Uani 1 1 d .
C19 C -0.1051(5) 0.4323(3) 0.8093(3) 0.1004(11) Uani 1 1 d .
H19A H -0.1749 0.4814 0.8560 0.151 Uiso 1 1 calc R
H19B H -0.0127 0.3898 0.8490 0.151 Uiso 1 1 calc R
H19C H -0.1718 0.3650 0.7789 0.151 Uiso 1 1 calc R
C22 C 0.3994(5) 0.6894(4) 0.8947(4) 0.1230(16) Uani 1 1 d .
H22A H 0.4912 0.6472 0.9351 0.184 Uiso 1 1 calc R
H22B H 0.3336 0.7441 0.9394 0.184 Uiso 1 1 calc R
H22C H 0.4442 0.7445 0.8357 0.184 Uiso 1 1 calc R
C21 C 0.3886(5) 0.4853(4) 0.7906(4) 0.1232(15) Uani 1 1 d .
H21A H 0.4373 0.5331 0.7291 0.185 Uiso 1 1 calc R
H21B H 0.3160 0.4161 0.7682 0.185 Uiso 1 1 calc R
H21C H 0.4777 0.4453 0.8347 0.185 Uiso 1 1 calc R
C18 C -0.1756(6) 0.5863(4) 0.6517(4) 0.1360(18) Uani 1 1 d .
H18A H -0.2554 0.5175 0.6389 0.204 Uiso 1 1 calc R
H18B H -0.1292 0.6223 0.5852 0.204 Uiso 1 1 calc R
H18C H -0.2321 0.6567 0.6866 0.204 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
C1 Si1 C17 113.84(12)
C1 Si1 C20 114.69(13)
C17 Si1 C20 111.28(13)
C1 Si1 C16 90.81(10)
C17 Si1 C16 112.24(12)
C20 Si1 C16 112.55(11)
C11 C10 C16 120.0(2)
C11 C10 C9 128.4(2)
C16 C10 C9 111.58(19)
C9 N1 C7 107.1(2)
C9 N1 C8 128.5(2)
C7 N1 C8 124.4(2)
C9 C1 C2 105.6(2)
C9 C1 Si1 108.94(16)
C2 C1 Si1 145.34(19)
C15 C16 C10 118.8(2)
C15 C16 Si1 131.2(2)
C10 C16 Si1 109.95(16)
C1 C9 N1 111.2(2)
C1 C9 C10 118.7(2)
N1 C9 C10 130.1(2)
C12 C11 C10 119.8(2)
C12 C11 H11 120.1
C10 C11 H11 120.1
C12 C13 C15 119.8(2)
C12 C13 C14 120.7(2)
C15 C13 C14 119.5(3)
C6 C7 N1 129.0(3)
C6 C7 C2 122.3(3)
N1 C7 C2 108.6(2)
C16 C15 C13 120.5(2)
C16 C15 H15 119.8
C13 C15 H15 119.8
C13 C12 C11 121.1(2)
C13 C12 H12 119.4
C11 C12 H12 119.4
C3 C2 C7 118.6(3)
C3 C2 C1 133.9(3)
C7 C2 C1 107.5(2)
C5 C6 C7 117.9(3)
C5 C6 H6 121.0
C7 C6 H6 121.0
C18 C17 C19 110.8(3)
C18 C17 Si1 112.7(2)
C19 C17 Si1 113.7(2)
C18 C17 H17 106.4
C19 C17 H17 106.4
Si1 C17 H17 106.4
N1 C8 H8A 109.5
N1 C8 H8B 109.5
H8A C8 H8B 109.5
N1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N2 C14 C13 179.0(4)
C4 C3 C2 118.6(3)
C4 C3 H3 120.7
C2 C3 H3 120.7
C21 C20 C22 111.1(3)
C21 C20 Si1 110.8(2)
C22 C20 Si1 111.0(2)
C21 C20 H20 108.0
C22 C20 H20 108.0
Si1 C20 H20 108.0
C3 C4 C5 121.2(3)
C3 C4 H4 119.4
C5 C4 H4 119.4
C6 C5 C4 121.3(3)
C6 C5 H5 119.4
C4 C5 H5 119.4
C17 C19 H19A 109.5
C17 C19 H19B 109.5
H19A C19 H19B 109.5
C17 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C20 C22 H22A 109.5
C20 C22 H22B 109.5
H22A C22 H22B 109.5
C20 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Si1 C1 1.838(3)
Si1 C17 1.878(3)
Si1 C20 1.884(3)
Si1 C16 1.888(2)
C10 C11 1.392(3)
C10 C16 1.415(3)
C10 C9 1.468(3)
N1 C9 1.382(3)
N1 C7 1.395(3)
N1 C8 1.443(3)
C1 C9 1.379(3)
C1 C2 1.442(3)
C16 C15 1.380(3)
C11 C12 1.375(3)
C11 H11 0.9300
C13 C12 1.368(4)
C13 C15 1.403(3)
C13 C14 1.446(3)
C7 C6 1.392(4)
C7 C2 1.399(4)
C15 H15 0.9300
C12 H12 0.9300
C2 C3 1.398(3)
C6 C5 1.352(4)
C6 H6 0.9300
C17 C18 1.494(5)
C17 C19 1.516(5)
C17 H17 0.9800
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C14 N2 1.124(4)
C3 C4 1.380(4)
C3 H3 0.9300
C20 C21 1.508(4)
C20 C22 1.530(5)
C20 H20 0.9800
C4 C5 1.397(5)
C4 H4 0.9300
C5 H5 0.9300
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
