#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:44:03 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178791 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/45/4104564.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_4104564
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            'C21 H24 Cl N Si'
_chemical_formula_weight         353.95
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9398(8)
_cell_length_b                   10.6673(7)
_cell_length_c                   15.4012(11)
_cell_measurement_reflns_used    5480
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.56
_cell_volume                     1961.6(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11406
_diffrn_reflns_theta_full        27.03
_diffrn_reflns_theta_max         27.03
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.8819
_exptl_absorpt_correction_T_min  0.8819
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4179
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0430
_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)+(0.0798P)²+0.0332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                3751
_reflns_number_total             4179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja901622b_5n.cif
_cod_data_source_block           5n
_cod_database_code               4104564
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
C1 C 0.25468(18) 0.7357(2) 0.64820(14) 0.0611(5) Uani 1 1 d .
C2 C 0.3414(2) 0.7700(3) 0.59319(18) 0.0791(7) Uani 1 1 d .
H2 H 0.3506 0.8535 0.5773 0.095 Uiso 1 1 calc R
C3 C 0.4147(3) 0.6792(4) 0.5618(2) 0.0915(9) Uani 1 1 d .
H3 H 0.4718 0.7022 0.5239 0.110 Uiso 1 1 calc R
C4 C 0.4036(2) 0.5568(4) 0.5860(2) 0.0905(9) Uani 1 1 d .
H4 H 0.4542 0.4975 0.5654 0.109 Uiso 1 1 calc R
C5 C 0.3174(2) 0.5196(3) 0.64121(19) 0.0773(6) Uani 1 1 d .
H5 H 0.3104 0.4361 0.6578 0.093 Uiso 1 1 calc R
C6 C 0.24211(18) 0.6088(2) 0.67121(14) 0.0598(5) Uani 1 1 d .
C7 C 0.14598(16) 0.58972(18) 0.73031(13) 0.0555(4) Uani 1 1 d .
C8 C 0.08691(17) 0.69439(17) 0.75780(13) 0.0540(4) Uani 1 1 d .
C9 C 0.00061(17) 0.64741(18) 0.81372(13) 0.0540(4) Uani 1 1 d .
C10 C -0.08541(18) 0.7048(2) 0.86099(14) 0.0603(5) Uani 1 1 d .
H10 H -0.0950 0.7913 0.8598 0.072 Uiso 1 1 calc R
C11 C -0.15530(18) 0.6299(3) 0.90915(16) 0.0688(6) Uani 1 1 d .
C12 C -0.1436(2) 0.4994(3) 0.9123(2) 0.0791(7) Uani 1 1 d .
H12 H -0.1926 0.4517 0.9456 0.095 Uiso 1 1 calc R
C13 C -0.0599(2) 0.4420(2) 0.86619(18) 0.0753(6) Uani 1 1 d .
H13 H -0.0513 0.3554 0.8681 0.090 Uiso 1 1 calc R
C14 C 0.0123(2) 0.5155(2) 0.81623(14) 0.0612(5) Uani 1 1 d .
C15 C 0.0497(2) 0.9203(3) 0.63198(18) 0.0781(7) Uani 1 1 d .
H15 H -0.0059 0.9628 0.6683 0.094 Uiso 1 1 calc R
C16 C -0.0121(5) 0.8326(4) 0.5743(4) 0.175(3) Uani 1 1 d .
H16A H -0.0479 0.8791 0.5287 0.262 Uiso 1 1 calc R
H16B H -0.0678 0.7887 0.6074 0.262 Uiso 1 1 calc R
H16C H 0.0393 0.7734 0.5495 0.262 Uiso 1 1 calc R
C17 C 0.1095(3) 1.0213(3) 0.5791(3) 0.1032(11) Uani 1 1 d .
H17A H 0.1815 0.9907 0.5610 0.155 Uiso 1 1 calc R
H17B H 0.1192 1.0949 0.6141 0.155 Uiso 1 1 calc R
H17C H 0.0655 1.0417 0.5289 0.155 Uiso 1 1 calc R
C18 C 0.21346(19) 0.9463(2) 0.78601(17) 0.0677(5) Uani 1 1 d .
H18 H 0.2463 1.0156 0.7528 0.081 Uiso 1 1 calc R
C19 C 0.1262(3) 1.0014(4) 0.8470(3) 0.1142(13) Uani 1 1 d .
H19A H 0.0920 0.9353 0.8799 0.171 Uiso 1 1 calc R
H19B H 0.0699 1.0442 0.8137 0.171 Uiso 1 1 calc R
H19C H 0.1615 1.0596 0.8858 0.171 Uiso 1 1 calc R
C20 C 0.3067(3) 0.8842(4) 0.8366(3) 0.1083(11) Uani 1 1 d .
H20A H 0.3396 0.9439 0.8757 0.163 Uiso 1 1 calc R
H20B H 0.3628 0.8541 0.7972 0.163 Uiso 1 1 calc R
H20C H 0.2769 0.8151 0.8693 0.163 Uiso 1 1 calc R
C21 C 0.1295(3) 0.3522(2) 0.7427(2) 0.0850(8) Uani 1 1 d .
H21A H 0.0735 0.2972 0.7660 0.128 Uiso 1 1 calc R
H21B H 0.2011 0.3316 0.7673 0.128 Uiso 1 1 calc R
H21C H 0.1327 0.3426 0.6808 0.128 Uiso 1 1 calc R
Cl1 Cl -0.26135(6) 0.69982(7) 0.96959(5) 0.0928(2) Uani 1 1 d .
N1 N 0.10105(16) 0.48258(15) 0.76420(14) 0.0630(4) Uani 1 1 d .
Si1 Si 0.14722(4) 0.83506(5) 0.70654(4) 0.05333(14) Uani 1 1 d .
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 119.2(2)
C2 C1 Si1 130.4(2)
C6 C1 Si1 110.31(16)
C1 C2 C3 119.8(3)
C1 C2 H2 120.1
C3 C2 H2 120.1
C4 C3 C2 120.6(3)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 120.8(3)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C5 C4 119.1(3)
C6 C5 H5 120.5
C4 C5 H5 120.5
C5 C6 C1 120.4(2)
C5 C6 C7 127.8(2)
C1 C6 C7 111.75(18)
N1 C7 C8 110.93(18)
N1 C7 C6 130.94(19)
C8 C7 C6 118.13(18)
C7 C8 C9 105.52(17)
C7 C8 Si1 109.04(15)
C9 C8 Si1 145.42(16)
C10 C9 C14 119.54(19)
C10 C9 C8 133.40(18)
C14 C9 C8 107.06(19)
C11 C10 C9 118.2(2)
C11 C10 H10 120.9
C9 C10 H10 120.9
C10 C11 C12 122.4(2)
C10 C11 Cl1 118.8(2)
C12 C11 Cl1 118.74(18)
C13 C12 C11 120.0(2)
C13 C12 H12 120.0
C11 C12 H12 120.0
C12 C13 C14 119.0(2)
C12 C13 H13 120.5
C14 C13 H13 120.5
N1 C14 C13 130.8(2)
N1 C14 C9 108.32(18)
C13 C14 C9 120.9(2)
C16 C15 C17 110.9(3)
C16 C15 Si1 111.7(2)
C17 C15 Si1 112.3(2)
C16 C15 H15 107.2
C17 C15 H15 107.2
Si1 C15 H15 107.2
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C15 C17 H17A 109.5
C15 C17 H17B 109.5
H17A C17 H17B 109.5
C15 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C20 C18 C19 110.8(3)
C20 C18 Si1 111.63(19)
C19 C18 Si1 110.96(19)
C20 C18 H18 107.7
C19 C18 H18 107.7
Si1 C18 H18 107.7
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C18 C20 H20A 109.5
C18 C20 H20B 109.5
H20A C20 H20B 109.5
C18 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
N1 C21 H21A 109.5
N1 C21 H21B 109.5
H21A C21 H21B 109.5
N1 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C7 N1 C14 108.16(16)
C7 N1 C21 127.9(2)
C14 N1 C21 123.5(2)
C8 Si1 C15 114.56(11)
C8 Si1 C18 113.57(11)
C15 Si1 C18 110.76(13)
C8 Si1 C1 90.70(10)
C15 Si1 C1 113.77(12)
C18 Si1 C1 112.20(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.388(3)
C1 C6 1.407(3)
C1 Si1 1.891(2)
C2 C3 1.392(4)
C2 H2 0.9300
C3 C4 1.365(5)
C3 H3 0.9300
C4 C5 1.392(4)
C4 H4 0.9300
C5 C6 1.389(3)
C5 H5 0.9300
C6 C7 1.479(3)
C7 N1 1.366(3)
C7 C8 1.387(3)
C8 C9 1.433(3)
C8 Si1 1.8422(19)
C9 C10 1.400(3)
C9 C14 1.414(3)
C10 C11 1.373(3)
C10 H10 0.9300
C11 C12 1.400(4)
C11 Cl1 1.740(3)
C12 C13 1.370(4)
C12 H12 0.9300
C13 C14 1.397(3)
C13 H13 0.9300
C14 N1 1.374(3)
C15 C16 1.487(5)
C15 C17 1.528(4)
C15 Si1 1.871(3)
C15 H15 0.9800
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 C20 1.512(4)
C18 C19 1.521(4)
C18 Si1 1.879(2)
C18 H18 0.9800
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C21 N1 1.469(3)
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
