#------------------------------------------------------------------------------
#$Date: 2016-03-23 14:53:57 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179311 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/08/4320855.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_4320855
loop_
_publ_author_name
'Amy T. Levy'
'Marilyn M. Olmstead'
'Timothy E. Patten'
_publ_contact_author
; Dr. Timothy E. Patten
  Department of Chemistry
  University of California
  One Shields Ave.
  Davis, CA 95616-5295
  USA
;
_publ_contact_author_email       patten@indigo.ucdavis.edu
_publ_contact_author_fax         530-752-8995
_publ_contact_author_phone       530-754-6181
_publ_section_title
;
 Synthesis, Characterization, and Polymerization Activity of
 [Bis(4,4'-bis(neophyldimethylsilylmethyl)-2,2'-bipyridyl)copper(I)] +
 CuBr2- and Implications for Copper(I) Catalyst Structures in Atom
 Transfer Radical Polymerization
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1628
_journal_page_last               1634
_journal_paper_doi               10.1021/ic990567k
_journal_volume                  39
_journal_year                    2000
_chemical_formula_sum            'C28 H48 N2 Si2'
_chemical_formula_weight         468.86
_chemical_name_common            dTHEXbipy
_chemical_name_systematic
; 
 4,4'-di-(dimethylthexylsilylmethyl)-2,2'-bipyridine 
;
_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                100.21(2)
_cell_angle_beta                 90.82(2)
_cell_angle_gamma                109.64(2)
_cell_formula_units_Z            1
_cell_length_a                   7.067(2)
_cell_length_b                   8.820(2)
_cell_length_c                   12.329(3)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      29.7
_cell_measurement_theta_min      3.7
_cell_volume                     710.0(3)
_computing_cell_refinement       'Siemens P3'
_computing_data_collection       'Siemens P3'
_computing_data_reduction        'Siemens XDISK'
_computing_molecular_graphics    'SHELXTL 5 (Sheldrick, 1994)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.756
_diffrn_measured_fraction_theta_max 0.756
_diffrn_measurement_device_type  'Syntex P2₁'
_diffrn_measurement_method       2θ-ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2050
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.00
_diffrn_reflns_theta_min         3.65
_diffrn_standards_decay_%        <0.1
_diffrn_standards_interval_count 198
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_T_max  0.8857
_exptl_absorpt_correction_T_min  0.7066
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;XABS2: an empirical absorption correction program. Parkin, S.; Moezzi,
 B.; Hope, H. J. Appl. Cryst. 1995, 28, 53-56.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             258
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         1919
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.529
_refine_ls_shift/su_mean         0.027
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0701P)²+1.4388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1437
_reflns_number_gt                1725
_reflns_number_total             1919
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic990567k_2.cif
_cod_data_source_block           mn879
_cod_database_code               4320855
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.32615(12) 0.42785(10) 0.21819(7) 0.0213(3) Uani 1 1 d . A .
N1 N 0.2294(4) 0.9438(3) 0.4842(2) 0.0229(6) Uani 1 1 d . . .
C1 C 0.4102(4) 0.9246(3) 0.4811(2) 0.0186(7) Uani 1 1 d . . .
C2 C 0.4321(4) 0.7730(4) 0.4454(2) 0.0206(7) Uani 1 1 d . . .
H2 H 0.5630 0.7654 0.4444 0.025 Uiso 1 1 calc R . .
C3 C 0.2643(4) 0.6330(4) 0.4114(2) 0.0204(7) Uani 1 1 d . . .
C4 C 0.0776(5) 0.6546(4) 0.4149(3) 0.0258(7) Uani 1 1 d . . .
H4 H -0.0428 0.5632 0.3926 0.031 Uiso 1 1 calc R . .
C5 C 0.0681(5) 0.8087(4) 0.4508(3) 0.0279(8) Uani 1 1 d . . .
H5 H -0.0611 0.8198 0.4520 0.034 Uiso 1 1 calc R . .
C6 C 0.2825(5) 0.4689(4) 0.3707(2) 0.0237(7) Uani 1 1 d . . .
H6A H 0.1577 0.3828 0.3842 0.028 Uiso 1 1 calc R . .
H6B H 0.3957 0.4601 0.4144 0.028 Uiso 1 1 calc R . .
C7 C 0.1208(6) 0.4494(4) 0.1319(3) 0.0373(9) Uani 1 1 d . . .
H7A H 0.1110 0.5583 0.1565 0.056 Uiso 1 1 calc R . .
H7B H -0.0075 0.3650 0.1398 0.056 Uiso 1 1 calc R . .
H7C H 0.1511 0.4363 0.0542 0.056 Uiso 1 1 calc R . .
C8 C 0.5666(5) 0.5915(4) 0.1982(3) 0.0383(9) Uani 1 1 d . . .
H8A H 0.5978 0.5720 0.1209 0.057 Uiso 1 1 calc R . .
H8B H 0.6766 0.5889 0.2463 0.057 Uiso 1 1 calc R . .
H8C H 0.5509 0.6991 0.2170 0.057 Uiso 1 1 calc R . .
C9 C 0.3536(5) 0.2177(4) 0.1784(3) 0.0261(7) Uani 1 1 d . . .
C10A C 0.350(2) 0.185(2) 0.0571(12) 0.054(4) Uani 0.50 1 d PD A 1
H10A H 0.3053 0.2648 0.0279 0.081 Uiso 0.50 1 calc PR A 1
H10B H 0.2564 0.0739 0.0276 0.081 Uiso 0.50 1 calc PR A 1
H10C H 0.4854 0.1943 0.0351 0.081 Uiso 0.50 1 calc PR A 1
C11A C 0.1964(12) 0.0849(8) 0.2285(8) 0.0333(17) Uani 0.50 1 d PD A 1
H11A H 0.2624 0.0785 0.2990 0.040 Uiso 0.50 1 calc PR A 1
C12A C 0.1679(16) -0.0995(11) 0.1346(7) 0.037(2) Uani 0.50 1 d PD A 1
H12A H 0.2992 -0.1136 0.1277 0.056 Uiso 0.50 1 calc PR A 1
H12B H 0.1138 -0.0947 0.0622 0.056 Uiso 0.50 1 calc PR A 1
H12C H 0.0748 -0.1924 0.1621 0.056 Uiso 0.50 1 calc PR A 1
C13A C 0.0095(19) 0.073(2) 0.2479(11) 0.039(4) Uani 0.50 1 d PD A 1
H13A H -0.0811 -0.0389 0.2181 0.058 Uiso 0.50 1 calc PR A 1
H13B H -0.0288 0.1505 0.2121 0.058 Uiso 0.50 1 calc PR A 1
H13C H -0.0005 0.0990 0.3277 0.058 Uiso 0.50 1 calc PR A 1
C14A C 0.5707(15) 0.2367(16) 0.2281(11) 0.057(3) Uani 0.50 1 d PD A 1
H14A H 0.5751 0.2582 0.3090 0.086 Uiso 0.50 1 calc PR A 1
H14B H 0.6724 0.3283 0.2038 0.086 Uiso 0.50 1 calc PR A 1
H14C H 0.5986 0.1353 0.2021 0.086 Uiso 0.50 1 calc PR A 1
C10B C 0.446(2) 0.211(3) 0.0613(15) 0.062(5) Uani 0.50 1 d PD A 2
H10D H 0.4987 0.3216 0.0451 0.092 Uiso 0.50 1 calc PR A 2
H10E H 0.3414 0.1398 0.0038 0.092 Uiso 0.50 1 calc PR A 2
H10F H 0.5564 0.1667 0.0630 0.092 Uiso 0.50 1 calc PR A 2
C11B C 0.1418(12) 0.0706(8) 0.1576(8) 0.0323(17) Uani 0.50 1 d PD A 2
H11B H 0.1055 0.0438 0.0761 0.039 Uiso 0.50 1 calc PR A 2
C12B C 0.2118(19) -0.0890(12) 0.1893(8) 0.050(3) Uani 0.50 1 d PD A 2
H12D H 0.3198 -0.1021 0.1438 0.075 Uiso 0.50 1 calc PR A 2
H12E H 0.0953 -0.1910 0.1744 0.075 Uiso 0.50 1 calc PR A 2
H12F H 0.2597 -0.0636 0.2677 0.075 Uiso 0.50 1 calc PR A 2
C13B C -0.022(2) 0.074(3) 0.2050(13) 0.057(5) Uani 0.50 1 d PD A 2
H13D H -0.0862 -0.0293 0.2301 0.085 Uiso 0.50 1 calc PR A 2
H13E H -0.1155 0.0891 0.1518 0.085 Uiso 0.50 1 calc PR A 2
H13F H 0.0133 0.1656 0.2686 0.085 Uiso 0.50 1 calc PR A 2
C14B C 0.4884(14) 0.1955(12) 0.2626(9) 0.042(2) Uani 0.50 1 d PD A 2
H14D H 0.4292 0.2001 0.3340 0.063 Uiso 0.50 1 calc PR A 2
H14E H 0.6201 0.2829 0.2695 0.063 Uiso 0.50 1 calc PR A 2
H14F H 0.5051 0.0887 0.2401 0.063 Uiso 0.50 1 calc PR A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 '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
C7 Si1 C8 107.14(17) . . ?
C7 Si1 C6 110.60(15) . . ?
C8 Si1 C6 106.85(15) . . ?
C7 Si1 C9 112.62(15) . . ?
C8 Si1 C9 109.64(16) . . ?
C6 Si1 C9 109.78(14) . . ?
C5 N1 C1 116.7(3) . . ?
N1 C1 C2 122.6(3) . . ?
N1 C1 C1 116.5(3) . 2_676 ?
C2 C1 C1 120.8(3) . 2_676 ?
C3 C2 C1 120.5(3) . . ?
C2 C3 C4 116.2(3) . . ?
C2 C3 C6 121.9(3) . . ?
C4 C3 C6 121.8(3) . . ?
C5 C4 C3 119.9(3) . . ?
N1 C5 C4 124.0(3) . . ?
C3 C6 Si1 114.1(2) . . ?
C10A C9 C14B 130.3(7) . . ?
C10A C9 C11A 115.4(8) . . ?
C14B C9 C11A 81.0(5) . . ?
C10A C9 C14A 108.6(7) . . ?
C14B C9 C14A 28.2(5) . . ?
C11A C9 C14A 107.8(6) . . ?
C10A C9 C10B 23.7(9) . . ?
C14B C9 C10B 110.5(7) . . ?
C11A C9 C10B 131.6(8) . . ?
C14A C9 C10B 85.9(8) . . ?
C10A C9 C11B 83.8(7) . . ?
C14B C9 C11B 111.4(5) . . ?
C11A C9 C11B 34.0(3) . . ?
C14A C9 C11B 133.6(6) . . ?
C10B C9 C11B 104.6(8) . . ?
C10A C9 Si1 105.6(7) . . ?
C14B C9 Si1 110.2(4) . . ?
C11A C9 Si1 112.5(3) . . ?
C14A C9 Si1 106.4(5) . . ?
C10B C9 Si1 107.0(7) . . ?
C11B C9 Si1 112.9(3) . . ?
C13A C11A C9 128.0(10) . . ?
C13A C11A C12A 103.5(9) . . ?
C9 C11A C12A 103.7(6) . . ?
C13B C11B C9 124.8(11) . . ?
C13B C11B C12B 110.4(10) . . ?
C9 C11B C12B 100.9(6) . . ?
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 C7 1.868(3) . ?
Si1 C8 1.876(3) . ?
Si1 C6 1.901(3) . ?
Si1 C9 1.907(3) . ?
N1 C5 1.337(4) . ?
N1 C1 1.344(4) . ?
C1 C2 1.392(4) . ?
C1 C1 1.491(6) 2_676 ?
C2 C3 1.387(4) . ?
C3 C4 1.395(4) . ?
C3 C6 1.495(4) . ?
C4 C5 1.377(4) . ?
C9 C10A 1.470(15) . ?
C9 C14B 1.481(11) . ?
C9 C11A 1.546(8) . ?
C9 C14A 1.587(11) . ?
C9 C10B 1.594(15) . ?
C9 C11B 1.599(8) . ?
C11A C13A 1.318(11) . ?
C11A C12A 1.770(10) . ?
C11B C13B 1.311(12) . ?
C11B C12B 1.743(10) . ?
