#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:06:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178635 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/46/4074661.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_4074661
loop_
_publ_author_name
'Nanjo, Masato'
'Matsudo, Kazuhiko'
'Kurihara, Mari'
'Nakamura, Sayaka'
'Sakaguchi, Yoshio'
'Hayashi, Hisaharu'
'Mochida, Kunio'
_publ_section_title
;
 Preparation, Structural Characterization, and Photochemical Reactions of
 Silyl- and Germylborates
;
_journal_issue                   4
_journal_name_full               Organometallics
_journal_page_first              832
_journal_paper_doi               10.1021/om050733y
_journal_volume                  25
_journal_year                    2006
_chemical_formula_sum            'C24 H30 B Ge Li'
_chemical_formula_weight         408.82
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.114(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1640(12)
_cell_length_b                   11.3280(5)
_cell_length_c                   16.1220(14)
_cell_measurement_temperature    293(2)
_cell_volume                     2187.0(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3066
_diffrn_reflns_theta_full        23.33
_diffrn_reflns_theta_max         23.33
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    1.405
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0052(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1153
_reflns_number_gt                2647
_reflns_number_total             3066
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om050733ysi20050825_031322.cif
_cod_data_source_block           shelxl
_cod_database_code               4074661
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Ge1 Ge -0.02101(3) 0.15933(3) 0.790011(19) 0.02600(19) Uani 1 1 d .
C1 C -0.1557(3) 0.1962(3) 0.7050(2) 0.0433(9) Uani 1 1 d .
H1A H -0.2253 0.1799 0.7417 0.066(13) Uiso 1 1 d R
H1B H -0.1583 0.2879 0.6926 0.053(11) Uiso 1 1 d R
C2 C -0.1715(4) 0.1313(4) 0.6225(3) 0.0662(13) Uani 1 1 d .
H2A H -0.2437 0.1464 0.5855 0.095(18) Uiso 1 1 d R
H2B H -0.1547 0.0448 0.6364 0.098(18) Uiso 1 1 d R
H2C H -0.0827 0.1609 0.5992 0.17(3) Uiso 1 1 d R
C3 C -0.0271(3) -0.0155(3) 0.8028(2) 0.0380(8) Uani 1 1 d .
H3A H 0.0355 -0.0479 0.8447 0.054(11) Uiso 1 1 d R
H3B H -0.0135 -0.0496 0.7413 0.077(14) Uiso 1 1 d R
C4 C -0.1388(3) -0.0588(3) 0.8214(3) 0.0572(12) Uani 1 1 d .
H4A H -0.1397 -0.1507 0.8339 0.072(14) Uiso 1 1 d R
H4B H -0.2114 -0.0324 0.7771 0.093(16) Uiso 1 1 d R
H4C H -0.1676 -0.0302 0.8822 0.17(3) Uiso 1 1 d R
C5 C -0.0681(3) 0.2205(3) 0.8937(2) 0.0418(9) Uani 1 1 d .
H5A H -0.1416 0.1806 0.9001 0.046(11) Uiso 1 1 d R
H5B H -0.0815 0.3175 0.8844 0.057(11) Uiso 1 1 d R
C6 C 0.0079(4) 0.1921(4) 0.9768(2) 0.0528(11) Uani 1 1 d .
H6A H 0.0809 0.2313 0.9820 0.063(13) Uiso 1 1 d R
H6B H 0.0247 0.1050 0.9804 0.051(11) Uiso 1 1 d R
H6C H -0.0122 0.2149 1.0344 0.075(14) Uiso 1 1 d R
C7 C 0.0883(3) 0.3824(3) 0.7755(2) 0.0284(7) Uani 1 1 d .
C8 C 0.1062(3) 0.4395(3) 0.8542(2) 0.0345(8) Uani 1 1 d .
H8 H 0.1636 0.3958 0.9060 0.033(8) Uiso 1 1 d R
C9 C 0.0549(3) 0.5476(3) 0.8667(3) 0.0487(10) Uani 1 1 d .
H9 H 0.0669 0.5870 0.9206 0.035(9) Uiso 1 1 d R
C10 C -0.0124(3) 0.6036(3) 0.8008(3) 0.0537(12) Uani 1 1 d .
H10 H -0.0439 0.6755 0.8043 0.063(13) Uiso 1 1 d R
C11 C -0.0288(3) 0.5519(3) 0.7222(3) 0.0487(10) Uani 1 1 d .
H11 H -0.0794 0.5934 0.6698 0.057(12) Uiso 1 1 d R
C12 C 0.0213(3) 0.4434(3) 0.7096(2) 0.0369(9) Uani 1 1 d .
H12 H -0.0029 0.3988 0.6482 0.056(11) Uiso 1 1 d R
C13 C 0.1523(3) 0.2152(2) 0.67170(19) 0.0258(7) Uani 1 1 d .
C14 C 0.1254(3) 0.1080(3) 0.63044(19) 0.0280(7) Uani 1 1 d .
H14 H 0.0880 0.0432 0.6568 0.038(9) Uiso 1 1 d R
C15 C 0.1519(3) 0.0830(3) 0.5512(2) 0.0356(8) Uani 1 1 d .
H15 H 0.1214 0.0051 0.5218 0.049(10) Uiso 1 1 d R
C16 C 0.2069(3) 0.1645(3) 0.5108(2) 0.0371(9) Uani 1 1 d .
H16 H 0.2304 0.1447 0.4549 0.035(9) Uiso 1 1 d R
C17 C 0.2370(3) 0.2720(3) 0.5502(2) 0.0361(8) Uani 1 1 d .
H17 H 0.2762 0.3346 0.5212 0.024(8) Uiso 1 1 d R
C18 C 0.2109(3) 0.2959(3) 0.6290(2) 0.0317(7) Uani 1 1 d .
H18 H 0.2359 0.3752 0.6519 0.040(9) Uiso 1 1 d R
C19 C 0.2388(3) 0.2139(2) 0.83520(18) 0.0250(7) Uani 1 1 d .
C20 C 0.2505(3) 0.1211(3) 0.8935(2) 0.0326(8) Uani 1 1 d .
H20 H 0.1851 0.0719 0.8907 0.038(9) Uiso 1 1 d R
C21 C 0.3473(3) 0.1041(3) 0.9523(2) 0.0417(9) Uani 1 1 d .
H21 H 0.3446 0.0474 0.9863 0.041(10) Uiso 1 1 d R
C22 C 0.4376(3) 0.1776(3) 0.9553(2) 0.0427(9) Uani 1 1 d .
H22 H 0.5115 0.1639 1.0004 0.050(11) Uiso 1 1 d R
C23 C 0.4316(3) 0.2686(3) 0.8973(2) 0.0402(9) Uani 1 1 d .
H23 H 0.5035 0.3246 0.8997 0.048(11) Uiso 1 1 d R
C24 C 0.3344(3) 0.2856(3) 0.8389(2) 0.0342(8) Uani 1 1 d .
H24 H 0.3290 0.3582 0.7934 0.045(10) Uiso 1 1 d R
B1 B 0.1276(3) 0.2451(3) 0.7664(2) 0.0237(7) Uani 1 1 d .
Li1 Li 0.1707(5) 0.6003(5) 0.7660(4) 0.0425(15) 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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li -0.0003 0.0001 '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
C5 Ge1 C1 100.52(16) . .
C5 Ge1 C3 103.79(14) . .
C1 Ge1 C3 103.83(15) . .
C5 Ge1 B1 111.61(14) . .
C1 Ge1 B1 113.64(15) . .
C3 Ge1 B1 121.06(13) . .
C2 C1 Ge1 118.0(3) . .
C2 C1 H1A 113.1 . .
Ge1 C1 H1A 102.0 . .
C2 C1 H1B 108.6 . .
Ge1 C1 H1B 109.3 . .
H1A C1 H1B 105.0 . .
C1 C2 H2A 114.4 . .
C1 C2 H2B 106.7 . .
H2A C2 H2B 115.0 . .
C1 C2 H2C 98.7 . .
H2A C2 H2C 119.8 . .
H2B C2 H2C 100.0 . .
C4 C3 Ge1 112.9(2) . .
C4 C3 H3A 110.5 . .
Ge1 C3 H3A 113.5 . .
C4 C3 H3B 110.1 . .
Ge1 C3 H3B 103.9 . .
H3A C3 H3B 105.3 . .
C3 C4 H4A 113.1 . .
C3 C4 H4B 115.9 . .
H4A C4 H4B 111.4 . .
C3 C4 H4C 119.7 . .
H4A C4 H4C 95.8 . .
H4B C4 H4C 98.7 . .
C6 C5 Ge1 116.6(3) . .
C6 C5 H5A 103.0 . .
Ge1 C5 H5A 108.5 . .
C6 C5 H5B 112.2 . .
Ge1 C5 H5B 106.7 . .
H5A C5 H5B 109.8 . .
C5 C6 H6A 112.3 . .
C5 C6 H6B 110.1 . .
H6A C6 H6B 105.5 . .
C5 C6 H6C 122.3 . .
H6A C6 H6C 99.4 . .
H6B C6 H6C 105.7 . .
C12 C7 C8 115.8(3) . .
C12 C7 B1 122.6(3) . .
C8 C7 B1 121.0(3) . .
C12 C7 Li1 71.1(2) . .
C8 C7 Li1 68.1(2) . .
B1 C7 Li1 138.6(2) . .
C9 C8 C7 121.9(3) . .
C9 C8 Li1 69.0(3) . .
C7 C8 Li1 80.7(2) . .
C9 C8 H8 121.2 . .
C7 C8 H8 116.9 . .
Li1 C8 H8 122.1 . .
C10 C9 C8 120.6(4) . .
C10 C9 Li1 72.7(3) . .
C8 C9 Li1 78.0(3) . .
C10 C9 H9 117.2 . .
C8 C9 H9 122.1 . .
Li1 C9 H9 118.6 . .
C9 C10 C11 119.0(3) . .
C9 C10 Li1 73.9(3) . .
C11 C10 Li1 76.7(3) . .
C9 C10 H10 124.5 . .
C11 C10 H10 116.4 . .
Li1 C10 H10 116.8 . .
C10 C11 C12 120.6(4) . .
C10 C11 Li1 70.5(3) . .
C12 C11 Li1 78.7(3) . .
C10 C11 H11 120.8 . .
C12 C11 H11 118.5 . .
Li1 C11 H11 122.1 . .
C11 C12 C7 122.0(3) . .
C11 C12 Li1 69.2(3) . .
C7 C12 Li1 78.1(2) . .
C11 C12 H12 118.5 . .
C7 C12 H12 118.8 . .
Li1 C12 H12 133.5 . .
C14 C13 C18 115.3(3) . .
C14 C13 B1 123.8(3) . .
C18 C13 B1 120.7(3) . .
C14 C13 Li1 81.7(2) . 2_546
C18 C13 Li1 93.4(2) . 2_546
B1 C13 Li1 91.1(2) . 2_546
C13 C14 C15 122.6(3) . .
C13 C14 Li1 68.0(2) . 2_546
C15 C14 Li1 102.7(2) . 2_546
C13 C14 H14 121.6 . .
C15 C14 H14 115.9 . .
Li1 C14 H14 98.6 2_546 .
C16 C15 C14 120.5(3) . .
C16 C15 H15 121.3 . .
C14 C15 H15 117.8 . .
C15 C16 C17 118.9(3) . .
C15 C16 H16 120.6 . .
C17 C16 H16 120.3 . .
C18 C17 C16 120.3(3) . .
C18 C17 H17 119.1 . .
C16 C17 H17 120.6 . .
C17 C18 C13 122.4(3) . .
C17 C18 H18 114.2 . .
C13 C18 H18 123.4 . .
C20 C19 C24 114.7(3) . .
C20 C19 B1 126.4(3) . .
C24 C19 B1 118.9(3) . .
C20 C19 Li1 92.7(2) . 2_546
C24 C19 Li1 82.4(2) . 2_546
B1 C19 Li1 94.4(2) . 2_546
C21 C20 C19 122.4(3) . .
C21 C20 H20 123.0 . .
C19 C20 H20 114.6 . .
C22 C21 C20 121.1(3) . .
C22 C21 H21 123.9 . .
C20 C21 H21 114.9 . .
C21 C22 C23 118.8(3) . .
C21 C22 H22 120.7 . .
C23 C22 H22 120.5 . .
C24 C23 C22 119.9(3) . .
C24 C23 H23 122.2 . .
C22 C23 H23 117.9 . .
C23 C24 C19 123.1(3) . .
C23 C24 Li1 104.0(2) . 2_546
C19 C24 Li1 66.2(2) . 2_546
C23 C24 H24 120.1 . .
C19 C24 H24 116.8 . .
Li1 C24 H24 99.9 2_546 .
C19 B1 C7 111.4(2) . .
C19 B1 C13 108.8(2) . .
C7 B1 C13 112.5(2) . .
C19 B1 Ge1 113.9(2) . .
C7 B1 Ge1 98.4(2) . .
C13 B1 Ge1 111.6(2) . .
C10 Li1 C9 33.38(16) . .
C10 Li1 C11 32.90(16) . .
C9 Li1 C11 58.28(19) . .
C10 Li1 C19 133.2(3) . 2_556
C9 Li1 C19 162.3(3) . 2_556
C11 Li1 C19 117.1(3) . 2_556
C10 Li1 C8 58.92(18) . .
C9 Li1 C8 33.07(13) . .
C11 Li1 C8 67.18(18) . .
C19 Li1 C8 164.5(3) 2_556 .
C10 Li1 C13 130.7(3) . 2_556
C9 Li1 C13 114.4(3) . 2_556
C11 Li1 C13 160.2(3) . 2_556
C19 Li1 C13 63.63(16) 2_556 2_556
C8 Li1 C13 118.0(3) . 2_556
C10 Li1 C12 57.86(17) . .
C9 Li1 C12 66.95(18) . .
C11 Li1 C12 32.09(13) . .
C19 Li1 C12 119.3(3) 2_556 .
C8 Li1 C12 55.45(15) . .
C13 Li1 C12 167.1(3) 2_556 .
C10 Li1 C7 68.12(18) . .
C9 Li1 C7 57.50(15) . .
C11 Li1 C7 56.78(15) . .
C19 Li1 C7 136.8(3) 2_556 .
C8 Li1 C7 31.17(11) . .
C13 Li1 C7 137.9(3) 2_556 .
C12 Li1 C7 30.81(12) . .
C10 Li1 C24 102.4(2) . 2_556
C9 Li1 C24 131.8(3) . 2_556
C11 Li1 C24 94.6(2) . 2_556
C19 Li1 C24 31.35(12) 2_556 2_556
C8 Li1 C24 160.7(3) . 2_556
C13 Li1 C24 77.02(17) 2_556 2_556
C12 Li1 C24 112.2(3) . 2_556
C7 Li1 C24 142.0(3) . 2_556
C10 Li1 C14 129.7(3) . 2_556
C9 Li1 C14 99.9(2) . 2_556
C11 Li1 C14 157.2(3) . 2_556
C19 Li1 C14 85.74(19) 2_556 2_556
C8 Li1 C14 91.0(2) . 2_556
C13 Li1 C14 30.31(12) 2_556 2_556
C12 Li1 C14 137.8(2) . 2_556
C7 Li1 C14 107.6(2) . 2_556
C24 Li1 C14 106.1(2) 2_556 2_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ge1 C5 1.984(3) .
Ge1 C1 1.987(4) .
Ge1 C3 1.994(3) .
Ge1 B1 2.145(4) .
C1 C2 1.502(6) .
C1 H1A 1.1300 .
C1 H1B 1.0573 .
C2 H2A 0.9861 .
C2 H2B 1.0179 .
C2 H2C 1.2501 .
C3 C4 1.523(5) .
C3 H3A 0.9951 .
C3 H3B 1.1033 .
C4 H4A 1.0608 .
C4 H4B 1.0761 .
C4 H4C 1.1442 .
C5 C6 1.523(6) .
C5 H5A 1.0231 .
C5 H5B 1.1171 .
C6 H6A 0.9831 .
C6 H6B 1.0072 .
C6 H6C 1.0337 .
C7 C12 1.402(5) .
C7 C8 1.405(5) .
C7 B1 1.642(4) .
C7 Li1 2.679(6) .
C8 C9 1.406(5) .
C8 Li1 2.519(6) .
C8 H8 1.1069 .
C9 C10 1.377(6) .
C9 Li1 2.405(7) .
C9 H9 0.9649 .
C10 C11 1.378(6) .
C10 Li1 2.390(7) .
C10 H10 0.9061 .
C11 C12 1.403(5) .
C11 Li1 2.468(7) .
C11 H11 1.0634 .
C12 Li1 2.590(6) .
C12 H12 1.1043 .
C13 C14 1.396(4) .
C13 C18 1.411(4) .
C13 B1 1.642(4) .
C13 Li1 2.565(6) 2_546
C14 C15 1.400(5) .
C14 Li1 2.737(7) 2_546
C14 H14 0.9975 .
C15 C16 1.370(5) .
C15 H15 1.0389 .
C16 C17 1.392(5) .
C16 H16 1.0172 .
C17 C18 1.389(5) .
C17 H17 1.0135 .
C18 H18 0.9982 .
C19 C20 1.401(4) .
C19 C24 1.411(5) .
C19 B1 1.630(4) .
C19 Li1 2.482(6) 2_546
C20 C21 1.390(5) .
C20 H20 0.9659 .
C21 C22 1.372(5) .
C21 H21 0.8488 .
C22 C23 1.385(5) .
C22 H22 1.0636 .
C23 C24 1.390(5) .
C23 H23 1.0756 .
C24 Li1 2.689(6) 2_546
C24 H24 1.0963 .
Li1 C19 2.482(6) 2_556
Li1 C13 2.565(6) 2_556
Li1 C24 2.689(6) 2_556
Li1 C14 2.737(7) 2_556
