#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:06:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178635 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/46/4074664.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_4074664
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 Na'
_chemical_formula_weight         424.87
_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                 102.449(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4970(5)
_cell_length_b                   11.6750(6)
_cell_length_c                   15.5740(6)
_cell_measurement_temperature    293(2)
_cell_volume                     2218.86(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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    0.0193
_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       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3157
_diffrn_reflns_theta_full        23.29
_diffrn_reflns_theta_max         23.29
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    1.406
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0064(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.427
_refine_ls_shift/su_mean         0.071
_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          0.1107
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                3050
_reflns_number_total             3157
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om050733ysi20050825_031538.cif
_cod_data_source_block           shelxl
_cod_database_code               4074664
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 1.030005(16) 0.337448(17) 0.210769(13) 0.02395(19) Uani 1 1 d .
Na1 Na 0.66446(7) 0.38055(9) 0.26917(6) 0.0472(3) Uani 1 1 d .
H1A H 1.2391 0.3214 0.2727 0.047(7) Uiso 1 1 d R
H1B H 1.1700 0.2107 0.3076 0.068(8) Uiso 1 1 d R
C1 C 1.16392(17) 0.3027(2) 0.30150(15) 0.0396(5) Uani 1 1 d .
H2A H 1.2436 0.3421 0.4260 0.109(13) Uiso 1 1 d R
H2B H 1.1146 0.3545 0.4226 0.074(11) Uiso 1 1 d R
H2C H 1.1800 0.4598 0.3804 0.133(16) Uiso 1 1 d R
C2 C 1.1770(2) 0.3638(3) 0.38888(17) 0.0575(7) Uani 1 1 d .
H3A H 1.1505 0.3217 0.1044 0.054(9) Uiso 1 1 d R
H3B H 1.0923 0.1991 0.1052 0.057(7) Uiso 1 1 d R
C3 C 1.07677(18) 0.2877(2) 0.10252(14) 0.0400(5) Uani 1 1 d .
H4A H 1.0240 0.2952 -0.0417 0.080(9) Uiso 1 1 d R
H4B H 0.9272 0.2757 0.0110 0.067(9) Uiso 1 1 d R
H4C H 0.9844 0.3883 0.0146 0.055(8) Uiso 1 1 d R
C4 C 0.9975(2) 0.3139(2) 0.01646(16) 0.0497(6) Uani 1 1 d .
H5A H 1.0085 0.5395 0.2538 0.044(6) Uiso 1 1 d R
H5B H 0.9671 0.5318 0.1564 0.055(8) Uiso 1 1 d R
C5 C 1.02807(15) 0.5074(2) 0.20329(14) 0.0377(6) Uani 1 1 d .
H6A H 1.1941 0.5352 0.2406 0.114(13) Uiso 1 1 d R
H6B H 1.1339 0.6386 0.1881 0.071(9) Uiso 1 1 d R
H6C H 1.1672 0.5197 0.1313 0.115(13) Uiso 1 1 d R
C6 C 1.1378(2) 0.5584(2) 0.1929(2) 0.0612(8) Uani 1 1 d .
C7 C 0.77616(15) 0.27293(16) 0.15907(11) 0.0244(4) Uani 1 1 d .
H8 H 0.8245 0.4320 0.1089 0.044(6) Uiso 1 1 d R
C8 C 0.75614(17) 0.3714(2) 0.10713(13) 0.0328(5) Uani 1 1 d .
H9 H 0.6513 0.4632 0.0213 0.050(7) Uiso 1 1 d R
C9 C 0.65377(19) 0.3953(2) 0.05307(15) 0.0415(6) Uani 1 1 d .
H10 H 0.4947 0.3383 0.0112 0.042(7) Uiso 1 1 d R
C10 C 0.56720(19) 0.3220(2) 0.05015(16) 0.0425(6) Uani 1 1 d .
H11 H 0.5259 0.1743 0.1016 0.055(9) Uiso 1 1 d R
C11 C 0.58338(16) 0.22322(19) 0.10090(14) 0.0384(5) Uani 1 1 d .
H12 H 0.6967 0.1284 0.1868 0.043(6) Uiso 1 1 d R
C12 C 0.68508(16) 0.20005(19) 0.15311(13) 0.0326(5) Uani 1 1 d .
C13 C 0.86312(14) 0.26984(16) 0.32659(11) 0.0233(4) Uani 1 1 d .
H14 H 0.7960 0.1115 0.3426 0.029(5) Uiso 1 1 d R
C14 C 0.80619(16) 0.1904(2) 0.36817(14) 0.0299(5) Uani 1 1 d .
H15 H 0.7226 0.1565 0.4670 0.088(13) Uiso 1 1 d R
C15 C 0.76980(18) 0.2152(2) 0.44362(14) 0.0370(5) Uani 1 1 d .
H16 H 0.7651 0.3451 0.5389 0.055(9) Uiso 1 1 d R
C16 C 0.7892(2) 0.3224(2) 0.48327(16) 0.0384(7) Uani 1 1 d .
H17 H 0.8696 0.4818 0.4741 0.059(8) Uiso 1 1 d R
C17 C 0.84546(17) 0.4037(2) 0.44474(13) 0.0347(5) Uani 1 1 d .
H18 H 0.9250 0.4379 0.3392 0.051(7) Uiso 1 1 d R
C18 C 0.88205(17) 0.3767(2) 0.36847(13) 0.0290(5) Uani 1 1 d .
C19 C 0.93207(14) 0.11420(17) 0.21860(12) 0.0252(4) Uani 1 1 d .
H20 H 0.8702 0.1031 0.0829 0.027(5) Uiso 1 1 d R
C20 C 0.91523(16) 0.06093(17) 0.13565(12) 0.0300(5) Uani 1 1 d .
H21 H 0.9517 -0.0740 0.0630 0.058(7) Uiso 1 1 d R
C21 C 0.96631(18) -0.04007(19) 0.12057(15) 0.0386(5) Uani 1 1 d .
H22 H 1.0746 -0.1707 0.1822 0.060(9) Uiso 1 1 d R
C22 C 1.03678(17) -0.0947(2) 0.18927(19) 0.0432(6) Uani 1 1 d .
H23 H 1.1020 -0.0850 0.3256 0.053(8) Uiso 1 1 d R
C23 C 1.05244(16) -0.0481(2) 0.27295(16) 0.0400(6) Uani 1 1 d .
H24 H 1.0203 0.0935 0.3511 0.030(5) Uiso 1 1 d R
C24 C 1.00127(17) 0.05358(18) 0.28728(13) 0.0314(5) Uani 1 1 d .
B1 B 0.89022(16) 0.24377(18) 0.23012(13) 0.0227(5) 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'
Ge Ge 0.1547 1.8001 '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'
Na Na 0.0362 0.0249 '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
C3 Ge1 C5 104.13(9) . .
C3 Ge1 C1 100.79(10) . .
C5 Ge1 C1 104.10(9) . .
C3 Ge1 B1 111.67(8) . .
C5 Ge1 B1 121.28(8) . .
C1 Ge1 B1 112.59(9) . .
C7 Na1 C22 144.37(8) . 2_655
C7 Na1 C13 56.35(6) . .
C22 Na1 C13 140.90(8) 2_655 .
C7 Na1 C21 171.56(7) . 2_655
C22 Na1 C21 29.10(7) 2_655 2_655
C13 Na1 C21 124.25(7) . 2_655
C7 Na1 C23 126.39(7) . 2_655
C22 Na1 C23 29.10(8) 2_655 2_655
C13 Na1 C23 167.87(8) . 2_655
C21 Na1 C23 50.97(7) 2_655 2_655
C7 Na1 C18 77.00(6) . .
C22 Na1 C18 134.09(8) 2_655 .
C13 Na1 C18 29.06(6) . .
C21 Na1 C18 107.02(7) 2_655 .
C23 Na1 C18 155.53(7) 2_655 .
C7 Na1 C12 29.27(6) . .
C22 Na1 C12 116.37(8) 2_655 .
C13 Na1 C12 70.09(6) . .
C21 Na1 C12 142.47(7) 2_655 .
C23 Na1 C12 106.96(7) 2_655 .
C18 Na1 C12 97.40(7) . .
C7 Na1 C20 159.92(7) . 2_655
C22 Na1 C20 50.52(7) 2_655 2_655
C13 Na1 C20 124.15(6) . 2_655
C21 Na1 C20 28.32(6) 2_655 2_655
C23 Na1 C20 58.18(6) 2_655 2_655
C18 Na1 C20 97.41(6) . 2_655
C12 Na1 C20 165.11(7) . 2_655
C7 Na1 C24 123.96(6) . 2_655
C22 Na1 C24 50.60(7) 2_655 2_655
C13 Na1 C24 163.22(7) . 2_655
C21 Na1 C24 58.37(6) 2_655 2_655
C23 Na1 C24 28.29(7) 2_655 2_655
C18 Na1 C24 136.03(7) . 2_655
C12 Na1 C24 119.01(7) . 2_655
C20 Na1 C24 48.68(6) 2_655 2_655
C7 Na1 C8 27.79(6) . .
C22 Na1 C8 137.76(8) 2_655 .
C13 Na1 C8 77.06(6) . .
C21 Na1 C8 156.76(7) 2_655 .
C23 Na1 C8 110.09(7) 2_655 .
C18 Na1 C8 87.86(6) . .
C12 Na1 C8 47.83(6) . .
C20 Na1 C8 134.42(7) 2_655 .
C24 Na1 C8 98.51(7) 2_655 .
C7 Na1 C19 136.21(7) . 2_655
C22 Na1 C19 59.25(7) 2_655 2_655
C13 Na1 C19 138.33(6) . 2_655
C21 Na1 C19 50.14(6) 2_655 2_655
C23 Na1 C19 50.04(6) 2_655 2_655
C18 Na1 C19 109.39(6) . 2_655
C12 Na1 C19 144.21(6) . 2_655
C20 Na1 C19 27.60(5) 2_655 2_655
C24 Na1 C19 27.63(5) 2_655 2_655
C8 Na1 C19 108.54(7) . 2_655
C7 Na1 C14 70.31(6) . .
C22 Na1 C14 114.84(8) 2_655 .
C13 Na1 C14 27.53(6) . .
C21 Na1 C14 106.64(7) 2_655 .
C23 Na1 C14 140.39(8) 2_655 .
C18 Na1 C14 47.52(7) . .
C12 Na1 C14 69.91(6) . .
C20 Na1 C14 120.11(6) 2_655 .
C24 Na1 C14 164.61(7) 2_655 .
C8 Na1 C14 96.58(6) . .
C19 Na1 C14 145.86(6) 2_655 .
C2 C1 Ge1 117.01(17) . .
C2 C1 H1A 108.9 . .
Ge1 C1 H1A 108.6 . .
C2 C1 H1B 113.5 . .
Ge1 C1 H1B 107.3 . .
H1A C1 H1B 100.1 . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 117.4 . .
H2A C2 H2B 108.9 . .
C1 C2 H2C 111.2 . .
H2A C2 H2C 107.0 . .
H2B C2 H2C 102.2 . .
C4 C3 Ge1 115.83(16) . .
C4 C3 H3A 111.6 . .
Ge1 C3 H3A 107.3 . .
C4 C3 H3B 108.2 . .
Ge1 C3 H3B 109.8 . .
H3A C3 H3B 103.2 . .
C3 C4 H4A 116.9 . .
C3 C4 H4B 113.0 . .
H4A C4 H4B 106.0 . .
C3 C4 H4C 108.0 . .
H4A C4 H4C 105.5 . .
H4B C4 H4C 106.8 . .
C6 C5 Ge1 113.17(16) . .
C6 C5 H5A 109.2 . .
Ge1 C5 H5A 110.4 . .
C6 C5 H5B 112.2 . .
Ge1 C5 H5B 109.4 . .
H5A C5 H5B 101.9 . .
C5 C6 H6A 109.6 . .
C5 C6 H6B 111.2 . .
H6A C6 H6B 111.4 . .
C5 C6 H6C 112.1 . .
H6A C6 H6C 102.6 . .
H6B C6 H6C 109.5 . .
C8 C7 C12 114.70(17) . .
C8 C7 B1 125.62(17) . .
C12 C7 B1 119.44(17) . .
C8 C7 Na1 86.16(12) . .
C12 C7 Na1 78.73(12) . .
B1 C7 Na1 99.14(11) . .
C7 C8 C9 122.6(2) . .
C7 C8 Na1 66.05(11) . .
C9 C8 Na1 91.93(14) . .
C7 C8 H8 118.2 . .
C9 C8 H8 119.3 . .
Na1 C8 H8 113.0 . .
C10 C9 C8 120.5(2) . .
C10 C9 H9 125.3 . .
C8 C9 H9 114.2 . .
C9 C10 C11 118.8(2) . .
C9 C10 H10 120.6 . .
C11 C10 H10 120.5 . .
C12 C11 C10 120.07(19) . .
C12 C11 H11 119.6 . .
C10 C11 H11 120.3 . .
C11 C12 C7 123.3(2) . .
C11 C12 Na1 91.80(14) . .
C7 C12 Na1 72.00(11) . .
C11 C12 H12 119.6 . .
C7 C12 H12 117.1 . .
Na1 C12 H12 108.5 . .
C18 C13 C14 115.03(18) . .
C18 C13 B1 122.93(17) . .
C14 C13 B1 121.59(17) . .
C18 C13 Na1 77.58(11) . .
C14 C13 Na1 87.11(11) . .
B1 C13 Na1 97.97(10) . .
C15 C14 C13 123.0(2) . .
C15 C14 Na1 90.87(14) . .
C13 C14 Na1 65.36(11) . .
C15 C14 H14 119.8 . .
C13 C14 H14 117.2 . .
Na1 C14 H14 117.3 . .
C14 C15 C16 120.6(2) . .
C14 C15 H15 118.9 . .
C16 C15 H15 120.3 . .
C17 C16 C15 118.5(2) . .
C17 C16 H16 117.5 . .
C15 C16 H16 124.0 . .
C16 C17 C18 120.1(2) . .
C16 C17 H17 122.5 . .
C18 C17 H17 117.1 . .
C17 C18 C13 122.8(2) . .
C17 C18 Na1 90.51(13) . .
C13 C18 Na1 73.37(11) . .
C17 C18 H18 120.3 . .
C13 C18 H18 116.9 . .
Na1 C18 H18 105.8 . .
C20 C19 C24 114.81(18) . .
C20 C19 B1 121.67(16) . .
C24 C19 B1 122.86(16) . .
C20 C19 Na1 71.01(11) . 2_645
C24 C19 Na1 71.68(12) . 2_645
B1 C19 Na1 134.08(12) . 2_645
C21 C20 C19 123.26(18) . .
C21 C20 Na1 71.77(12) . 2_645
C19 C20 Na1 81.39(11) . 2_645
C21 C20 H20 118.1 . .
C19 C20 H20 118.3 . .
Na1 C20 H20 125.3 2_645 .
C20 C21 C22 120.0(2) . .
C20 C21 Na1 79.91(13) . 2_645
C22 C21 Na1 74.30(14) . 2_645
C20 C21 H21 120.5 . .
C22 C21 H21 119.4 . .
Na1 C21 H21 114.9 2_645 .
C23 C22 C21 118.8(2) . .
C23 C22 Na1 76.73(14) . 2_645
C21 C22 Na1 76.60(13) . 2_645
C23 C22 H22 117.9 . .
C21 C22 H22 123.2 . .
Na1 C22 H22 113.8 2_645 .
C22 C23 C24 120.64(19) . .
C22 C23 Na1 74.17(13) . 2_645
C24 C23 Na1 80.47(12) . 2_645
C22 C23 H23 122.2 . .
C24 C23 H23 117.2 . .
Na1 C23 H23 117.4 2_645 .
C23 C24 C19 122.31(19) . .
C23 C24 Na1 71.24(12) . 2_645
C19 C24 Na1 80.69(12) . 2_645
C23 C24 H24 120.0 . .
C19 C24 H24 117.4 . .
Na1 C24 H24 125.8 2_645 .
C19 B1 C13 114.19(14) . .
C19 B1 C7 111.88(14) . .
C13 B1 C7 104.99(14) . .
C19 B1 Ge1 99.71(12) . .
C13 B1 Ge1 111.79(12) . .
C7 B1 Ge1 114.61(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ge1 C3 1.986(2) .
Ge1 C5 1.988(2) .
Ge1 C1 1.986(2) .
Ge1 B1 2.137(2) .
Na1 C7 2.739(2) .
Na1 C22 2.744(3) 2_655
Na1 C13 2.7706(19) .
Na1 C21 2.773(2) 2_655
Na1 C23 2.776(2) 2_655
Na1 C18 2.824(2) .
Na1 C12 2.824(2) .
Na1 C20 2.874(2) 2_655
Na1 C24 2.891(2) 2_655
Na1 C8 2.990(2) .
Na1 C19 3.005(2) 2_655
Na1 C14 3.044(2) .
C1 C2 1.514(4) .
C1 H1A 1.1458 .
C1 H1B 1.0796 .
C2 H2A 0.9408 .
C2 H2B 1.0349 .
C2 H2C 1.1297 .
C3 C4 1.516(4) .
C3 H3A 0.9973 .
C3 H3B 1.0519 .
C4 H4A 1.0517 .
C4 H4B 0.9729 .
C4 H4C 0.8835 .
C5 C6 1.535(3) .
C5 H5A 0.9491 .
C5 H5B 0.9777 .
C6 H6A 0.9456 .
C6 H6B 0.9398 .
C6 H6C 1.1880 .
C7 C8 1.397(3) .
C7 C12 1.408(3) .
C7 B1 1.641(3) .
C8 C9 1.399(3) .
C8 H8 1.1048 .
C9 C10 1.372(3) .
C9 H9 0.9320 .
C10 C11 1.388(3) .
C10 H10 0.9945 .
C11 C12 1.380(3) .
C11 H11 0.9197 .
C12 H12 0.9813 .
C13 C18 1.404(3) .
C13 C14 1.409(3) .
C13 B1 1.638(3) .
C14 C15 1.379(3) .
C14 H14 0.9998 .
C15 C16 1.393(4) .
C15 H15 1.0217 .
C16 C17 1.391(4) .
C16 H16 1.0125 .
C17 C18 1.398(3) .
C17 H17 1.0355 .
C18 H18 1.0536 .
C19 C20 1.408(3) .
C19 C24 1.412(3) .
C19 B1 1.623(3) .
C19 Na1 3.005(2) 2_645
C20 C21 1.385(3) .
C20 Na1 2.874(2) 2_645
C20 H20 1.0173 .
C21 C22 1.386(3) .
C21 Na1 2.773(2) 2_645
C21 H21 0.9603 .
C22 C23 1.387(4) .
C22 Na1 2.744(3) 2_645
C22 H22 1.0219 .
C23 C24 1.389(3) .
C23 Na1 2.776(2) 2_645
C23 H23 1.0107 .
C24 Na1 2.891(2) 2_645
C24 H24 1.0761 .
