#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/61/4086160.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_4086160
loop_
_publ_author_name
'Hadlington, Terrance J.'
'Li, Jiaye'
'Hermann, Markus'
'Davey, Amelia'
'Frenking, Gernot'
'Jones, Cameron'
_publ_section_title
;
 Reactivity of Amido-Digermynes, LGeGeL (L = Bulky Amide), toward Olefins
 and Related Molecules: Facile Reduction, C--H Activation, and Reversible
 Cycloaddition of Unsaturated Substrates
;
_journal_issue                   13
_journal_name_full               Organometallics
_journal_page_first              3175
_journal_paper_doi               10.1021/acs.organomet.5b00206
_journal_volume                  34
_journal_year                    2015
_chemical_formula_sum            'C94 H112 Ge2 N6 O2 Si2'
_chemical_formula_weight         1559.26
_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
_cell_angle_alpha                103.86(3)
_cell_angle_beta                 108.34(3)
_cell_angle_gamma                103.40(3)
_cell_formula_units_Z            1
_cell_length_a                   12.865(3)
_cell_length_b                   13.810(3)
_cell_length_c                   13.816(3)
_cell_measurement_temperature    123(2)
_cell_volume                     2132.8(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Gemini Ultra'
_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  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31110
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             826
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.495
_refine_diff_density_min         -0.892
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     486
_refine_ls_number_reflns         8353
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0391P)²+2.0954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                7213
_reflns_number_total             8353
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00206_si_002.cif
_cod_data_source_block           compound11
_cod_original_cell_volume        2132.8(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4086160
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
Ge1 Ge 0.50877(2) 0.013275(17) 0.100525(19) 0.02019(8) Uani 1 1 d .
Si1 Si 0.69420(5) 0.24435(4) 0.13801(5) 0.01579(13) Uani 1 1 d .
O1 O 1.18425(18) -0.33020(15) 0.22736(16) 0.0425(5) Uani 1 1 d .
N1 N 0.60839(15) 0.16012(13) 0.17940(14) 0.0146(4) Uani 1 1 d .
N2 N 0.63664(18) -0.06204(15) 0.13274(16) 0.0255(4) Uani 1 1 d .
N3 N 0.87893(19) -0.21671(19) 0.2131(2) 0.0404(6) Uani 1 1 d .
C1 C 0.59516(18) 0.20354(15) 0.27883(17) 0.0145(4) Uani 1 1 d .
C2 C 0.51037(18) 0.25207(16) 0.28137(17) 0.0165(4) Uani 1 1 d .
C3 C 0.5010(2) 0.29556(17) 0.37879(18) 0.0216(5) Uani 1 1 d .
H3 H 0.4422 0.3266 0.3782 0.026 Uiso 1 1 calc R
C4 C 0.5740(2) 0.29528(18) 0.47651(19) 0.0254(5) Uani 1 1 d .
C5 C 0.6552(2) 0.24503(18) 0.47366(18) 0.0245(5) Uani 1 1 d .
H5 H 0.7050 0.2420 0.5395 0.029 Uiso 1 1 calc R
C6 C 0.66652(19) 0.19868(17) 0.37766(18) 0.0197(5) Uani 1 1 d .
C7 C 0.5637(3) 0.3467(2) 0.5812(2) 0.0399(7) Uani 1 1 d .
H7A H 0.6265 0.3445 0.6423 0.060 Uiso 1 1 calc R
H7B H 0.4886 0.3086 0.5798 0.060 Uiso 1 1 calc R
H7C H 0.5695 0.4205 0.5893 0.060 Uiso 1 1 calc R
C8 C 0.42581(18) 0.25934(17) 0.17980(17) 0.0175(4) Uani 1 1 d .
H8 H 0.4348 0.2138 0.1168 0.021 Uiso 1 1 calc R
C9 C 0.30078(19) 0.21061(17) 0.16812(18) 0.0196(5) Uani 1 1 d .
C10 C 0.2244(2) 0.2662(2) 0.1693(2) 0.0320(6) Uani 1 1 d .
H10 H 0.2499 0.3399 0.1810 0.038 Uiso 1 1 calc R
C11 C 0.1103(2) 0.2153(2) 0.1534(3) 0.0435(7) Uani 1 1 d .
H11 H 0.0589 0.2547 0.1544 0.052 Uiso 1 1 calc R
C12 C 0.0715(2) 0.1091(2) 0.1364(2) 0.0376(6) Uani 1 1 d .
H12 H -0.0068 0.0744 0.1238 0.045 Uiso 1 1 calc R
C13 C 0.1476(2) 0.0535(2) 0.1377(2) 0.0328(6) Uani 1 1 d .
H13 H 0.1218 -0.0201 0.1267 0.039 Uiso 1 1 calc R
C14 C 0.2612(2) 0.10391(19) 0.1549(2) 0.0259(5) Uani 1 1 d .
H14 H 0.3133 0.0648 0.1577 0.031 Uiso 1 1 calc R
C15 C 0.45128(19) 0.37056(17) 0.17270(18) 0.0192(5) Uani 1 1 d .
C16 C 0.3886(2) 0.38384(19) 0.07686(19) 0.0243(5) Uani 1 1 d .
H16 H 0.3313 0.3239 0.0184 0.029 Uiso 1 1 calc R
C17 C 0.4082(2) 0.4822(2) 0.0652(2) 0.0306(6) Uani 1 1 d .
H17 H 0.3639 0.4894 -0.0005 0.037 Uiso 1 1 calc R
C18 C 0.4921(2) 0.57019(19) 0.1488(2) 0.0298(6) Uani 1 1 d .
H18 H 0.5056 0.6380 0.1411 0.036 Uiso 1 1 calc R
C19 C 0.5559(2) 0.55851(19) 0.2432(2) 0.0270(5) Uani 1 1 d .
H19 H 0.6146 0.6184 0.3005 0.032 Uiso 1 1 calc R
C20 C 0.5351(2) 0.45950(18) 0.25567(19) 0.0221(5) Uani 1 1 d .
H20 H 0.5790 0.4529 0.3219 0.027 Uiso 1 1 calc R
C21 C 0.75586(19) 0.14234(17) 0.38254(18) 0.0201(5) Uani 1 1 d .
H21 H 0.7332 0.0953 0.3067 0.024 Uiso 1 1 calc R
C22 C 0.7488(2) 0.06876(18) 0.44992(19) 0.0240(5) Uani 1 1 d .
C23 C 0.6411(2) 0.00967(19) 0.4415(2) 0.0294(6) Uani 1 1 d .
H23 H 0.5730 0.0185 0.3975 0.035 Uiso 1 1 calc R
C24 C 0.6311(3) -0.0619(2) 0.4961(2) 0.0394(7) Uani 1 1 d .
H24 H 0.5566 -0.1016 0.4891 0.047 Uiso 1 1 calc R
C25 C 0.7293(3) -0.0756(2) 0.5605(3) 0.0464(8) Uani 1 1 d .
H25 H 0.7227 -0.1246 0.5981 0.056 Uiso 1 1 calc R
C26 C 0.8362(3) -0.0179(2) 0.5698(3) 0.0492(8) Uani 1 1 d .
H26 H 0.9039 -0.0272 0.6138 0.059 Uiso 1 1 calc R
C27 C 0.8468(2) 0.0544(2) 0.5153(2) 0.0362(6) Uani 1 1 d .
H27 H 0.9216 0.0942 0.5230 0.043 Uiso 1 1 calc R
C28 C 0.8788(2) 0.21693(18) 0.41687(18) 0.0223(5) Uani 1 1 d .
C29 C 0.9216(2) 0.31887(19) 0.4919(2) 0.0309(6) Uani 1 1 d .
H29 H 0.8735 0.3439 0.5244 0.037 Uiso 1 1 calc R
C30 C 1.0339(2) 0.3843(2) 0.5197(2) 0.0396(7) Uani 1 1 d .
H30 H 1.0616 0.4538 0.5705 0.048 Uiso 1 1 calc R
C31 C 1.1053(2) 0.3494(2) 0.4744(3) 0.0435(7) Uani 1 1 d .
H31 H 1.1820 0.3945 0.4939 0.052 Uiso 1 1 calc R
C32 C 1.0648(2) 0.2488(2) 0.4008(2) 0.0410(7) Uani 1 1 d .
H32 H 1.1138 0.2239 0.3696 0.049 Uiso 1 1 calc R
C33 C 0.9521(2) 0.1836(2) 0.3722(2) 0.0307(6) Uani 1 1 d .
H33 H 0.9248 0.1145 0.3208 0.037 Uiso 1 1 calc R
C34 C 0.6112(2) 0.27811(18) 0.02073(19) 0.0226(5) Uani 1 1 d .
H34A H 0.5737 0.2147 -0.0443 0.034 Uiso 1 1 calc R
H34B H 0.6645 0.3326 0.0085 0.034 Uiso 1 1 calc R
H34C H 0.5519 0.3047 0.0364 0.034 Uiso 1 1 calc R
C35 C 0.7972(2) 0.18856(18) 0.0931(2) 0.0242(5) Uani 1 1 d .
H35A H 0.8406 0.1640 0.1487 0.036 Uiso 1 1 calc R
H35B H 0.8514 0.2434 0.0821 0.036 Uiso 1 1 calc R
H35C H 0.7534 0.1290 0.0249 0.036 Uiso 1 1 calc R
C36 C 0.7841(2) 0.37207(17) 0.2515(2) 0.0250(5) Uani 1 1 d .
H36A H 0.7351 0.3979 0.2858 0.038 Uiso 1 1 calc R
H36B H 0.8174 0.4244 0.2229 0.038 Uiso 1 1 calc R
H36C H 0.8468 0.3609 0.3051 0.038 Uiso 1 1 calc R
C37 C 0.6397(2) -0.11391(18) 0.2046(2) 0.0280(5) Uani 1 1 d .
H37 H 0.5836 -0.1157 0.2359 0.034 Uiso 1 1 calc R
C38 C 0.7187(2) -0.16441(19) 0.2353(2) 0.0304(6) Uani 1 1 d .
H38 H 0.7168 -0.1986 0.2871 0.037 Uiso 1 1 calc R
C39 C 0.8019(2) -0.16521(19) 0.1898(2) 0.0315(6) Uani 1 1 d .
C40 C 0.7987(2) -0.11165(19) 0.1144(2) 0.0295(6) Uani 1 1 d .
H40 H 0.8531 -0.1090 0.0811 0.035 Uiso 1 1 calc R
C41 C 0.7167(2) -0.06334(18) 0.0893(2) 0.0265(5) Uani 1 1 d .
H41 H 0.7164 -0.0285 0.0378 0.032 Uiso 1 1 calc R
C42 C 0.9589(3) -0.2212(3) 0.1614(3) 0.0571(9) Uani 1 1 d .
H42A H 0.9160 -0.2620 0.0840 0.086 Uiso 1 1 calc R
H42B H 1.0124 -0.2554 0.1944 0.086 Uiso 1 1 calc R
H42C H 1.0031 -0.1493 0.1703 0.086 Uiso 1 1 calc R
C43 C 0.8749(3) -0.2764(3) 0.2865(3) 0.0522(8) Uani 1 1 d .
H43A H 0.8750 -0.2315 0.3532 0.078 Uiso 1 1 calc R
H43B H 0.9429 -0.2996 0.3039 0.078 Uiso 1 1 calc R
H43C H 0.8040 -0.3384 0.2516 0.078 Uiso 1 1 calc R
C44 C 1.2988(3) -0.1578(3) 0.2528(3) 0.0539(9) Uani 1 1 d .
H44A H 1.2361 -0.1323 0.2613 0.081 Uiso 1 1 calc R
H44B H 1.3395 -0.1157 0.2196 0.081 Uiso 1 1 calc R
H44C H 1.3535 -0.1509 0.3239 0.081 Uiso 1 1 calc R
C45 C 1.2491(3) -0.2708(3) 0.1822(3) 0.0547(9) Uani 1 1 d .
H45A H 1.1980 -0.2776 0.1085 0.066 Uiso 1 1 calc R
H45B H 1.3123 -0.2981 0.1764 0.066 Uiso 1 1 calc R
C46 C 1.1388(4) -0.4399(3) 0.1683(4) 0.0758(12) Uani 1 1 d .
H46A H 1.2024 -0.4670 0.1630 0.091 Uiso 1 1 calc R
H46B H 1.0836 -0.4535 0.0940 0.091 Uiso 1 1 calc R
C47 C 1.0781(5) -0.4943(3) 0.2265(5) 0.1062(17) Uani 1 1 d U
H47A H 1.1352 -0.4877 0.2964 0.159 Uiso 1 1 calc R
H47B H 1.0381 -0.5692 0.1827 0.159 Uiso 1 1 calc R
H47C H 1.0214 -0.4614 0.2387 0.159 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'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_3
N1 Ge1 N2 99.26(8) .
N1 Ge1 Ge1 103.50(6) 2_655
N2 Ge1 Ge1 93.30(6) 2_655
N1 Si1 C34 114.49(10) .
N1 Si1 C36 110.49(10) .
C34 Si1 C36 106.90(11) .
N1 Si1 C35 113.25(10) .
C34 Si1 C35 104.34(11) .
C36 Si1 C35 106.83(11) .
C46 O1 C45 113.0(3) .
C1 N1 Si1 118.43(13) .
C1 N1 Ge1 112.56(13) .
Si1 N1 Ge1 128.58(10) .
C41 N2 C37 115.5(2) .
C41 N2 Ge1 126.81(16) .
C37 N2 Ge1 117.68(17) .
C39 N3 C42 121.8(2) .
C39 N3 C43 119.4(3) .
C42 N3 C43 118.6(2) .
C2 C1 C6 117.42(19) .
C2 C1 N1 121.48(19) .
C6 C1 N1 121.10(19) .
C3 C2 C1 120.4(2) .
C3 C2 C8 117.1(2) .
C1 C2 C8 122.46(19) .
C4 C3 C2 122.4(2) .
C3 C4 C5 117.2(2) .
C3 C4 C7 120.8(2) .
C5 C4 C7 122.0(2) .
C4 C5 C6 122.4(2) .
C5 C6 C1 120.1(2) .
C5 C6 C21 118.4(2) .
C1 C6 C21 121.51(19) .
C2 C8 C15 113.95(18) .
C2 C8 C9 109.74(17) .
C15 C8 C9 112.88(18) .
C10 C9 C14 117.8(2) .
C10 C9 C8 124.0(2) .
C14 C9 C8 118.2(2) .
C9 C10 C11 120.7(2) .
C12 C11 C10 120.7(3) .
C11 C12 C13 119.1(2) .
C12 C13 C14 120.4(2) .
C13 C14 C9 121.3(2) .
C20 C15 C16 117.7(2) .
C20 C15 C8 123.6(2) .
C16 C15 C8 118.7(2) .
C17 C16 C15 121.4(2) .
C16 C17 C18 120.2(2) .
C19 C18 C17 119.3(2) .
C18 C19 C20 120.6(2) .
C15 C20 C19 120.8(2) .
C6 C21 C28 113.49(18) .
C6 C21 C22 111.48(19) .
C28 C21 C22 113.01(18) .
C27 C22 C23 117.9(2) .
C27 C22 C21 122.3(2) .
C23 C22 C21 119.7(2) .
C24 C23 C22 121.3(2) .
C25 C24 C23 120.2(3) .
C26 C25 C24 119.3(3) .
C25 C26 C27 120.8(3) .
C22 C27 C26 120.5(3) .
C33 C28 C29 117.7(2) .
C33 C28 C21 119.5(2) .
C29 C28 C21 122.8(2) .
C30 C29 C28 120.6(3) .
C31 C30 C29 120.6(3) .
C30 C31 C32 119.5(3) .
C31 C32 C33 119.9(3) .
C28 C33 C32 121.6(3) .
N2 C37 C38 124.4(2) .
C37 C38 C39 119.8(2) .
N3 C39 C38 122.8(2) .
N3 C39 C40 121.2(3) .
C38 C39 C40 116.0(2) .
C41 C40 C39 119.9(2) .
N2 C41 C40 124.4(2) .
O1 C45 C44 109.2(3) .
O1 C46 C47 108.0(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ge1 N1 1.9494(19) .
Ge1 N2 2.131(2) .
Ge1 Ge1 2.6420(8) 2_655
Si1 N1 1.7377(18) .
Si1 C34 1.867(2) .
Si1 C36 1.869(3) .
Si1 C35 1.869(2) .
O1 C46 1.414(4) .
O1 C45 1.419(4) .
N1 C1 1.441(3) .
N2 C41 1.347(3) .
N2 C37 1.352(3) .
N3 C39 1.351(3) .
N3 C42 1.430(4) .
N3 C43 1.457(4) .
C1 C2 1.411(3) .
C1 C6 1.413(3) .
C2 C3 1.391(3) .
C2 C8 1.523(3) .
C3 C4 1.383(3) .
C4 C5 1.386(3) .
C4 C7 1.512(3) .
C5 C6 1.396(3) .
C6 C21 1.524(3) .
C8 C15 1.528(3) .
C8 C9 1.533(3) .
C9 C10 1.382(3) .
C9 C14 1.389(3) .
C10 C11 1.393(4) .
C11 C12 1.370(4) .
C12 C13 1.376(4) .
C13 C14 1.382(3) .
C15 C20 1.385(3) .
C15 C16 1.396(3) .
C16 C17 1.381(3) .
C17 C18 1.382(4) .
C18 C19 1.375(4) .
C19 C20 1.394(3) .
C21 C28 1.526(3) .
C21 C22 1.540(3) .
C22 C27 1.389(3) .
C22 C23 1.389(4) .
C23 C24 1.385(4) .
C24 C25 1.382(4) .
C25 C26 1.370(5) .
C26 C27 1.393(4) .
C28 C33 1.383(4) .
C28 C29 1.394(3) .
C29 C30 1.390(4) .
C30 C31 1.374(4) .
C31 C32 1.375(4) .
C32 C33 1.390(4) .
C37 C38 1.378(4) .
C38 C39 1.403(4) .
C39 C40 1.410(4) .
C40 C41 1.373(4) .
C44 C45 1.486(5) .
C46 C47 1.494(6) .
