#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/61/4086159.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_4086159
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            'C92 H102 Ge2 N4 O2 Si2'
_chemical_formula_weight         1497.14
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 113.787(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   32.6327(12)
_cell_length_b                   13.2336(4)
_cell_length_c                   20.1143(8)
_cell_measurement_temperature    123(2)
_cell_volume                     7948.4(6)
_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  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26058
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3160
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.197
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         7801
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0459
_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)+(0.0680P)²+6.1019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1319
_reflns_number_gt                6014
_reflns_number_total             7801
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00206_si_002.cif
_cod_data_source_block           compound10
_cod_original_cell_volume        7948.4(5)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4086159
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.445548(9) 0.26175(2) 0.208281(16) 0.02133(12) Uani 1 1 d .
Si1 Si 0.41137(3) 0.26335(6) 0.34271(4) 0.02303(19) Uani 1 1 d .
O1 O 0.29699(12) -0.2430(2) 0.1187(2) 0.0837(12) Uani 1 1 d D
N1 N 0.40558(8) 0.24185(16) 0.25276(13) 0.0195(5) Uani 1 1 d .
N2 N 0.47896(7) 0.37575(17) 0.25326(13) 0.0221(5) Uani 1 1 d .
C1 C 0.36743(8) 0.1804(2) 0.20844(14) 0.0191(6) Uani 1 1 d .
C2 C 0.32596(9) 0.2286(2) 0.16885(16) 0.0217(6) Uani 1 1 d .
C3 C 0.28777(9) 0.1696(2) 0.13507(16) 0.0244(6) Uani 1 1 d .
H3 H 0.2596 0.2021 0.1117 0.029 Uiso 1 1 calc R
C4 C 0.28960(9) 0.0653(2) 0.13442(16) 0.0261(7) Uani 1 1 d .
C5 C 0.33121(9) 0.0197(2) 0.16575(16) 0.0245(6) Uani 1 1 d .
H5 H 0.3334 -0.0514 0.1612 0.029 Uiso 1 1 calc R
C6 C 0.37028(9) 0.0754(2) 0.20404(15) 0.0199(6) Uani 1 1 d .
C7 C 0.24766(10) 0.0026(2) 0.10052(19) 0.0356(8) Uani 1 1 d .
H7A H 0.2391 -0.0236 0.1387 0.053 Uiso 1 1 calc R
H7B H 0.2532 -0.0540 0.0738 0.053 Uiso 1 1 calc R
H7C H 0.2234 0.0446 0.0670 0.053 Uiso 1 1 calc R
C8 C 0.32467(9) 0.3421(2) 0.15668(15) 0.0221(6) Uani 1 1 d .
H8 H 0.3457 0.3734 0.2032 0.027 Uiso 1 1 calc R
C9 C 0.34237(9) 0.3674(2) 0.09886(15) 0.0241(6) Uani 1 1 d .
C10 C 0.34769(11) 0.2962(3) 0.05302(17) 0.0350(7) Uani 1 1 d .
H10 H 0.3401 0.2277 0.0567 0.042 Uiso 1 1 calc R
C11 C 0.36402(12) 0.3234(3) 0.00134(19) 0.0468(10) Uani 1 1 d .
H11 H 0.3673 0.2733 -0.0300 0.056 Uiso 1 1 calc R
C12 C 0.37532(11) 0.4213(3) -0.00487(19) 0.0434(9) Uani 1 1 d .
H12 H 0.3870 0.4389 -0.0396 0.052 Uiso 1 1 calc R
C13 C 0.36969(11) 0.4940(3) 0.03946(19) 0.0412(8) Uani 1 1 d .
H13 H 0.3772 0.5623 0.0352 0.049 Uiso 1 1 calc R
C14 C 0.35300(10) 0.4674(2) 0.09030(18) 0.0318(7) Uani 1 1 d .
H14 H 0.3487 0.5184 0.1201 0.038 Uiso 1 1 calc R
C15 C 0.27881(9) 0.3897(2) 0.13797(16) 0.0224(6) Uani 1 1 d .
C16 C 0.26656(10) 0.4229(2) 0.19252(18) 0.0334(7) Uani 1 1 d .
H16 H 0.2867 0.4146 0.2419 0.040 Uiso 1 1 calc R
C17 C 0.22540(12) 0.4681(3) 0.1764(2) 0.0437(9) Uani 1 1 d .
H17 H 0.2176 0.4909 0.2145 0.052 Uiso 1 1 calc R
C18 C 0.19564(11) 0.4803(3) 0.10504(19) 0.0385(8) Uani 1 1 d .
H18 H 0.1675 0.5120 0.0939 0.046 Uiso 1 1 calc R
C19 C 0.20702(10) 0.4462(2) 0.05049(19) 0.0351(8) Uani 1 1 d .
H19 H 0.1866 0.4538 0.0013 0.042 Uiso 1 1 calc R
C20 C 0.24820(10) 0.4007(2) 0.06655(17) 0.0305(7) Uani 1 1 d .
H20 H 0.2555 0.3768 0.0282 0.037 Uiso 1 1 calc R
C21 C 0.41456(9) 0.0172(2) 0.23855(15) 0.0212(6) Uani 1 1 d .
H21 H 0.4390 0.0689 0.2527 0.025 Uiso 1 1 calc R
C22 C 0.42156(9) -0.0527(2) 0.18274(16) 0.0233(6) Uani 1 1 d .
C23 C 0.41396(9) -0.0163(2) 0.11376(16) 0.0278(7) Uani 1 1 d .
H23 H 0.4041 0.0513 0.1014 0.033 Uiso 1 1 calc R
C24 C 0.42058(10) -0.0770(3) 0.06308(18) 0.0343(8) Uani 1 1 d .
H24 H 0.4150 -0.0513 0.0161 0.041 Uiso 1 1 calc R
C25 C 0.43540(11) -0.1755(3) 0.08093(18) 0.0367(8) Uani 1 1 d .
H25 H 0.4397 -0.2177 0.0460 0.044 Uiso 1 1 calc R
C26 C 0.44388(11) -0.2120(3) 0.14917(19) 0.0364(8) Uani 1 1 d .
H26 H 0.4546 -0.2791 0.1619 0.044 Uiso 1 1 calc R
C27 C 0.43672(10) -0.1510(2) 0.19949(18) 0.0312(7) Uani 1 1 d .
H27 H 0.4423 -0.1771 0.2464 0.037 Uiso 1 1 calc R
C28 C 0.42008(9) -0.0380(2) 0.30755(16) 0.0242(6) Uani 1 1 d .
C29 C 0.46117(10) -0.0374(2) 0.36618(16) 0.0303(7) Uani 1 1 d .
H29 H 0.4856 -0.0026 0.3623 0.036 Uiso 1 1 calc R
C30 C 0.46745(11) -0.0863(3) 0.43035(17) 0.0353(8) Uani 1 1 d .
H30 H 0.4959 -0.0844 0.4700 0.042 Uiso 1 1 calc R
C31 C 0.43254(12) -0.1376(3) 0.43698(19) 0.0408(9) Uani 1 1 d .
H31 H 0.4365 -0.1697 0.4814 0.049 Uiso 1 1 calc R
C32 C 0.39198(12) -0.1418(3) 0.3785(2) 0.0491(10) Uani 1 1 d .
H32 H 0.3680 -0.1787 0.3821 0.059 Uiso 1 1 calc R
C33 C 0.38566(11) -0.0929(3) 0.31461(19) 0.0401(8) Uani 1 1 d .
H33 H 0.3573 -0.0967 0.2747 0.048 Uiso 1 1 calc R
C34 C 0.37448(11) 0.1731(3) 0.36378(17) 0.0340(8) Uani 1 1 d .
H34A H 0.3434 0.1831 0.3294 0.051 Uiso 1 1 calc R
H34B H 0.3770 0.1850 0.4134 0.051 Uiso 1 1 calc R
H34C H 0.3837 0.1037 0.3597 0.051 Uiso 1 1 calc R
C35 C 0.39406(11) 0.3903(2) 0.36225(18) 0.0357(8) Uani 1 1 d .
H35A H 0.4146 0.4417 0.3584 0.054 Uiso 1 1 calc R
H35B H 0.3949 0.3909 0.4115 0.054 Uiso 1 1 calc R
H35C H 0.3636 0.4050 0.3271 0.054 Uiso 1 1 calc R
C36 C 0.47089(11) 0.2425(2) 0.40513(17) 0.0307(7) Uani 1 1 d .
H36A H 0.4788 0.1715 0.4029 0.046 Uiso 1 1 calc R
H36B H 0.4751 0.2592 0.4549 0.046 Uiso 1 1 calc R
H36C H 0.4902 0.2857 0.3905 0.046 Uiso 1 1 calc R
C37 C 0.47444(9) 0.4611(2) 0.29383(17) 0.0251(6) Uani 1 1 d .
C38 C 0.43882(11) 0.5268(2) 0.2628(2) 0.0366(8) Uani 1 1 d .
H38 H 0.4171 0.5153 0.2149 0.044 Uiso 1 1 calc R
C39 C 0.43501(13) 0.6106(3) 0.3025(3) 0.0508(10) Uani 1 1 d .
H39 H 0.4108 0.6563 0.2813 0.061 Uiso 1 1 calc R
C40 C 0.46624(14) 0.6271(3) 0.3723(3) 0.0531(11) Uani 1 1 d .
H40 H 0.4631 0.6830 0.3996 0.064 Uiso 1 1 calc R
C41 C 0.50175(13) 0.5623(3) 0.4020(2) 0.0497(10) Uani 1 1 d .
H41 H 0.5234 0.5738 0.4499 0.060 Uiso 1 1 calc R
C42 C 0.50638(11) 0.4804(3) 0.36313(18) 0.0357(8) Uani 1 1 d .
H42 H 0.5316 0.4371 0.3839 0.043 Uiso 1 1 calc R
C43 C 0.31360(18) -0.2046(4) 0.0172(3) 0.0945(18) Uani 1 1 d D
H43A H 0.2821 -0.1865 -0.0098 0.142 Uiso 1 1 calc R
H43B H 0.3254 -0.2344 -0.0162 0.142 Uiso 1 1 calc R
H43C H 0.3308 -0.1439 0.0395 0.142 Uiso 1 1 calc R
C44 C 0.31733(18) -0.2771(4) 0.0733(2) 0.0732(14) Uani 1 1 d D
H44A H 0.3031 -0.3414 0.0502 0.088 Uiso 1 1 calc R
H44B H 0.3494 -0.2908 0.1030 0.088 Uiso 1 1 calc R
C45 C 0.29800(19) -0.3066(4) 0.1716(2) 0.0888(18) Uani 1 1 d D
H45A H 0.3296 -0.3182 0.2049 0.107 Uiso 1 1 calc R
H45B H 0.2853 -0.3723 0.1493 0.107 Uiso 1 1 calc R
C46 C 0.2736(2) -0.2717(5) 0.2145(4) 0.109(2) Uani 1 1 d DU
H46A H 0.2770 -0.1984 0.2211 0.164 Uiso 1 1 calc R
H46B H 0.2857 -0.3050 0.2621 0.164 Uiso 1 1 calc R
H46C H 0.2418 -0.2884 0.1890 0.164 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_1
N2 Ge1 N1 105.37(10) .
N1 Si1 C36 108.60(13) .
N1 Si1 C34 108.56(13) .
C36 Si1 C34 110.25(15) .
N1 Si1 C35 116.44(13) .
C36 Si1 C35 108.33(15) .
C34 Si1 C35 104.55(15) .
C45 O1 C44 116.5(4) .
C1 N1 Si1 115.48(17) .
C1 N1 Ge1 112.02(17) .
Si1 N1 Ge1 131.26(13) .
N2 N2 C37 112.01(18) 2_655
N2 N2 Ge1 110.49(13) 2_655
C37 N2 Ge1 137.48(18) .
C6 C1 C2 119.0(2) .
C6 C1 N1 122.2(2) .
C2 C1 N1 118.8(2) .
C3 C2 C1 119.2(3) .
C3 C2 C8 120.9(2) .
C1 C2 C8 119.6(2) .
C4 C3 C2 122.0(3) .
C3 C4 C5 118.0(3) .
C3 C4 C7 121.3(3) .
C5 C4 C7 120.7(3) .
C4 C5 C6 121.9(3) .
C1 C6 C5 119.2(2) .
C1 C6 C21 123.0(2) .
C5 C6 C21 117.8(2) .
C2 C8 C15 114.1(2) .
C2 C8 C9 110.1(2) .
C15 C8 C9 110.8(2) .
C10 C9 C14 117.5(3) .
C10 C9 C8 123.2(3) .
C14 C9 C8 119.3(3) .
C9 C10 C11 120.8(3) .
C12 C11 C10 120.8(3) .
C11 C12 C13 119.5(3) .
C12 C13 C14 119.8(3) .
C13 C14 C9 121.6(3) .
C16 C15 C20 118.1(3) .
C16 C15 C8 120.3(3) .
C20 C15 C8 121.6(3) .
C15 C16 C17 121.0(3) .
C18 C17 C16 120.3(3) .
C19 C18 C17 119.3(3) .
C18 C19 C20 120.5(3) .
C19 C20 C15 120.8(3) .
C28 C21 C6 113.5(2) .
C28 C21 C22 112.3(2) .
C6 C21 C22 111.2(2) .
C27 C22 C23 118.1(3) .
C27 C22 C21 122.0(3) .
C23 C22 C21 119.9(3) .
C24 C23 C22 121.0(3) .
C23 C24 C25 119.9(3) .
C26 C25 C24 119.9(3) .
C25 C26 C27 119.9(3) .
C22 C27 C26 121.3(3) .
C29 C28 C33 117.4(3) .
C29 C28 C21 119.7(3) .
C33 C28 C21 122.9(3) .
C30 C29 C28 121.4(3) .
C31 C30 C29 120.3(3) .
C32 C31 C30 119.1(3) .
C31 C32 C33 120.7(3) .
C32 C33 C28 121.1(3) .
C38 C37 C42 119.4(3) .
C38 C37 N2 119.9(3) .
C42 C37 N2 120.6(3) .
C37 C38 C39 119.5(3) .
C40 C39 C38 120.5(4) .
C41 C40 C39 119.5(3) .
C40 C41 C42 120.7(4) .
C41 C42 C37 120.3(3) .
O1 C44 C43 112.4(4) .
O1 C45 C46 115.0(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ge1 N2 1.867(2) .
Ge1 N1 1.874(2) .
Si1 N1 1.765(2) .
Si1 C36 1.860(3) .
Si1 C34 1.862(3) .
Si1 C35 1.864(3) .
O1 C45 1.347(5) .
O1 C44 1.403(5) .
N1 C1 1.453(3) .
N2 N2 1.431(4) 2_655
N2 C37 1.435(4) .
C1 C6 1.399(4) .
C1 C2 1.415(4) .
C2 C3 1.393(4) .
C2 C8 1.520(4) .
C3 C4 1.383(4) .
C4 C5 1.384(4) .
C4 C7 1.508(4) .
C5 C6 1.403(4) .
C6 C21 1.534(4) .
C8 C15 1.525(4) .
C8 C9 1.530(4) .
C9 C10 1.378(4) .
C9 C14 1.396(4) .
C10 C11 1.393(5) .
C11 C12 1.366(5) .
C12 C13 1.374(5) .
C13 C14 1.384(4) .
C15 C16 1.382(4) .
C15 C20 1.387(4) .
C16 C17 1.384(4) .
C17 C18 1.379(5) .
C18 C19 1.369(5) .
C19 C20 1.386(4) .
C21 C28 1.514(4) .
C21 C22 1.542(4) .
C22 C27 1.383(4) .
C22 C23 1.393(4) .
C23 C24 1.382(4) .
C24 C25 1.386(5) .
C25 C26 1.374(5) .
C26 C27 1.387(4) .
C28 C29 1.383(4) .
C28 C33 1.392(4) .
C29 C30 1.383(4) .
C30 C31 1.378(5) .
C31 C32 1.372(5) .
C32 C33 1.378(5) .
C37 C38 1.383(4) .
C37 C42 1.387(4) .
C38 C39 1.401(5) .
C39 C40 1.379(6) .
C40 C41 1.370(6) .
C41 C42 1.380(5) .
C43 C44 1.449(5) .
C45 C46 1.464(5) .
