#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:33:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180187 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/83/7108397.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_7108397
loop_
_publ_author_name
'Cameron Jones'
'Anastas Sidiropoulos'
'Nicole Holzmann'
'Gernot Frenking'
'Andreas Stasch'
_publ_section_title
;
 An N-heterocyclic carbene adduct of diatomic tin, :Sn[double bond, length
 as m-dash]Sn:
;
_journal_name_full               Chem.Commun.
_journal_page_first              9855
_journal_paper_doi               10.1039/c2cc35228a
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C78 H96 Ge2 N4'
_chemical_formula_weight         1234.77
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 108.3710(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.2533(7)
_cell_length_b                   22.8619(12)
_cell_length_c                   13.0395(7)
_cell_measurement_reflns_used    4183
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      24.81
_cell_measurement_theta_min      2.43
_cell_volume                     3466.6(3)
_computing_cell_refinement       'Apex2 v2012.2.0 (Bruker AXS, 2012)'
_computing_data_collection       'Apex2 v2012.2.0 (Bruker AXS, 2012)'
_computing_data_reduction        'Apex2 v2012.2.0 (Bruker AXS, 2012)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Apex X8'
_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  0.0815
_diffrn_reflns_av_sigmaI/netI    0.1055
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17684
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.911
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         6102
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0345P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                3832
_reflns_number_total             6102
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc35228a.cif
_cod_data_source_block           compound2(benzene)4
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7108397
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.07476(3) 0.018694(16) 0.57255(3) 0.02243(12) Uani 1 1 d .
N1 N -0.0758(2) 0.11763(12) 0.6112(2) 0.0173(7) Uani 1 1 d .
C1 C -0.0034(3) 0.09783(14) 0.5574(3) 0.0170(8) Uani 1 1 d .
N2 N 0.0098(2) 0.14522(12) 0.4984(2) 0.0187(7) Uani 1 1 d .
C2 C -0.1065(3) 0.17550(15) 0.5850(3) 0.0246(9) Uani 1 1 d .
H2 H -0.1565 0.1986 0.6113 0.030 Uiso 1 1 calc R
C3 C -0.0524(3) 0.19253(15) 0.5159(3) 0.0257(9) Uani 1 1 d .
H3 H -0.0559 0.2303 0.4845 0.031 Uiso 1 1 calc R
C4 C -0.0997(3) 0.08601(15) 0.6978(3) 0.0200(8) Uani 1 1 d .
C5 C -0.0203(3) 0.09128(16) 0.8013(3) 0.0255(9) Uani 1 1 d .
C6 C -0.0453(4) 0.06133(17) 0.8845(3) 0.0335(10) Uani 1 1 d .
H6 H 0.0064 0.0638 0.9561 0.040 Uiso 1 1 calc R
C7 C -0.1434(4) 0.02834(17) 0.8644(3) 0.0372(11) Uani 1 1 d .
H7 H -0.1586 0.0080 0.9220 0.045 Uiso 1 1 calc R
C8 C -0.2199(3) 0.02445(17) 0.7620(3) 0.0324(10) Uani 1 1 d .
H8 H -0.2871 0.0013 0.7496 0.039 Uiso 1 1 calc R
C9 C -0.2008(3) 0.05378(15) 0.6757(3) 0.0232(9) Uani 1 1 d .
C10 C 0.0867(3) 0.12808(17) 0.8243(3) 0.0318(10) Uani 1 1 d .
H10 H 0.0922 0.1422 0.7535 0.038 Uiso 1 1 calc R
C11 C 0.1950(4) 0.09221(19) 0.8792(4) 0.0528(13) Uani 1 1 d .
H11A H 0.1931 0.0788 0.9499 0.079 Uiso 1 1 calc R
H11B H 0.2633 0.1166 0.8885 0.079 Uiso 1 1 calc R
H11C H 0.1980 0.0583 0.8341 0.079 Uiso 1 1 calc R
C12 C 0.0806(4) 0.18204(19) 0.8922(4) 0.0585(14) Uani 1 1 d .
H12A H 0.0085 0.2030 0.8582 0.088 Uiso 1 1 calc R
H12B H 0.1457 0.2079 0.8969 0.088 Uiso 1 1 calc R
H12C H 0.0835 0.1697 0.9650 0.088 Uiso 1 1 calc R
C13 C -0.2890(3) 0.05195(16) 0.5639(3) 0.0262(9) Uani 1 1 d .
H13 H -0.2494 0.0639 0.5108 0.031 Uiso 1 1 calc R
C14 C -0.3396(3) -0.00895(16) 0.5319(3) 0.0392(11) Uani 1 1 d .
H14A H -0.2773 -0.0370 0.5383 0.059 Uiso 1 1 calc R
H14B H -0.3908 -0.0082 0.4571 0.059 Uiso 1 1 calc R
H14C H -0.3832 -0.0208 0.5799 0.059 Uiso 1 1 calc R
C15 C -0.3836(3) 0.09683(17) 0.5575(3) 0.0358(10) Uani 1 1 d .
H15A H -0.4215 0.0873 0.6113 0.054 Uiso 1 1 calc R
H15B H -0.4403 0.0959 0.4851 0.054 Uiso 1 1 calc R
H15C H -0.3497 0.1360 0.5719 0.054 Uiso 1 1 calc R
C16 C 0.0900(3) 0.14763(14) 0.4377(3) 0.0216(9) Uani 1 1 d .
C17 C 0.2053(3) 0.16078(15) 0.4933(3) 0.0262(9) Uani 1 1 d .
C18 C 0.2803(3) 0.16404(16) 0.4325(3) 0.0340(10) Uani 1 1 d .
H18 H 0.3590 0.1729 0.4673 0.041 Uiso 1 1 calc R
C19 C 0.2421(4) 0.15463(17) 0.3225(4) 0.0395(11) Uani 1 1 d .
H19 H 0.2947 0.1571 0.2825 0.047 Uiso 1 1 calc R
C20 C 0.1285(4) 0.14168(17) 0.2701(3) 0.0382(11) Uani 1 1 d .
H20 H 0.1039 0.1353 0.1942 0.046 Uiso 1 1 calc R
C21 C 0.0488(3) 0.13773(15) 0.3262(3) 0.0268(9) Uani 1 1 d .
C22 C 0.2498(3) 0.17067(17) 0.6142(3) 0.0337(10) Uani 1 1 d .
H22 H 0.1878 0.1578 0.6441 0.040 Uiso 1 1 calc R
C23 C 0.3556(4) 0.1357(2) 0.6711(4) 0.0709(17) Uani 1 1 d .
H23A H 0.4195 0.1485 0.6464 0.106 Uiso 1 1 calc R
H23B H 0.3404 0.0941 0.6548 0.106 Uiso 1 1 calc R
H23C H 0.3758 0.1419 0.7493 0.106 Uiso 1 1 calc R
C24 C 0.2720(6) 0.2344(2) 0.6418(4) 0.097(2) Uani 1 1 d U
H24A H 0.3371 0.2478 0.6195 0.146 Uiso 1 1 calc R
H24B H 0.2899 0.2397 0.7200 0.146 Uiso 1 1 calc R
H24C H 0.2034 0.2572 0.6040 0.146 Uiso 1 1 calc R
C25 C -0.0759(3) 0.12513(16) 0.2672(3) 0.0289(10) Uani 1 1 d .
H25 H -0.1114 0.1100 0.3213 0.035 Uiso 1 1 calc R
C26 C -0.0932(4) 0.07852(17) 0.1789(3) 0.0406(11) Uani 1 1 d .
H26A H -0.0667 0.0938 0.1206 0.061 Uiso 1 1 calc R
H26B H -0.1750 0.0685 0.1500 0.061 Uiso 1 1 calc R
H26C H -0.0490 0.0435 0.2096 0.061 Uiso 1 1 calc R
C27 C -0.1399(4) 0.18132(17) 0.2185(3) 0.0405(11) Uani 1 1 d .
H27A H -0.1312 0.2103 0.2759 0.061 Uiso 1 1 calc R
H27B H -0.2216 0.1726 0.1844 0.061 Uiso 1 1 calc R
H27C H -0.1076 0.1969 0.1642 0.061 Uiso 1 1 calc R
C28 C 0.3761(4) -0.0407(2) 0.7594(4) 0.0462(12) Uani 1 1 d .
H28 H 0.3047 -0.0218 0.7256 0.055 Uiso 1 1 calc R
C29 C 0.4631(4) -0.0112(2) 0.8368(3) 0.0446(11) Uani 1 1 d .
H29 H 0.4516 0.0279 0.8559 0.054 Uiso 1 1 calc R
C30 C 0.5665(3) -0.03903(18) 0.8859(3) 0.0368(11) Uani 1 1 d .
H30 H 0.6261 -0.0193 0.9394 0.044 Uiso 1 1 calc R
C31 C 0.5829(3) -0.0957(2) 0.8568(3) 0.0387(11) Uani 1 1 d .
H31 H 0.6543 -0.1147 0.8900 0.046 Uiso 1 1 calc R
C32 C 0.4963(4) -0.1247(2) 0.7802(3) 0.0417(11) Uani 1 1 d .
H32 H 0.5078 -0.1638 0.7608 0.050 Uiso 1 1 calc R
C33 C 0.3932(4) -0.0970(2) 0.7317(3) 0.0446(12) Uani 1 1 d .
H33 H 0.3335 -0.1170 0.6787 0.053 Uiso 1 1 calc R
C34 C 0.3466(4) -0.2673(2) 0.6409(4) 0.0562(14) Uani 1 1 d .
H34 H 0.3232 -0.2375 0.6804 0.067 Uiso 1 1 calc R
C35 C 0.4166(4) -0.2540(2) 0.5810(4) 0.0563(14) Uani 1 1 d .
H35 H 0.4415 -0.2148 0.5786 0.068 Uiso 1 1 calc R
C36 C 0.4514(4) -0.2968(2) 0.5241(3) 0.0474(12) Uani 1 1 d .
H36 H 0.5006 -0.2875 0.4829 0.057 Uiso 1 1 calc R
C37 C 0.4145(4) -0.35306(19) 0.5275(3) 0.0438(12) Uani 1 1 d .
H37 H 0.4378 -0.3828 0.4880 0.053 Uiso 1 1 calc R
C38 C 0.3441(4) -0.36665(19) 0.5873(4) 0.0467(12) Uani 1 1 d .
H38 H 0.3189 -0.4058 0.5895 0.056 Uiso 1 1 calc R
C39 C 0.3099(4) -0.3238(2) 0.6442(4) 0.0547(13) Uani 1 1 d .
H39 H 0.2610 -0.3332 0.6857 0.066 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'
Ge Ge 0.1547 1.8001 '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
C1 Ge1 Ge1 91.25(9) 3_556
C1 N1 C2 111.0(3) .
C1 N1 C4 123.9(3) .
C2 N1 C4 124.2(3) .
N2 C1 N1 103.7(3) .
N2 C1 Ge1 128.8(2) .
N1 C1 Ge1 127.4(2) .
C1 N2 C3 111.0(3) .
C1 N2 C16 124.0(3) .
C3 N2 C16 124.5(3) .
C3 C2 N1 106.9(3) .
C2 C3 N2 107.5(3) .
C9 C4 C5 123.3(3) .
C9 C4 N1 119.3(3) .
C5 C4 N1 117.4(3) .
C6 C5 C4 116.8(4) .
C6 C5 C10 120.6(4) .
C4 C5 C10 122.5(3) .
C7 C6 C5 121.0(4) .
C8 C7 C6 120.6(4) .
C7 C8 C9 121.3(4) .
C4 C9 C8 117.0(3) .
C4 C9 C13 122.1(3) .
C8 C9 C13 120.9(3) .
C5 C10 C11 111.4(3) .
C5 C10 C12 111.4(3) .
C11 C10 C12 110.7(3) .
C9 C13 C14 113.1(3) .
C9 C13 C15 109.4(3) .
C14 C13 C15 111.1(3) .
C21 C16 C17 123.2(3) .
C21 C16 N2 118.5(3) .
C17 C16 N2 118.3(3) .
C18 C17 C16 117.1(4) .
C18 C17 C22 120.0(4) .
C16 C17 C22 122.9(3) .
C19 C18 C17 121.1(4) .
C20 C19 C18 120.7(4) .
C19 C20 C21 121.2(4) .
C20 C21 C16 116.8(4) .
C20 C21 C25 120.6(4) .
C16 C21 C25 122.5(3) .
C23 C22 C24 109.5(4) .
C23 C22 C17 113.9(3) .
C24 C22 C17 111.9(4) .
C21 C25 C26 113.2(3) .
C21 C25 C27 110.8(3) .
C26 C25 C27 109.8(3) .
C33 C28 C29 120.0(4) .
C30 C29 C28 119.6(4) .
C29 C30 C31 119.8(4) .
C32 C31 C30 120.4(4) .
C33 C32 C31 119.8(4) .
C28 C33 C32 120.4(4) .
C35 C34 C39 119.9(4) .
C34 C35 C36 120.5(4) .
C37 C36 C35 119.3(4) .
C36 C37 C38 120.4(4) .
C37 C38 C39 120.1(4) .
C38 C39 C34 119.8(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ge1 C1 2.027(3) .
Ge1 Ge1 2.3413(8) 3_556
N1 C1 1.370(4) .
N1 C2 1.388(4) .
N1 C4 1.446(4) .
C1 N2 1.367(4) .
N2 C3 1.383(4) .
N2 C16 1.445(4) .
C2 C3 1.334(4) .
C4 C9 1.391(5) .
C4 C5 1.398(5) .
C5 C6 1.397(5) .
C5 C10 1.506(5) .
C6 C7 1.373(5) .
C7 C8 1.372(5) .
C8 C9 1.391(5) .
C9 C13 1.518(5) .
C10 C11 1.532(5) .
C10 C12 1.535(5) .
C13 C14 1.528(5) .
C13 C15 1.531(5) .
C16 C21 1.399(5) .
C16 C17 1.402(5) .
C17 C18 1.392(5) .
C17 C22 1.514(5) .
C18 C19 1.377(5) .
C19 C20 1.375(5) .
C20 C21 1.396(5) .
C21 C25 1.506(5) .
C22 C23 1.505(5) .
C22 C24 1.505(6) .
C25 C26 1.534(5) .
C25 C27 1.534(5) .
C28 C33 1.372(6) .
C28 C29 1.390(6) .
C29 C30 1.381(5) .
C30 C31 1.381(5) .
C31 C32 1.378(5) .
C32 C33 1.376(5) .
C34 C35 1.365(6) .
C34 C39 1.373(6) .
C35 C36 1.375(6) .
C36 C37 1.368(5) .
C37 C38 1.369(5) .
C38 C39 1.371(6) .
