 
data_compound2(benzene)4 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C78 H96 Ge2 N4' 
_chemical_formula_weight          1234.77 
 
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' 
 
_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    P2(1)/c 
 
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' 
 
_cell_length_a                    12.2533(7) 
_cell_length_b                    22.8619(12) 
_cell_length_c                    13.0395(7) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  108.3710(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      3466.6(3) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     123(2) 
_cell_measurement_reflns_used     4183 
_cell_measurement_theta_min       2.43 
_cell_measurement_theta_max       24.81 
 
_exptl_crystal_description        'block' 
_exptl_crystal_colour             'red' 
_exptl_crystal_size_max           0.18 
_exptl_crystal_size_mid           0.15 
_exptl_crystal_size_min           0.12 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.183 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1312 
_exptl_absorpt_coefficient_mu     0.911 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.851 
_exptl_absorpt_correction_T_max   0.898 
_exptl_absorpt_process_details    'Sortav (Blessing, 1995)'
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       123(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker Apex X8' 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             17684 
_diffrn_reflns_av_R_equivalents   0.0815 
_diffrn_reflns_av_sigmaI/netI     0.1055 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        14 
_diffrn_reflns_limit_k_min        -25 
_diffrn_reflns_limit_k_max        27 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        9 
_diffrn_reflns_theta_min          2.67 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              6102 
_reflns_number_gt                 3832 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Apex2 v2012.2.0 (Bruker AXS, 2012)' 
_computing_cell_refinement        'Apex2 v2012.2.0 (Bruker AXS, 2012)' 
_computing_data_reduction         'Apex2 v2012.2.0 (Bruker AXS, 2012)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'X-Seed (Barbour, 2001)' 
_computing_publication_material   'CIFTAB (Sheldrick, 1997)' 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. Two molecules of benzene of
 crystallisation were refined, with their carbon atoms anisotropic, in the
 asymmetric unit of the crystal structure. The ISOR command of Shelxl was
 used to apply a mild isotropic restraint to atom C24.
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0345P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          6102 
_refine_ls_number_parameters      387 
_refine_ls_number_restraints      6 
_refine_ls_R_factor_all           0.0994 
_refine_ls_R_factor_gt            0.0492 
_refine_ls_wR_factor_ref          0.1041 
_refine_ls_wR_factor_gt           0.0881 
_refine_ls_goodness_of_fit_ref    0.988 
_refine_ls_restrained_S_all       1.002 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
 
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 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
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 . . 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
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) . ? 
 
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 
 _geom_angle_publ_flag 
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) . . ? 
 
_diffrn_measured_fraction_theta_max    0.997 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.997 
_refine_diff_density_max    0.408 
_refine_diff_density_min   -0.495 
_refine_diff_density_rms    0.072 
