#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:47:07 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179128 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/90/4309037.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_4309037
loop_
_publ_author_name
'Sergey S. Karlov'
'Elmira Kh. Lermontova'
'Maxim V. Zabalov'
'Anastasia A. Selina'
'Andrei V. Churakov'
'Judith A. K. Howard'
'Mikhail Yu. Antipin'
'Galina S. Zaitseva'
_publ_contact_author
; Dr Galina S. Zaitseva
  Department of Chemistry, Moscow State University
  Leninskie Gory, Moscow 119899, Russia
;
_publ_contact_author_email       zait@org.chem.msu.su
_publ_section_title
;
Synthesis, X-ray Diffraction Studies, and DFT Calculations on
Hexacoordinated Germanium Derivatives: The Case of Germaspirobis(ocanes)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4879
_journal_page_last               4886
_journal_paper_doi               10.1021/ic048165m
_journal_volume                  44
_journal_year                    2005
_chemical_formula_moiety         'C20 H26 Ge N2 O4, C7 H8'
_chemical_formula_sum            'C27 H34 Ge N2 O4'
_chemical_formula_weight         523.15
_chemical_name_systematic
; 
Bis(N-phenyl-diethanolamine)germanium toluene solvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 118.135(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.0253(7)
_cell_length_b                   18.4791(7)
_cell_length_c                   17.4343(7)
_cell_measurement_reflns_used    7473
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.021
_cell_measurement_theta_min      2.204
_cell_volume                     4836.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27669
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_T_max  0.7805
_exptl_absorpt_correction_T_min  0.7805
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.568
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     885
_refine_ls_number_reflns         11658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0605P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                7700
_reflns_number_total             11658
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic048165msi20041228_094930_2.cif
_cod_data_source_block           z
_cod_database_code               4309037
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge1 Ge 0.761391(15) -0.141159(12) 1.254694(15) 0.01948(8) Uani 1 1 d . . .
N1 N 0.62582(13) -0.05641(10) 1.10154(14) 0.0264(5) Uani 1 1 d . . .
O11 O 0.68395(10) -0.20165(8) 1.17844(11) 0.0239(4) Uani 1 1 d . . .
O12 O 0.81038(10) -0.08880(9) 1.20476(10) 0.0258(4) Uani 1 1 d . . .
C11 C 0.59172(15) -0.18040(13) 1.13241(17) 0.0243(5) Uani 1 1 d . . .
C12 C 0.57600(16) -0.12251(14) 1.06467(17) 0.0257(5) Uani 1 1 d . . .
C13 C 0.77092(16) -0.08995(14) 1.11252(16) 0.0262(5) Uani 1 1 d . . .
C14 C 0.69173(19) -0.03950(16) 1.0724(2) 0.0333(6) Uani 1 1 d . . .
C15 C 0.58702(14) -0.00074(12) 1.12681(15) 0.0216(5) Uani 1 1 d . . .
C16 C 0.50977(16) -0.01270(13) 1.13454(17) 0.0269(5) Uani 1 1 d . . .
C17 C 0.47196(16) 0.04152(14) 1.16131(17) 0.0296(6) Uani 1 1 d . . .
C18 C 0.50837(18) 0.11000(14) 1.18025(17) 0.0301(6) Uani 1 1 d . . .
C19 C 0.58586(18) 0.12298(15) 1.17462(16) 0.0311(6) Uani 1 1 d . . .
C20 C 0.62492(16) 0.06872(13) 1.14873(16) 0.0260(5) Uani 1 1 d . . .
N2 N 0.88197(12) -0.05623(10) 1.39281(12) 0.0215(4) Uani 1 1 d . . .
O21 O 0.70098(10) -0.10552(8) 1.30348(11) 0.0260(4) Uani 1 1 d . . .
O22 O 0.84361(10) -0.20218(8) 1.32310(11) 0.0248(4) Uani 1 1 d . . .
C21 C 0.72201(17) -0.03882(15) 1.34777(18) 0.0333(6) Uani 1 1 d . . .
C22 C 0.81652(16) -0.03690(15) 1.42236(17) 0.0263(5) Uani 1 1 d . . .
C23 C 0.93268(15) -0.17614(13) 1.37226(17) 0.0233(5) Uani 1 1 d . . .
C24 C 0.93988(16) -0.11825(13) 1.43659(16) 0.0239(5) Uani 1 1 d . . .
C25 C 0.91879(15) 0.00179(12) 1.36711(15) 0.0221(5) Uani 1 1 d . . .
C26 C 0.87532(16) 0.06900(13) 1.34197(16) 0.0257(5) Uani 1 1 d . . .
C27 C 0.91082(18) 0.12545(14) 1.31597(17) 0.0309(6) Uani 1 1 d . . .
C28 C 0.99069(19) 0.11664(14) 1.31375(17) 0.0313(6) Uani 1 1 d . . .
C29 C 1.03413(17) 0.05101(14) 1.33750(17) 0.0307(6) Uani 1 1 d . . .
C30 C 0.99890(16) -0.00575(13) 1.36357(16) 0.0252(5) Uani 1 1 d . . .
Ge2 Ge 0.749990(14) 0.387393(13) 0.742720(15) 0.01874(8) Uani 1 1 d . . .
N3 N 0.61050(12) 0.30320(10) 0.58732(13) 0.0245(4) Uani 1 1 d . . .
O31 O 0.66962(10) 0.44667(8) 0.66745(10) 0.0225(3) Uani 1 1 d . . .
O32 O 0.79518(10) 0.33268(9) 0.69092(10) 0.0253(4) Uani 1 1 d . . .
C31 C 0.57776(15) 0.42546(13) 0.62416(16) 0.0222(5) Uani 1 1 d . . .
C32 C 0.55940(15) 0.36977(13) 0.55339(16) 0.0227(5) Uani 1 1 d . . .
C33 C 0.75532(16) 0.33678(14) 0.59812(15) 0.0254(5) Uani 1 1 d . . .
C34 C 0.67469(17) 0.28776(14) 0.55626(18) 0.0278(6) Uani 1 1 d . . .
C35 C 0.57692(15) 0.24717(12) 0.61748(15) 0.0216(5) Uani 1 1 d . . .
C36 C 0.49761(15) 0.25621(13) 0.62345(16) 0.0257(5) Uani 1 1 d . . .
C37 C 0.46458(17) 0.20076(14) 0.65398(17) 0.0300(6) Uani 1 1 d . . .
C38 C 0.50825(18) 0.13552(13) 0.67989(17) 0.0305(6) Uani 1 1 d . . .
C39 C 0.58686(18) 0.12640(15) 0.67594(17) 0.0302(6) Uani 1 1 d . . .
C40 C 0.62123(16) 0.18071(13) 0.64615(16) 0.0260(5) Uani 1 1 d . . .
N4 N 0.87506(12) 0.30578(10) 0.87988(12) 0.0209(4) Uani 1 1 d . . .
O41 O 0.69223(10) 0.35147(8) 0.79444(10) 0.0233(4) Uani 1 1 d . . .
O42 O 0.83248(10) 0.44992(8) 0.80666(11) 0.0259(4) Uani 1 1 d . . .
C41 C 0.71805(16) 0.28544(13) 0.84218(17) 0.0268(5) Uani 1 1 d . . .
C42 C 0.81281(16) 0.28822(14) 0.91420(16) 0.0240(5) Uani 1 1 d . . .
C43 C 0.92262(15) 0.42536(13) 0.85359(17) 0.0257(5) Uani 1 1 d . . .
C44 C 0.93377(15) 0.36819(13) 0.92049(17) 0.0240(5) Uani 1 1 d . . .
C45 C 0.91050(14) 0.24666(12) 0.85448(14) 0.0212(5) Uani 1 1 d . . .
C46 C 0.87090(16) 0.17843(12) 0.83877(16) 0.0238(5) Uani 1 1 d . . .
C47 C 0.90647(17) 0.12091(14) 0.81410(16) 0.0283(5) Uani 1 1 d . . .
C48 C 0.98254(17) 0.12946(14) 0.80492(17) 0.0285(6) Uani 1 1 d . . .
C49 C 1.02113(17) 0.19684(14) 0.81875(17) 0.0293(6) Uani 1 1 d . . .
C50 C 0.98628(15) 0.25488(13) 0.84327(16) 0.0243(5) Uani 1 1 d . . .
C61 C 0.70915(15) 0.08505(12) 0.50262(15) 0.0238(5) Uani 1 1 d . . .
C62 C 0.78670(16) 0.11021(13) 0.57430(17) 0.0272(6) Uani 1 1 d . . .
C63 C 0.83662(16) 0.16506(14) 0.56522(19) 0.0330(6) Uani 1 1 d . . .
C64 C 0.81154(17) 0.19585(14) 0.48456(19) 0.0323(6) Uani 1 1 d . . .
C65 C 0.73479(18) 0.17211(14) 0.41308(18) 0.0308(6) Uani 1 1 d . . .
C66 C 0.68407(17) 0.11801(14) 0.42228(17) 0.0283(6) Uani 1 1 d . . .
C67 C 0.6561(2) 0.02542(16) 0.5138(2) 0.0342(6) Uani 1 1 d . . .
C71 C 0.71294(15) 0.15864(12) 0.99980(16) 0.0258(5) Uani 1 1 d . . .
C72 C 0.79033(16) 0.13857(13) 1.07437(17) 0.0277(6) Uani 1 1 d . . .
C73 C 0.84528(16) 0.08487(15) 1.07139(19) 0.0330(6) Uani 1 1 d . . .
C74 C 0.82525(17) 0.05028(14) 0.99406(19) 0.0330(6) Uani 1 1 d . . .
C75 C 0.74863(18) 0.06928(13) 0.91933(18) 0.0311(6) Uani 1 1 d . . .
C76 C 0.69347(16) 0.12244(14) 0.92259(17) 0.0277(5) Uani 1 1 d . . .
C77 C 0.6544(2) 0.21747(16) 1.0040(2) 0.0359(7) Uani 1 1 d . . .
H11A H 0.5730(14) -0.1647(11) 1.1724(14) 0.012(6) Uiso 1 1 d . . .
H11B H 0.5604(15) -0.2219(12) 1.0994(15) 0.019(6) Uiso 1 1 d . . .
H12A H 0.5941(17) -0.1407(13) 1.0262(17) 0.031(7) Uiso 1 1 d . . .
H12B H 0.5114(18) -0.1145(13) 1.0321(17) 0.034(8) Uiso 1 1 d . . .
H13A H 0.7497(16) -0.1429(12) 1.0887(16) 0.031(7) Uiso 1 1 d . . .
H13B H 0.8177(16) -0.0731(12) 1.0959(16) 0.030(7) Uiso 1 1 d . . .
H14A H 0.7147(17) 0.0049(15) 1.0900(17) 0.039(8) Uiso 1 1 d . . .
H14B H 0.6637(19) -0.0392(15) 1.012(2) 0.052(9) Uiso 1 1 d . . .
H16A H 0.4855(18) -0.0544(14) 1.1272(18) 0.044(9) Uiso 1 1 d . . .
H17A H 0.4181(17) 0.0276(13) 1.1654(16) 0.035(7) Uiso 1 1 d . . .
H18A H 0.4856(18) 0.1423(13) 1.1963(18) 0.029(8) Uiso 1 1 d . . .
H19A H 0.618(2) 0.1669(17) 1.189(2) 0.059(10) Uiso 1 1 d . . .
H20A H 0.6795(17) 0.0820(14) 1.1492(17) 0.035(7) Uiso 1 1 d . . .
H21A H 0.684(2) -0.0449(16) 1.386(2) 0.068(10) Uiso 1 1 d . . .
H21B H 0.7123(19) 0.0061(15) 1.3010(18) 0.059(9) Uiso 1 1 d . . .
H22A H 0.8288(17) 0.0055(15) 1.4527(17) 0.040(8) Uiso 1 1 d . . .
H22B H 0.811(2) -0.0802(18) 1.453(2) 0.075(11) Uiso 1 1 d . . .
H23A H 0.9498(16) -0.1595(13) 1.3341(16) 0.024(7) Uiso 1 1 d . . .
H23B H 0.9676(15) -0.2146(12) 1.4053(15) 0.018(6) Uiso 1 1 d . . .
H24A H 0.9216(15) -0.1381(11) 1.4753(15) 0.014(6) Uiso 1 1 d . . .
H24B H 1.0045(18) -0.1031(13) 1.4746(17) 0.035(8) Uiso 1 1 d . . .
H26A H 0.8218(16) 0.0767(13) 1.3433(16) 0.028(7) Uiso 1 1 d . . .
H27A H 0.873(2) 0.1644(17) 1.298(2) 0.057(10) Uiso 1 1 d . . .
H28A H 1.0098(18) 0.1481(14) 1.2962(17) 0.028(8) Uiso 1 1 d . . .
H29A H 1.0924(16) 0.0413(12) 1.3387(15) 0.025(6) Uiso 1 1 d . . .
H30A H 1.0323(16) -0.0451(13) 1.3796(16) 0.027(7) Uiso 1 1 d . . .
H31A H 0.5427(15) 0.4663(12) 0.5940(15) 0.021(6) Uiso 1 1 d . . .
H31B H 0.5620(16) 0.4062(13) 0.6674(16) 0.026(7) Uiso 1 1 d . . .
H32A H 0.492(2) 0.3607(14) 0.5202(19) 0.052(9) Uiso 1 1 d . . .
H32B H 0.5736(15) 0.3875(11) 0.5101(15) 0.019(6) Uiso 1 1 d . . .
H33A H 0.8000(16) 0.3180(13) 0.5829(16) 0.034(7) Uiso 1 1 d . . .
H33B H 0.7341(15) 0.3891(11) 0.5741(15) 0.021(6) Uiso 1 1 d . . .
H34A H 0.6483(17) 0.2936(13) 0.4970(18) 0.036(8) Uiso 1 1 d . . .
H34B H 0.6971(16) 0.2427(14) 0.5681(16) 0.031(7) Uiso 1 1 d . . .
H36A H 0.4635(16) 0.2969(13) 0.6069(15) 0.025(6) Uiso 1 1 d . . .
H37A H 0.4073(17) 0.2125(13) 0.6573(17) 0.038(7) Uiso 1 1 d . . .
H38A H 0.4882(17) 0.1014(14) 0.6987(17) 0.030(7) Uiso 1 1 d . . .
H39A H 0.6180(19) 0.0895(16) 0.6917(19) 0.042(9) Uiso 1 1 d . . .
H40A H 0.6715(19) 0.1727(16) 0.6452(18) 0.044(8) Uiso 1 1 d . . .
H41A H 0.7068(15) 0.2434(12) 0.7957(15) 0.027(6) Uiso 1 1 d . . .
H41B H 0.6805(17) 0.2820(13) 0.8735(17) 0.043(8) Uiso 1 1 d . . .
H42A H 0.8159(17) 0.3316(14) 0.9550(17) 0.040(8) Uiso 1 1 d . . .
H42B H 0.8299(16) 0.2456(14) 0.9475(16) 0.032(7) Uiso 1 1 d . . .
H43A H 0.9574(16) 0.4653(13) 0.8850(16) 0.029(7) Uiso 1 1 d . . .
H43B H 0.9394(15) 0.4076(12) 0.8114(16) 0.023(6) Uiso 1 1 d . . .
H44A H 0.9971(19) 0.3528(13) 0.9492(18) 0.038(8) Uiso 1 1 d . . .
H44B H 0.9199(16) 0.3905(12) 0.9633(16) 0.021(7) Uiso 1 1 d . . .
H46A H 0.8209(16) 0.1693(13) 0.8433(16) 0.025(7) Uiso 1 1 d . . .
H47A H 0.8776(19) 0.0817(15) 0.8077(18) 0.041(8) Uiso 1 1 d . . .
H48A H 1.005(2) 0.0956(15) 0.7893(19) 0.050(9) Uiso 1 1 d . . .
H49A H 1.0736(18) 0.2035(14) 0.8130(17) 0.041(8) Uiso 1 1 d . . .
H50A H 1.0195(16) 0.2964(13) 0.8547(15) 0.025(7) Uiso 1 1 d . . .
H62A H 0.8035(15) 0.0877(12) 0.6287(15) 0.021(6) Uiso 1 1 d . . .
H63A H 0.8865(17) 0.1828(13) 0.6176(17) 0.037(7) Uiso 1 1 d . . .
H64A H 0.8468(15) 0.2321(12) 0.4772(15) 0.021(6) Uiso 1 1 d . . .
H65A H 0.7169(16) 0.1934(13) 0.3560(17) 0.032(7) Uiso 1 1 d . . .
H66A H 0.6330(16) 0.1011(12) 0.3747(16) 0.024(7) Uiso 1 1 d . . .
H67A H 0.691(2) -0.0122(17) 0.546(2) 0.067(11) Uiso 1 1 d . . .
H67B H 0.6162(19) 0.0023(14) 0.4569(19) 0.051(9) Uiso 1 1 d . . .
H67C H 0.624(2) 0.0403(18) 0.542(2) 0.084(12) Uiso 1 1 d . . .
H72A H 0.8034(15) 0.1658(12) 1.1282(16) 0.026(6) Uiso 1 1 d . . .
H73A H 0.8976(18) 0.0706(14) 1.1252(18) 0.045(8) Uiso 1 1 d . . .
H74A H 0.8651(16) 0.0152(13) 0.9942(16) 0.027(7) Uiso 1 1 d . . .
H75A H 0.7337(17) 0.0462(13) 0.8659(17) 0.040(8) Uiso 1 1 d . . .
H76A H 0.6398(16) 0.1350(12) 0.8707(16) 0.026(7) Uiso 1 1 d . . .
H77A H 0.6068(19) 0.2266(14) 0.9514(19) 0.045(9) Uiso 1 1 d . . .
H77B H 0.692(2) 0.2685(18) 1.030(2) 0.081(11) Uiso 1 1 d . . .
H77C H 0.636(2) 0.2079(16) 1.043(2) 0.060(10) Uiso 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'
N N 0.0061 0.0033 '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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O21 Ge1 O12 124.19(8) . . ?
O21 Ge1 O22 112.10(8) . . ?
O12 Ge1 O22 106.16(7) . . ?
O21 Ge1 O11 101.78(7) . . ?
O12 Ge1 O11 109.72(7) . . ?
O22 Ge1 O11 100.28(8) . . ?
O21 Ge1 N2 74.35(6) . . ?
O12 Ge1 N2 77.87(6) . . ?
O22 Ge1 N2 75.45(6) . . ?
O11 Ge1 N2 172.23(7) . . ?
O21 Ge1 N1 81.63(7) . . ?
O12 Ge1 N1 67.58(6) . . ?
O22 Ge1 N1 165.37(7) . . ?
O11 Ge1 N1 70.93(6) . . ?
N2 Ge1 N1 114.56(6) . . ?
C15 N1 C12 119.54(19) . . ?
C15 N1 C14 120.2(2) . . ?
C12 N1 C14 114.1(2) . . ?
C15 N1 Ge1 112.35(14) . . ?
C12 N1 Ge1 89.91(13) . . ?
C14 N1 Ge1 91.48(14) . . ?
C11 O11 Ge1 118.60(14) . . ?
C13 O12 Ge1 118.17(14) . . ?
O11 C11 C12 111.8(2) . . ?
O11 C11 H11A 109.5(13) . . ?
C12 C11 H11A 111.2(13) . . ?
O11 C11 H11B 105.6(13) . . ?
C12 C11 H11B 104.6(13) . . ?
H11A C11 H11B 113.9(19) . . ?
N1 C12 C11 113.3(2) . . ?
N1 C12 H12A 107.6(16) . . ?
C11 C12 H12A 108.1(16) . . ?
N1 C12 H12B 112.9(15) . . ?
C11 C12 H12B 107.2(15) . . ?
H12A C12 H12B 107(2) . . ?
O12 C13 C14 110.9(2) . . ?
O12 C13 H13A 110.5(13) . . ?
C14 C13 H13A 108.9(13) . . ?
O12 C13 H13B 107.6(14) . . ?
C14 C13 H13B 109.1(13) . . ?
H13A C13 H13B 109.9(18) . . ?
N1 C14 C13 111.7(2) . . ?
N1 C14 H14A 111.0(17) . . ?
C13 C14 H14A 104.8(18) . . ?
N1 C14 H14B 109.1(18) . . ?
C13 C14 H14B 113.3(18) . . ?
H14A C14 H14B 107(2) . . ?
N1 C15 C16 121.2(2) . . ?
N1 C15 C20 122.1(2) . . ?
C16 C15 C20 116.7(2) . . ?
C17 C16 C15 121.6(2) . . ?
C17 C16 H16A 115.7(19) . . ?
C15 C16 H16A 122.5(19) . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17A 123.4(15) . . ?
C16 C17 H17A 115.5(15) . . ?
C17 C18 C19 118.4(2) . . ?
C17 C18 H18A 120.9(19) . . ?
C19 C18 H18A 120.7(19) . . ?
C18 C19 C20 120.9(2) . . ?
C18 C19 H19A 125.4(19) . . ?
C20 C19 H19A 113.6(19) . . ?
C19 C20 C15 121.2(2) . . ?
C19 C20 H20A 115.0(16) . . ?
C15 C20 H20A 123.7(16) . . ?
C25 N2 C24 117.77(18) . . ?
C25 N2 C22 116.54(19) . . ?
C24 N2 C22 116.10(19) . . ?
C25 N2 Ge1 114.02(14) . . ?
C24 N2 Ge1 92.86(13) . . ?
C22 N2 Ge1 93.90(13) . . ?
C21 O21 Ge1 122.83(15) . . ?
C23 O22 Ge1 118.19(14) . . ?
O21 C21 C22 112.5(2) . . ?
O21 C21 H21A 99.6(16) . . ?
C22 C21 H21A 99.7(16) . . ?
O21 C21 H21B 109.7(14) . . ?
C22 C21 H21B 109.8(15) . . ?
H21A C21 H21B 125(2) . . ?
N2 C22 C21 111.4(2) . . ?
N2 C22 H22A 113.9(17) . . ?
C21 C22 H22A 112.2(17) . . ?
N2 C22 H22B 106.4(19) . . ?
C21 C22 H22B 96.2(19) . . ?
H22A C22 H22B 115(2) . . ?
O22 C23 C24 112.03(19) . . ?
O22 C23 H23A 107.1(16) . . ?
C24 C23 H23A 111.5(16) . . ?
O22 C23 H23B 107.6(14) . . ?
C24 C23 H23B 106.0(14) . . ?
H23A C23 H23B 113(2) . . ?
N2 C24 C23 111.5(2) . . ?
N2 C24 H24A 108.0(13) . . ?
C23 C24 H24A 108.6(14) . . ?
N2 C24 H24B 112.1(14) . . ?
C23 C24 H24B 111.2(14) . . ?
H24A C24 H24B 105(2) . . ?
C30 C25 C26 117.0(2) . . ?
C30 C25 N2 121.6(2) . . ?
C26 C25 N2 121.4(2) . . ?
C27 C26 C25 121.4(2) . . ?
C27 C26 H26A 118.4(16) . . ?
C25 C26 H26A 120.3(16) . . ?
C26 C27 C28 120.4(3) . . ?
C26 C27 H27A 111(2) . . ?
C28 C27 H27A 129(2) . . ?
C29 C28 C27 119.3(2) . . ?
C29 C28 H28A 120(2) . . ?
C27 C28 H28A 121(2) . . ?
C28 C29 C30 120.7(2) . . ?
C28 C29 H29A 123.4(13) . . ?
C30 C29 H29A 115.9(13) . . ?
C29 C30 C25 121.3(2) . . ?
C29 C30 H30A 114.4(16) . . ?
C25 C30 H30A 124.3(16) . . ?
O41 Ge2 O42 113.52(8) . . ?
O41 Ge2 O32 122.40(8) . . ?
O42 Ge2 O32 107.01(8) . . ?
O41 Ge2 O31 101.08(7) . . ?
O42 Ge2 O31 99.90(8) . . ?
O32 Ge2 O31 110.47(7) . . ?
O41 Ge2 N4 74.89(6) . . ?
O42 Ge2 N4 75.61(6) . . ?
O32 Ge2 N4 77.67(6) . . ?
O31 Ge2 N4 171.71(6) . . ?
O41 Ge2 N3 82.70(7) . . ?
O42 Ge2 N3 162.59(7) . . ?
O32 Ge2 N3 66.21(6) . . ?
O31 Ge2 N3 69.51(6) . . ?
N4 Ge2 N3 116.52(5) . . ?
C35 N3 C34 120.34(19) . . ?
C35 N3 C32 120.28(18) . . ?
C34 N3 C32 114.9(2) . . ?
C35 N3 Ge2 109.14(14) . . ?
C34 N3 Ge2 91.35(13) . . ?
C32 N3 Ge2 89.76(12) . . ?
C31 O31 Ge2 119.58(14) . . ?
C33 O32 Ge2 117.50(14) . . ?
O31 C31 C32 111.57(19) . . ?
O31 C31 H31A 108.6(14) . . ?
C32 C31 H31A 104.6(14) . . ?
O31 C31 H31B 108.7(14) . . ?
C32 C31 H31B 110.7(14) . . ?
H31A C31 H31B 112.7(19) . . ?
N3 C32 C31 112.7(2) . . ?
N3 C32 H32A 112.7(15) . . ?
C31 C32 H32A 108.2(16) . . ?
N3 C32 H32B 106.6(13) . . ?
C31 C32 H32B 112.2(14) . . ?
H32A C32 H32B 104(2) . . ?
O32 C33 C34 110.6(2) . . ?
O32 C33 H33A 105.8(15) . . ?
C34 C33 H33A 107.5(14) . . ?
O32 C33 H33B 113.0(12) . . ?
C34 C33 H33B 107.2(12) . . ?
H33A C33 H33B 112.6(18) . . ?
N3 C34 C33 111.8(2) . . ?
N3 C34 H34A 110.0(16) . . ?
C33 C34 H34A 108.8(16) . . ?
N3 C34 H34B 114.1(16) . . ?
C33 C34 H34B 104.6(16) . . ?
H34A C34 H34B 107(2) . . ?
N3 C35 C40 122.3(2) . . ?
N3 C35 C36 121.0(2) . . ?
C40 C35 C36 116.7(2) . . ?
C37 C36 C35 121.0(2) . . ?
C37 C36 H36A 114.7(15) . . ?
C35 C36 H36A 124.3(15) . . ?
C38 C37 C36 121.2(2) . . ?
C38 C37 H37A 123.2(14) . . ?
C36 C37 H37A 115.6(14) . . ?
C37 C38 C39 118.5(2) . . ?
C37 C38 H38A 121.4(18) . . ?
C39 C38 H38A 120.1(18) . . ?
C40 C39 C38 121.5(2) . . ?
C40 C39 H39A 114(2) . . ?
C38 C39 H39A 125(2) . . ?
C39 C40 C35 121.2(2) . . ?
C39 C40 H40A 118(2) . . ?
C35 C40 H40A 120(2) . . ?
C45 N4 C44 117.53(18) . . ?
C45 N4 C42 116.73(18) . . ?
C44 N4 C42 115.57(19) . . ?
C45 N4 Ge2 114.59(13) . . ?
C44 N4 Ge2 93.43(12) . . ?
C42 N4 Ge2 93.60(12) . . ?
C41 O41 Ge2 122.19(14) . . ?
C43 O42 Ge2 118.44(14) . . ?
O41 C41 C42 111.8(2) . . ?
O41 C41 H41A 106.5(12) . . ?
C42 C41 H41A 113.2(12) . . ?
O41 C41 H41B 105.6(14) . . ?
C42 C41 H41B 104.5(15) . . ?
H41A C41 H41B 115.1(19) . . ?
N4 C42 C41 111.13(19) . . ?
N4 C42 H42A 106.7(14) . . ?
C41 C42 H42A 106.3(14) . . ?
N4 C42 H42B 111.2(15) . . ?
C41 C42 H42B 112.6(16) . . ?
H42A C42 H42B 109(2) . . ?
O42 C43 C44 111.8(2) . . ?
O42 C43 H43A 107.1(14) . . ?
C44 C43 H43A 106.4(15) . . ?
O42 C43 H43B 107.2(14) . . ?
C44 C43 H43B 112.0(14) . . ?
H43A C43 H43B 112(2) . . ?
N4 C44 C43 111.4(2) . . ?
N4 C44 H44A 110.4(15) . . ?
C43 C44 H44A 107.4(15) . . ?
N4 C44 H44B 110.2(14) . . ?
C43 C44 H44B 107.8(14) . . ?
H44A C44 H44B 109(2) . . ?
C46 C45 C50 117.5(2) . . ?
C46 C45 N4 121.4(2) . . ?
C50 C45 N4 121.1(2) . . ?
C47 C46 C45 120.8(2) . . ?
C47 C46 H46A 116.7(16) . . ?
C45 C46 H46A 122.5(16) . . ?
C48 C47 C46 121.1(2) . . ?
C48 C47 H47A 126.5(19) . . ?
C46 C47 H47A 112.4(19) . . ?
C49 C48 C47 118.5(2) . . ?
C49 C48 H48A 118(2) . . ?
C47 C48 H48A 123(2) . . ?
C48 C49 C50 121.0(2) . . ?
C48 C49 H49A 119.5(16) . . ?
C50 C49 H49A 119.5(16) . . ?
C49 C50 C45 121.0(2) . . ?
C49 C50 H50A 113.9(15) . . ?
C45 C50 H50A 125.0(15) . . ?
C66 C61 C62 117.6(2) . . ?
C66 C61 C67 122.3(2) . . ?
C62 C61 C67 120.1(2) . . ?
C63 C62 C61 120.9(2) . . ?
C63 C62 H62A 121.7(14) . . ?
C61 C62 H62A 117.4(14) . . ?
C62 C63 C64 120.5(3) . . ?
C62 C63 H63A 117.2(15) . . ?
C64 C63 H63A 122.2(16) . . ?
C65 C64 C63 119.5(3) . . ?
C65 C64 H64A 119.4(15) . . ?
C63 C64 H64A 121.1(15) . . ?
C66 C65 C64 120.1(3) . . ?
C66 C65 H65A 120.0(15) . . ?
C64 C65 H65A 119.9(15) . . ?
C65 C66 C61 121.4(2) . . ?
C65 C66 H66A 120.9(15) . . ?
C61 C66 H66A 117.7(15) . . ?
C61 C67 H67A 113(2) . . ?
C61 C67 H67B 110.8(16) . . ?
H67A C67 H67B 103(2) . . ?
C61 C67 H67C 113(2) . . ?
H67A C67 H67C 105(3) . . ?
H67B C67 H67C 111(3) . . ?
C72 C71 C76 117.5(2) . . ?
C72 C71 C77 120.3(2) . . ?
C76 C71 C77 122.3(2) . . ?
C73 C72 C71 121.0(2) . . ?
C73 C72 H72A 123.0(14) . . ?
C71 C72 H72A 116.0(14) . . ?
C72 C73 C74 120.6(3) . . ?
C72 C73 H73A 119.0(16) . . ?
C74 C73 H73A 120.4(16) . . ?
C73 C74 C75 119.3(2) . . ?
C73 C74 H74A 118.1(15) . . ?
C75 C74 H74A 122.5(15) . . ?
C76 C75 C74 120.0(3) . . ?
C76 C75 H75A 119.4(16) . . ?
C74 C75 H75A 120.6(16) . . ?
C75 C76 C71 121.6(2) . . ?
C75 C76 H76A 119.8(14) . . ?
C71 C76 H76A 118.6(14) . . ?
C71 C77 H77A 112.4(18) . . ?
C71 C77 H77B 111.7(17) . . ?
H77A C77 H77B 109(2) . . ?
C71 C77 H77C 112(2) . . ?
H77A C77 H77C 110(3) . . ?
H77B C77 H77C 101(2) . . ?
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 O21 1.7435(15) . ?
Ge1 O12 1.7534(15) . ?
Ge1 O22 1.7547(16) . ?
Ge1 O11 1.7613(15) . ?
Ge1 N2 2.7953(19) . ?
Ge1 N1 3.016(2) . ?
N1 C15 1.401(3) . ?
N1 C12 1.453(3) . ?
N1 C14 1.467(3) . ?
O11 C11 1.441(3) . ?
O12 C13 1.421(3) . ?
C11 C12 1.521(3) . ?
C11 H11A 0.94(2) . ?
C11 H11B 0.96(2) . ?
C12 H12A 0.92(3) . ?
C12 H12B 0.98(3) . ?
C13 C14 1.512(3) . ?
C13 H13A 1.06(2) . ?
C13 H13B 1.02(2) . ?
C14 H14A 0.90(3) . ?
C14 H14B 0.93(3) . ?
C15 C16 1.401(3) . ?
C15 C20 1.406(3) . ?
C16 C17 1.385(3) . ?
C16 H16A 0.86(3) . ?
C17 C18 1.379(3) . ?
C17 H17A 0.99(2) . ?
C18 C19 1.389(4) . ?
C18 H18A 0.83(3) . ?
C19 C20 1.391(4) . ?
C19 H19A 0.94(3) . ?
C20 H20A 0.96(3) . ?
N2 C25 1.417(3) . ?
N2 C24 1.469(3) . ?
N2 C22 1.475(3) . ?
O21 C21 1.408(3) . ?
O22 C23 1.428(3) . ?
C21 C22 1.519(3) . ?
C21 H21A 1.12(3) . ?
C21 H21B 1.12(3) . ?
C22 H22A 0.91(3) . ?
C22 H22B 1.00(3) . ?
C23 C24 1.513(3) . ?
C23 H23A 0.90(2) . ?
C23 H23B 0.93(2) . ?
C24 H24A 0.94(2) . ?
C24 H24B 1.02(3) . ?
C25 C30 1.401(3) . ?
C25 C26 1.406(3) . ?
C26 C27 1.385(4) . ?
C26 H26A 0.93(2) . ?
C27 C28 1.388(4) . ?
C27 H27A 0.91(3) . ?
C28 C29 1.379(4) . ?
C28 H28A 0.79(3) . ?
C29 C30 1.387(3) . ?
C29 H29A 1.00(2) . ?
C30 H30A 0.88(2) . ?
Ge2 O41 1.7485(15) . ?
Ge2 O42 1.7532(16) . ?
Ge2 O32 1.7564(15) . ?
Ge2 O31 1.7609(15) . ?
Ge2 N4 2.7793(19) . ?
Ge2 N3 3.055(2) . ?
N3 C35 1.400(3) . ?
N3 C34 1.458(3) . ?
N3 C32 1.461(3) . ?
O31 C31 1.434(3) . ?
O32 C33 1.431(3) . ?
C31 C32 1.522(3) . ?
C31 H31A 0.95(2) . ?
C31 H31B 0.98(2) . ?
C32 H32A 1.03(3) . ?
C32 H32B 0.95(2) . ?
C33 C34 1.514(3) . ?
C33 H33A 0.98(2) . ?
C33 H33B 1.05(2) . ?
C34 H34A 0.92(3) . ?
C34 H34B 0.90(3) . ?
C35 C40 1.404(3) . ?
C35 C36 1.412(3) . ?
C36 C37 1.390(3) . ?
C36 H36A 0.91(2) . ?
C37 C38 1.376(3) . ?
C37 H37A 1.03(3) . ?
C38 C39 1.383(4) . ?
C38 H38A 0.85(3) . ?
C39 C40 1.381(4) . ?
C39 H39A 0.83(3) . ?
C40 H40A 0.88(3) . ?
N4 C45 1.416(3) . ?
N4 C44 1.471(3) . ?
N4 C42 1.478(3) . ?
O41 C41 1.425(3) . ?
O42 C43 1.430(3) . ?
C41 C42 1.507(3) . ?
C41 H41A 1.07(2) . ?
C41 H41B 1.02(3) . ?
C42 H42A 1.06(3) . ?
C42 H42B 0.94(3) . ?
C43 C44 1.518(3) . ?
C43 H43A 0.94(2) . ?
C43 H43B 0.96(2) . ?
C44 H44A 0.99(3) . ?
C44 H44B 0.97(2) . ?
C45 C46 1.395(3) . ?
C45 C50 1.401(3) . ?
C46 C47 1.388(3) . ?
C46 H46A 0.91(2) . ?
C47 C48 1.387(4) . ?
C47 H47A 0.85(3) . ?
C48 C49 1.375(4) . ?
C48 H48A 0.85(3) . ?
C49 C50 1.387(3) . ?
C49 H49A 0.95(3) . ?
C50 H50A 0.92(2) . ?
C61 C66 1.397(3) . ?
C61 C62 1.402(3) . ?
C61 C67 1.495(3) . ?
C62 C63 1.379(4) . ?
C62 H62A 0.95(2) . ?
C63 C64 1.385(4) . ?
C63 H63A 0.96(3) . ?
C64 C65 1.385(4) . ?
C64 H64A 0.95(2) . ?
C65 C66 1.379(4) . ?
C65 H65A 0.98(2) . ?
C66 H66A 0.93(2) . ?
C67 H67A 0.92(3) . ?
C67 H67B 1.00(3) . ?
C67 H67C 0.93(4) . ?
C71 C72 1.396(3) . ?
C71 C76 1.396(3) . ?
C71 C77 1.500(4) . ?
C72 C73 1.381(4) . ?
C72 H72A 0.99(2) . ?
C73 C74 1.382(4) . ?
C73 H73A 0.98(3) . ?
C74 C75 1.385(4) . ?
C74 H74A 0.94(2) . ?
C75 C76 1.379(4) . ?
C75 H75A 0.94(3) . ?
C76 H76A 0.96(2) . ?
C77 H77A 0.91(3) . ?
C77 H77B 1.11(3) . ?
C77 H77C 0.89(3) . ?
