##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
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##############################################################################
data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2006-04-28
_journal_date_accepted     2006-05-23
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2006
_journal_volume     62
_journal_issue      7
_journal_page_first     m303
_journal_page_last     m305
_journal_paper_category     FM
_journal_coeditor_code     SQ3019
_publ_contact_author_name     'Alexander A. Korlyukov'
_publ_contact_author_address
;
28 Vavilov Street
Moscow 119991
Russian Federation
;
_publ_contact_author_email     alex@xrlab.ineos.ac.ru
_publ_contact_author_fax     '+7(495)1355085'
_publ_contact_author_phone     '+7(495)1359214'
_publ_section_title
;
Two germatranes with bulky substituents
;
loop_
    _publ_author_name
    _publ_author_address
    'Korlyukov, Alexander A.'
;
A. N. Nesmeyanov Institute of Organoelement Compounds
Russian Academy of Science
28 Vavilov Street
Moscow 119991
Russian Federation
;
    'Komissarov, Eugene A.'
;
A. N. Nesmeyanov Institute of Organoelement Compounds
Russian Academy of Science
28 Vavilov Street
Moscow 119991
Russian Federation
;
    'Alekseev, Nikolay V.'
;
State Research Institute of Chemistry and Technology of Organoelement Compounds
38 Entuziastov Sh.
Moscow 111123
Russian Federation
;
    'Pavlov, Konstantin V.'
;
State Research Institute of Chemistry and Technology of Organoelement Compounds
38 Entuziastov Sh.
Moscow 111123
Russian Federation
;
    'Krivolapova, Olga V.'
;
State Research Institute of Chemistry and Technology of Organoelement Compounds
38 Entuziastov Sh.
Moscow 111123
Russian Federation
;
    'Lachtin, Valentin G.'
;
State Research Institute of Chemistry and Technology of Organoelement Compounds
38 Entuziastov Sh.
Moscow 111123
Russian Federation
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
1-adamantyl-2,8,9-trioxa-5-aza-1-germabicyclo[3.3.3]undecane
;
_chemical_name_common     '1-adamantylgermatrane'
_chemical_formula_moiety     'C16 H27 Ge N O3'
_chemical_formula_sum     'C16 H27 Ge N O3'
_chemical_formula_iupac     '[Ge (C10 H15) (C6 H12 N O3)]'
_chemical_formula_weight     353.98
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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     10.641(6)
_cell_length_b     7.292(4)
_cell_length_c     19.943(11)
_cell_angle_alpha     90.00
_cell_angle_beta     90.001(12)
_cell_angle_gamma     90.00
_cell_volume     1547.3(14)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     898
_cell_measurement_theta_min     2.78
_cell_measurement_theta_max     30.02
_cell_measurement_temperature     120(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.520
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     744
_exptl_absorpt_coefficient_mu     1.990
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1998)'
_exptl_absorpt_correction_T_min     0.5866
_exptl_absorpt_correction_T_max     0.8258
_exptl_special_details
;
  ?
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     15300
_diffrn_reflns_av_R_equivalents     0.0593
_diffrn_reflns_av_sigmaI/netI     0.0792
_diffrn_reflns_theta_min     1.02
_diffrn_reflns_theta_max     30.03
_diffrn_reflns_theta_full     30.03
_diffrn_measured_fraction_theta_max     0.973
_diffrn_measured_fraction_theta_full     0.973
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     28
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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.
;
_reflns_number_total     4396
_reflns_number_gt     3193
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0510
_refine_ls_R_factor_gt     0.0376
_refine_ls_wR_factor_gt     0.0969
_refine_ls_wR_factor_ref     0.1077
_refine_ls_goodness_of_fit_ref     0.965
_refine_ls_restrained_S_all     0.965
_refine_ls_number_reflns     4396
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0517P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.022
_refine_diff_density_min     -0.564
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 1998)'
_computing_data_reduction     'SAINT-Plus'
_computing_structure_solution     'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Ge Ge1 0.74872(5) 0.08892(4) 0.080204(15) 0.01452(9) Uani d . 1 . .
    O O1 0.6713(3) -0.0777(4) 0.02609(13) 0.0227(6) Uani d . 1 . .
    O O2 0.9186(2) 0.1143(4) 0.07117(13) 0.0220(6) Uani d . 1 . .
    O O3 0.6560(3) 0.2863(4) 0.10614(13) 0.0235(6) Uani d . 1 . .
    N N1 0.7550(4) 0.2496(4) -0.01702(12) 0.0160(5) Uani d . 1 . .
    C C1 0.6727(4) -0.0516(5) -0.04451(18) 0.0221(8) Uani d . 1 . .
    H H1A 0.6001 -0.1156 -0.0649 0.027 Uiso calc R 1 . .
    H H1B 0.7506 -0.1047 -0.0635 0.027 Uiso calc R 1 . .
    C C2 0.9686(4) 0.2383(6) 0.02363(18) 0.0219(8) Uani d . 1 . .
    H H2A 1.0555 0.2016 0.0120 0.026 Uiso calc R 1 . .
    H H2B 0.9714 0.3631 0.0431 0.026 Uiso calc R 1 . .
    C C3 0.6147(4) 0.4150(5) 0.05792(18) 0.0206(8) Uani d . 1 . .
    H H3A 0.6006 0.5352 0.0797 0.025 Uiso calc R 1 . .
    H H3B 0.5341 0.3737 0.0383 0.025 Uiso calc R 1 . .
    C C4 0.6663(4) 0.1536(5) -0.06110(18) 0.0206(8) Uani d . 1 . .
    H H4A 0.6890 0.1743 -0.1086 0.025 Uiso calc R 1 . .
    H H4B 0.5800 0.2002 -0.0537 0.025 Uiso calc R 1 . .
    C C5 0.8877(3) 0.2389(6) -0.03910(18) 0.0203(8) Uani d . 1 . .
    H H5A 0.9089 0.3457 -0.0676 0.024 Uiso calc R 1 . .
    H H5B 0.9019 0.1256 -0.0654 0.024 Uiso calc R 1 . .
    C C6 0.7141(4) 0.4351(5) 0.00207(19) 0.0203(8) Uani d . 1 . .
    H H6A 0.6774 0.4990 -0.0371 0.024 Uiso calc R 1 . .
    H H6B 0.7865 0.5075 0.0185 0.024 Uiso calc R 1 . .
    C C7 0.7430(4) -0.0452(4) 0.16570(14) 0.0122(6) Uani d . 1 . .
    C C8 0.6081(3) -0.1016(5) 0.18285(17) 0.0156(7) Uani d . 1 . .
    H H8A 0.5757 -0.1846 0.1476 0.019 Uiso calc R 1 . .
    H H8B 0.5539 0.0088 0.1839 0.019 Uiso calc R 1 . .
    C C9 0.7931(4) 0.0828(5) 0.22203(18) 0.0205(8) Uani d . 1 . .
    H H9A 0.7418 0.1960 0.2238 0.025 Uiso calc R 1 . .
    H H9B 0.8811 0.1179 0.2122 0.025 Uiso calc R 1 . .
    C C10 0.8281(3) -0.2189(5) 0.16362(18) 0.0196(8) Uani d . 1 . .
    H H10A 0.9161 -0.1830 0.1541 0.024 Uiso calc R 1 . .
    H H10B 0.7995 -0.3023 0.1275 0.024 Uiso calc R 1 . .
    C C11 0.6020(3) -0.2001(5) 0.25195(19) 0.0173(7) Uani d . 1 . .
    H H11A 0.5132 -0.2357 0.2620 0.021 Uiso calc R 1 . .
    C C12 0.6847(4) -0.3729(5) 0.2481(2) 0.0219(9) Uani d . 1 . .
    H H12A 0.6812 -0.4396 0.2913 0.026 Uiso calc R 1 . .
    H H12B 0.6527 -0.4554 0.2126 0.026 Uiso calc R 1 . .
    C C13 0.6507(4) -0.0712(5) 0.30642(19) 0.0215(8) Uani d . 1 . .
    H H13A 0.6466 -0.1329 0.3506 0.026 Uiso calc R 1 . .
    H H13B 0.5976 0.0402 0.3083 0.026 Uiso calc R 1 . .
    C C14 0.7868(4) -0.0177(6) 0.29079(19) 0.0231(9) Uani d . 1 . .
    H H14A 0.8188 0.0657 0.3267 0.028 Uiso calc R 1 . .
    C C15 0.8210(4) -0.3190(6) 0.2326(2) 0.0236(9) Uani d . 1 . .
    H H15A 0.8744 -0.4318 0.2312 0.028 Uiso calc R 1 . .
    C C16 0.8704(4) -0.1888(6) 0.2872(2) 0.0260(9) Uani d . 1 . .
    H H16C 0.8704 -0.2522 0.3311 0.031 Uiso calc R 1 . .
    H H16A 0.9579 -0.1525 0.2767 0.031 Uiso calc R 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Ge1 O3 . 1.820(3) ?
    Ge1 O1 . 1.822(3) ?
    Ge1 O2 . 1.825(3) ?
    Ge1 C7 . 1.966(3) ?
    Ge1 N1 . 2.266(3) ?
    O1 C1 . 1.421(4) ?
    O2 C2 . 1.414(4) ?
    O3 C3 . 1.414(4) ?
    N1 C4 . 1.468(5) ?
    N1 C6 . 1.471(5) ?
    N1 C5 . 1.481(5) ?
    C1 C4 . 1.534(6) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 C5 . 1.518(5) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C6 . 1.543(5) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 C8 . 1.531(6) ?
    C7 C9 . 1.555(5) ?
    C7 C10 . 1.559(5) ?
    C8 C11 . 1.555(5) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C14 . 1.556(5) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C15 . 1.559(5) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 C13 . 1.527(5) ?
    C11 C12 . 1.539(5) ?
    C11 H11A . 1.0000 ?
    C12 C15 . 1.534(5) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C14 . 1.532(6) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 C16 . 1.534(6) ?
    C14 H14A . 1.0000 ?
    C15 C16 . 1.537(6) ?
    C15 H15A . 1.0000 ?
    C16 H16C . 0.9900 ?
    C16 H16A . 0.9900 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O3 Ge1 O1 . . 116.78(14) ?
    O3 Ge1 O2 . . 118.99(13) ?
    O1 Ge1 O2 . . 117.17(13) ?
    O3 Ge1 C7 . . 97.46(13) ?
    O1 Ge1 C7 . . 99.67(13) ?
    O2 Ge1 C7 . . 99.60(16) ?
    O3 Ge1 N1 . . 81.40(11) ?
    O1 Ge1 N1 . . 81.45(12) ?
    O2 Ge1 N1 . . 80.43(13) ?
    C7 Ge1 N1 . . 178.69(11) ?
    C1 O1 Ge1 . . 119.5(2) ?
    C2 O2 Ge1 . . 120.3(2) ?
    C3 O3 Ge1 . . 120.0(2) ?
    C4 N1 C6 . . 113.7(3) ?
    C4 N1 C5 . . 114.2(3) ?
    C6 N1 C5 . . 114.1(3) ?
    C4 N1 Ge1 . . 104.3(2) ?
    C6 N1 Ge1 . . 104.2(2) ?
    C5 N1 Ge1 . . 104.8(2) ?
    O1 C1 C4 . . 110.1(3) ?
    O1 C1 H1A . . 109.6 ?
    C4 C1 H1A . . 109.6 ?
    O1 C1 H1B . . 109.6 ?
    C4 C1 H1B . . 109.6 ?
    H1A C1 H1B . . 108.2 ?
    O2 C2 C5 . . 109.9(3) ?
    O2 C2 H2A . . 109.7 ?
    C5 C2 H2A . . 109.7 ?
    O2 C2 H2B . . 109.7 ?
    C5 C2 H2B . . 109.7 ?
    H2A C2 H2B . . 108.2 ?
    O3 C3 C6 . . 109.9(3) ?
    O3 C3 H3A . . 109.7 ?
    C6 C3 H3A . . 109.7 ?
    O3 C3 H3B . . 109.7 ?
    C6 C3 H3B . . 109.7 ?
    H3A C3 H3B . . 108.2 ?
    N1 C4 C1 . . 107.9(3) ?
    N1 C4 H4A . . 110.1 ?
    C1 C4 H4A . . 110.1 ?
    N1 C4 H4B . . 110.1 ?
    C1 C4 H4B . . 110.1 ?
    H4A C4 H4B . . 108.4 ?
    N1 C5 C2 . . 107.2(3) ?
    N1 C5 H5A . . 110.3 ?
    C2 C5 H5A . . 110.3 ?
    N1 C5 H5B . . 110.3 ?
    C2 C5 H5B . . 110.3 ?
    H5A C5 H5B . . 108.5 ?
    N1 C6 C3 . . 107.6(3) ?
    N1 C6 H6A . . 110.2 ?
    C3 C6 H6A . . 110.2 ?
    N1 C6 H6B . . 110.2 ?
    C3 C6 H6B . . 110.2 ?
    H6A C6 H6B . . 108.5 ?
    C8 C7 C9 . . 108.7(3) ?
    C8 C7 C10 . . 109.4(3) ?
    C9 C7 C10 . . 107.9(3) ?
    C8 C7 Ge1 . . 110.9(2) ?
    C9 C7 Ge1 . . 108.5(2) ?
    C10 C7 Ge1 . . 111.3(2) ?
    C7 C8 C11 . . 111.2(3) ?
    C7 C8 H8A . . 109.4 ?
    C11 C8 H8A . . 109.4 ?
    C7 C8 H8B . . 109.4 ?
    C11 C8 H8B . . 109.4 ?
    H8A C8 H8B . . 108.0 ?
    C7 C9 C14 . . 109.8(3) ?
    C7 C9 H9A . . 109.7 ?
    C14 C9 H9A . . 109.7 ?
    C7 C9 H9B . . 109.7 ?
    C14 C9 H9B . . 109.7 ?
    H9A C9 H9B . . 108.2 ?
    C7 C10 C15 . . 109.2(3) ?
    C7 C10 H10A . . 109.8 ?
    C15 C10 H10A . . 109.8 ?
    C7 C10 H10B . . 109.8 ?
    C15 C10 H10B . . 109.8 ?
    H10A C10 H10B . . 108.3 ?
    C13 C11 C12 . . 110.2(3) ?
    C13 C11 C8 . . 109.4(3) ?
    C12 C11 C8 . . 108.0(3) ?
    C13 C11 H11A . . 109.7 ?
    C12 C11 H11A . . 109.7 ?
    C8 C11 H11A . . 109.7 ?
    C15 C12 C11 . . 109.9(3) ?
    C15 C12 H12A . . 109.7 ?
    C11 C12 H12A . . 109.7 ?
    C15 C12 H12B . . 109.7 ?
    C11 C12 H12B . . 109.7 ?
    H12A C12 H12B . . 108.2 ?
    C11 C13 C14 . . 109.5(3) ?
    C11 C13 H13A . . 109.8 ?
    C14 C13 H13A . . 109.8 ?
    C11 C13 H13B . . 109.8 ?
    C14 C13 H13B . . 109.8 ?
    H13A C13 H13B . . 108.2 ?
    C13 C14 C16 . . 110.5(3) ?
    C13 C14 C9 . . 109.9(3) ?
    C16 C14 C9 . . 108.4(3) ?
    C13 C14 H14A . . 109.3 ?
    C16 C14 H14A . . 109.3 ?
    C9 C14 H14A . . 109.3 ?
    C12 C15 C16 . . 109.9(4) ?
    C12 C15 C10 . . 110.1(3) ?
    C16 C15 C10 . . 108.6(3) ?
    C12 C15 H15A . . 109.4 ?
    C16 C15 H15A . . 109.4 ?
    C10 C15 H15A . . 109.4 ?
    C14 C16 C15 . . 109.7(3) ?
    C14 C16 H16C . . 109.7 ?
    C15 C16 H16C . . 109.7 ?
    C14 C16 H16A . . 109.7 ?
    C15 C16 H16A . . 109.7 ?
    H16C C16 H16A . . 108.2 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O3 Ge1 O1 C1 . . . . 87.0(3) ?
    O2 Ge1 O1 C1 . . . . -63.4(3) ?
    C7 Ge1 O1 C1 . . . . -169.5(3) ?
    N1 Ge1 O1 C1 . . . . 11.2(3) ?
    O3 Ge1 O2 C2 . . . . -62.0(3) ?
    O1 Ge1 O2 C2 . . . . 87.7(3) ?
    C7 Ge1 O2 C2 . . . . -166.1(3) ?
    N1 Ge1 O2 C2 . . . . 12.5(3) ?
    O1 Ge1 O3 C3 . . . . -65.1(3) ?
    O2 Ge1 O3 C3 . . . . 84.8(3) ?
    C7 Ge1 O3 C3 . . . . -169.9(3) ?
    N1 Ge1 O3 C3 . . . . 10.8(3) ?
    O3 Ge1 N1 C4 . . . . -104.2(2) ?
    O1 Ge1 N1 C4 . . . . 14.7(2) ?
    O2 Ge1 N1 C4 . . . . 134.3(2) ?
    O3 Ge1 N1 C6 . . . . 15.3(2) ?
    O1 Ge1 N1 C6 . . . . 134.2(3) ?
    O2 Ge1 N1 C6 . . . . -106.2(2) ?
    O3 Ge1 N1 C5 . . . . 135.4(2) ?
    O1 Ge1 N1 C5 . . . . -105.6(2) ?
    O2 Ge1 N1 C5 . . . . 13.9(2) ?
    Ge1 O1 C1 C4 . . . . -34.7(4) ?
    Ge1 O2 C2 C5 . . . . -36.7(4) ?
    Ge1 O3 C3 C6 . . . . -34.3(4) ?
    C6 N1 C4 C1 . . . . -147.0(3) ?
    C5 N1 C4 C1 . . . . 79.7(4) ?
    Ge1 N1 C4 C1 . . . . -34.2(3) ?
    O1 C1 C4 N1 . . . . 45.3(4) ?
    C4 N1 C5 C2 . . . . -147.6(3) ?
    C6 N1 C5 C2 . . . . 79.2(4) ?
    Ge1 N1 C5 C2 . . . . -34.1(3) ?
    O2 C2 C5 N1 . . . . 45.8(4) ?
    C4 N1 C6 C3 . . . . 78.4(4) ?
    C5 N1 C6 C3 . . . . -148.2(3) ?
    Ge1 N1 C6 C3 . . . . -34.5(3) ?
    O3 C3 C6 N1 . . . . 45.3(4) ?
    O3 Ge1 C7 C8 . . . . 64.0(2) ?
    O1 Ge1 C7 C8 . . . . -54.9(2) ?
    O2 Ge1 C7 C8 . . . . -174.8(2) ?
    O3 Ge1 C7 C9 . . . . -55.3(3) ?
    O1 Ge1 C7 C9 . . . . -174.2(3) ?
    O2 Ge1 C7 C9 . . . . 65.9(3) ?
    O3 Ge1 C7 C10 . . . . -173.9(3) ?
    O1 Ge1 C7 C10 . . . . 67.2(3) ?
    O2 Ge1 C7 C10 . . . . -52.7(3) ?
    C9 C7 C8 C11 . . . . -58.2(4) ?
    C10 C7 C8 C11 . . . . 59.4(4) ?
    Ge1 C7 C8 C11 . . . . -177.5(2) ?
    C8 C7 C9 C14 . . . . 57.9(4) ?
    C10 C7 C9 C14 . . . . -60.7(4) ?
    Ge1 C7 C9 C14 . . . . 178.6(3) ?
    C8 C7 C10 C15 . . . . -57.6(4) ?
    C9 C7 C10 C15 . . . . 60.6(4) ?
    Ge1 C7 C10 C15 . . . . 179.6(3) ?
    C7 C8 C11 C13 . . . . 59.6(4) ?
    C7 C8 C11 C12 . . . . -60.3(4) ?
    C13 C11 C12 C15 . . . . -59.1(4) ?
    C8 C11 C12 C15 . . . . 60.4(4) ?
    C12 C11 C13 C14 . . . . 58.9(4) ?
    C8 C11 C13 C14 . . . . -59.7(4) ?
    C11 C13 C14 C16 . . . . -59.1(4) ?
    C11 C13 C14 C9 . . . . 60.6(4) ?
    C7 C9 C14 C13 . . . . -59.7(4) ?
    C7 C9 C14 C16 . . . . 61.2(4) ?
    C11 C12 C15 C16 . . . . 58.6(4) ?
    C11 C12 C15 C10 . . . . -61.0(4) ?
    C7 C10 C15 C12 . . . . 58.8(4) ?
    C7 C10 C15 C16 . . . . -61.5(4) ?
    C13 C14 C16 C15 . . . . 58.9(4) ?
    C9 C14 C16 C15 . . . . -61.6(4) ?
    C12 C15 C16 C14 . . . . -58.4(4) ?
    C10 C15 C16 C14 . . . . 62.1(4) ?
data_II
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_chemical_name_systematic
;
(2,8,9-trioxa-5-aza-1-germabicyclo[3.3.3]undecan-1-yl)methyl
N-cyclohexylcarbamate
;
_chemical_name_common     '[(germatran-1-yl)methyl] N-cyclohexylcarbamate'
_chemical_formula_moiety     'C14 H26 Ge N2 O5'
_chemical_formula_sum     'C14 H26 Ge N2 O5'
_chemical_formula_iupac     '[Ge (C6 H12 N O3) (C8 H14 N O2)]'
_chemical_formula_weight     374.96
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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     9.4398(13)
_cell_length_b     16.690(2)
_cell_length_c     10.3361(16)
_cell_angle_alpha     90.00
_cell_angle_beta     97.740(3)
_cell_angle_gamma     90.00
_cell_volume     1613.6(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     759
_cell_measurement_theta_min     2.33
_cell_measurement_theta_max     29.21
_cell_measurement_temperature     120(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.543
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     784
_exptl_absorpt_coefficient_mu     1.923
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1998)'
_exptl_absorpt_correction_T_min     0.6996
_exptl_absorpt_correction_T_max     0.9446
_exptl_special_details
;
  ?
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Smart CCD 1000 area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8957
_diffrn_reflns_av_R_equivalents     0.0476
_diffrn_reflns_av_sigmaI/netI     0.0731
_diffrn_reflns_theta_min     2.44
_diffrn_reflns_theta_max     27.10
_diffrn_reflns_theta_full     27.10
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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.
;
_reflns_number_total     3487
_reflns_number_gt     2310
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0751
_refine_ls_R_factor_gt     0.0472
_refine_ls_wR_factor_gt     0.1009
_refine_ls_wR_factor_ref     0.1079
_refine_ls_goodness_of_fit_ref     1.050
_refine_ls_restrained_S_all     1.050
_refine_ls_number_reflns     3487
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0462P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.533
_refine_diff_density_min     -0.388
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 1998)'
_computing_data_reduction     'SAINT-Plus'
_computing_structure_solution     'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Ge Ge1 0.39838(4) 0.64542(2) 1.00349(4) 0.02019(14) Uani d . 1 . .
    O O1 0.4131(3) 0.75377(14) 1.0155(2) 0.0233(6) Uani d . 1 . .
    O O2 0.4545(3) 0.58764(15) 1.1476(2) 0.0265(6) Uani d . 1 . .
    O O3 0.2663(3) 0.60820(15) 0.8771(2) 0.0257(6) Uani d . 1 . .
    O O4 0.5703(2) 0.64959(14) 0.7982(2) 0.0212(6) Uani d . 1 . .
    O O5 0.7879(3) 0.59277(15) 0.7956(2) 0.0253(6) Uani d . 1 . .
    N N1 0.2102(3) 0.66659(17) 1.1044(3) 0.0204(7) Uani d . 1 . .
    N N2 0.6731(3) 0.65629(19) 0.6172(3) 0.0246(7) Uani d . 1 . .
    H H2C 0.6004 0.6876 0.5891 0.029 Uiso calc R 1 . .
    C C1 0.3003(4) 0.7972(2) 1.0607(4) 0.0261(9) Uani d . 1 . .
    H H1A 0.2284 0.8117 0.9857 0.031 Uiso calc R 1 . .
    H H1B 0.3385 0.8474 1.1031 0.031 Uiso calc R 1 . .
    C C2 0.3769(4) 0.5907(2) 1.2545(3) 0.0258(9) Uani d . 1 . .
    H H2A 0.4133 0.6349 1.3136 0.031 Uiso calc R 1 . .
    H H2B 0.3892 0.5398 1.3040 0.031 Uiso calc R 1 . .
    C C3 0.1258(4) 0.5936(2) 0.9069(4) 0.0284(9) Uani d . 1 . .
    H H3A 0.1213 0.5398 0.9464 0.034 Uiso calc R 1 . .
    H H3B 0.0569 0.5952 0.8258 0.034 Uiso calc R 1 . .
    C C4 0.2300(4) 0.7480(2) 1.1571(4) 0.0250(9) Uani d . 1 . .
    H H4A 0.2911 0.7469 1.2428 0.030 Uiso calc R 1 . .
    H H4B 0.1365 0.7717 1.1691 0.030 Uiso calc R 1 . .
    C C5 0.2186(4) 0.6041(2) 1.2052(3) 0.0239(9) Uani d . 1 . .
    H H5A 0.1746 0.5539 1.1681 0.029 Uiso calc R 1 . .
    H H5B 0.1673 0.6213 1.2779 0.029 Uiso calc R 1 . .
    C C6 0.0872(4) 0.6568(2) 1.0012(3) 0.0233(8) Uani d . 1 . .
    H H6A 0.0657 0.7082 0.9549 0.028 Uiso calc R 1 . .
    H H6B 0.0016 0.6400 1.0401 0.028 Uiso calc R 1 . .
    C C7 0.5727(4) 0.6186(2) 0.9296(3) 0.0221(8) Uani d . 1 . .
    H H7A 0.6563 0.6410 0.9861 0.026 Uiso calc R 1 . .
    H H7B 0.5837 0.5596 0.9281 0.026 Uiso calc R 1 . .
    C C8 0.6877(4) 0.6301(2) 0.7406(4) 0.0227(8) Uani d . 1 . .
    C C9 0.7740(4) 0.6346(2) 0.5276(3) 0.0242(9) Uani d . 1 . .
    H H9A 0.8729 0.6370 0.5764 0.029 Uiso calc R 1 . .
    C C10 0.7638(4) 0.6949(2) 0.4172(4) 0.0286(9) Uani d . 1 . .
    H H10A 0.7927 0.7483 0.4533 0.034 Uiso calc R 1 . .
    H H10B 0.6632 0.6986 0.3758 0.034 Uiso calc R 1 . .
    C C11 0.8581(4) 0.6726(2) 0.3135(4) 0.0310(10) Uani d . 1 . .
    H H11A 0.8427 0.7116 0.2408 0.037 Uiso calc R 1 . .
    H H11B 0.9598 0.6753 0.3519 0.037 Uiso calc R 1 . .
    C C14 0.7470(4) 0.5497(2) 0.4762(4) 0.0293(9) Uani d . 1 . .
    H H14A 0.7657 0.5114 0.5497 0.035 Uiso calc R 1 . .
    H H14B 0.6453 0.5444 0.4386 0.035 Uiso calc R 1 . .
    C C13 0.8411(5) 0.5282(2) 0.3723(4) 0.0291(9) Uani d . 1 . .
    H H13B 0.9423 0.5265 0.4124 0.035 Uiso calc R 1 . .
    H H13C 0.8147 0.4743 0.3369 0.035 Uiso calc R 1 . .
    C C12 0.8242(4) 0.5890(2) 0.2612(4) 0.0274(9) Uani d . 1 . .
    H H12B 0.8893 0.5751 0.1972 0.033 Uiso calc R 1 . .
    H H12C 0.7249 0.5875 0.2159 0.033 Uiso calc R 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Ge1 O3 . 1.791(2) ?
    Ge1 O2 . 1.794(2) ?
    Ge1 O1 . 1.817(2) ?
    Ge1 C7 . 1.957(4) ?
    Ge1 N1 . 2.206(3) ?
    O1 C1 . 1.418(4) ?
    O2 C2 . 1.406(4) ?
    O3 C3 . 1.422(4) ?
    O4 C8 . 1.366(4) ?
    O4 C7 . 1.451(4) ?
    O5 C8 . 1.209(4) ?
    N1 C4 . 1.467(4) ?
    N1 C5 . 1.469(4) ?
    N1 C6 . 1.476(4) ?
    N2 C8 . 1.337(5) ?
    N2 C9 . 1.460(4) ?
    N2 H2C . 0.8800 ?
    C1 C4 . 1.511(5) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 C5 . 1.529(5) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C6 . 1.515(5) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C9 C10 . 1.515(5) ?
    C9 C14 . 1.524(5) ?
    C9 H9A . 1.0000 ?
    C10 C11 . 1.528(5) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 C12 . 1.514(5) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C14 C13 . 1.526(5) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C13 C12 . 1.525(5) ?
    C13 H13B . 0.9900 ?
    C13 H13C . 0.9900 ?
    C12 H12B . 0.9900 ?
    C12 H12C . 0.9900 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O3 Ge1 O2 . . 121.20(12) ?
    O3 Ge1 O1 . . 115.75(11) ?
    O2 Ge1 O1 . . 117.84(12) ?
    O3 Ge1 C7 . . 100.09(14) ?
    O2 Ge1 C7 . . 91.80(13) ?
    O1 Ge1 C7 . . 101.19(14) ?
    O3 Ge1 N1 . . 82.80(11) ?
    O2 Ge1 N1 . . 81.96(11) ?
    O1 Ge1 N1 . . 82.36(11) ?
    C7 Ge1 N1 . . 173.73(13) ?
    C1 O1 Ge1 . . 118.5(2) ?
    C2 O2 Ge1 . . 120.4(2) ?
    C3 O3 Ge1 . . 118.7(2) ?
    C8 O4 C7 . . 114.3(3) ?
    C4 N1 C5 . . 113.8(3) ?
    C4 N1 C6 . . 114.8(3) ?
    C5 N1 C6 . . 113.4(3) ?
    C4 N1 Ge1 . . 104.7(2) ?
    C5 N1 Ge1 . . 104.6(2) ?
    C6 N1 Ge1 . . 104.2(2) ?
    C8 N2 C9 . . 122.1(3) ?
    C8 N2 H2C . . 118.9 ?
    C9 N2 H2C . . 118.9 ?
    O1 C1 C4 . . 110.8(3) ?
    O1 C1 H1A . . 109.5 ?
    C4 C1 H1A . . 109.5 ?
    O1 C1 H1B . . 109.5 ?
    C4 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 108.1 ?
    O2 C2 C5 . . 109.5(3) ?
    O2 C2 H2A . . 109.8 ?
    C5 C2 H2A . . 109.8 ?
    O2 C2 H2B . . 109.8 ?
    C5 C2 H2B . . 109.8 ?
    H2A C2 H2B . . 108.2 ?
    O3 C3 C6 . . 109.4(3) ?
    O3 C3 H3A . . 109.8 ?
    C6 C3 H3A . . 109.8 ?
    O3 C3 H3B . . 109.8 ?
    C6 C3 H3B . . 109.8 ?
    H3A C3 H3B . . 108.2 ?
    N1 C4 C1 . . 107.7(3) ?
    N1 C4 H4A . . 110.2 ?
    C1 C4 H4A . . 110.2 ?
    N1 C4 H4B . . 110.2 ?
    C1 C4 H4B . . 110.2 ?
    H4A C4 H4B . . 108.5 ?
    N1 C5 C2 . . 107.3(3) ?
    N1 C5 H5A . . 110.3 ?
    C2 C5 H5A . . 110.3 ?
    N1 C5 H5B . . 110.3 ?
    C2 C5 H5B . . 110.3 ?
    H5A C5 H5B . . 108.5 ?
    N1 C6 C3 . . 108.0(3) ?
    N1 C6 H6A . . 110.1 ?
    C3 C6 H6A . . 110.1 ?
    N1 C6 H6B . . 110.1 ?
    C3 C6 H6B . . 110.1 ?
    H6A C6 H6B . . 108.4 ?
    O4 C7 Ge1 . . 112.1(2) ?
    O4 C7 H7A . . 109.2 ?
    Ge1 C7 H7A . . 109.2 ?
    O4 C7 H7B . . 109.2 ?
    Ge1 C7 H7B . . 109.2 ?
    H7A C7 H7B . . 107.9 ?
    O5 C8 N2 . . 126.2(4) ?
    O5 C8 O4 . . 123.1(3) ?
    N2 C8 O4 . . 110.6(3) ?
    N2 C9 C10 . . 109.4(3) ?
    N2 C9 C14 . . 111.0(3) ?
    C10 C9 C14 . . 111.4(3) ?
    N2 C9 H9A . . 108.3 ?
    C10 C9 H9A . . 108.3 ?
    C14 C9 H9A . . 108.3 ?
    C9 C10 C11 . . 112.5(3) ?
    C9 C10 H10A . . 109.1 ?
    C11 C10 H10A . . 109.1 ?
    C9 C10 H10B . . 109.1 ?
    C11 C10 H10B . . 109.1 ?
    H10A C10 H10B . . 107.8 ?
    C12 C11 C10 . . 111.1(3) ?
    C12 C11 H11A . . 109.4 ?
    C10 C11 H11A . . 109.4 ?
    C12 C11 H11B . . 109.4 ?
    C10 C11 H11B . . 109.4 ?
    H11A C11 H11B . . 108.0 ?
    C13 C14 C9 . . 112.2(3) ?
    C13 C14 H14A . . 109.2 ?
    C9 C14 H14A . . 109.2 ?
    C13 C14 H14B . . 109.2 ?
    C9 C14 H14B . . 109.2 ?
    H14A C14 H14B . . 107.9 ?
    C12 C13 C14 . . 111.2(3) ?
    C12 C13 H13B . . 109.4 ?
    C14 C13 H13B . . 109.4 ?
    C12 C13 H13C . . 109.4 ?
    C14 C13 H13C . . 109.4 ?
    H13B C13 H13C . . 108.0 ?
    C11 C12 C13 . . 110.4(3) ?
    C11 C12 H12B . . 109.6 ?
    C13 C12 H12B . . 109.6 ?
    C11 C12 H12C . . 109.6 ?
    C13 C12 H12C . . 109.6 ?
    H12B C12 H12C . . 108.1 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O3 Ge1 O1 C1 . . . . 70.1(3) ?
    O2 Ge1 O1 C1 . . . . -84.8(3) ?
    C7 Ge1 O1 C1 . . . . 177.2(2) ?
    N1 Ge1 O1 C1 . . . . -8.1(2) ?
    O3 Ge1 O2 C2 . . . . -85.2(3) ?
    O1 Ge1 O2 C2 . . . . 68.2(3) ?
    C7 Ge1 O2 C2 . . . . 171.9(3) ?
    N1 Ge1 O2 C2 . . . . -8.7(3) ?
    O2 Ge1 O3 C3 . . . . 63.0(3) ?
    O1 Ge1 O3 C3 . . . . -90.9(3) ?
    C7 Ge1 O3 C3 . . . . 161.4(3) ?
    N1 Ge1 O3 C3 . . . . -13.0(3) ?
    O3 Ge1 N1 C4 . . . . -133.9(2) ?
    O2 Ge1 N1 C4 . . . . 103.1(2) ?
    O1 Ge1 N1 C4 . . . . -16.6(2) ?
    O3 Ge1 N1 C5 . . . . 106.2(2) ?
    O2 Ge1 N1 C5 . . . . -16.8(2) ?
    O1 Ge1 N1 C5 . . . . -136.5(2) ?
    O3 Ge1 N1 C6 . . . . -13.0(2) ?
    O2 Ge1 N1 C6 . . . . -136.0(2) ?
    O1 Ge1 N1 C6 . . . . 104.3(2) ?
    Ge1 O1 C1 C4 . . . . 31.3(4) ?
    Ge1 O2 C2 C5 . . . . 32.0(4) ?
    Ge1 O3 C3 C6 . . . . 36.4(4) ?
    C5 N1 C4 C1 . . . . 148.6(3) ?
    C6 N1 C4 C1 . . . . -78.6(4) ?
    Ge1 N1 C4 C1 . . . . 35.0(3) ?
    O1 C1 C4 N1 . . . . -44.0(4) ?
    C4 N1 C5 C2 . . . . -78.3(4) ?
    C6 N1 C5 C2 . . . . 148.2(3) ?
    Ge1 N1 C5 C2 . . . . 35.3(3) ?
    O2 C2 C5 N1 . . . . -44.1(4) ?
    C4 N1 C6 C3 . . . . 147.2(3) ?
    C5 N1 C6 C3 . . . . -79.8(4) ?
    Ge1 N1 C6 C3 . . . . 33.3(3) ?
    O3 C3 C6 N1 . . . . -45.3(4) ?
    C8 O4 C7 Ge1 . . . . -177.9(2) ?
    O3 Ge1 C7 O4 . . . . 53.2(3) ?
    O2 Ge1 C7 O4 . . . . 175.3(2) ?
    O1 Ge1 C7 O4 . . . . -65.8(3) ?
    C9 N2 C8 O5 . . . . 6.7(6) ?
    C9 N2 C8 O4 . . . . -171.8(3) ?
    C7 O4 C8 O5 . . . . -2.6(5) ?
    C7 O4 C8 N2 . . . . 175.9(3) ?
    C8 N2 C9 C10 . . . . -159.1(3) ?
    C8 N2 C9 C14 . . . . 77.5(4) ?
    N2 C9 C10 C11 . . . . -175.5(3) ?
    C14 C9 C10 C11 . . . . -52.4(5) ?
    C9 C10 C11 C12 . . . . 55.2(5) ?
    N2 C9 C14 C13 . . . . 174.4(3) ?
    C10 C9 C14 C13 . . . . 52.2(4) ?
    C9 C14 C13 C12 . . . . -54.7(4) ?
    C10 C11 C12 C13 . . . . -56.8(5) ?
    C14 C13 C12 C11 . . . . 56.8(4) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N2 H2C O1 4_575 0.88 2.077 2.951(4) 172 no
