#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:47:07 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179128 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/90/4309036.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_4309036
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         'C22 H30 Ge N2 O4'
_chemical_formula_sum            'C22 H30 Ge N2 O4'
_chemical_formula_weight         459.07
_chemical_name_systematic
; 
Bis[N-methyl-(2-oxy-2-phenylethyl)-(2-oxyethyl)amine]germanium
;
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6124(1)
_cell_length_b                   11.6124(1)
_cell_length_c                   15.5183(2)
_cell_measurement_reflns_used    8939
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.870
_cell_measurement_theta_min      2.480
_cell_volume                     2092.61(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 1K'
_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  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15351
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    1.495
_exptl_absorpt_correction_T_max  0.8649
_exptl_absorpt_correction_T_min  0.7542
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.007(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0246
_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)+(0.0339P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0570
_reflns_number_gt                2362
_reflns_number_total             2540
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic048165msi20041228_094930_1.cif
_cod_data_source_block           k
_cod_database_code               4309036
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -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 0.311153(16) 0.311153(16) 0.0000 0.01682(7) Uani 1 2 d S . .
N1 N 0.30649(16) 0.48671(13) 0.06946(10) 0.0228(3) Uani 1 1 d . . .
O1 O 0.16286(10) 0.30572(12) 0.03800(8) 0.0215(3) Uani 1 1 d . . .
O2 O 0.39563(12) 0.27564(12) 0.09621(9) 0.0241(3) Uani 1 1 d . . .
C1 C 0.1868(2) 0.48881(17) 0.10510(13) 0.0251(4) Uani 1 1 d . . .
C2 C 0.10977(17) 0.41466(16) 0.04722(12) 0.0217(4) Uani 1 1 d . . .
C3 C -0.00873(17) 0.40253(18) 0.08684(12) 0.0241(4) Uani 1 1 d . . .
C4 C -0.0800(2) 0.4993(2) 0.09356(15) 0.0384(6) Uani 1 1 d . . .
C5 C -0.1886(3) 0.4893(3) 0.13010(16) 0.0497(7) Uani 1 1 d . . .
C6 C -0.2286(2) 0.3856(3) 0.15832(16) 0.0453(7) Uani 1 1 d . . .
C7 C -0.1592(2) 0.2895(2) 0.15183(18) 0.0459(7) Uani 1 1 d . . .
C8 C -0.04916(19) 0.2980(2) 0.11637(14) 0.0308(5) Uani 1 1 d . . .
C9 C 0.3911(2) 0.47563(19) 0.13984(15) 0.0285(5) Uani 1 1 d . . .
C10 C 0.39152(19) 0.34961(19) 0.16847(13) 0.0273(5) Uani 1 1 d . . .
C11 C 0.3277(2) 0.59119(18) 0.01798(15) 0.0329(5) Uani 1 1 d . . .
H11 H 0.187(2) 0.4524(19) 0.1595(14) 0.025(5) Uiso 1 1 d . . .
H102 H 0.320(2) 0.3354(19) 0.2036(15) 0.027(5) Uiso 1 1 d . . .
H113 H 0.327(2) 0.654(2) 0.0543(15) 0.030(6) Uiso 1 1 d . . .
H12 H 0.1638(18) 0.564(2) 0.1137(13) 0.021(5) Uiso 1 1 d . . .
H112 H 0.4039(19) 0.5864(19) -0.0055(14) 0.024(5) Uiso 1 1 d . . .
H2 H 0.1001(17) 0.4553(19) -0.0078(15) 0.027(5) Uiso 1 1 d . . .
H101 H 0.4601(18) 0.3332(17) 0.2040(13) 0.019(5) Uiso 1 1 d . . .
H92 H 0.467(2) 0.497(2) 0.1161(18) 0.047(8) Uiso 1 1 d . . .
H4 H -0.052(2) 0.571(2) 0.0701(18) 0.046(7) Uiso 1 1 d . . .
H5 H -0.233(2) 0.556(3) 0.1343(19) 0.050(8) Uiso 1 1 d . . .
H7 H -0.182(3) 0.217(3) 0.170(2) 0.062(9) Uiso 1 1 d . . .
H6 H -0.301(2) 0.379(2) 0.1821(17) 0.041(7) Uiso 1 1 d . . .
H111 H 0.266(2) 0.598(2) -0.0268(19) 0.051(8) Uiso 1 1 d . . .
H8 H -0.005(2) 0.235(2) 0.1083(16) 0.035(7) Uiso 1 1 d . . .
H91 H 0.3700(19) 0.527(2) 0.1864(16) 0.027(6) 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
O1 Ge1 O1 92.25(9) . 7 ?
O1 Ge1 O2 103.56(6) . . ?
O1 Ge1 O2 93.99(6) 7 . ?
O1 Ge1 O2 93.99(6) . 7 ?
O1 Ge1 O2 103.56(6) 7 7 ?
O2 Ge1 O2 154.67(9) . 7 ?
O1 Ge1 N1 170.44(6) . 7 ?
O1 Ge1 N1 81.79(6) 7 7 ?
O2 Ge1 N1 84.40(6) . 7 ?
O2 Ge1 N1 80.26(6) 7 7 ?
O1 Ge1 N1 81.79(6) . . ?
O1 Ge1 N1 170.44(6) 7 . ?
O2 Ge1 N1 80.26(6) . . ?
O2 Ge1 N1 84.40(6) 7 . ?
N1 Ge1 N1 105.06(9) 7 . ?
C11 N1 C9 111.21(17) . . ?
C11 N1 C1 110.03(17) . . ?
C9 N1 C1 110.28(16) . . ?
C11 N1 Ge1 118.07(12) . . ?
C9 N1 Ge1 104.67(12) . . ?
C1 N1 Ge1 102.06(11) . . ?
C2 O1 Ge1 114.45(11) . . ?
C10 O2 Ge1 119.43(12) . . ?
N1 C1 C2 108.45(15) . . ?
N1 C1 H11 108.8(15) . . ?
C2 C1 H11 105.8(14) . . ?
N1 C1 H12 109.6(13) . . ?
C2 C1 H12 116.7(13) . . ?
H11 C1 H12 107.2(19) . . ?
O1 C2 C3 110.74(15) . . ?
O1 C2 C1 107.91(16) . . ?
C3 C2 C1 110.17(16) . . ?
O1 C2 H2 113.0(13) . . ?
C3 C2 H2 107.1(12) . . ?
C1 C2 H2 107.8(12) . . ?
C8 C3 C4 118.7(2) . . ?
C8 C3 C2 121.74(17) . . ?
C4 C3 C2 119.5(2) . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 122.2(17) . . ?
C3 C4 H4 117.7(17) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 121.4(18) . . ?
C4 C5 H5 117.6(18) . . ?
C5 C6 C7 119.5(2) . . ?
C5 C6 H6 120.8(16) . . ?
C7 C6 H6 119.8(16) . . ?
C6 C7 C8 120.4(3) . . ?
C6 C7 H7 123(2) . . ?
C8 C7 H7 117(2) . . ?
C3 C8 C7 120.3(2) . . ?
C3 C8 H8 118.6(16) . . ?
C7 C8 H8 120.9(16) . . ?
N1 C9 C10 107.50(16) . . ?
N1 C9 H92 107.4(16) . . ?
C10 C9 H92 110.2(16) . . ?
N1 C9 H91 109.4(14) . . ?
C10 C9 H91 111.7(14) . . ?
H92 C9 H91 111(2) . . ?
O2 C10 C9 110.56(16) . . ?
O2 C10 H102 111.0(12) . . ?
C9 C10 H102 108.2(13) . . ?
O2 C10 H101 107.4(12) . . ?
C9 C10 H101 110.5(12) . . ?
H102 C10 H101 109.2(18) . . ?
N1 C11 H113 108.7(15) . . ?
N1 C11 H112 108.2(13) . . ?
H113 C11 H112 107(2) . . ?
N1 C11 H111 108.7(16) . . ?
H113 C11 H111 111(2) . . ?
H112 C11 H111 114(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 O1 1.8213(12) . ?
Ge1 O1 1.8213(12) 7 ?
Ge1 O2 1.8335(13) . ?
Ge1 O2 1.8335(13) 7 ?
Ge1 N1 2.3067(15) 7 ?
Ge1 N1 2.3067(15) . ?
N1 C11 1.473(2) . ?
N1 C9 1.475(3) . ?
N1 C1 1.496(3) . ?
O1 C2 1.415(2) . ?
O2 C10 1.413(2) . ?
C1 C2 1.532(3) . ?
C1 H11 0.94(2) . ?
C1 H12 0.93(2) . ?
C2 C3 1.514(3) . ?
C2 H2 0.98(2) . ?
C3 C8 1.380(3) . ?
C3 C4 1.400(3) . ?
C4 C5 1.388(4) . ?
C4 H4 0.97(3) . ?
C5 C6 1.362(4) . ?
C5 H5 0.93(3) . ?
C6 C7 1.381(4) . ?
C6 H6 0.92(3) . ?
C7 C8 1.395(3) . ?
C7 H7 0.93(3) . ?
C8 H8 0.90(3) . ?
C9 C10 1.529(3) . ?
C9 H92 0.99(3) . ?
C9 H91 0.97(2) . ?
C10 H102 1.01(2) . ?
C10 H101 0.99(2) . ?
C11 H113 0.92(2) . ?
C11 H112 0.96(2) . ?
C11 H111 1.00(3) . ?
