#------------------------------------------------------------------------------
#$Date: 2021-07-01 10:33:58 +0300 (Thu, 01 Jul 2021) $
#$Revision: 266858 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/38/1563832.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_1563832
loop_
_publ_author_name
'Schwarzer, Sandra'
'Böhme, Uwe'
'Fels, Sabine'
'Günther, Betty'
'Brendler, Erica'
_publ_section_title
;
 (S)-N-[(2-hydroxynaphthalen-1-yl)methylidene]valine -- A valuable ligand
 for the preparation of chiral complexes
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              136
_journal_page_last               147
_journal_paper_doi               10.1016/j.ica.2018.08.011
_journal_volume                  483
_journal_year                    2018
_chemical_formula_moiety         '2(C44 H40 Ge2 N2 O7), C H Cl3'
_chemical_formula_sum            'C89 H81 Cl3 Ge4 N4 O14'
_chemical_formula_weight         1827.28
_chemical_melting_point          537
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                110.740(4)
_cell_angle_beta                 100.151(4)
_cell_angle_gamma                100.061(4)
_cell_formula_units_Z            1
_cell_length_a                   11.4185(5)
_cell_length_b                   12.0876(6)
_cell_length_c                   16.5054(8)
_cell_measurement_reflns_used    9200
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.52
_cell_volume                     2026.38(19)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_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  0.0630
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9200
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.590
_exptl_absorpt_coefficient_mu    1.636
_exptl_absorpt_correction_T_max  0.7355
_exptl_absorpt_correction_T_min  0.5606
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'X-RED; Stoe, 2009'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       Prism
_exptl_crystal_F_000             934
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.205
_refine_diff_density_min         -1.416
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         9200
_refine_ls_number_restraints     56
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1230P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.1726
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6324
_reflns_number_total             9200
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            k105f_7.cif
_cod_data_source_block           k105f_7
_cod_original_cell_volume        2026.37(18)
_cod_database_code               1563832
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.561
_shelx_estimated_absorpt_t_max   0.736
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge1 Ge 0.28091(4) 0.60732(4) 0.25766(3) 0.02710(13) Uani 1 1 d . U . . .
O1 O 0.3981(3) 0.5668(3) 0.19405(19) 0.0233(4) Uani 1 1 d . U . . .
O2 O 0.1905(2) 0.6640(3) 0.34539(19) 0.0224(6) Uani 1 1 d . . . . .
O3 O 0.2030(3) 0.7655(3) 0.4898(2) 0.0306(7) Uani 1 1 d . . . . .
N1 N 0.4155(3) 0.7162(3) 0.3567(2) 0.0207(5) Uani 1 1 d . U . . .
C1 C 0.5416(3) 0.7642(3) 0.2637(2) 0.0165(7) Uani 1 1 d . . . . .
C2 C 0.4864(3) 0.6514(4) 0.1913(3) 0.0192(7) Uani 1 1 d . . . . .
C3 C 0.5283(4) 0.6217(4) 0.1120(3) 0.0242(8) Uani 1 1 d . . . . .
H3 H 0.4941 0.5432 0.0645 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6167(4) 0.7048(4) 0.1034(3) 0.0251(8) Uani 1 1 d . . . . .
H4 H 0.6429 0.6834 0.0496 0.030 Uiso 1 1 calc R U . . .
C5 C 0.7592(4) 0.9117(4) 0.1613(3) 0.0256(8) Uani 1 1 d . . . . .
H5 H 0.7853 0.8899 0.1075 0.031 Uiso 1 1 calc R U . . .
C6 C 0.8066(4) 1.0271(4) 0.2264(3) 0.0271(9) Uani 1 1 d . . . . .
H6 H 0.8637 1.0859 0.2171 0.033 Uiso 1 1 calc R U . . .
C7 C 0.7705(4) 1.0588(4) 0.3074(3) 0.0246(8) Uani 1 1 d . . . . .
H7 H 0.8041 1.1390 0.3528 0.029 Uiso 1 1 calc R U . . .
C8 C 0.6875(4) 0.9753(4) 0.3217(3) 0.0211(7) Uani 1 1 d . . . . .
H8 H 0.6649 0.9982 0.3769 0.025 Uiso 1 1 calc R U . . .
C9 C 0.6346(3) 0.8544(3) 0.2545(2) 0.0172(7) Uani 1 1 d . . . . .
C10 C 0.6712(3) 0.8235(4) 0.1731(3) 0.0193(7) Uani 1 1 d . . . . .
C11 C 0.5101(3) 0.7850(3) 0.3469(2) 0.0164(7) Uani 1 1 d . . . . .
H11 H 0.5609 0.8531 0.3985 0.020 Uiso 1 1 calc R U . . .
C12 C 0.3911(3) 0.7478(3) 0.4459(2) 0.0188(7) Uani 1 1 d . . . . .
H12 H 0.4317 0.8362 0.4839 0.023 Uiso 1 1 calc R U . . .
C13 C 0.2514(4) 0.7262(4) 0.4289(3) 0.0213(7) Uani 1 1 d . . . . .
C14 C 0.4389(4) 0.6679(4) 0.4932(3) 0.0231(8) Uani 1 1 d . . . . .
H14A H 0.3812 0.5842 0.4645 0.028 Uiso 0.486(14) 1 calc R U P A 1
H14B H 0.5248 0.6675 0.4882 0.028 Uiso 0.514(14) 1 calc R U P A 2
C15 C 0.4416(5) 0.7210(5) 0.5922(3) 0.0386(11) Uani 1 1 d . . . . .
H15A H 0.4932 0.8054 0.6205 0.058 Uiso 1 1 calc R U . . .
H15B H 0.4757 0.6715 0.6214 0.058 Uiso 1 1 calc R U . . .
H15C H 0.3578 0.7204 0.5984 0.058 Uiso 1 1 calc R U . . .
C16A C 0.5730(8) 0.6553(9) 0.4843(7) 0.030(2) Uani 0.486(14) 1 d . . P A 1
H16A H 0.6304 0.7368 0.5103 0.045 Uiso 0.486(14) 1 calc R U P A 1
H16B H 0.5709 0.6154 0.4208 0.045 Uiso 0.486(14) 1 calc R U P A 1
H16C H 0.6003 0.6060 0.5162 0.045 Uiso 0.486(14) 1 calc R U P A 1
C16B C 0.3600(8) 0.5355(9) 0.4497(7) 0.033(2) Uani 0.514(14) 1 d . . P A 2
H16D H 0.3916 0.4886 0.4822 0.049 Uiso 0.514(14) 1 calc R U P A 2
H16E H 0.3633 0.4989 0.3871 0.049 Uiso 0.514(14) 1 calc R U P A 2
H16F H 0.2746 0.5343 0.4519 0.049 Uiso 0.514(14) 1 calc R U P A 2
C17 C 0.1983(4) 0.4394(4) 0.2201(3) 0.0253(8) Uani 1 1 d . . . . .
C18 C 0.0710(4) 0.4076(4) 0.2092(3) 0.0260(8) Uani 1 1 d . . . . .
H18 H 0.0294 0.4701 0.2272 0.031 Uiso 1 1 calc R U . . .
C19 C 0.0049(4) 0.2858(4) 0.1724(3) 0.0307(9) Uani 1 1 d . . . . .
H19 H -0.0819 0.2652 0.1636 0.037 Uiso 1 1 calc R U . . .
C20 C 0.0655(5) 0.1945(4) 0.1487(4) 0.0408(12) Uani 1 1 d . . . . .
H20 H 0.0203 0.1110 0.1233 0.049 Uiso 1 1 calc R U . . .
C21 C 0.1915(6) 0.2242(5) 0.1619(5) 0.0565(16) Uani 1 1 d . U . . .
H21 H 0.2334 0.1612 0.1477 0.068 Uiso 1 1 calc R U . . .
C22 C 0.2572(5) 0.3456(5) 0.1957(5) 0.0462(13) Uani 1 1 d . U . . .
H22 H 0.3436 0.3651 0.2024 0.055 Uiso 1 1 calc R U . . .
Ge2 Ge 0.17938(4) 0.81288(4) 0.20396(3) 0.02711(13) Uani 1 1 d . . . . .
O4 O 0.0352(3) 0.7365(3) 0.11145(19) 0.0273(6) Uani 1 1 d . . . . .
O5 O 0.3031(3) 0.9104(3) 0.31495(18) 0.0227(6) Uani 1 1 d . . . . .
O6 O 0.3429(3) 1.0244(3) 0.4602(2) 0.0317(7) Uani 1 1 d . . . . .
N2 N 0.0744(3) 0.8420(3) 0.2856(2) 0.0236(7) Uani 1 1 d . . . . .
C23 C -0.0897(4) 0.6580(4) 0.1909(3) 0.0240(8) Uani 1 1 d . . . . .
C24 C -0.0562(4) 0.6522(4) 0.1112(3) 0.0251(8) Uani 1 1 d . . . . .
C25 C -0.1224(4) 0.5550(5) 0.0276(3) 0.0301(9) Uani 1 1 d . . . . .
H25 H -0.1037 0.5546 -0.0263 0.036 Uiso 1 1 calc R U . . .
C26 C -0.2119(4) 0.4630(5) 0.0251(3) 0.0308(9) Uani 1 1 d . . . . .
H26 H -0.2527 0.3970 -0.0308 0.037 Uiso 1 1 calc R U . . .
C27 C -0.3406(5) 0.3647(4) 0.0991(4) 0.0364(10) Uani 1 1 d . . . . .
H27 H -0.3779 0.2975 0.0431 0.044 Uiso 1 1 calc R U . . .
C28 C -0.3782(7) 0.3651(5) 0.1726(4) 0.0515(15) Uani 1 1 d . . . . .
H28 H -0.4420 0.2996 0.1681 0.062 Uiso 1 1 calc R U . . .
C29 C -0.3211(7) 0.4646(5) 0.2562(4) 0.0574(18) Uani 1 1 d . . . . .
H29 H -0.3469 0.4653 0.3080 0.069 Uiso 1 1 calc R U . . .
C30 C -0.2290(6) 0.5600(5) 0.2633(3) 0.0433(13) Uani 1 1 d . . . . .
H30 H -0.1918 0.6256 0.3201 0.052 Uiso 1 1 calc R U . . .
C31 C -0.1883(4) 0.5619(4) 0.1871(3) 0.0281(9) Uani 1 1 d . . . . .
C32 C -0.2469(4) 0.4625(4) 0.1040(3) 0.0295(9) Uani 1 1 d . . . . .
C33 C -0.0273(4) 0.7596(4) 0.2718(3) 0.0248(8) Uani 1 1 d . . . . .
H33 H -0.0624 0.7696 0.3212 0.030 Uiso 1 1 calc R U . . .
C34 C 0.1318(4) 0.9356(4) 0.3772(3) 0.0285(9) Uani 1 1 d D . . . .
H34A H 0.1144 0.8956 0.4190 0.034 Uiso 0.54(3) 1 calc R U P B 3
H34B H 0.1080 0.9071 0.4234 0.034 Uiso 0.46(3) 1 calc R U P B 4
C35 C 0.2708(4) 0.9615(4) 0.3879(3) 0.0225(8) Uani 1 1 d . . . . .
C36A C 0.0674(11) 1.0372(10) 0.3943(5) 0.022(2) Uani 0.54(3) 1 d D U P B 3
H36A H -0.0237 1.0013 0.3730 0.026 Uiso 0.54(3) 1 calc R U P B 3
C37A C 0.1076(14) 1.1073(12) 0.3383(8) 0.027(3) Uani 0.54(3) 1 d D . P B 3
H37A H 0.0764 1.1806 0.3522 0.041 Uiso 0.54(3) 1 calc R U P B 3
H37B H 0.0744 1.0547 0.2744 0.041 Uiso 0.54(3) 1 calc R U P B 3
H37C H 0.1977 1.1314 0.3524 0.041 Uiso 0.54(3) 1 calc R U P B 3
C38A C 0.1021(14) 1.1204(14) 0.4944(6) 0.028(3) Uani 0.54(3) 1 d D . P B 3
H38A H 0.0923 1.0701 0.5293 0.042 Uiso 0.54(3) 1 calc R U P B 3
H38B H 0.0482 1.1760 0.5054 0.042 Uiso 0.54(3) 1 calc R U P B 3
H38C H 0.1879 1.1683 0.5126 0.042 Uiso 0.54(3) 1 calc R U P B 3
C36B C 0.1021(12) 1.0670(10) 0.3892(5) 0.015(3) Uani 0.46(3) 1 d D U P B 4
H36B H 0.0103 1.0502 0.3713 0.018 Uiso 0.46(3) 1 calc R U P B 4
C37B C 0.150(2) 1.1308(18) 0.3319(11) 0.035(4) Uani 0.46(3) 1 d D . P B 4
H37D H 0.2401 1.1454 0.3445 0.052 Uiso 0.46(3) 1 calc R U P B 4
H37E H 0.1285 1.2092 0.3461 0.052 Uiso 0.46(3) 1 calc R U P B 4
H37F H 0.1134 1.0787 0.2682 0.052 Uiso 0.46(3) 1 calc R U P B 4
C38B C 0.1437(18) 1.1570(16) 0.4889(7) 0.030(3) Uani 0.46(3) 1 d D . P B 4
H38D H 0.2318 1.1966 0.5047 0.045 Uiso 0.46(3) 1 calc R U P B 4
H38E H 0.1285 1.1120 0.5267 0.045 Uiso 0.46(3) 1 calc R U P B 4
H38F H 0.0972 1.2193 0.4984 0.045 Uiso 0.46(3) 1 calc R U P B 4
C39 C 0.2534(4) 0.9018(4) 0.1413(3) 0.0252(8) Uani 1 1 d . . . . .
C40 C 0.1911(5) 0.8922(4) 0.0573(3) 0.0353(11) Uani 1 1 d . . . . .
H40 H 0.1076 0.8463 0.0319 0.042 Uiso 1 1 calc R U . . .
C41 C 0.2508(6) 0.9496(5) 0.0107(3) 0.0444(13) Uani 1 1 d . . . . .
H41 H 0.2070 0.9432 -0.0460 0.053 Uiso 1 1 calc R U . . .
C42 C 0.3721(5) 1.0154(5) 0.0451(3) 0.0379(11) Uani 1 1 d . . . . .
H42 H 0.4115 1.0546 0.0128 0.045 Uiso 1 1 calc R U . . .
C43 C 0.4361(5) 1.0238(5) 0.1273(4) 0.0375(11) Uani 1 1 d . . . . .
H43 H 0.5202 1.0683 0.1512 0.045 Uiso 1 1 calc R U . . .
C44 C 0.3777(4) 0.9673(5) 0.1753(3) 0.0326(10) Uani 1 1 d . . . . .
H44 H 0.4226 0.9734 0.2316 0.039 Uiso 1 1 calc R U . . .
O7 O 0.2202(3) 0.6774(3) 0.19108(19) 0.0239(4) Uani 1 1 d . U . . .
C45 C 0.0353(11) 0.5314(11) 0.4905(8) 0.044(2) Uani 0.5 1 d . . P C -1
H45 H 0.0714 0.6061 0.4811 0.053 Uiso 0.5 1 calc R U P C -1
Cl1 Cl 0.1473(2) 0.4409(2) 0.4836(2) 0.0444(6) Uani 0.5 1 d . . P C -1
Cl2 Cl -0.0957(3) 0.4510(4) 0.4058(2) 0.0657(10) Uani 0.5 1 d . . P C -1
Cl3 Cl 0.0121(3) 0.5794(3) 0.5965(2) 0.0506(7) Uani 0.5 1 d . . P C -1
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'
Cl Cl 0.1484 0.1585 '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
O7 Ge1 O1 93.40(13) . .
O7 Ge1 C17 114.18(17) . .
O1 Ge1 C17 91.83(15) . .
O7 Ge1 N1 113.04(14) . .
O1 Ge1 N1 86.94(13) . .
C17 Ge1 N1 132.75(17) . .
O7 Ge1 O2 94.28(13) . .
O1 Ge1 O2 167.59(13) . .
C17 Ge1 O2 93.89(15) . .
N1 Ge1 O2 81.09(13) . .
C2 O1 Ge1 122.0(2) . .
C13 O2 Ge1 118.6(2) . .
C11 N1 C12 119.5(3) . .
C11 N1 Ge1 122.4(3) . .
C12 N1 Ge1 115.6(2) . .
C2 C1 C11 118.9(3) . .
C2 C1 C9 119.7(3) . .
C11 C1 C9 121.3(3) . .
O1 C2 C1 122.8(3) . .
O1 C2 C3 117.1(3) . .
C1 C2 C3 120.0(3) . .
C4 C3 C2 120.5(4) . .
C4 C3 H3 119.8 . .
C2 C3 H3 119.8 . .
C3 C4 C10 121.7(4) . .
C3 C4 H4 119.2 . .
C10 C4 H4 119.2 . .
C6 C5 C10 120.9(4) . .
C6 C5 H5 119.6 . .
C10 C5 H5 119.6 . .
C5 C6 C7 119.7(4) . .
C5 C6 H6 120.1 . .
C7 C6 H6 120.1 . .
C8 C7 C6 121.0(4) . .
C8 C7 H7 119.5 . .
C6 C7 H7 119.5 . .
C7 C8 C9 120.8(4) . .
C7 C8 H8 119.6 . .
C9 C8 H8 119.6 . .
C10 C9 C8 117.9(3) . .
C10 C9 C1 118.7(3) . .
C8 C9 C1 123.4(3) . .
C9 C10 C5 119.8(4) . .
C9 C10 C4 119.2(3) . .
C5 C10 C4 121.0(3) . .
N1 C11 C1 124.3(3) . .
N1 C11 H11 117.8 . .
C1 C11 H11 117.8 . .
N1 C12 C13 105.4(3) . .
N1 C12 C14 111.6(3) . .
C13 C12 C14 111.2(3) . .
N1 C12 H12 109.5 . .
C13 C12 H12 109.5 . .
C14 C12 H12 109.5 . .
O3 C13 O2 123.8(4) . .
O3 C13 C12 121.6(4) . .
O2 C13 C12 114.6(3) . .
C15 C14 C16B 109.2(5) . .
C15 C14 C12 110.8(4) . .
C16B C14 C12 111.9(4) . .
C15 C14 C16A 108.8(5) . .
C12 C14 C16A 112.2(4) . .
C15 C14 H14A 108.3 . .
C12 C14 H14A 108.3 . .
C16A C14 H14A 108.3 . .
C15 C14 H14B 108.3 . .
C16B C14 H14B 108.3 . .
C12 C14 H14B 108.3 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C14 C16A H16A 109.5 . .
C14 C16A H16B 109.5 . .
H16A C16A H16B 109.5 . .
C14 C16A H16C 109.5 . .
H16A C16A H16C 109.5 . .
H16B C16A H16C 109.5 . .
C14 C16B H16D 109.5 . .
C14 C16B H16E 109.5 . .
H16D C16B H16E 109.5 . .
C14 C16B H16F 109.5 . .
H16D C16B H16F 109.5 . .
H16E C16B H16F 109.5 . .
C22 C17 C18 118.2(4) . .
C22 C17 Ge1 122.8(3) . .
C18 C17 Ge1 118.8(3) . .
C19 C18 C17 120.8(4) . .
C19 C18 H18 119.6 . .
C17 C18 H18 119.6 . .
C20 C19 C18 119.8(4) . .
C20 C19 H19 120.1 . .
C18 C19 H19 120.1 . .
C21 C20 C19 120.2(5) . .
C21 C20 H20 119.9 . .
C19 C20 H20 119.9 . .
C20 C21 C22 120.1(5) . .
C20 C21 H21 120.0 . .
C22 C21 H21 120.0 . .
C21 C22 C17 120.9(5) . .
C21 C22 H22 119.6 . .
C17 C22 H22 119.6 . .
O7 Ge2 O4 93.88(14) . .
O7 Ge2 C39 114.69(15) . .
O4 Ge2 C39 93.00(16) . .
O7 Ge2 O5 95.14(13) . .
O4 Ge2 O5 166.46(13) . .
C39 Ge2 O5 92.39(16) . .
O7 Ge2 N2 109.85(15) . .
O4 Ge2 N2 86.83(13) . .
C39 Ge2 N2 135.36(16) . .
O5 Ge2 N2 80.61(13) . .
C24 O4 Ge2 123.7(3) . .
C35 O5 Ge2 120.1(3) . .
C33 N2 C34 118.6(4) . .
C33 N2 Ge2 121.4(3) . .
C34 N2 Ge2 116.6(3) . .
C33 C23 C24 118.8(4) . .
C33 C23 C31 121.9(4) . .
C24 C23 C31 119.3(4) . .
O4 C24 C23 121.7(4) . .
O4 C24 C25 118.2(4) . .
C23 C24 C25 120.2(4) . .
C26 C25 C24 120.0(4) . .
C26 C25 H25 120.0 . .
C24 C25 H25 120.0 . .
C25 C26 C32 122.0(4) . .
C25 C26 H26 119.0 . .
C32 C26 H26 119.0 . .
C28 C27 C32 121.3(5) . .
C28 C27 H27 119.4 . .
C32 C27 H27 119.4 . .
C27 C28 C29 119.2(6) . .
C27 C28 H28 120.4 . .
C29 C28 H28 120.4 . .
C30 C29 C28 120.9(5) . .
C30 C29 H29 119.6 . .
C28 C29 H29 119.6 . .
C29 C30 C31 121.0(5) . .
C29 C30 H30 119.5 . .
C31 C30 H30 119.5 . .
C32 C31 C30 117.4(5) . .
C32 C31 C23 119.1(4) . .
C30 C31 C23 123.5(4) . .
C31 C32 C27 120.3(4) . .
C31 C32 C26 119.2(4) . .
C27 C32 C26 120.6(4) . .
N2 C33 C23 126.6(4) . .
N2 C33 H33 116.7 . .
C23 C33 H33 116.7 . .
N2 C34 C36A 109.2(4) . .
N2 C34 C35 106.2(3) . .
C36A C34 C35 121.3(6) . .
N2 C34 C36B 111.9(4) . .
C35 C34 C36B 103.8(6) . .
N2 C34 H34A 106.4 . .
C36A C34 H34A 106.4 . .
C35 C34 H34A 106.4 . .
N2 C34 H34B 111.5 . .
C35 C34 H34B 111.5 . .
C36B C34 H34B 111.5 . .
O6 C35 O5 124.1(4) . .
O6 C35 C34 121.2(4) . .
O5 C35 C34 114.8(3) . .
C34 C36A C37A 105.8(7) . .
C34 C36A C38A 111.0(6) . .
C37A C36A C38A 111.7(8) . .
C34 C36A H36A 109.4 . .
C37A C36A H36A 109.4 . .
C38A C36A H36A 109.4 . .
C36A C37A H37A 109.5 . .
C36A C37A H37B 109.5 . .
H37A C37A H37B 109.5 . .
C36A C37A H37C 109.5 . .
H37A C37A H37C 109.5 . .
H37B C37A H37C 109.5 . .
C36A C38A H38A 109.5 . .
C36A C38A H38B 109.5 . .
H38A C38A H38B 109.5 . .
C36A C38A H38C 109.5 . .
H38A C38A H38C 109.5 . .
H38B C38A H38C 109.5 . .
C37B C36B C38B 109.5(11) . .
C37B C36B C34 117.2(9) . .
C38B C36B C34 111.0(7) . .
C37B C36B H36B 106.1 . .
C38B C36B H36B 106.1 . .
C34 C36B H36B 106.1 . .
C36B C37B H37D 109.5 . .
C36B C37B H37E 109.5 . .
H37D C37B H37E 109.5 . .
C36B C37B H37F 109.5 . .
H37D C37B H37F 109.5 . .
H37E C37B H37F 109.5 . .
C36B C38B H38D 109.5 . .
C36B C38B H38E 109.5 . .
H38D C38B H38E 109.5 . .
C36B C38B H38F 109.5 . .
H38D C38B H38F 109.5 . .
H38E C38B H38F 109.5 . .
C40 C39 C44 118.1(4) . .
C40 C39 Ge2 121.9(4) . .
C44 C39 Ge2 119.7(3) . .
C41 C40 C39 120.3(5) . .
C41 C40 H40 119.8 . .
C39 C40 H40 119.8 . .
C42 C41 C40 121.2(5) . .
C42 C41 H41 119.4 . .
C40 C41 H41 119.4 . .
C41 C42 C43 119.4(5) . .
C41 C42 H42 120.3 . .
C43 C42 H42 120.3 . .
C42 C43 C44 120.2(5) . .
C42 C43 H43 119.9 . .
C44 C43 H43 119.9 . .
C43 C44 C39 120.8(4) . .
C43 C44 H44 119.6 . .
C39 C44 H44 119.6 . .
Ge2 O7 Ge1 138.68(18) . .
Cl2 C45 Cl3 114.5(7) . .
Cl2 C45 Cl1 109.8(7) . .
Cl3 C45 Cl1 109.6(6) . .
Cl2 C45 H45 107.5 . .
Cl3 C45 H45 107.5 . .
Cl1 C45 H45 107.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ge1 O7 1.733(3) .
Ge1 O1 1.869(3) .
Ge1 C17 1.904(4) .
Ge1 N1 1.910(3) .
Ge1 O2 1.924(3) .
O1 C2 1.324(5) .
O2 C13 1.302(5) .
O3 C13 1.221(5) .
N1 C11 1.315(5) .
N1 C12 1.475(5) .
C1 C2 1.402(5) .
C1 C11 1.428(5) .
C1 C9 1.452(5) .
C2 C3 1.422(5) .
C3 C4 1.358(6) .
C3 H3 0.9500 .
C4 C10 1.427(6) .
C4 H4 0.9500 .
C5 C6 1.365(6) .
C5 C10 1.423(6) .
C5 H5 0.9500 .
C6 C7 1.412(6) .
C6 H6 0.9500 .
C7 C8 1.373(6) .
C7 H7 0.9500 .
C8 C9 1.427(5) .
C8 H8 0.9500 .
C9 C10 1.420(5) .
C11 H11 0.9500 .
C12 C13 1.529(5) .
C12 C14 1.551(5) .
C12 H12 1.0000 .
C14 C15 1.521(6) .
C14 C16B 1.530(10) .
C14 C16A 1.592(9) .
C14 H14A 1.0000 .
C14 H14B 1.0000 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16A H16A 0.9800 .
C16A H16B 0.9800 .
C16A H16C 0.9800 .
C16B H16D 0.9800 .
C16B H16E 0.9800 .
C16B H16F 0.9800 .
C17 C22 1.393(6) .
C17 C18 1.398(6) .
C18 C19 1.387(6) .
C18 H18 0.9500 .
C19 C20 1.381(7) .
C19 H19 0.9500 .
C20 C21 1.379(8) .
C20 H20 0.9500 .
C21 C22 1.384(8) .
C21 H21 0.9500 .
C22 H22 0.9500 .
Ge2 O7 1.732(3) .
Ge2 O4 1.865(3) .
Ge2 C39 1.928(4) .
Ge2 O5 1.928(3) .
Ge2 N2 1.938(3) .
O4 C24 1.323(6) .
O5 C35 1.294(5) .
O6 C35 1.214(5) .
N2 C33 1.316(6) .
N2 C34 1.476(5) .
C23 C33 1.413(6) .
C23 C24 1.415(5) .
C23 C31 1.444(6) .
C24 C25 1.425(6) .
C25 C26 1.356(7) .
C25 H25 0.9500 .
C26 C32 1.430(6) .
C26 H26 0.9500 .
C27 C28 1.354(8) .
C27 C32 1.417(7) .
C27 H27 0.9500 .
C28 C29 1.418(9) .
C28 H28 0.9500 .
C29 C30 1.373(8) .
C29 H29 0.9500 .
C30 C31 1.423(6) .
C30 H30 0.9500 .
C31 C32 1.414(6) .
C33 H33 0.9500 .
C34 C36A 1.507(8) .
C34 C35 1.529(6) .
C34 C36B 1.632(10) .
C34 H34A 1.0000 .
C34 H34B 1.0000 .
C36A C37A 1.534(12) .
C36A C38A 1.534(9) .
C36A H36A 1.0000 .
C37A H37A 0.9800 .
C37A H37B 0.9800 .
C37A H37C 0.9800 .
C38A H38A 0.9800 .
C38A H38B 0.9800 .
C38A H38C 0.9800 .
C36B C37B 1.532(13) .
C36B C38B 1.546(11) .
C36B H36B 1.0000 .
C37B H37D 0.9800 .
C37B H37E 0.9800 .
C37B H37F 0.9800 .
C38B H38D 0.9800 .
C38B H38E 0.9800 .
C38B H38F 0.9800 .
C39 C40 1.397(6) .
C39 C44 1.403(7) .
C40 C41 1.391(7) .
C40 H40 0.9500 .
C41 C42 1.375(8) .
C41 H41 0.9500 .
C42 C43 1.382(7) .
C42 H42 0.9500 .
C43 C44 1.396(7) .
C43 H43 0.9500 .
C44 H44 0.9500 .
C45 Cl2 1.712(12) .
C45 Cl3 1.722(13) .
C45 Cl1 1.815(13) .
C45 H45 1.0000 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 O6 0.95 2.22 3.136(5) 162.1 2_676
C12 H12 O6 1.00 2.62 3.406(5) 135.6 2_676
C34 H34A O3 1.00 2.51 3.332(6) 139.2 .
C45 H45 O3 1.00 2.17 3.132(11) 160.9 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O7 Ge1 O1 C2 63.5(3) . . . .
C17 Ge1 O1 C2 177.9(3) . . . .
N1 Ge1 O1 C2 -49.4(3) . . . .
O2 Ge1 O1 C2 -64.6(7) . . . .
Ge1 O1 C2 C1 34.0(5) . . . .
Ge1 O1 C2 C3 -148.5(3) . . . .
C11 C1 C2 O1 6.1(6) . . . .
C9 C1 C2 O1 -177.6(3) . . . .
C11 C1 C2 C3 -171.3(4) . . . .
C9 C1 C2 C3 5.0(6) . . . .
O1 C2 C3 C4 178.5(4) . . . .
C1 C2 C3 C4 -3.9(6) . . . .
C2 C3 C4 C10 0.5(7) . . . .
C10 C5 C6 C7 1.6(7) . . . .
C5 C6 C7 C8 -0.4(7) . . . .
C6 C7 C8 C9 -0.6(6) . . . .
C7 C8 C9 C10 0.4(6) . . . .
C7 C8 C9 C1 -176.6(4) . . . .
C2 C1 C9 C10 -2.7(5) . . . .
C11 C1 C9 C10 173.5(3) . . . .
C2 C1 C9 C8 174.3(4) . . . .
C11 C1 C9 C8 -9.6(6) . . . .
C8 C9 C10 C5 0.8(5) . . . .
C1 C9 C10 C5 177.9(4) . . . .
C8 C9 C10 C4 -177.8(4) . . . .
C1 C9 C10 C4 -0.7(5) . . . .
C6 C5 C10 C9 -1.8(6) . . . .
C6 C5 C10 C4 176.7(4) . . . .
C3 C4 C10 C9 1.8(6) . . . .
C3 C4 C10 C5 -176.8(4) . . . .
C12 N1 C11 C1 -179.2(3) . . . .
Ge1 N1 C11 C1 -18.1(5) . . . .
C2 C1 C11 N1 -14.0(6) . . . .
C9 C1 C11 N1 169.8(4) . . . .
C11 N1 C12 C13 139.1(3) . . . .
Ge1 N1 C12 C13 -23.2(4) . . . .
C11 N1 C12 C14 -100.0(4) . . . .
Ge1 N1 C12 C14 97.7(3) . . . .
Ge1 O2 C13 O3 -179.4(3) . . . .
Ge1 O2 C13 C12 0.9(4) . . . .
N1 C12 C13 O3 -165.9(4) . . . .
C14 C12 C13 O3 73.1(5) . . . .
N1 C12 C13 O2 13.9(4) . . . .
C14 C12 C13 O2 -107.2(4) . . . .
N1 C12 C14 C15 166.3(4) . . . .
C13 C12 C14 C15 -76.4(4) . . . .
N1 C12 C14 C16B -71.6(5) . . . .
C13 C12 C14 C16B 45.7(6) . . . .
N1 C12 C14 C16A 44.5(6) . . . .
C13 C12 C14 C16A 161.9(5) . . . .
C22 C17 C18 C19 -2.0(7) . . . .
Ge1 C17 C18 C19 172.7(3) . . . .
C17 C18 C19 C20 2.0(7) . . . .
C18 C19 C20 C21 0.3(9) . . . .
C19 C20 C21 C22 -2.5(11) . . . .
C20 C21 C22 C17 2.5(11) . . . .
C18 C17 C22 C21 -0.2(9) . . . .
Ge1 C17 C22 C21 -174.7(5) . . . .
O7 Ge2 O4 C24 60.5(3) . . . .
C39 Ge2 O4 C24 175.5(3) . . . .
O5 Ge2 O4 C24 -71.1(7) . . . .
N2 Ge2 O4 C24 -49.2(3) . . . .
Ge2 O4 C24 C23 36.3(5) . . . .
Ge2 O4 C24 C25 -144.6(3) . . . .
C33 C23 C24 O4 3.0(6) . . . .
C31 C23 C24 O4 -178.6(4) . . . .
C33 C23 C24 C25 -176.0(4) . . . .
C31 C23 C24 C25 2.4(6) . . . .
O4 C24 C25 C26 176.2(4) . . . .
C23 C24 C25 C26 -4.7(6) . . . .
C24 C25 C26 C32 2.8(7) . . . .
C32 C27 C28 C29 -1.0(9) . . . .
C27 C28 C29 C30 0.2(11) . . . .
C28 C29 C30 C31 0.1(11) . . . .
C29 C30 C31 C32 0.4(8) . . . .
C29 C30 C31 C23 -178.3(6) . . . .
C33 C23 C31 C32 -179.9(4) . . . .
C24 C23 C31 C32 1.7(6) . . . .
C33 C23 C31 C30 -1.3(7) . . . .
C24 C23 C31 C30 -179.7(5) . . . .
C30 C31 C32 C27 -1.1(7) . . . .
C23 C31 C32 C27 177.6(4) . . . .
C30 C31 C32 C26 177.7(4) . . . .
C23 C31 C32 C26 -3.6(6) . . . .
C28 C27 C32 C31 1.5(8) . . . .
C28 C27 C32 C26 -177.4(5) . . . .
C25 C26 C32 C31 1.3(7) . . . .
C25 C26 C32 C27 -179.8(4) . . . .
C34 N2 C33 C23 -174.6(4) . . . .
Ge2 N2 C33 C23 -16.3(6) . . . .
C24 C23 C33 N2 -12.4(6) . . . .
C31 C23 C33 N2 169.2(4) . . . .
C33 N2 C34 C36A -82.1(7) . . . .
Ge2 N2 C34 C36A 118.5(7) . . . .
C33 N2 C34 C35 145.5(4) . . . .
Ge2 N2 C34 C35 -13.9(4) . . . .
C33 N2 C34 C36B -101.9(7) . . . .
Ge2 N2 C34 C36B 98.7(6) . . . .
Ge2 O5 C35 O6 -179.7(3) . . . .
Ge2 O5 C35 C34 1.0(5) . . . .
N2 C34 C35 O6 -171.2(4) . . . .
C36A C34 C35 O6 63.5(6) . . . .
C36B C34 C35 O6 70.7(5) . . . .
N2 C34 C35 O5 8.1(5) . . . .
C36A C34 C35 O5 -117.2(5) . . . .
C36B C34 C35 O5 -110.0(5) . . . .
N2 C34 C36A C37A -72.2(7) . . . .
C35 C34 C36A C37A 51.7(7) . . . .
N2 C34 C36A C38A 166.4(7) . . . .
C35 C34 C36A C38A -69.7(9) . . . .
N2 C34 C36B C37B -62.8(10) . . . .
C35 C34 C36B C37B 51.3(9) . . . .
N2 C34 C36B C38B 170.4(8) . . . .
C35 C34 C36B C38B -75.6(9) . . . .
C44 C39 C40 C41 -1.9(7) . . . .
Ge2 C39 C40 C41 -174.7(4) . . . .
C39 C40 C41 C42 0.8(8) . . . .
C40 C41 C42 C43 0.5(8) . . . .
C41 C42 C43 C44 -0.8(8) . . . .
C42 C43 C44 C39 -0.3(8) . . . .
C40 C39 C44 C43 1.6(7) . . . .
Ge2 C39 C44 C43 174.6(4) . . . .
O4 Ge2 O7 Ge1 -138.7(3) . . . .
C39 Ge2 O7 Ge1 126.2(3) . . . .
O5 Ge2 O7 Ge1 31.2(3) . . . .
N2 Ge2 O7 Ge1 -50.7(3) . . . .
O1 Ge1 O7 Ge2 -131.7(3) . . . .
C17 Ge1 O7 Ge2 134.8(3) . . . .
N1 Ge1 O7 Ge2 -43.5(3) . . . .
O2 Ge1 O7 Ge2 38.6(3) . . . .
