# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b20002
_database_code_depnum_ccdc_archive 'CCDC 2090115'
loop_
_audit_author_name
_audit_author_address
'Paul Boyle'
;The University of Western Ontario
Canada
;
_audit_update_record             
;
2021-06-15 deposited with the CCDC.	2021-10-18 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H56 Ge O6'
_chemical_formula_weight         657.39
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.091(2)
_cell_length_b                   18.355(5)
_cell_length_c                   12.889(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.130(14)
_cell_angle_gamma                90
_cell_volume                     1673.2(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    110
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      31.86
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    0.959
_shelx_estimated_absorpt_T_min   0.766
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6334
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Axis Apex2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56754
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.727
_diffrn_reflns_theta_max         33.841
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6714
_reflns_number_gt                5108
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       Apex3
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    Mercury
_computing_publication_material  cif2tables.py
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+1.9778P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6714
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.500000 0.500000 0.500000 0.01356(7) Uani 1 2 d S . P . .
O1 O 0.40734(18) 0.58917(7) 0.45986(9) 0.0156(2) Uani 1 1 d . . . . .
O2 O 0.42246(18) 0.46357(7) 0.37182(9) 0.0143(2) Uani 1 1 d . . . . .
O3 O 0.76621(19) 0.53043(7) 0.45013(10) 0.0178(2) Uani 1 1 d . . . . .
C1 C 0.3616(2) 0.58827(9) 0.35505(12) 0.0129(3) Uani 1 1 d . . . . .
C2 C 0.3655(2) 0.52001(9) 0.30728(13) 0.0131(3) Uani 1 1 d . . . . .
C3 C 0.3187(2) 0.51243(9) 0.20005(13) 0.0137(3) Uani 1 1 d . . . . .
C4 C 0.2787(2) 0.57729(10) 0.14440(13) 0.0146(3) Uani 1 1 d . . . . .
H4 H 0.247157 0.573910 0.071664 0.018 Uiso 1 1 calc R U . . .
C5 C 0.2828(2) 0.64635(10) 0.19015(13) 0.0143(3) Uani 1 1 d . . . . .
C6 C 0.3233(2) 0.65111(10) 0.29830(13) 0.0147(3) Uani 1 1 d . . . . .
H6 H 0.324339 0.697124 0.332090 0.018 Uiso 1 1 calc R U . . .
C7 C 0.3121(2) 0.43693(9) 0.14742(12) 0.0136(3) Uani 1 1 d . . . . .
C8 C 0.2602(3) 0.44171(11) 0.03027(14) 0.0194(3) Uani 1 1 d . . . . .
H8A H 0.355053 0.470929 -0.002548 0.029 Uiso 1 1 calc R U . . .
H8B H 0.135753 0.464654 0.018015 0.029 Uiso 1 1 calc R U . . .
H8C H 0.256425 0.392604 0.000343 0.029 Uiso 1 1 calc R U . . .
C9 C 0.1597(3) 0.39078(11) 0.19634(15) 0.0245(4) Uani 1 1 d . . . . .
H9A H 0.158095 0.341658 0.166492 0.037 Uiso 1 1 calc R U . . .
H9B H 0.035614 0.413577 0.181881 0.037 Uiso 1 1 calc R U . . .
H9C H 0.188607 0.387786 0.271727 0.037 Uiso 1 1 calc R U . . .
C10 C 0.5029(3) 0.39878(11) 0.16425(15) 0.0220(4) Uani 1 1 d . . . . .
H10A H 0.495382 0.350538 0.131627 0.033 Uiso 1 1 calc R U . . .
H10B H 0.536097 0.393446 0.238995 0.033 Uiso 1 1 calc R U . . .
H10C H 0.599913 0.427839 0.132933 0.033 Uiso 1 1 calc R U . . .
C11 C 0.2584(3) 0.71671(10) 0.12647(14) 0.0175(3) Uani 1 1 d . . . . .
C12 C 0.1391(3) 0.77284(12) 0.18134(17) 0.0280(4) Uani 1 1 d . . . . .
H12A H 0.132055 0.818152 0.141030 0.042 Uiso 1 1 calc R U . . .
H12B H 0.197746 0.782606 0.251129 0.042 Uiso 1 1 calc R U . . .
H12C H 0.011318 0.753536 0.186840 0.042 Uiso 1 1 calc R U . . .
C13 C 0.1605(3) 0.70356(12) 0.01840(16) 0.0280(4) Uani 1 1 d . . . . .
H13A H 0.238177 0.670909 -0.021008 0.042 Uiso 1 1 calc R U . . .
H13B H 0.144195 0.750097 -0.018422 0.042 Uiso 1 1 calc R U . . .
H13C H 0.036549 0.681241 0.025398 0.042 Uiso 1 1 calc R U . . .
C14 C 0.4548(3) 0.74878(12) 0.11336(17) 0.0267(4) Uani 1 1 d . . . . .
H14A H 0.528295 0.714677 0.073899 0.040 Uiso 1 1 calc R U . . .
H14B H 0.519995 0.757041 0.181998 0.040 Uiso 1 1 calc R U . . .
H14C H 0.441681 0.795137 0.075807 0.040 Uiso 1 1 calc R U . . .
C15 C 0.8407(3) 0.50790(11) 0.35253(15) 0.0219(4) Uani 1 1 d . . . . .
H15A H 0.765066 0.467400 0.320390 0.026 Uiso 1 1 calc R U . . .
H15B H 0.973921 0.491937 0.364117 0.026 Uiso 1 1 calc R U . . .
C16 C 0.8257(3) 0.57545(12) 0.28379(15) 0.0239(4) Uani 1 1 d . . . . .
H16A H 0.706688 0.574966 0.238632 0.029 Uiso 1 1 calc R U . . .
H16B H 0.933785 0.578404 0.239460 0.029 Uiso 1 1 calc R U . . .
C17 C 0.8283(3) 0.63978(12) 0.36087(16) 0.0235(4) Uani 1 1 d . . . . .
H17A H 0.939783 0.671284 0.353175 0.028 Uiso 1 1 calc R U . . .
H17B H 0.712289 0.669568 0.349414 0.028 Uiso 1 1 calc R U . . .
C18 C 0.8383(3) 0.60435(11) 0.46766(15) 0.0227(4) Uani 1 1 d . . . . .
H18A H 0.970229 0.603256 0.498476 0.027 Uiso 1 1 calc R U . . .
H18B H 0.759433 0.631337 0.515035 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ge1 O1 1.8247(13) 3_666 ?
Ge1 O1 1.8247(13) . ?
Ge1 O2 1.8297(13) 3_666 ?
Ge1 O2 1.8298(13) . ?
Ge1 O3 2.1126(14) 3_666 ?
Ge1 O3 2.1126(14) . ?
O1 C1 1.366(2) . ?
O2 C2 1.371(2) . ?
O3 C15 1.459(2) . ?
O3 C18 1.462(2) . ?
C1 C6 1.382(2) . ?
C1 C2 1.397(2) . ?
C2 C3 1.405(2) . ?
C3 C4 1.408(2) . ?
C3 C7 1.542(2) . ?
C4 C5 1.397(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(2) . ?
C5 C11 1.533(2) . ?
C6 H6 0.9500 . ?
C7 C10 1.525(3) . ?
C7 C8 1.531(2) . ?
C7 C9 1.543(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.530(3) . ?
C11 C14 1.532(3) . ?
C11 C12 1.538(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.523(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.542(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.519(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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 180.0 3_666 . ?
O1 Ge1 O2 89.60(6) 3_666 3_666 ?
O1 Ge1 O2 90.40(6) . 3_666 ?
O1 Ge1 O2 90.40(6) 3_666 . ?
O1 Ge1 O2 89.60(6) . . ?
O2 Ge1 O2 180.0 3_666 . ?
O1 Ge1 O3 89.31(6) 3_666 3_666 ?
O1 Ge1 O3 90.69(6) . 3_666 ?
O2 Ge1 O3 92.23(6) 3_666 3_666 ?
O2 Ge1 O3 87.77(6) . 3_666 ?
O1 Ge1 O3 90.69(6) 3_666 . ?
O1 Ge1 O3 89.31(6) . . ?
O2 Ge1 O3 87.77(6) 3_666 . ?
O2 Ge1 O3 92.23(6) . . ?
O3 Ge1 O3 180.0 3_666 . ?
C1 O1 Ge1 108.93(11) . . ?
C2 O2 Ge1 109.15(11) . . ?
C15 O3 C18 104.60(14) . . ?
C15 O3 Ge1 125.06(11) . . ?
C18 O3 Ge1 120.57(11) . . ?
O1 C1 C6 122.46(15) . . ?
O1 C1 C2 115.83(15) . . ?
C6 C1 C2 121.63(15) . . ?
O2 C2 C1 115.11(15) . . ?
O2 C2 C3 124.09(16) . . ?
C1 C2 C3 120.77(15) . . ?
C2 C3 C4 116.23(15) . . ?
C2 C3 C7 121.29(15) . . ?
C4 C3 C7 122.48(15) . . ?
C5 C4 C3 123.69(15) . . ?
C5 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
C4 C5 C6 118.13(16) . . ?
C4 C5 C11 122.69(15) . . ?
C6 C5 C11 119.04(16) . . ?
C1 C6 C5 119.42(16) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C10 C7 C8 108.33(14) . . ?
C10 C7 C3 110.57(14) . . ?
C8 C7 C3 112.33(14) . . ?
C10 C7 C9 109.27(16) . . ?
C8 C7 C9 107.99(15) . . ?
C3 C7 C9 108.28(14) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C11 C14 108.46(17) . . ?
C13 C11 C5 112.37(16) . . ?
C14 C11 C5 108.33(15) . . ?
C13 C11 C12 107.21(17) . . ?
C14 C11 C12 109.15(17) . . ?
C5 C11 C12 111.26(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 C16 104.85(16) . . ?
O3 C15 H15A 110.8 . . ?
C16 C15 H15A 110.8 . . ?
O3 C15 H15B 110.8 . . ?
C16 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
C15 C16 C17 104.56(16) . . ?
C15 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
C18 C17 C16 104.67(17) . . ?
C18 C17 H17A 110.8 . . ?
C16 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C16 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
O3 C18 C17 105.34(15) . . ?
O3 C18 H18A 110.7 . . ?
C17 C18 H18A 110.7 . . ?
O3 C18 H18B 110.7 . . ?
C17 C18 H18B 110.7 . . ?
H18A C18 H18B 108.8 . . ?

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
_geom_torsion_publ_flag
O2 Ge1 O1 C1 169.25(11) 3_666 . . . ?
O2 Ge1 O1 C1 -10.75(11) . . . . ?
O3 Ge1 O1 C1 -98.52(11) 3_666 . . . ?
O3 Ge1 O1 C1 81.48(11) . . . . ?
O1 Ge1 O2 C2 -170.55(11) 3_666 . . . ?
O1 Ge1 O2 C2 9.45(11) . . . . ?
O3 Ge1 O2 C2 100.16(11) 3_666 . . . ?
O3 Ge1 O2 C2 -79.84(11) . . . . ?
Ge1 O1 C1 C6 -166.94(13) . . . . ?
Ge1 O1 C1 C2 9.83(18) . . . . ?
Ge1 O2 C2 C1 -6.04(18) . . . . ?
Ge1 O2 C2 C3 172.12(13) . . . . ?
O1 C1 C2 O2 -2.6(2) . . . . ?
C6 C1 C2 O2 174.22(15) . . . . ?
O1 C1 C2 C3 179.20(15) . . . . ?
C6 C1 C2 C3 -4.0(3) . . . . ?
O2 C2 C3 C4 -174.78(15) . . . . ?
C1 C2 C3 C4 3.3(2) . . . . ?
O2 C2 C3 C7 5.3(3) . . . . ?
C1 C2 C3 C7 -176.69(15) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C7 C3 C4 C5 179.68(16) . . . . ?
C3 C4 C5 C6 -2.1(3) . . . . ?
C3 C4 C5 C11 173.63(16) . . . . ?
O1 C1 C6 C5 178.10(15) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
C4 C5 C6 C1 1.4(2) . . . . ?
C11 C5 C6 C1 -174.42(15) . . . . ?
C2 C3 C7 C10 -58.2(2) . . . . ?
C4 C3 C7 C10 121.79(17) . . . . ?
C2 C3 C7 C8 -179.39(15) . . . . ?
C4 C3 C7 C8 0.6(2) . . . . ?
C2 C3 C7 C9 61.4(2) . . . . ?
C4 C3 C7 C9 -118.53(18) . . . . ?
C4 C5 C11 C13 20.9(2) . . . . ?
C6 C5 C11 C13 -163.43(17) . . . . ?
C4 C5 C11 C14 -98.9(2) . . . . ?
C6 C5 C11 C14 76.8(2) . . . . ?
C4 C5 C11 C12 141.14(18) . . . . ?
C6 C5 C11 C12 -43.2(2) . . . . ?
C18 O3 C15 C16 -39.55(18) . . . . ?
Ge1 O3 C15 C16 106.02(15) . . . . ?
O3 C15 C16 C17 24.91(19) . . . . ?
C15 C16 C17 C18 -1.75(19) . . . . ?
C15 O3 C18 C17 38.50(19) . . . . ?
Ge1 O3 C18 C17 -108.98(14) . . . . ?
C16 C17 C18 O3 -22.0(2) . . . . ?

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
C15 H15A O2 0.99 2.56 3.103(2) 114.0 .

_refine_diff_density_max         2.679
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.089


_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Bruker Apex2'
_diffrn_measurement_device       'κ-geometry diffractometer'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b21079
_database_code_depnum_ccdc_archive 'CCDC 2090117'
loop_
_audit_author_name
_audit_author_address
'Paul Boyle'
;The University of Western Ontario
Canada
;
_audit_update_record             
;
2021-06-15 deposited with the CCDC.	2021-10-18 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H36 Br8 Cl Ge N O4'
_chemical_formula_weight         1197.90
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'
Cl Cl 0.1484 0.1585 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.864(5)
_cell_length_b                   11.942(6)
_cell_length_c                   16.473(7)
_cell_angle_alpha                84.984(10)
_cell_angle_beta                 88.202(8)
_cell_angle_gamma                73.534(13)
_cell_volume                     1853.6(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    223
_cell_measurement_reflns_used    9198
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      30.45
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.144
_exptl_absorpt_coefficient_mu    9.554
_shelx_estimated_absorpt_T_min   0.133
_shelx_estimated_absorpt_T_max   0.340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3819
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Axis Apex2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            112781
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.241
_diffrn_reflns_theta_max         30.556
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11316
_reflns_number_gt                8838
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       Apex3
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    Mercury
_computing_publication_material  cif2tables.py
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0219P)²+1.5099P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11316
_refine_ls_number_parameters     392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0571
_refine_ls_wR_factor_gt          0.0518
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.95230(2) 0.23707(2) 0.24993(2) 0.02174(5) Uani 1 1 d . . . . .
Cl1 Cl 0.92190(7) 0.42396(6) 0.24691(4) 0.03627(14) Uani 1 1 d . . . . .
O1 O 1.10112(16) 0.17952(16) 0.18089(9) 0.0295(4) Uani 1 1 d . . . . .
O2 O 0.83324(16) 0.22850(16) 0.16734(9) 0.0290(4) Uani 1 1 d . . . . .
O3 O 1.08107(15) 0.18722(15) 0.33389(9) 0.0265(3) Uani 1 1 d . . . . .
O4 O 0.81578(15) 0.21317(15) 0.32232(9) 0.0258(3) Uani 1 1 d . . . . .
C1 C 1.0544(2) 0.1735(2) 0.10585(13) 0.0244(5) Uani 1 1 d . . . . .
C2 C 0.9075(2) 0.2011(2) 0.09824(13) 0.0234(4) Uani 1 1 d . . . . .
C3 C 0.8481(2) 0.1982(2) 0.02360(13) 0.0249(5) Uani 1 1 d . . . . .
C4 C 0.9365(3) 0.1662(2) -0.04400(13) 0.0273(5) Uani 1 1 d . . . . .
C5 C 1.0820(2) 0.1386(2) -0.03607(13) 0.0281(5) Uani 1 1 d . . . . .
C6 C 1.1418(2) 0.1416(2) 0.03939(13) 0.0269(5) Uani 1 1 d . . . . .
C7 C 1.0136(2) 0.1746(2) 0.40459(12) 0.0216(4) Uani 1 1 d . . . . .
C8 C 0.8684(2) 0.1881(2) 0.39847(12) 0.0218(4) Uani 1 1 d . . . . .
C9 C 0.7885(2) 0.1763(2) 0.46753(13) 0.0237(4) Uani 1 1 d . . . . .
C10 C 0.8537(2) 0.1490(2) 0.54384(12) 0.0230(4) Uani 1 1 d . . . . .
C11 C 0.9976(2) 0.1360(2) 0.55030(12) 0.0225(4) Uani 1 1 d . . . . .
C12 C 1.0778(2) 0.1501(2) 0.48022(13) 0.0228(4) Uani 1 1 d . . . . .
Br3 Br 0.65042(3) 0.23903(3) 0.01602(2) 0.04020(7) Uani 1 1 d . . . . .
Br4 Br 0.85689(3) 0.15986(3) -0.14561(2) 0.03922(7) Uani 1 1 d . . . . .
Br5 Br 1.20210(3) 0.09683(3) -0.12633(2) 0.04976(8) Uani 1 1 d . . . . .
Br6 Br 1.33837(3) 0.10198(3) 0.05452(2) 0.04287(7) Uani 1 1 d . . . . .
Br9 Br 0.59281(2) 0.20305(3) 0.45511(2) 0.04084(7) Uani 1 1 d . . . . .
Br10 Br 0.74437(3) 0.13002(3) 0.63699(2) 0.03403(6) Uani 1 1 d . . . . .
Br11 Br 1.08484(3) 0.10109(2) 0.65307(2) 0.03391(6) Uani 1 1 d . . . . .
Br12 Br 1.27139(2) 0.13851(3) 0.48492(2) 0.03694(7) Uani 1 1 d . . . . .
N1 N 0.36557(19) 0.44409(16) 0.24130(11) 0.0221(4) Uani 1 1 d . . . . .
C13 C 0.4795(2) 0.32777(19) 0.23916(13) 0.0216(4) Uani 1 1 d . . . . .
H13A H 0.527021 0.325892 0.185942 0.026 Uiso 1 1 calc R U . . .
H13B H 0.550091 0.324036 0.280620 0.026 Uiso 1 1 calc R U . . .
C14 C 0.4274(2) 0.2196(2) 0.25350(14) 0.0246(4) Uani 1 1 d . . . . .
H14A H 0.350113 0.225403 0.215959 0.029 Uiso 1 1 calc R U . . .
H14B H 0.391051 0.214321 0.309329 0.029 Uiso 1 1 calc R U . . .
C15 C 0.5475(2) 0.1103(2) 0.24012(15) 0.0289(5) Uani 1 1 d . . . . .
H15A H 0.574544 0.110557 0.182364 0.035 Uiso 1 1 calc R U . . .
H15B H 0.629907 0.110912 0.271663 0.035 Uiso 1 1 calc R U . . .
C16 C 0.5044(3) 0.0002(2) 0.26585(18) 0.0408(6) Uani 1 1 d . . . . .
H16A H 0.492594 -0.006601 0.324582 0.061 Uiso 1 1 calc R U . . .
H16B H 0.577158 -0.067679 0.249420 0.061 Uiso 1 1 calc R U . . .
H16C H 0.415930 0.004287 0.239996 0.061 Uiso 1 1 calc R U . . .
C17 C 0.2552(2) 0.4573(2) 0.17609(14) 0.0268(5) Uani 1 1 d . . . . .
H17A H 0.201985 0.400393 0.190772 0.032 Uiso 1 1 calc R U . . .
H17B H 0.188545 0.535643 0.176743 0.032 Uiso 1 1 calc R U . . .
C18 C 0.3106(3) 0.4408(3) 0.09021(15) 0.0356(6) Uani 1 1 d . . . . .
H18A H 0.374664 0.361681 0.087573 0.043 Uiso 1 1 calc R U . . .
H18B H 0.363679 0.497253 0.073981 0.043 Uiso 1 1 calc R U . . .
C19 C 0.1877(3) 0.4587(3) 0.03258(16) 0.0442(7) Uani 1 1 d . . . . .
H19A H 0.131614 0.405310 0.051139 0.053 Uiso 1 1 calc R U . . .
H19B H 0.126539 0.539101 0.033515 0.053 Uiso 1 1 calc R U . . .
C20 C 0.2389(4) 0.4363(4) -0.05385(19) 0.0716(11) Uani 1 1 d . . . . .
H20A H 0.288849 0.492621 -0.073667 0.107 Uiso 1 1 calc R U . . .
H20B H 0.158476 0.444441 -0.088586 0.107 Uiso 1 1 calc R U . . .
H20C H 0.302024 0.357641 -0.054590 0.107 Uiso 1 1 calc R U . . .
C21 C 0.4334(2) 0.5434(2) 0.22574(14) 0.0269(5) Uani 1 1 d . . . . .
H21A H 0.357810 0.616818 0.216571 0.032 Uiso 1 1 calc R U . . .
H21B H 0.488863 0.531510 0.175216 0.032 Uiso 1 1 calc R U . . .
C22 C 0.5288(3) 0.5583(2) 0.29218(15) 0.0307(5) Uani 1 1 d . . . . .
H22A H 0.605004 0.485683 0.303129 0.037 Uiso 1 1 calc R U . . .
H22B H 0.474388 0.575871 0.342572 0.037 Uiso 1 1 calc R U . . .
C23 C 0.5909(3) 0.6583(2) 0.26381(16) 0.0345(6) Uani 1 1 d . . . . .
H23A H 0.649322 0.637767 0.215131 0.041 Uiso 1 1 calc R U . . .
H23B H 0.513783 0.728744 0.248748 0.041 Uiso 1 1 calc R U . . .
C24 C 0.6802(3) 0.6851(3) 0.3288(2) 0.0483(7) Uani 1 1 d . . . . .
H24A H 0.620928 0.712583 0.375171 0.072 Uiso 1 1 calc R U . . .
H24B H 0.722978 0.745150 0.306747 0.072 Uiso 1 1 calc R U . . .
H24C H 0.753830 0.614561 0.345968 0.072 Uiso 1 1 calc R U . . .
C25 C 0.2920(2) 0.4466(2) 0.32386(13) 0.0270(5) Uani 1 1 d . . . . .
H25A H 0.246626 0.383213 0.329311 0.032 Uiso 1 1 calc R U . . .
H25B H 0.364360 0.429656 0.366179 0.032 Uiso 1 1 calc R U . . .
C26 C 0.1814(3) 0.5601(2) 0.34057(16) 0.0367(6) Uani 1 1 d . . . . .
H26A H 0.224690 0.624795 0.336097 0.044 Uiso 1 1 calc R U . . .
H26B H 0.105978 0.577413 0.300116 0.044 Uiso 1 1 calc R U . . .
C27 C 0.1200(4) 0.5488(3) 0.4251(2) 0.0610(10) Uani 1 1 d . . . . .
H27A H 0.042058 0.619147 0.432851 0.073 Uiso 1 1 calc R U . . .
H27B H 0.081018 0.481566 0.429602 0.073 Uiso 1 1 calc R U . . .
C28 C 0.2265(6) 0.5329(4) 0.4918(2) 0.0907(16) Uani 1 1 d . . . . .
H28A H 0.290464 0.454346 0.493355 0.136 Uiso 1 1 calc R U . . .
H28B H 0.177696 0.544703 0.543753 0.136 Uiso 1 1 calc R U . . .
H28C H 0.279861 0.589609 0.481213 0.136 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ge1 O4 1.8369(16) . ?
Ge1 O1 1.8387(16) . ?
Ge1 O3 1.8489(16) . ?
Ge1 O2 1.8529(16) . ?
Ge1 Cl1 2.1622(13) . ?
O1 C1 1.347(3) . ?
O2 C2 1.348(3) . ?
O3 C7 1.341(2) . ?
O4 C8 1.349(2) . ?
C1 C6 1.384(3) . ?
C1 C2 1.399(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.403(3) . ?
C3 Br3 1.877(2) . ?
C4 C5 1.387(3) . ?
C4 Br4 1.887(2) . ?
C5 C6 1.400(3) . ?
C5 Br5 1.883(2) . ?
C6 Br6 1.881(2) . ?
C7 C12 1.385(3) . ?
C7 C8 1.401(3) . ?
C8 C9 1.384(3) . ?
C9 C10 1.400(3) . ?
C9 Br9 1.880(2) . ?
C10 C11 1.390(3) . ?
C10 Br10 1.882(2) . ?
C11 C12 1.404(3) . ?
C11 Br11 1.883(2) . ?
C12 Br12 1.879(2) . ?
N1 C21 1.518(3) . ?
N1 C25 1.520(3) . ?
N1 C17 1.520(3) . ?
N1 C13 1.521(3) . ?
C13 C14 1.518(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.521(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.516(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 C18 1.509(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 C19 1.519(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C19 C20 1.516(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C22 1.520(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 C23 1.523(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 C24 1.517(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C25 C26 1.520(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C26 C27 1.511(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C27 C28 1.506(6) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 H28C 0.9700 . ?

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
O4 Ge1 O1 150.29(8) . . ?
O4 Ge1 O3 87.88(7) . . ?
O1 Ge1 O3 86.63(8) . . ?
O4 Ge1 O2 87.33(8) . . ?
O1 Ge1 O2 87.46(8) . . ?
O3 Ge1 O2 158.98(8) . . ?
O4 Ge1 Cl1 103.03(6) . . ?
O1 Ge1 Cl1 106.68(6) . . ?
O3 Ge1 Cl1 99.60(6) . . ?
O2 Ge1 Cl1 101.42(6) . . ?
C1 O1 Ge1 110.80(13) . . ?
C2 O2 Ge1 110.38(13) . . ?
C7 O3 Ge1 110.10(13) . . ?
C8 O4 Ge1 110.26(13) . . ?
O1 C1 C6 124.2(2) . . ?
O1 C1 C2 115.40(18) . . ?
C6 C1 C2 120.4(2) . . ?
O2 C2 C3 124.6(2) . . ?
O2 C2 C1 115.24(18) . . ?
C3 C2 C1 120.16(19) . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 Br3 118.54(16) . . ?
C4 C3 Br3 121.93(17) . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 Br4 120.02(17) . . ?
C3 C4 Br4 119.90(18) . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 Br5 120.67(17) . . ?
C6 C5 Br5 119.03(17) . . ?
C1 C6 C5 119.5(2) . . ?
C1 C6 Br6 118.21(17) . . ?
C5 C6 Br6 122.29(16) . . ?
O3 C7 C12 124.53(19) . . ?
O3 C7 C8 115.51(18) . . ?
C12 C7 C8 119.96(19) . . ?
O4 C8 C9 124.19(19) . . ?
O4 C8 C7 115.41(18) . . ?
C9 C8 C7 120.40(19) . . ?
C8 C9 C10 119.74(19) . . ?
C8 C9 Br9 117.96(16) . . ?
C10 C9 Br9 122.27(16) . . ?
C11 C10 C9 120.09(19) . . ?
C11 C10 Br10 120.66(16) . . ?
C9 C10 Br10 119.24(16) . . ?
C10 C11 C12 119.98(19) . . ?
C10 C11 Br11 120.09(16) . . ?
C12 C11 Br11 119.93(16) . . ?
C7 C12 C11 119.81(19) . . ?
C7 C12 Br12 117.98(16) . . ?
C11 C12 Br12 122.21(16) . . ?
C21 N1 C25 111.91(17) . . ?
C21 N1 C17 108.46(17) . . ?
C25 N1 C17 108.01(17) . . ?
C21 N1 C13 109.07(17) . . ?
C25 N1 C13 108.32(16) . . ?
C17 N1 C13 111.09(17) . . ?
C14 C13 N1 115.22(17) . . ?
C14 C13 H13A 108.5 . . ?
N1 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
N1 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C13 C14 C15 110.04(18) . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C14 111.1(2) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N1 116.04(18) . . ?
C18 C17 H17A 108.3 . . ?
N1 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
N1 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C17 C18 C19 109.5(2) . . ?
C17 C18 H18A 109.8 . . ?
C19 C18 H18A 109.8 . . ?
C17 C18 H18B 109.8 . . ?
C19 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C20 C19 C18 111.4(3) . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 C22 116.65(19) . . ?
N1 C21 H21A 108.1 . . ?
C22 C21 H21A 108.1 . . ?
N1 C21 H21B 108.1 . . ?
C22 C21 H21B 108.1 . . ?
H21A C21 H21B 107.3 . . ?
C21 C22 C23 108.7(2) . . ?
C21 C22 H22A 110.0 . . ?
C23 C22 H22A 110.0 . . ?
C21 C22 H22B 110.0 . . ?
C23 C22 H22B 110.0 . . ?
H22A C22 H22B 108.3 . . ?
C24 C23 C22 112.4(2) . . ?
C24 C23 H23A 109.1 . . ?
C22 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C22 C23 H23B 109.1 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 N1 116.44(19) . . ?
C26 C25 H25A 108.2 . . ?
N1 C25 H25A 108.2 . . ?
C26 C25 H25B 108.2 . . ?
N1 C25 H25B 108.2 . . ?
H25A C25 H25B 107.3 . . ?
C27 C26 C25 109.8(2) . . ?
C27 C26 H26A 109.7 . . ?
C25 C26 H26A 109.7 . . ?
C27 C26 H26B 109.7 . . ?
C25 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?
C28 C27 C26 113.3(3) . . ?
C28 C27 H27A 108.9 . . ?
C26 C27 H27A 108.9 . . ?
C28 C27 H27B 108.9 . . ?
C26 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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
_geom_torsion_publ_flag
O4 Ge1 O1 C1 87.4(2) . . . . ?
O3 Ge1 O1 C1 167.10(16) . . . . ?
O2 Ge1 O1 C1 7.27(16) . . . . ?
Cl1 Ge1 O1 C1 -93.89(15) . . . . ?
O4 Ge1 O2 C2 -158.38(16) . . . . ?
O1 Ge1 O2 C2 -7.64(16) . . . . ?
O3 Ge1 O2 C2 -81.4(2) . . . . ?
Cl1 Ge1 O2 C2 98.86(15) . . . . ?
O4 Ge1 O3 C7 -8.19(15) . . . . ?
O1 Ge1 O3 C7 -158.98(16) . . . . ?
O2 Ge1 O3 C7 -85.1(2) . . . . ?
Cl1 Ge1 O3 C7 94.66(14) . . . . ?
O1 Ge1 O4 C8 87.25(19) . . . . ?
O3 Ge1 O4 C8 7.84(15) . . . . ?
O2 Ge1 O4 C8 167.37(16) . . . . ?
Cl1 Ge1 O4 C8 -91.52(15) . . . . ?
Ge1 O1 C1 C6 175.2(2) . . . . ?
Ge1 O1 C1 C2 -5.5(3) . . . . ?
Ge1 O2 C2 C3 -174.0(2) . . . . ?
Ge1 O2 C2 C1 6.5(3) . . . . ?
O1 C1 C2 O2 -0.7(3) . . . . ?
C6 C1 C2 O2 178.6(2) . . . . ?
O1 C1 C2 C3 179.7(2) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
O2 C2 C3 C4 -178.8(2) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
O2 C2 C3 Br3 1.8(3) . . . . ?
C1 C2 C3 Br3 -178.70(18) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
Br3 C3 C4 C5 178.89(19) . . . . ?
C2 C3 C4 Br4 179.10(18) . . . . ?
Br3 C3 C4 Br4 -1.5(3) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
Br4 C4 C5 C6 -179.08(19) . . . . ?
C3 C4 C5 Br5 -179.45(18) . . . . ?
Br4 C4 C5 Br5 0.9(3) . . . . ?
O1 C1 C6 C5 -179.8(2) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
O1 C1 C6 Br6 0.8(3) . . . . ?
C2 C1 C6 Br6 -178.48(18) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
Br5 C5 C6 C1 179.22(19) . . . . ?
C4 C5 C6 Br6 178.66(19) . . . . ?
Br5 C5 C6 Br6 -1.4(3) . . . . ?
Ge1 O3 C7 C12 -173.08(19) . . . . ?
Ge1 O3 C7 C8 6.8(2) . . . . ?
Ge1 O4 C8 C9 173.79(19) . . . . ?
Ge1 O4 C8 C7 -5.9(2) . . . . ?
O3 C7 C8 O4 -0.6(3) . . . . ?
C12 C7 C8 O4 179.3(2) . . . . ?
O3 C7 C8 C9 179.6(2) . . . . ?
C12 C7 C8 C9 -0.5(4) . . . . ?
O4 C8 C9 C10 179.4(2) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
O4 C8 C9 Br9 -2.7(3) . . . . ?
C7 C8 C9 Br9 176.99(17) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
Br9 C9 C10 C11 -176.64(18) . . . . ?
C8 C9 C10 Br10 -178.72(18) . . . . ?
Br9 C9 C10 Br10 3.5(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
Br10 C10 C11 C12 179.81(17) . . . . ?
C9 C10 C11 Br11 179.26(18) . . . . ?
Br10 C10 C11 Br11 -0.9(3) . . . . ?
O3 C7 C12 C11 -178.5(2) . . . . ?
C8 C7 C12 C11 1.6(3) . . . . ?
O3 C7 C12 Br12 2.2(3) . . . . ?
C8 C7 C12 Br12 -177.76(17) . . . . ?
C10 C11 C12 C7 -1.3(3) . . . . ?
Br11 C11 C12 C7 179.39(17) . . . . ?
C10 C11 C12 Br12 177.98(17) . . . . ?
Br11 C11 C12 Br12 -1.3(3) . . . . ?
C21 N1 C13 C14 -179.78(18) . . . . ?
C25 N1 C13 C14 58.2(2) . . . . ?
C17 N1 C13 C14 -60.3(2) . . . . ?
N1 C13 C14 C15 173.45(18) . . . . ?
C13 C14 C15 C16 171.7(2) . . . . ?
C21 N1 C17 C18 66.4(3) . . . . ?
C25 N1 C17 C18 -172.2(2) . . . . ?
C13 N1 C17 C18 -53.5(3) . . . . ?
N1 C17 C18 C19 -179.1(2) . . . . ?
C17 C18 C19 C20 -176.9(3) . . . . ?
C25 N1 C21 C22 50.9(3) . . . . ?
C17 N1 C21 C22 169.9(2) . . . . ?
C13 N1 C21 C22 -69.0(2) . . . . ?
N1 C21 C22 C23 177.7(2) . . . . ?
C21 C22 C23 C24 176.1(2) . . . . ?
C21 N1 C25 C26 55.3(3) . . . . ?
C17 N1 C25 C26 -64.0(3) . . . . ?
C13 N1 C25 C26 175.5(2) . . . . ?
N1 C25 C26 C27 -179.3(2) . . . . ?
C25 C26 C27 C28 64.6(3) . . . . ?

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
C13 H13B O4 0.98 2.66 3.484(3) 141.8 .
C13 H13B Br9 0.98 3.09 3.808(3) 131.5 .
C14 H14B Br9 0.98 3.14 3.711(3) 119.0 .
C17 H17A Cl1 0.98 2.83 3.570(3) 132.9 1_455
C18 H18A Br3 0.98 2.96 3.770(3) 140.5 .
C21 H21A Br4 0.98 3.06 4.020(3) 166.4 2_665
C26 H26A Br10 0.98 3.10 4.020(3) 157.1 2_666

_refine_diff_density_max         0.941
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.099


_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Bruker Apex2'
_diffrn_measurement_device       'κ-geometry diffractometer'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b21074
_database_code_depnum_ccdc_archive 'CCDC 2090116'
loop_
_audit_author_name
_audit_author_address
'Paul Boyle'
;The University of Western Ontario
Canada
;
_audit_update_record             
;
2021-06-15 deposited with the CCDC.	2021-10-18 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H70 Ge O6 P2'
_chemical_formula_weight         781.49
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.012(3)
_cell_length_b                   9.945(4)
_cell_length_c                   14.528(6)
_cell_angle_alpha                109.138(11)
_cell_angle_beta                 92.133(9)
_cell_angle_gamma                95.396(13)
_cell_volume                     1085.9(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    110
_cell_measurement_reflns_used    9440
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      37.29
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.167
_exptl_absorpt_coefficient_mu    0.819
_shelx_estimated_absorpt_T_min   0.750
_shelx_estimated_absorpt_T_max   0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6804
_exptl_absorpt_correction_T_max  0.7483
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Axis Apex2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            125120
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.867
_diffrn_reflns_theta_max         42.168
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             15267
_reflns_number_gt                13141
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       Apex3
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    Mercury
_computing_publication_material  cif2tables.py
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0399P)²+0.0621P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         15267
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0733
_refine_ls_wR_factor_gt          0.0700
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.500000 0.500000 0.000000 0.00834(2) Uani 1 2 d S . P . .
P1 P 0.19946(2) 0.48634(2) 0.14644(2) 0.01144(3) Uani 1 1 d . . . . .
O1 O 0.28582(5) 0.52363(5) 0.06510(3) 0.01248(7) Uani 1 1 d . . . . .
O2 O 0.60106(5) 0.46967(4) 0.10674(3) 0.01029(6) Uani 1 1 d . . . . .
O3 O 0.56594(5) 0.69376(4) 0.05858(3) 0.01186(6) Uani 1 1 d . . . . .
C1 C 0.63338(6) 0.59702(6) 0.17967(4) 0.01065(8) Uani 1 1 d . . . . .
C2 C 0.61560(7) 0.72022(6) 0.15365(4) 0.01136(8) Uani 1 1 d . . . . .
C3 C 0.64568(8) 0.85658(6) 0.22413(4) 0.01428(9) Uani 1 1 d . . . . .
C4 C 0.68614(8) 0.86359(7) 0.32101(4) 0.01672(10) Uani 1 1 d . . . . .
H4 H 0.704899 0.955223 0.370157 0.020 Uiso 1 1 calc R U . . .
C5 C 0.70002(8) 0.74311(7) 0.34839(4) 0.01550(9) Uani 1 1 d . . . . .
C6 C 0.67559(7) 0.60783(6) 0.27536(4) 0.01310(8) Uani 1 1 d . . . . .
H6 H 0.687993 0.524001 0.291540 0.016 Uiso 1 1 calc R U . . .
C7 C 0.63580(9) 0.99084(6) 0.19540(5) 0.01819(10) Uani 1 1 d . . . . .
C8 C 0.45888(10) 0.99062(8) 0.15108(7) 0.02810(15) Uani 1 1 d . . . . .
H8A H 0.377100 0.992703 0.199905 0.042 Uiso 1 1 calc R U . . .
H8B H 0.431248 0.903815 0.094160 0.042 Uiso 1 1 calc R U . . .
H8C H 0.455291 1.075193 0.130867 0.042 Uiso 1 1 calc R U . . .
C9 C 0.76323(10) 0.99291(8) 0.11939(6) 0.02479(13) Uani 1 1 d . . . . .
H9A H 0.757462 1.078934 0.101093 0.037 Uiso 1 1 calc R U . . .
H9B H 0.736830 0.907530 0.061332 0.037 Uiso 1 1 calc R U . . .
H9C H 0.876749 0.993570 0.147216 0.037 Uiso 1 1 calc R U . . .
C10 C 0.67609(14) 1.12976(8) 0.28276(6) 0.03166(17) Uani 1 1 d . . . . .
H10A H 0.594883 1.132147 0.331922 0.047 Uiso 1 1 calc R U . . .
H10B H 0.669292 1.212335 0.260661 0.047 Uiso 1 1 calc R U . . .
H10C H 0.789805 1.133435 0.311433 0.047 Uiso 1 1 calc R U . . .
C11 C 0.73635(9) 0.75152(8) 0.45468(4) 0.01940(11) Uani 1 1 d . . . . .
C12 C 0.75067(13) 0.90525(9) 0.52626(5) 0.03083(17) Uani 1 1 d . . . . .
H12A H 0.845345 0.962429 0.511128 0.046 Uiso 1 1 calc R U . . .
H12B H 0.769258 0.904509 0.593140 0.046 Uiso 1 1 calc R U . . .
H12C H 0.646556 0.947123 0.520295 0.046 Uiso 1 1 calc R U . . .
C13 C 0.90177(11) 0.69002(12) 0.46511(6) 0.03239(17) Uani 1 1 d . . . . .
H13A H 0.893307 0.589917 0.422336 0.049 Uiso 1 1 calc R U . . .
H13B H 0.923730 0.695150 0.533055 0.049 Uiso 1 1 calc R U . . .
H13C H 0.993989 0.745702 0.446590 0.049 Uiso 1 1 calc R U . . .
C14 C 0.59164(11) 0.66454(10) 0.48370(5) 0.03033(17) Uani 1 1 d . . . . .
H14A H 0.485755 0.702895 0.475849 0.046 Uiso 1 1 calc R U . . .
H14B H 0.612476 0.671147 0.552028 0.046 Uiso 1 1 calc R U . . .
H14C H 0.584322 0.564067 0.441746 0.046 Uiso 1 1 calc R U . . .
C15 C 0.21055(8) 0.64047(8) 0.25559(4) 0.01888(11) Uani 1 1 d . . . . .
H15A H 0.159997 0.610938 0.308115 0.023 Uiso 1 1 calc R U . . .
H15B H 0.330152 0.675794 0.276747 0.023 Uiso 1 1 calc R U . . .
C16 C 0.12127(10) 0.76280(8) 0.24280(5) 0.02291(12) Uani 1 1 d . . . . .
H16A H 0.169352 0.791936 0.190283 0.034 Uiso 1 1 calc R U . . .
H16B H 0.135925 0.844302 0.303856 0.034 Uiso 1 1 calc R U . . .
H16C H 0.001195 0.730738 0.226061 0.034 Uiso 1 1 calc R U . . .
C17 C 0.28685(8) 0.34652(7) 0.17904(5) 0.01718(10) Uani 1 1 d . . . . .
H17A H 0.294949 0.264668 0.118778 0.021 Uiso 1 1 calc R U . . .
H17B H 0.402270 0.382382 0.209254 0.021 Uiso 1 1 calc R U . . .
C18 C 0.18447(10) 0.29329(9) 0.24979(6) 0.02474(13) Uani 1 1 d . . . . .
H18A H 0.175345 0.373618 0.309671 0.037 Uiso 1 1 calc R U . . .
H18B H 0.240760 0.219659 0.265844 0.037 Uiso 1 1 calc R U . . .
H18C H 0.071811 0.252562 0.219101 0.037 Uiso 1 1 calc R U . . .
C19 C -0.01752(7) 0.42531(7) 0.10696(5) 0.01555(9) Uani 1 1 d . . . . .
H19A H -0.077780 0.413266 0.162506 0.019 Uiso 1 1 calc R U . . .
H19B H -0.068406 0.498892 0.086487 0.019 Uiso 1 1 calc R U . . .
C20 C -0.04018(9) 0.28349(7) 0.02215(5) 0.02037(11) Uani 1 1 d . . . . .
H20A H 0.031279 0.290942 -0.029660 0.031 Uiso 1 1 calc R U . . .
H20B H -0.158064 0.261957 -0.003520 0.031 Uiso 1 1 calc R U . . .
H20C H -0.008270 0.206651 0.045241 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ge1 O2 1.8467(7) 2_665 ?
Ge1 O2 1.8467(7) . ?
Ge1 O3 1.8484(8) . ?
Ge1 O3 1.8484(8) 2_665 ?
Ge1 O1 1.9862(8) 2_665 ?
Ge1 O1 1.9863(8) . ?
P1 O1 1.5208(7) . ?
P1 C19 1.7940(9) . ?
P1 C17 1.7996(8) . ?
P1 C15 1.8006(9) . ?
O2 C1 1.3535(8) . ?
O3 C2 1.3551(9) . ?
C1 C6 1.3851(10) . ?
C1 C2 1.4132(9) . ?
C2 C3 1.3984(9) . ?
C3 C4 1.4101(10) . ?
C3 C7 1.5317(10) . ?
C4 C5 1.3930(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.4048(9) . ?
C5 C11 1.5341(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.5344(12) . ?
C7 C9 1.5353(11) . ?
C7 C10 1.5362(11) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.5322(12) . ?
C11 C13 1.5335(13) . ?
C11 C14 1.5353(11) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.5259(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.5321(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.5284(11) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
O2 Ge1 O2 179.999(12) 2_665 . ?
O2 Ge1 O3 91.39(3) 2_665 . ?
O2 Ge1 O3 88.61(3) . . ?
O2 Ge1 O3 88.61(3) 2_665 2_665 ?
O2 Ge1 O3 91.39(3) . 2_665 ?
O3 Ge1 O3 180.0 . 2_665 ?
O2 Ge1 O1 90.25(3) 2_665 2_665 ?
O2 Ge1 O1 89.75(3) . 2_665 ?
O3 Ge1 O1 90.36(3) . 2_665 ?
O3 Ge1 O1 89.64(3) 2_665 2_665 ?
O2 Ge1 O1 89.75(3) 2_665 . ?
O2 Ge1 O1 90.25(3) . . ?
O3 Ge1 O1 89.64(3) . . ?
O3 Ge1 O1 90.36(3) 2_665 . ?
O1 Ge1 O1 180.0 2_665 . ?
O1 P1 C19 108.75(4) . . ?
O1 P1 C17 113.76(3) . . ?
C19 P1 C17 107.18(4) . . ?
O1 P1 C15 111.03(4) . . ?
C19 P1 C15 108.60(3) . . ?
C17 P1 C15 107.34(4) . . ?
P1 O1 Ge1 139.50(3) . . ?
C1 O2 Ge1 108.56(4) . . ?
C2 O3 Ge1 109.15(4) . . ?
O2 C1 C6 122.69(5) . . ?
O2 C1 C2 116.12(5) . . ?
C6 C1 C2 121.15(5) . . ?
O3 C2 C3 124.76(5) . . ?
O3 C2 C1 114.96(5) . . ?
C3 C2 C1 120.27(6) . . ?
C2 C3 C4 117.05(6) . . ?
C2 C3 C7 120.54(6) . . ?
C4 C3 C7 122.41(5) . . ?
C5 C4 C3 123.41(5) . . ?
C5 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
C4 C5 C6 118.25(6) . . ?
C4 C5 C11 122.98(6) . . ?
C6 C5 C11 118.75(6) . . ?
C1 C6 C5 119.80(6) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C3 C7 C8 110.25(6) . . ?
C3 C7 C9 109.33(6) . . ?
C8 C7 C9 108.91(7) . . ?
C3 C7 C10 112.53(7) . . ?
C8 C7 C10 107.95(7) . . ?
C9 C7 C10 107.78(6) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C13 108.07(7) . . ?
C12 C11 C5 112.61(6) . . ?
C13 C11 C5 109.95(6) . . ?
C12 C11 C14 107.68(7) . . ?
C13 C11 C14 109.59(8) . . ?
C5 C11 C14 108.89(6) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 P1 113.68(5) . . ?
C16 C15 H15A 108.8 . . ?
P1 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
P1 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 P1 113.84(5) . . ?
C18 C17 H17A 108.8 . . ?
P1 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
P1 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 P1 112.37(5) . . ?
C20 C19 H19A 109.1 . . ?
P1 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
P1 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
_geom_torsion_publ_flag
C19 P1 O1 Ge1 -137.84(5) . . . . ?
C17 P1 O1 Ge1 -18.48(5) . . . . ?
C15 P1 O1 Ge1 102.73(5) . . . . ?
O3 Ge1 O2 C1 14.22(4) . . . . ?
O3 Ge1 O2 C1 -165.77(3) 2_665 . . . ?
O1 Ge1 O2 C1 104.59(4) 2_665 . . . ?
O1 Ge1 O2 C1 -75.41(4) . . . . ?
O2 Ge1 O3 C2 166.10(4) 2_665 . . . ?
O2 Ge1 O3 C2 -13.90(4) . . . . ?
O1 Ge1 O3 C2 -103.64(4) 2_665 . . . ?
O1 Ge1 O3 C2 76.36(4) . . . . ?
Ge1 O2 C1 C6 165.99(4) . . . . ?
Ge1 O2 C1 C2 -11.73(5) . . . . ?
Ge1 O3 C2 C3 -168.34(5) . . . . ?
Ge1 O3 C2 C1 10.50(6) . . . . ?
O2 C1 C2 O3 0.86(7) . . . . ?
C6 C1 C2 O3 -176.90(5) . . . . ?
O2 C1 C2 C3 179.76(5) . . . . ?
C6 C1 C2 C3 2.00(8) . . . . ?
O3 C2 C3 C4 176.00(5) . . . . ?
C1 C2 C3 C4 -2.78(8) . . . . ?
O3 C2 C3 C7 -4.49(9) . . . . ?
C1 C2 C3 C7 176.73(5) . . . . ?
C2 C3 C4 C5 1.18(9) . . . . ?
C7 C3 C4 C5 -178.32(6) . . . . ?
C3 C4 C5 C6 1.26(9) . . . . ?
C3 C4 C5 C11 -177.19(6) . . . . ?
O2 C1 C6 C5 -177.07(5) . . . . ?
C2 C1 C6 C5 0.54(8) . . . . ?
C4 C5 C6 C1 -2.11(9) . . . . ?
C11 C5 C6 C1 176.41(5) . . . . ?
C2 C3 C7 C8 60.50(8) . . . . ?
C4 C3 C7 C8 -120.01(7) . . . . ?
C2 C3 C7 C9 -59.20(8) . . . . ?
C4 C3 C7 C9 120.28(7) . . . . ?
C2 C3 C7 C10 -178.93(6) . . . . ?
C4 C3 C7 C10 0.56(9) . . . . ?
C4 C5 C11 C12 1.50(9) . . . . ?
C6 C5 C11 C12 -176.94(6) . . . . ?
C4 C5 C11 C13 -119.07(8) . . . . ?
C6 C5 C11 C13 62.48(8) . . . . ?
C4 C5 C11 C14 120.85(8) . . . . ?
C6 C5 C11 C14 -57.59(9) . . . . ?
O1 P1 C15 C16 62.26(6) . . . . ?
C19 P1 C15 C16 -57.27(6) . . . . ?
C17 P1 C15 C16 -172.84(5) . . . . ?
O1 P1 C17 C18 -171.40(5) . . . . ?
C19 P1 C17 C18 -51.15(6) . . . . ?
C15 P1 C17 C18 65.36(6) . . . . ?
O1 P1 C19 C20 66.33(6) . . . . ?
C17 P1 C19 C20 -57.05(6) . . . . ?
C15 P1 C19 C20 -172.73(5) . . . . ?

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
C17 H17B O2 0.99 2.50 3.0661(12) 115.7 .

_refine_diff_density_max         0.687
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.063


_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Bruker Apex2'
_diffrn_measurement_device       'κ-geometry diffractometer'
