# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1915517'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2019-05-12 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 O2 Si'
_chemical_formula_sum            'C18 H16 O2 Si'
_chemical_formula_weight         292.40

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8022(3)
_cell_length_b                   11.3939(3)
_cell_length_c                   14.9070(4)
_cell_angle_alpha                88.3116(11)
_cell_angle_beta                 89.7934(11)
_cell_angle_gamma                65.7475(10)
_cell_volume                     1517.23(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7128
_cell_measurement_theta_min      2.647
_cell_measurement_theta_max      30.475

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9402
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17101
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         27.00
_reflns_number_total             6582
_reflns_number_gt                5395
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0346P)²+0.7851P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6582
_refine_ls_number_parameters     507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.76427(5) 0.74448(4) 0.98026(3) 0.02163(11) Uani 1 1 d . . .
Si2 Si 0.24349(5) 0.74013(4) 0.47198(3) 0.02051(11) Uani 1 1 d . . .
O11 O 0.49476(15) 0.88728(14) 0.93562(10) 0.0422(4) Uani 1 1 d . . .
O12 O 0.63546(13) 0.89707(12) 0.96136(8) 0.0303(3) Uani 1 1 d . . .
O21 O 0.33133(15) 0.50263(12) 0.50512(10) 0.0346(3) Uani 1 1 d . . .
O22 O 0.37069(13) 0.59131(11) 0.44696(8) 0.0266(3) Uani 1 1 d . . .
C11 C 0.71014(18) 0.65969(17) 1.07306(11) 0.0245(4) Uani 1 1 d . . .
C12 C 0.5909(2) 0.62305(19) 1.06358(13) 0.0321(4) Uani 1 1 d . . .
C13 C 0.5546(2) 0.5555(2) 1.13146(14) 0.0384(5) Uani 1 1 d . . .
C14 C 0.6376(2) 0.52164(19) 1.21054(14) 0.0371(5) Uani 1 1 d . . .
C15 C 0.7551(2) 0.55685(18) 1.22196(13) 0.0335(4) Uani 1 1 d . . .
C16 C 0.7911(2) 0.62498(18) 1.15377(12) 0.0286(4) Uani 1 1 d . . .
C21 C 0.92812(18) 0.77850(16) 1.01069(11) 0.0224(3) Uani 1 1 d . . .
C22 C 0.9209(2) 0.85981(19) 1.08112(13) 0.0326(4) Uani 1 1 d . . .
C23 C 1.0436(2) 0.8828(2) 1.10481(14) 0.0397(5) Uani 1 1 d . . .
C24 C 1.1766(2) 0.8258(2) 1.05914(14) 0.0351(4) Uani 1 1 d . . .
C25 C 1.1872(2) 0.74453(19) 0.99008(13) 0.0303(4) Uani 1 1 d . . .
C26 C 1.06396(19) 0.72140(17) 0.96562(11) 0.0250(4) Uani 1 1 d . . .
C31 C 0.79306(17) 0.65772(16) 0.87341(11) 0.0213(3) Uani 1 1 d . . .
C32 C 0.82109(19) 0.71526(18) 0.79513(11) 0.0266(4) Uani 1 1 d . . .
C33 C 0.8426(2) 0.6547(2) 0.71378(13) 0.0330(4) Uani 1 1 d . . .
C34 C 0.8375(2) 0.5358(2) 0.70870(13) 0.0347(4) Uani 1 1 d . . .
C35 C 0.8114(2) 0.47647(19) 0.78472(13) 0.0318(4) Uani 1 1 d . . .
C36 C 0.78951(19) 0.53725(17) 0.86650(12) 0.0260(4) Uani 1 1 d . . .
C41 C 0.26191(19) 0.76877(16) 0.59268(11) 0.0230(3) Uani 1 1 d . . .
C42 C 0.1399(2) 0.81143(17) 0.65044(12) 0.0280(4) Uani 1 1 d . . .
C43 C 0.1570(2) 0.83340(19) 0.74011(13) 0.0348(4) Uani 1 1 d . . .
C44 C 0.2958(2) 0.81463(19) 0.77307(13) 0.0357(5) Uani 1 1 d . . .
C45 C 0.4192(2) 0.77105(19) 0.71764(13) 0.0332(4) Uani 1 1 d . . .
C46 C 0.4024(2) 0.74783(18) 0.62854(12) 0.0288(4) Uani 1 1 d . . .
C51 C 0.31001(18) 0.83931(16) 0.39720(11) 0.0226(3) Uani 1 1 d . . .
C52 C 0.3214(2) 0.95044(17) 0.42693(13) 0.0289(4) Uani 1 1 d . . .
C53 C 0.3761(2) 1.02029(19) 0.37106(14) 0.0353(4) Uani 1 1 d . . .
C54 C 0.4205(2) 0.98123(19) 0.28492(13) 0.0326(4) Uani 1 1 d . . .
C55 C 0.4105(2) 0.87195(19) 0.25391(13) 0.0315(4) Uani 1 1 d . . .
C56 C 0.3552(2) 0.80192(19) 0.30958(12) 0.0281(4) Uani 1 1 d . . .
C61 C 0.05246(18) 0.75548(15) 0.44259(11) 0.0211(3) Uani 1 1 d . . .
C62 C -0.0313(2) 0.84054(17) 0.37388(12) 0.0281(4) Uani 1 1 d . . .
C63 C -0.1730(2) 0.8512(2) 0.35101(13) 0.0350(4) Uani 1 1 d . . .
C64 C -0.2339(2) 0.77643(19) 0.39578(13) 0.0313(4) Uani 1 1 d . . .
C65 C -0.1533(2) 0.69110(18) 0.46408(12) 0.0274(4) Uani 1 1 d . . .
C66 C -0.01215(19) 0.68110(16) 0.48721(11) 0.0235(3) Uani 1 1 d . . .
H1 H 0.433(4) 0.957(3) 0.973(2) 0.096(11) Uiso 1 1 d . . .
H2 H 0.431(4) 0.461(3) 0.537(2) 0.093(10) Uiso 1 1 d . . .
H12 H 0.531(2) 0.6466(19) 1.0077(14) 0.036(5) Uiso 1 1 d . . .
H13 H 0.472(3) 0.532(2) 1.1235(15) 0.051(7) Uiso 1 1 d . . .
H14 H 0.612(2) 0.475(2) 1.2586(15) 0.041(6) Uiso 1 1 d . . .
H15 H 0.814(2) 0.534(2) 1.2781(15) 0.046(6) Uiso 1 1 d . . .
H16 H 0.872(2) 0.649(2) 1.1620(13) 0.036(5) Uiso 1 1 d . . .
H22 H 0.828(2) 0.9001(19) 1.1147(13) 0.031(5) Uiso 1 1 d . . .
H23 H 1.036(3) 0.939(2) 1.1516(16) 0.050(6) Uiso 1 1 d . . .
H24 H 1.262(2) 0.841(2) 1.0751(14) 0.040(6) Uiso 1 1 d . . .
H25 H 1.281(2) 0.702(2) 0.9583(13) 0.035(5) Uiso 1 1 d . . .
H26 H 1.072(2) 0.6644(18) 0.9186(13) 0.025(5) Uiso 1 1 d . . .
H32 H 0.823(2) 0.799(2) 0.7980(13) 0.033(5) Uiso 1 1 d . . .
H33 H 0.860(2) 0.698(2) 0.6623(15) 0.043(6) Uiso 1 1 d . . .
H34 H 0.852(2) 0.492(2) 0.6523(15) 0.043(6) Uiso 1 1 d . . .
H35 H 0.806(2) 0.393(2) 0.7828(14) 0.040(6) Uiso 1 1 d . . .
H36 H 0.773(2) 0.4925(18) 0.9195(13) 0.026(5) Uiso 1 1 d . . .
H42 H 0.044(2) 0.8264(18) 0.6283(13) 0.028(5) Uiso 1 1 d . . .
H43 H 0.071(2) 0.862(2) 0.7765(15) 0.043(6) Uiso 1 1 d . . .
H44 H 0.306(2) 0.834(2) 0.8333(16) 0.048(6) Uiso 1 1 d . . .
H45 H 0.517(2) 0.7544(19) 0.7402(13) 0.035(5) Uiso 1 1 d . . .
H46 H 0.490(2) 0.7147(19) 0.5913(13) 0.033(5) Uiso 1 1 d . . .
H52 H 0.292(2) 0.9788(18) 0.4867(13) 0.027(5) Uiso 1 1 d . . .
H53 H 0.385(2) 1.096(2) 0.3961(14) 0.041(6) Uiso 1 1 d . . .
H54 H 0.456(2) 1.028(2) 0.2462(14) 0.038(6) Uiso 1 1 d . . .
H55 H 0.448(2) 0.8420(19) 0.1939(14) 0.032(5) Uiso 1 1 d . . .
H56 H 0.350(2) 0.727(2) 0.2888(13) 0.035(5) Uiso 1 1 d . . .
H62 H 0.011(2) 0.8904(19) 0.3420(13) 0.033(5) Uiso 1 1 d . . .
H63 H -0.229(2) 0.910(2) 0.3036(15) 0.042(6) Uiso 1 1 d . . .
H64 H -0.330(2) 0.7836(19) 0.3810(13) 0.034(5) Uiso 1 1 d . . .
H65 H -0.195(2) 0.6383(19) 0.4952(13) 0.030(5) Uiso 1 1 d . . .
H66 H 0.045(2) 0.6201(19) 0.5335(13) 0.030(5) Uiso 1 1 d . . .


_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
Si1 O12 1.6931(13) . ?
Si1 C31 1.8586(16) . ?
Si1 C21 1.8608(17) . ?
Si1 C11 1.8616(18) . ?
Si2 O22 1.6930(12) . ?
Si2 C61 1.8604(17) . ?
Si2 C41 1.8605(17) . ?
Si2 C51 1.8630(17) . ?
O11 O12 1.4814(17) . ?
O11 H1 0.97(3) . ?
O21 O22 1.4791(17) . ?
O21 H2 1.01(3) . ?
C11 C16 1.398(2) . ?
C11 C12 1.402(2) . ?
C12 C13 1.385(3) . ?
C12 H12 0.99(2) . ?
C13 C14 1.386(3) . ?
C13 H13 0.95(2) . ?
C14 C15 1.379(3) . ?
C14 H14 0.97(2) . ?
C15 C16 1.391(3) . ?
C15 H15 0.98(2) . ?
C16 H16 0.95(2) . ?
C21 C26 1.398(2) . ?
C21 C22 1.403(2) . ?
C22 C23 1.381(3) . ?
C22 H22 0.98(2) . ?
C23 C24 1.381(3) . ?
C23 H23 0.94(2) . ?
C24 C25 1.380(3) . ?
C24 H24 0.95(2) . ?
C25 C26 1.390(2) . ?
C25 H25 0.97(2) . ?
C26 H26 0.950(19) . ?
C31 C36 1.394(2) . ?
C31 C32 1.403(2) . ?
C32 C33 1.385(2) . ?
C32 H32 0.97(2) . ?
C33 C34 1.381(3) . ?
C33 H33 0.95(2) . ?
C34 C35 1.379(3) . ?
C34 H34 0.97(2) . ?
C35 C36 1.392(2) . ?
C35 H35 0.98(2) . ?
C36 H36 0.975(19) . ?
C41 C42 1.395(2) . ?
C41 C46 1.402(2) . ?
C42 C43 1.390(3) . ?
C42 H42 0.95(2) . ?
C43 C44 1.378(3) . ?
C43 H43 0.95(2) . ?
C44 C45 1.384(3) . ?
C44 H44 0.95(2) . ?
C45 C46 1.385(3) . ?
C45 H45 0.96(2) . ?
C46 H46 0.96(2) . ?
C51 C56 1.399(2) . ?
C51 C52 1.400(2) . ?
C52 C53 1.387(3) . ?
C52 H52 0.960(19) . ?
C53 C54 1.381(3) . ?
C53 H53 0.98(2) . ?
C54 C55 1.381(3) . ?
C54 H54 0.94(2) . ?
C55 C56 1.390(3) . ?
C55 H55 0.98(2) . ?
C56 H56 0.94(2) . ?
C61 C62 1.399(2) . ?
C61 C66 1.402(2) . ?
C62 C63 1.387(3) . ?
C62 H62 0.94(2) . ?
C63 C64 1.382(3) . ?
C63 H63 0.96(2) . ?
C64 C65 1.387(3) . ?
C64 H64 0.94(2) . ?
C65 C66 1.385(2) . ?
C65 H65 0.96(2) . ?
C66 H66 0.96(2) . ?

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
O12 Si1 C31 108.11(7) . . ?
O12 Si1 C21 99.49(7) . . ?
C31 Si1 C21 112.07(7) . . ?
O12 Si1 C11 112.46(7) . . ?
C31 Si1 C11 111.81(8) . . ?
C21 Si1 C11 112.24(7) . . ?
O22 Si2 C61 109.54(7) . . ?
O22 Si2 C41 109.35(7) . . ?
C61 Si2 C41 112.32(7) . . ?
O22 Si2 C51 99.59(7) . . ?
C61 Si2 C51 113.30(7) . . ?
C41 Si2 C51 111.94(7) . . ?
O12 O11 H1 93.7(18) . . ?
O11 O12 Si1 106.51(9) . . ?
O22 O21 H2 96.3(17) . . ?
O21 O22 Si2 104.63(9) . . ?
C16 C11 C12 117.24(17) . . ?
C16 C11 Si1 121.19(13) . . ?
C12 C11 Si1 121.52(14) . . ?
C13 C12 C11 121.37(18) . . ?
C13 C12 H12 119.3(12) . . ?
C11 C12 H12 119.3(12) . . ?
C12 C13 C14 120.09(18) . . ?
C12 C13 H13 119.8(14) . . ?
C14 C13 H13 120.2(14) . . ?
C15 C14 C13 119.85(18) . . ?
C15 C14 H14 119.5(13) . . ?
C13 C14 H14 120.6(13) . . ?
C14 C15 C16 119.95(19) . . ?
C14 C15 H15 120.6(13) . . ?
C16 C15 H15 119.4(13) . . ?
C15 C16 C11 121.50(17) . . ?
C15 C16 H16 119.5(12) . . ?
C11 C16 H16 119.0(12) . . ?
C26 C21 C22 117.63(16) . . ?
C26 C21 Si1 121.16(13) . . ?
C22 C21 Si1 121.19(13) . . ?
C23 C22 C21 121.11(18) . . ?
C23 C22 H22 119.2(11) . . ?
C21 C22 H22 119.7(11) . . ?
C22 C23 C24 120.31(18) . . ?
C22 C23 H23 119.5(14) . . ?
C24 C23 H23 120.1(14) . . ?
C25 C24 C23 119.77(17) . . ?
C25 C24 H24 119.4(13) . . ?
C23 C24 H24 120.8(13) . . ?
C24 C25 C26 120.21(18) . . ?
C24 C25 H25 120.7(12) . . ?
C26 C25 H25 119.1(12) . . ?
C25 C26 C21 120.95(17) . . ?
C25 C26 H26 120.0(11) . . ?
C21 C26 H26 119.0(11) . . ?
C36 C31 C32 117.68(15) . . ?
C36 C31 Si1 123.59(13) . . ?
C32 C31 Si1 118.73(13) . . ?
C33 C32 C31 120.90(17) . . ?
C33 C32 H32 119.8(12) . . ?
C31 C32 H32 119.3(12) . . ?
C34 C33 C32 120.23(18) . . ?
C34 C33 H33 121.8(13) . . ?
C32 C33 H33 118.0(13) . . ?
C35 C34 C33 120.12(17) . . ?
C35 C34 H34 118.5(13) . . ?
C33 C34 H34 121.4(13) . . ?
C34 C35 C36 119.73(18) . . ?
C34 C35 H35 121.7(12) . . ?
C36 C35 H35 118.6(12) . . ?
C35 C36 C31 121.34(17) . . ?
C35 C36 H36 118.1(11) . . ?
C31 C36 H36 120.5(11) . . ?
C42 C41 C46 117.59(16) . . ?
C42 C41 Si2 122.49(13) . . ?
C46 C41 Si2 119.92(13) . . ?
C43 C42 C41 121.16(18) . . ?
C43 C42 H42 119.2(12) . . ?
C41 C42 H42 119.6(12) . . ?
C44 C43 C42 119.99(19) . . ?
C44 C43 H43 122.3(13) . . ?
C42 C43 H43 117.8(13) . . ?
C43 C44 C45 120.15(18) . . ?
C43 C44 H44 119.6(14) . . ?
C45 C44 H44 120.2(14) . . ?
C44 C45 C46 119.81(18) . . ?
C44 C45 H45 121.1(12) . . ?
C46 C45 H45 119.1(12) . . ?
C45 C46 C41 121.27(18) . . ?
C45 C46 H46 118.9(12) . . ?
C41 C46 H46 119.9(12) . . ?
C56 C51 C52 117.75(16) . . ?
C56 C51 Si2 120.44(13) . . ?
C52 C51 Si2 121.78(13) . . ?
C53 C52 C51 120.77(17) . . ?
C53 C52 H52 119.2(11) . . ?
C51 C52 H52 120.0(11) . . ?
C54 C53 C52 120.41(18) . . ?
C54 C53 H53 122.2(12) . . ?
C52 C53 H53 117.3(12) . . ?
C53 C54 C55 120.02(17) . . ?
C53 C54 H54 121.3(13) . . ?
C55 C54 H54 118.7(13) . . ?
C54 C55 C56 119.76(18) . . ?
C54 C55 H55 119.2(11) . . ?
C56 C55 H55 120.9(11) . . ?
C55 C56 C51 121.29(17) . . ?
C55 C56 H56 119.7(12) . . ?
C51 C56 H56 119.0(12) . . ?
C62 C61 C66 117.44(15) . . ?
C62 C61 Si2 121.04(13) . . ?
C66 C61 Si2 121.51(13) . . ?
C63 C62 C61 121.26(17) . . ?
C63 C62 H62 119.7(12) . . ?
C61 C62 H62 119.0(12) . . ?
C64 C63 C62 120.16(18) . . ?
C64 C63 H63 119.6(13) . . ?
C62 C63 H63 120.2(13) . . ?
C63 C64 C65 119.85(17) . . ?
C63 C64 H64 120.7(12) . . ?
C65 C64 H64 119.4(12) . . ?
C66 C65 C64 119.92(17) . . ?
C66 C65 H65 119.9(11) . . ?
C64 C65 H65 120.2(12) . . ?
C65 C66 C61 121.37(16) . . ?
C65 C66 H66 119.8(11) . . ?
C61 C66 H66 118.8(11) . . ?

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
Si1 O12 O11 H1 136.3(19) . . . . ?
Si2 O22 O21 H2 -121.5(18) . . . . ?
C21 Si1 O12 O11 179.91(10) . . . . ?
C51 Si2 O22 O21 178.48(9) . . . . ?

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
O11 H1 O12 0.97(3) 1.83(3) 2.7670(18) 163(3) 2_677
O21 H2 O22 1.01(3) 1.80(3) 2.7548(18) 157(3) 2_666

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1915518'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2019-05-12 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H30 Ge2 O2'
_chemical_formula_sum            'C36 H30 Ge2 O2'
_chemical_formula_weight         639.78

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6748(2)
_cell_length_b                   9.4769(2)
_cell_length_c                   11.2572(3)
_cell_angle_alpha                65.780(1)
_cell_angle_beta                 88.888(1)
_cell_angle_gamma                66.382(1)
_cell_volume                     761.58(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6953
_cell_measurement_theta_min      2.602
_cell_measurement_theta_max      30.523

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             326
_exptl_absorpt_coefficient_mu    2.003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3794
_exptl_absorpt_correction_T_max  0.9065
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8232
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         27.99
_reflns_number_total             3637
_reflns_number_gt                3432
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0302P)²+0.2408P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3637
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0628
_refine_ls_wR_factor_gt          0.0620
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge1 Ge 0.669298(18) 0.369807(18) 0.679840(15) 0.01945(6) Uani 1 1 d . . .
O1 O 0.58054(14) 0.41978(14) 0.51583(11) 0.0277(2) Uani 1 1 d . . .
C11 C 0.87835(19) 0.1660(2) 0.71686(16) 0.0222(3) Uani 1 1 d . . .
C12 C 0.9786(2) 0.1542(2) 0.62023(19) 0.0348(4) Uani 1 1 d . . .
C13 C 1.1281(3) 0.0063(3) 0.6494(2) 0.0434(5) Uani 1 1 d . . .
C14 C 1.1790(2) -0.1289(2) 0.7737(2) 0.0373(4) Uani 1 1 d . . .
C15 C 1.0811(2) -0.1183(2) 0.87058(19) 0.0316(4) Uani 1 1 d . . .
C16 C 0.9314(2) 0.0286(2) 0.84189(16) 0.0249(3) Uani 1 1 d . . .
C21 C 0.51115(18) 0.32166(19) 0.79630(15) 0.0222(3) Uani 1 1 d . . .
C22 C 0.4821(2) 0.3726(2) 0.89664(17) 0.0286(3) Uani 1 1 d . . .
C23 C 0.3724(3) 0.3324(3) 0.98252(19) 0.0365(4) Uani 1 1 d . . .
C24 C 0.2919(2) 0.2393(3) 0.9676(2) 0.0370(4) Uani 1 1 d . . .
C25 C 0.3194(2) 0.1874(3) 0.8686(2) 0.0394(4) Uani 1 1 d . . .
C26 C 0.4277(2) 0.2291(2) 0.7819(2) 0.0322(4) Uani 1 1 d . . .
C31 C 0.7155(2) 0.5527(2) 0.68040(15) 0.0228(3) Uani 1 1 d . . .
C32 C 0.8819(2) 0.5202(3) 0.7211(2) 0.0362(4) Uani 1 1 d . . .
C33 C 0.9182(3) 0.6464(3) 0.7283(2) 0.0430(5) Uani 1 1 d . . .
C34 C 0.7887(3) 0.8075(3) 0.69441(19) 0.0390(4) Uani 1 1 d . . .
C35 C 0.6232(3) 0.8421(2) 0.6542(2) 0.0365(4) Uani 1 1 d . . .
C36 C 0.5859(2) 0.7159(2) 0.64671(17) 0.0287(3) Uani 1 1 d . . .
H12 H 0.941(3) 0.247(3) 0.536(3) 0.051(7) Uiso 1 1 d . . .
H13 H 1.190(3) -0.001(3) 0.580(3) 0.058(7) Uiso 1 1 d . . .
H14 H 1.280(3) -0.232(3) 0.795(2) 0.039(6) Uiso 1 1 d . . .
H15 H 1.117(3) -0.209(3) 0.956(2) 0.035(5) Uiso 1 1 d . . .
H16 H 0.871(3) 0.033(3) 0.907(2) 0.038(6) Uiso 1 1 d . . .
H22 H 0.535(3) 0.435(3) 0.909(2) 0.041(6) Uiso 1 1 d . . .
H23 H 0.358(3) 0.359(3) 1.049(3) 0.052(7) Uiso 1 1 d . . .
H24 H 0.224(3) 0.211(3) 1.024(2) 0.041(6) Uiso 1 1 d . . .
H25 H 0.268(3) 0.125(3) 0.857(3) 0.053(7) Uiso 1 1 d . . .
H26 H 0.448(3) 0.195(3) 0.713(2) 0.046(6) Uiso 1 1 d . . .
H32 H 0.971(3) 0.415(3) 0.741(2) 0.045(6) Uiso 1 1 d . . .
H33 H 1.038(3) 0.622(3) 0.757(3) 0.056(7) Uiso 1 1 d . . .
H34 H 0.814(3) 0.888(3) 0.701(2) 0.043(6) Uiso 1 1 d . . .
H35 H 0.536(3) 0.941(3) 0.635(2) 0.043(6) Uiso 1 1 d . . .
H36 H 0.470(3) 0.742(3) 0.618(2) 0.037(6) Uiso 1 1 d . . .


_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 1.8088(11) . ?
Ge1 C31 1.9313(15) . ?
Ge1 C21 1.9365(15) . ?
Ge1 C11 1.9376(15) . ?
O1 O1 1.505(2) 2_666 ?
C11 C16 1.389(2) . ?
C11 C12 1.392(2) . ?
C12 C13 1.391(3) . ?
C12 H12 0.94(3) . ?
C13 C14 1.376(3) . ?
C13 H13 0.95(3) . ?
C14 C15 1.381(3) . ?
C14 H14 0.95(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.93(2) . ?
C16 H16 0.89(2) . ?
C21 C22 1.383(2) . ?
C21 C26 1.396(2) . ?
C22 C23 1.392(2) . ?
C22 H22 0.94(2) . ?
C23 C24 1.384(3) . ?
C23 H23 0.87(3) . ?
C24 C25 1.373(3) . ?
C24 H24 0.89(2) . ?
C25 C26 1.391(3) . ?
C25 H25 0.92(3) . ?
C26 H26 0.95(3) . ?
C31 C36 1.393(2) . ?
C31 C32 1.394(2) . ?
C32 C33 1.385(3) . ?
C32 H32 0.92(2) . ?
C33 C34 1.379(3) . ?
C33 H33 1.00(3) . ?
C34 C35 1.379(3) . ?
C34 H34 0.91(2) . ?
C35 C36 1.391(2) . ?
C35 H35 0.88(2) . ?
C36 H36 0.96(2) . ?

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 C31 111.56(6) . . ?
O1 Ge1 C21 107.79(6) . . ?
C31 Ge1 C21 112.27(6) . . ?
O1 Ge1 C11 100.99(6) . . ?
C31 Ge1 C11 111.54(6) . . ?
C21 Ge1 C11 112.11(6) . . ?
O1 O1 Ge1 101.75(10) 2_666 . ?
C16 C11 C12 118.69(15) . . ?
C16 C11 Ge1 120.09(12) . . ?
C12 C11 Ge1 121.22(12) . . ?
C13 C12 C11 120.05(17) . . ?
C13 C12 H12 121.9(15) . . ?
C11 C12 H12 118.0(15) . . ?
C14 C13 C12 120.60(18) . . ?
C14 C13 H13 121.0(16) . . ?
C12 C13 H13 118.3(16) . . ?
C13 C14 C15 119.89(17) . . ?
C13 C14 H14 121.7(14) . . ?
C15 C14 H14 118.4(14) . . ?
C14 C15 C16 119.78(17) . . ?
C14 C15 H15 119.9(13) . . ?
C16 C15 H15 120.3(13) . . ?
C15 C16 C11 120.99(16) . . ?
C15 C16 H16 118.1(14) . . ?
C11 C16 H16 120.9(14) . . ?
C22 C21 C26 118.76(15) . . ?
C22 C21 Ge1 121.49(12) . . ?
C26 C21 Ge1 119.72(13) . . ?
C21 C22 C23 121.02(16) . . ?
C21 C22 H22 120.9(14) . . ?
C23 C22 H22 118.1(14) . . ?
C24 C23 C22 119.44(18) . . ?
C24 C23 H23 119.3(17) . . ?
C22 C23 H23 121.2(17) . . ?
C25 C24 C23 120.35(18) . . ?
C25 C24 H24 120.7(15) . . ?
C23 C24 H24 119.0(15) . . ?
C24 C25 C26 120.21(17) . . ?
C24 C25 H25 121.9(17) . . ?
C26 C25 H25 117.9(17) . . ?
C25 C26 C21 120.22(17) . . ?
C25 C26 H26 121.6(15) . . ?
C21 C26 H26 118.1(15) . . ?
C36 C31 C32 118.34(15) . . ?
C36 C31 Ge1 122.02(12) . . ?
C32 C31 Ge1 119.58(12) . . ?
C33 C32 C31 121.04(18) . . ?
C33 C32 H32 118.3(15) . . ?
C31 C32 H32 120.6(15) . . ?
C34 C33 C32 119.99(18) . . ?
C34 C33 H33 119.9(15) . . ?
C32 C33 H33 120.1(15) . . ?
C35 C34 C33 119.84(17) . . ?
C35 C34 H34 121.1(15) . . ?
C33 C34 H34 119.1(15) . . ?
C34 C35 C36 120.43(18) . . ?
C34 C35 H35 123.0(15) . . ?
C36 C35 H35 116.5(15) . . ?
C35 C36 C31 120.36(17) . . ?
C35 C36 H36 119.7(13) . . ?
C31 C36 H36 119.9(13) . . ?

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
C31 Ge1 O1 O1 -60.27(12) . . . 2_666 ?
C21 Ge1 O1 O1 63.42(12) . . . 2_666 ?
C11 Ge1 O1 O1 -178.88(11) . . . 2_666 ?
O1 Ge1 C11 C16 -139.29(12) . . . . ?
C31 Ge1 C11 C16 102.08(13) . . . . ?
C21 Ge1 C11 C16 -24.79(14) . . . . ?
O1 Ge1 C11 C12 41.11(15) . . . . ?
C31 Ge1 C11 C12 -77.52(15) . . . . ?
C21 Ge1 C11 C12 155.61(14) . . . . ?
C16 C11 C12 C13 0.5(3) . . . . ?
Ge1 C11 C12 C13 -179.92(16) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C12 C11 C16 C15 -0.1(2) . . . . ?
Ge1 C11 C16 C15 -179.76(13) . . . . ?
O1 Ge1 C21 C22 -142.68(13) . . . . ?
C31 Ge1 C21 C22 -19.42(16) . . . . ?
C11 Ge1 C21 C22 107.06(14) . . . . ?
O1 Ge1 C21 C26 39.22(15) . . . . ?
C31 Ge1 C21 C26 162.48(13) . . . . ?
C11 Ge1 C21 C26 -71.04(14) . . . . ?
C26 C21 C22 C23 0.2(3) . . . . ?
Ge1 C21 C22 C23 -177.88(14) . . . . ?
C21 C22 C23 C24 0.3(3) . . . . ?
C22 C23 C24 C25 -0.2(3) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C25 C26 C21 1.0(3) . . . . ?
C22 C21 C26 C25 -0.9(3) . . . . ?
Ge1 C21 C26 C25 177.22(15) . . . . ?
O1 Ge1 C31 C36 63.08(15) . . . . ?
C21 Ge1 C31 C36 -58.03(15) . . . . ?
C11 Ge1 C31 C36 175.19(13) . . . . ?
O1 Ge1 C31 C32 -119.79(14) . . . . ?
C21 Ge1 C31 C32 119.09(15) . . . . ?
C11 Ge1 C31 C32 -7.69(16) . . . . ?
C36 C31 C32 C33 0.1(3) . . . . ?
Ge1 C31 C32 C33 -177.10(16) . . . . ?
C31 C32 C33 C34 -0.3(3) . . . . ?
C32 C33 C34 C35 0.4(3) . . . . ?
C33 C34 C35 C36 -0.4(3) . . . . ?
C34 C35 C36 C31 0.3(3) . . . . ?
C32 C31 C36 C35 -0.2(3) . . . . ?
Ge1 C31 C36 C35 177.01(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1915519'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2019-05-12 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 Ge O2'
_chemical_formula_sum            'C18 H16 Ge O2'
_chemical_formula_weight         336.90

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'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8517(3)
_cell_length_b                   11.4503(3)
_cell_length_c                   15.0058(4)
_cell_angle_alpha                88.4868(9)
_cell_angle_beta                 89.8466(10)
_cell_angle_gamma                65.3416(9)
_cell_volume                     1537.77(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8393
_cell_measurement_theta_min      2.275
_cell_measurement_theta_max      30.531

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    1.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5028
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15171
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.00
_reflns_number_total             6668
_reflns_number_gt                5425
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0599P)²+0.2515P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6668
_refine_ls_number_parameters     507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge1 Ge 0.77416(3) 0.73674(3) 0.98171(2) 0.03190(10) Uani 1 1 d . . .
Ge2 Ge 0.23679(3) 0.74788(3) 0.471202(19) 0.02620(10) Uani 1 1 d . . .
O11 O 0.4965(3) 0.8918(2) 0.93441(18) 0.0554(7) Uani 1 1 d . . .
O12 O 0.6352(2) 0.9023(2) 0.95913(15) 0.0442(5) Uani 1 1 d . . .
O21 O 0.3354(2) 0.5005(2) 0.50300(17) 0.0436(6) Uani 1 1 d . . .
O22 O 0.3726(2) 0.58666(18) 0.44324(14) 0.0340(4) Uani 1 1 d . . .
C11 C 0.7119(3) 0.6542(3) 1.0769(2) 0.0361(7) Uani 1 1 d . . .
C12 C 0.5923(4) 0.6194(4) 1.0659(2) 0.0460(8) Uani 1 1 d . . .
C13 C 0.5538(4) 0.5560(4) 1.1321(3) 0.0520(9) Uani 1 1 d . . .
C14 C 0.6314(4) 0.5235(4) 1.2124(3) 0.0508(9) Uani 1 1 d . . .
C15 C 0.7504(4) 0.5559(3) 1.2252(2) 0.0487(8) Uani 1 1 d . . .
C16 C 0.7910(4) 0.6200(3) 1.1582(2) 0.0420(7) Uani 1 1 d . . .
C21 C 0.9411(3) 0.7742(3) 1.01332(19) 0.0329(6) Uani 1 1 d . . .
C22 C 0.9329(4) 0.8549(4) 1.0833(2) 0.0495(9) Uani 1 1 d . . .
C23 C 1.0548(5) 0.8800(4) 1.1051(3) 0.0601(10) Uani 1 1 d . . .
C24 C 1.1854(4) 0.8262(4) 1.0582(2) 0.0522(9) Uani 1 1 d . . .
C25 C 1.1959(4) 0.7449(4) 0.9886(2) 0.0448(8) Uani 1 1 d . . .
C26 C 1.0755(3) 0.7203(3) 0.96661(19) 0.0347(6) Uani 1 1 d . . .
C31 C 0.8003(3) 0.6508(3) 0.86996(19) 0.0316(6) Uani 1 1 d . . .
C32 C 0.8304(4) 0.7073(3) 0.7931(2) 0.0372(7) Uani 1 1 d . . .
C33 C 0.8478(4) 0.6495(4) 0.7125(2) 0.0455(8) Uani 1 1 d . . .
C34 C 0.8363(4) 0.5330(4) 0.7061(2) 0.0490(9) Uani 1 1 d . . .
C35 C 0.8085(4) 0.4751(3) 0.7807(2) 0.0450(8) Uani 1 1 d . . .
C36 C 0.7900(3) 0.5336(3) 0.8630(2) 0.0388(7) Uani 1 1 d . . .
C41 C 0.2614(3) 0.7711(3) 0.59604(17) 0.0283(6) Uani 1 1 d . . .
C42 C 0.1414(4) 0.8125(3) 0.6532(2) 0.0375(7) Uani 1 1 d . . .
C43 C 0.1611(5) 0.8345(3) 0.7422(2) 0.0464(8) Uani 1 1 d . . .
C44 C 0.3008(5) 0.8149(4) 0.7732(2) 0.0495(9) Uani 1 1 d . . .
C45 C 0.4219(4) 0.7706(3) 0.7181(2) 0.0452(8) Uani 1 1 d . . .
C46 C 0.4027(4) 0.7487(3) 0.6298(2) 0.0394(7) Uani 1 1 d . . .
C51 C 0.3060(3) 0.8491(3) 0.39364(19) 0.0286(6) Uani 1 1 d . . .
C52 C 0.3190(4) 0.9574(3) 0.4242(2) 0.0370(7) Uani 1 1 d . . .
C53 C 0.3743(4) 1.0265(3) 0.3685(3) 0.0453(8) Uani 1 1 d . . .
C54 C 0.4155(4) 0.9878(3) 0.2830(2) 0.0409(7) Uani 1 1 d . . .
C55 C 0.4048(4) 0.8802(4) 0.2520(2) 0.0424(8) Uani 1 1 d . . .
C56 C 0.3491(4) 0.8118(3) 0.3069(2) 0.0378(7) Uani 1 1 d . . .
C61 C 0.0410(3) 0.7589(3) 0.44115(18) 0.0266(6) Uani 1 1 d . . .
C62 C -0.0428(3) 0.8420(3) 0.3729(2) 0.0354(7) Uani 1 1 d . . .
C63 C -0.1831(4) 0.8504(3) 0.3507(2) 0.0422(8) Uani 1 1 d . . .
C64 C -0.2404(3) 0.7741(3) 0.3960(2) 0.0377(7) Uani 1 1 d . . .
C65 C -0.1586(3) 0.6910(3) 0.4630(2) 0.0343(7) Uani 1 1 d . . .
C66 C -0.0187(3) 0.6831(3) 0.4859(2) 0.0299(6) Uani 1 1 d . . .
H1 H 0.429(5) 0.965(4) 0.967(3) 0.067(12) Uiso 1 1 d . . .
H2 H 0.425(5) 0.475(4) 0.531(3) 0.089(15) Uiso 1 1 d . . .
H12 H 0.529(4) 0.648(3) 1.008(2) 0.039(9) Uiso 1 1 d . . .
H13 H 0.478(4) 0.533(3) 1.127(2) 0.054(10) Uiso 1 1 d . . .
H14 H 0.618(4) 0.488(4) 1.268(3) 0.066(12) Uiso 1 1 d . . .
H15 H 0.805(5) 0.526(4) 1.283(3) 0.071(12) Uiso 1 1 d . . .
H16 H 0.870(4) 0.644(3) 1.163(2) 0.051(10) Uiso 1 1 d . . .
H22 H 0.838(4) 0.905(3) 1.109(2) 0.048(10) Uiso 1 1 d . . .
H23 H 1.040(4) 0.939(3) 1.155(3) 0.057(10) Uiso 1 1 d . . .
H24 H 1.270(4) 0.845(3) 1.071(2) 0.051(10) Uiso 1 1 d . . .
H25 H 1.297(4) 0.701(4) 0.959(3) 0.058(11) Uiso 1 1 d . . .
H26 H 1.082(3) 0.658(3) 0.922(2) 0.041(9) Uiso 1 1 d . . .
H32 H 0.830(3) 0.787(3) 0.796(2) 0.030(8) Uiso 1 1 d . . .
H33 H 0.863(4) 0.694(3) 0.660(2) 0.047(9) Uiso 1 1 d . . .
H34 H 0.841(4) 0.494(4) 0.658(3) 0.060(11) Uiso 1 1 d . . .
H35 H 0.804(5) 0.396(4) 0.770(3) 0.072(12) Uiso 1 1 d . . .
H36 H 0.775(4) 0.497(3) 0.918(2) 0.048(10) Uiso 1 1 d . . .
H42 H 0.053(3) 0.830(2) 0.6330(18) 0.020(7) Uiso 1 1 d . . .
H43 H 0.081(4) 0.866(3) 0.775(2) 0.051(11) Uiso 1 1 d . . .
H44 H 0.303(4) 0.837(4) 0.824(3) 0.061(12) Uiso 1 1 d . . .
H45 H 0.510(4) 0.754(3) 0.746(2) 0.054(11) Uiso 1 1 d . . .
H46 H 0.479(4) 0.725(3) 0.596(3) 0.055(11) Uiso 1 1 d . . .
H52 H 0.291(3) 0.982(3) 0.480(2) 0.033(8) Uiso 1 1 d . . .
H53 H 0.378(4) 1.098(4) 0.388(3) 0.054(10) Uiso 1 1 d . . .
H54 H 0.457(4) 1.023(3) 0.243(2) 0.048(10) Uiso 1 1 d . . .
H55 H 0.431(3) 0.854(3) 0.197(2) 0.036(9) Uiso 1 1 d . . .
H56 H 0.346(4) 0.743(4) 0.281(3) 0.057(11) Uiso 1 1 d . . .
H62 H 0.000(3) 0.895(3) 0.347(2) 0.035(8) Uiso 1 1 d . . .
H63 H -0.237(4) 0.895(3) 0.306(2) 0.047(10) Uiso 1 1 d . . .
H64 H -0.332(4) 0.781(3) 0.385(2) 0.041(9) Uiso 1 1 d . . .
H65 H -0.196(4) 0.649(3) 0.496(2) 0.038(9) Uiso 1 1 d . . .
H66 H 0.034(3) 0.631(3) 0.530(2) 0.027(8) Uiso 1 1 d . . .


_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 O12 1.840(2) . ?
Ge1 C11 1.928(3) . ?
Ge1 C21 1.928(3) . ?
Ge1 C31 1.929(3) . ?
Ge2 O22 1.830(2) . ?
Ge2 C41 1.929(3) . ?
Ge2 C61 1.933(3) . ?
Ge2 C51 1.935(3) . ?
O11 O12 1.471(3) . ?
O11 H1 0.97(4) . ?
O21 O22 1.471(3) . ?
O21 H2 0.91(5) . ?
C11 C12 1.404(4) . ?
C11 C16 1.405(5) . ?
C12 C13 1.360(5) . ?
C12 H12 1.03(3) . ?
C13 C14 1.384(6) . ?
C13 H13 0.89(4) . ?
C14 C15 1.385(5) . ?
C14 H14 0.95(4) . ?
C15 C16 1.383(5) . ?
C15 H15 0.99(4) . ?
C16 H16 0.93(3) . ?
C21 C22 1.397(4) . ?
C21 C26 1.400(4) . ?
C22 C23 1.387(5) . ?
C22 H22 0.96(4) . ?
C23 C24 1.373(6) . ?
C23 H23 0.99(4) . ?
C24 C25 1.392(5) . ?
C24 H24 0.97(3) . ?
C25 C26 1.372(4) . ?
C25 H25 1.02(4) . ?
C26 H26 0.97(3) . ?
C31 C36 1.394(4) . ?
C31 C32 1.399(4) . ?
C32 C33 1.369(5) . ?
C32 H32 0.91(3) . ?
C33 C34 1.391(5) . ?
C33 H33 0.97(3) . ?
C34 C35 1.371(5) . ?
C34 H34 0.85(4) . ?
C35 C36 1.396(5) . ?
C35 H35 0.95(4) . ?
C36 H36 0.95(3) . ?
C41 C42 1.381(4) . ?
C41 C46 1.399(4) . ?
C42 C43 1.394(5) . ?
C42 H42 0.87(3) . ?
C43 C44 1.378(5) . ?
C43 H43 0.87(4) . ?
C44 C45 1.369(5) . ?
C44 H44 0.82(4) . ?
C45 C46 1.384(5) . ?
C45 H45 0.91(3) . ?
C46 H46 0.85(4) . ?
C51 C52 1.388(4) . ?
C51 C56 1.390(4) . ?
C52 C53 1.394(4) . ?
C52 H52 0.90(3) . ?
C53 C54 1.373(5) . ?
C53 H53 0.90(4) . ?
C54 C55 1.372(5) . ?
C54 H54 0.91(3) . ?
C55 C56 1.384(4) . ?
C55 H55 0.88(3) . ?
C56 H56 0.89(4) . ?
C61 C62 1.390(4) . ?
C61 C66 1.394(4) . ?
C62 C63 1.386(4) . ?
C62 H62 0.95(3) . ?
C63 C64 1.387(5) . ?
C63 H63 0.86(4) . ?
C64 C65 1.370(4) . ?
C64 H64 0.89(3) . ?
C65 C66 1.387(4) . ?
C65 H65 0.87(3) . ?
C66 H66 0.88(3) . ?

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
O12 Ge1 C11 111.61(12) . . ?
O12 Ge1 C21 98.52(11) . . ?
C11 Ge1 C21 113.54(12) . . ?
O12 Ge1 C31 105.60(11) . . ?
C11 Ge1 C31 113.19(12) . . ?
C21 Ge1 C31 113.14(12) . . ?
O22 Ge2 C41 107.78(11) . . ?
O22 Ge2 C61 107.20(10) . . ?
C41 Ge2 C61 113.51(11) . . ?
O22 Ge2 C51 99.39(10) . . ?
C41 Ge2 C51 113.06(11) . . ?
C61 Ge2 C51 114.52(11) . . ?
O12 O11 H1 97(2) . . ?
O11 O12 Ge1 105.89(15) . . ?
O22 O21 H2 90(3) . . ?
O21 O22 Ge2 104.12(14) . . ?
C12 C11 C16 117.6(3) . . ?
C12 C11 Ge1 121.5(2) . . ?
C16 C11 Ge1 120.8(2) . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 120.2(18) . . ?
C11 C12 H12 118.7(18) . . ?
C12 C13 C14 121.0(3) . . ?
C12 C13 H13 123(2) . . ?
C14 C13 H13 116(2) . . ?
C13 C14 C15 119.4(4) . . ?
C13 C14 H14 134(2) . . ?
C15 C14 H14 106(2) . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15 124(2) . . ?
C14 C15 H15 116(2) . . ?
C15 C16 C11 120.9(3) . . ?
C15 C16 H16 124(2) . . ?
C11 C16 H16 115(2) . . ?
C22 C21 C26 117.8(3) . . ?
C22 C21 Ge1 121.6(2) . . ?
C26 C21 Ge1 120.6(2) . . ?
C23 C22 C21 120.5(3) . . ?
C23 C22 H22 119(2) . . ?
C21 C22 H22 119(2) . . ?
C24 C23 C22 120.7(3) . . ?
C24 C23 H23 124(2) . . ?
C22 C23 H23 116(2) . . ?
C23 C24 C25 119.6(3) . . ?
C23 C24 H24 122(2) . . ?
C25 C24 H24 119(2) . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25 123(2) . . ?
C24 C25 H25 117(2) . . ?
C25 C26 C21 121.5(3) . . ?
C25 C26 H26 121.8(19) . . ?
C21 C26 H26 116.5(19) . . ?
C36 C31 C32 118.5(3) . . ?
C36 C31 Ge1 122.1(2) . . ?
C32 C31 Ge1 119.3(2) . . ?
C33 C32 C31 120.8(3) . . ?
C33 C32 H32 120(2) . . ?
C31 C32 H32 119(2) . . ?
C32 C33 C34 120.2(3) . . ?
C32 C33 H33 119(2) . . ?
C34 C33 H33 121(2) . . ?
C35 C34 C33 120.0(3) . . ?
C35 C34 H34 115(3) . . ?
C33 C34 H34 125(3) . . ?
C34 C35 C36 120.1(3) . . ?
C34 C35 H35 114(3) . . ?
C36 C35 H35 126(3) . . ?
C31 C36 C35 120.3(3) . . ?
C31 C36 H36 116(2) . . ?
C35 C36 H36 124(2) . . ?
C42 C41 C46 118.7(3) . . ?
C42 C41 Ge2 121.4(2) . . ?
C46 C41 Ge2 119.9(2) . . ?
C41 C42 C43 120.2(3) . . ?
C41 C42 H42 119.9(18) . . ?
C43 C42 H42 119.8(18) . . ?
C44 C43 C42 119.9(3) . . ?
C44 C43 H43 123(3) . . ?
C42 C43 H43 117(3) . . ?
C45 C44 C43 120.8(3) . . ?
C45 C44 H44 124(3) . . ?
C43 C44 H44 115(3) . . ?
C44 C45 C46 119.4(3) . . ?
C44 C45 H45 114(2) . . ?
C46 C45 H45 126(2) . . ?
C45 C46 C41 120.9(3) . . ?
C45 C46 H46 117(3) . . ?
C41 C46 H46 122(3) . . ?
C52 C51 C56 118.5(3) . . ?
C52 C51 Ge2 121.0(2) . . ?
C56 C51 Ge2 120.5(2) . . ?
C51 C52 C53 120.3(3) . . ?
C51 C52 H52 119.0(19) . . ?
C53 C52 H52 120.7(19) . . ?
C54 C53 C52 119.9(3) . . ?
C54 C53 H53 121(2) . . ?
C52 C53 H53 119(2) . . ?
C55 C54 C53 120.6(3) . . ?
C55 C54 H54 113(2) . . ?
C53 C54 H54 127(2) . . ?
C54 C55 C56 119.6(3) . . ?
C54 C55 H55 122(2) . . ?
C56 C55 H55 119(2) . . ?
C55 C56 C51 121.1(3) . . ?
C55 C56 H56 114(2) . . ?
C51 C56 H56 125(2) . . ?
C62 C61 C66 118.4(3) . . ?
C62 C61 Ge2 120.3(2) . . ?
C66 C61 Ge2 121.3(2) . . ?
C63 C62 C61 120.8(3) . . ?
C63 C62 H62 124.0(19) . . ?
C61 C62 H62 115.0(19) . . ?
C62 C63 C64 119.9(3) . . ?
C62 C63 H63 125(2) . . ?
C64 C63 H63 115(2) . . ?
C65 C64 C63 120.0(3) . . ?
C65 C64 H64 119(2) . . ?
C63 C64 H64 121(2) . . ?
C64 C65 C66 120.3(3) . . ?
C64 C65 H65 121(2) . . ?
C66 C65 H65 118(2) . . ?
C65 C66 C61 120.7(3) . . ?
C65 C66 H66 120.5(19) . . ?
C61 C66 H66 118.8(19) . . ?

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
Ge1 O12 O11 H1 139(2) . . . . ?
Ge2 O22 O21 H2 -115(3) . . . . ?
C21 Ge1 O12 O11 -179.32(18) . . . . ?
C51 Ge2 O22 O21 176.87(15) . . . . ?

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
O11 H1 O12 0.97(4) 1.79(4) 2.726(3) 160(3) 2_677
O21 H2 O22 0.91(5) 1.86(5) 2.738(3) 164(4) 2_666

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.939
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.076
