#------------------------------------------------------------------------------
#$Date: 2023-07-05 12:06:26 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284862 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/16/7131656.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7131656
loop_
_publ_author_name
'Caise, Alexa'
'Hicks, Jamie'
'Heilmann, Andreas'
'Aldridge, Simon'
_publ_section_title
;
 Redox flexibility in a germanium hydride manifold: hydrogen shuttling
 via oxidative addition and reductive elimination.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7251
_journal_page_last               7254
_journal_paper_doi               10.1039/d3cc01411h
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C30 H42 Ge N2 O'
_chemical_formula_sum            'C30 H42 Ge N2 O'
_chemical_formula_weight         519.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-02-15
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-16 deposited with the CCDC.	2023-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                102.491(3)
_cell_angle_beta                 100.285(3)
_cell_angle_gamma                93.091(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2011(3)
_cell_length_b                   10.5814(6)
_cell_length_c                   16.5784(5)
_cell_measurement_reflns_used    8407
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.9920
_cell_measurement_theta_min      5.4860
_cell_volume                     1375.61(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector_area_resol_mean 10.4102
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13167
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.498
_diffrn_reflns_theta_min         4.300
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5678
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0418P)²+0.3289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0744
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5403
_reflns_number_total             5678
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc01411h2.cif
_cod_data_source_block           compound-3
_cod_depositor_comments
'Adding full bibliography for 7131655--7131658.cif.'
_cod_database_code               7131656
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.877
_shelx_estimated_absorpt_t_min   0.719
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
N1 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
N1A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim C13A \\sim C14A: within 2A
with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
3. Others
 Sof(H7BC)=Sof(H7BD)=Sof(N1A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10D)=Sof(H10E)=
 Sof(H10F)=Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=Sof(C12A)=Sof(H12A)=
 Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C14A)=Sof(H14D)=Sof(H14E)=
 Sof(H14F)=1-FVAR(1)
 Sof(H7AA)=Sof(H7AB)=Sof(N1)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10A)=Sof(H10B)=
 Sof(H10C)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12)=Sof(H12)=Sof(C13)=
 Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C15(H15), C18(H18), C9(H9), C12(H12), C9A(H9A), C12A(H12A)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7AA,H7AB), C7(H7BC,H7BD), C8(H8A,H8B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27),
 C28(H28), C29(H29)
4.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,
 H14B,H14C), C10A(H10D,H10E,H10F), C11A(H11D,H11E,H11F), C13A(H13D,H13E,H13F),
 C14A(H14D,H14E,H14F)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge1 Ge 0.14912(2) 0.41218(2) 0.74866(2) 0.02203(6) Uani 1 1 d . . . . .
O1 O 0.35274(12) 0.36106(10) 0.80151(6) 0.0262(2) Uani 1 1 d . . . . .
N2 N 0.13639(13) 0.61779(11) 0.84520(7) 0.0201(2) Uani 1 1 d . . . . .
C1 C 0.27459(16) 0.53733(13) 0.70211(8) 0.0202(2) Uani 1 1 d . . . . .
C2 C 0.27334(16) 0.67041(13) 0.73321(8) 0.0217(2) Uani 1 1 d . . . . .
C3 C 0.3683(2) 0.75996(14) 0.70582(9) 0.0291(3) Uani 1 1 d . . . . .
H3 H 0.366165 0.850620 0.727069 0.035 Uiso 1 1 calc R U . . .
C4 C 0.4658(2) 0.71564(16) 0.64734(9) 0.0332(3) Uani 1 1 d . . . . .
H4 H 0.533700 0.776065 0.629832 0.040 Uiso 1 1 calc R U . . .
C5 C 0.46468(19) 0.58311(15) 0.61419(9) 0.0295(3) Uani 1 1 d . . . . .
H5 H 0.530244 0.553473 0.573335 0.035 Uiso 1 1 calc R U . . .
C6 C 0.36841(16) 0.49388(13) 0.64041(8) 0.0227(3) Uani 1 1 d . . . . .
C7 C 0.36534(17) 0.34993(14) 0.60334(9) 0.0264(3) Uani 1 1 d . . . . .
H7AA H 0.408652 0.336715 0.550388 0.032 Uiso 0.760(5) 1 calc R U P A 1
H7AB H 0.438414 0.310105 0.643226 0.032 Uiso 0.760(5) 1 calc R U P A 1
H7BC H 0.373210 0.336800 0.543249 0.032 Uiso 0.240(5) 1 calc R U P A 2
H7BD H 0.464349 0.316980 0.632671 0.032 Uiso 0.240(5) 1 calc R U P A 2
C8 C 0.16349(17) 0.71569(13) 0.79570(8) 0.0228(3) Uani 1 1 d . . . . .
H8A H 0.215751 0.798271 0.834577 0.027 Uiso 1 1 calc R U . . .
H8B H 0.054664 0.732645 0.765173 0.027 Uiso 1 1 calc R U . . .
C15 C -0.03840(16) 0.61271(14) 0.86273(9) 0.0250(3) Uani 1 1 d . . . . .
H15 H -0.052499 0.536347 0.888220 0.030 Uiso 1 1 calc R U . . .
C16 C -0.0716(2) 0.73232(17) 0.92586(11) 0.0357(3) Uani 1 1 d . . . . .
H16A H 0.000431 0.738031 0.980723 0.054 Uiso 1 1 calc R U . . .
H16B H -0.188451 0.724887 0.931500 0.054 Uiso 1 1 calc R U . . .
H16C H -0.048051 0.810699 0.905820 0.054 Uiso 1 1 calc R U . . .
C17 C -0.17273(18) 0.59001(17) 0.78251(10) 0.0341(3) Uani 1 1 d . . . . .
H17A H -0.184695 0.671826 0.764394 0.051 Uiso 1 1 calc R U . . .
H17B H -0.278971 0.558685 0.793975 0.051 Uiso 1 1 calc R U . . .
H17C H -0.140392 0.525012 0.737883 0.051 Uiso 1 1 calc R U . . .
C18 C 0.26408(17) 0.64920(13) 0.92644(8) 0.0232(3) Uani 1 1 d . . . . .
H18 H 0.246189 0.736929 0.958927 0.028 Uiso 1 1 calc R U . . .
C19 C 0.44244(17) 0.65586(14) 0.91156(9) 0.0263(3) Uani 1 1 d . . . . .
H19A H 0.463628 0.571111 0.879505 0.040 Uiso 1 1 calc R U . . .
H19B H 0.520240 0.678629 0.965873 0.040 Uiso 1 1 calc R U . . .
H19C H 0.457961 0.722127 0.879738 0.040 Uiso 1 1 calc R U . . .
C20 C 0.24340(19) 0.55254(15) 0.98090(9) 0.0294(3) Uani 1 1 d . . . . .
H20A H 0.134551 0.557508 0.997392 0.044 Uiso 1 1 calc R U . . .
H20B H 0.331552 0.573664 1.031460 0.044 Uiso 1 1 calc R U . . .
H20C H 0.250804 0.464330 0.948841 0.044 Uiso 1 1 calc R U . . .
C21 C 0.36266(17) 0.25696(13) 0.83616(8) 0.0231(3) Uani 1 1 d . . . . .
C22 C 0.23927(18) 0.21046(14) 0.87196(8) 0.0256(3) Uani 1 1 d . . . . .
H22 H 0.140146 0.252708 0.873243 0.031 Uiso 1 1 calc R U . . .
C23 C 0.25983(19) 0.10004(14) 0.90680(9) 0.0283(3) Uani 1 1 d . . . . .
H23 H 0.173657 0.069056 0.931074 0.034 Uiso 1 1 calc R U . . .
C24 C 0.4009(2) 0.03711(14) 0.90625(9) 0.0298(3) Uani 1 1 d . . . . .
H24 H 0.412453 -0.036417 0.930331 0.036 Uiso 1 1 calc R U . . .
C25 C 0.52946(18) 0.08145(14) 0.86985(9) 0.0287(3) Uani 1 1 d . . . . .
C26 C 0.6755(2) 0.01664(16) 0.86553(13) 0.0412(4) Uani 1 1 d . . . . .
H26 H 0.689549 -0.057043 0.889286 0.049 Uiso 1 1 calc R U . . .
C27 C 0.7961(2) 0.0583(2) 0.82786(15) 0.0495(5) Uani 1 1 d . . . . .
H27 H 0.892011 0.012423 0.824470 0.059 Uiso 1 1 calc R U . . .
C28 C 0.7792(2) 0.1696(2) 0.79373(13) 0.0446(4) Uani 1 1 d . . . . .
H28 H 0.864396 0.198685 0.768110 0.053 Uiso 1 1 calc R U . . .
C29 C 0.64049(19) 0.23534(15) 0.79755(10) 0.0322(3) Uani 1 1 d . . . . .
H29 H 0.630522 0.310329 0.774883 0.039 Uiso 1 1 calc R U . . .
C30 C 0.51182(17) 0.19281(13) 0.83490(9) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.1927(3) 0.2853(3) 0.58586(16) 0.0210(5) Uani 0.760(5) 1 d . U P A 1
C9 C 0.0732(2) 0.3410(2) 0.52749(11) 0.0242(5) Uani 0.760(5) 1 d . U P A 1
H9 H 0.096610 0.437674 0.546666 0.029 Uiso 0.760(5) 1 calc R U P A 1
C10 C -0.1060(4) 0.3092(3) 0.5356(2) 0.0343(6) Uani 0.760(5) 1 d . U P A 1
H10A H -0.138483 0.215974 0.512825 0.051 Uiso 0.760(5) 1 calc R U P A 1
H10B H -0.180037 0.359000 0.504036 0.051 Uiso 0.760(5) 1 calc R U P A 1
H10C H -0.114697 0.332042 0.595090 0.051 Uiso 0.760(5) 1 calc R U P A 1
C11 C 0.0885(5) 0.3065(4) 0.4345(2) 0.0365(7) Uani 0.760(5) 1 d . U P A 1
H11A H 0.202461 0.331860 0.429683 0.055 Uiso 0.760(5) 1 calc R U P A 1
H11B H 0.010505 0.353113 0.402436 0.055 Uiso 0.760(5) 1 calc R U P A 1
H11C H 0.062341 0.212651 0.412011 0.055 Uiso 0.760(5) 1 calc R U P A 1
C12 C 0.1823(2) 0.14040(18) 0.56299(12) 0.0270(5) Uani 0.760(5) 1 d . U P A 1
H12 H 0.068828 0.109738 0.528075 0.032 Uiso 0.760(5) 1 calc R U P A 1
C13 C 0.3070(4) 0.0830(2) 0.5102(2) 0.0468(7) Uani 0.760(5) 1 d . U P A 1
H13A H 0.301202 0.121727 0.461313 0.070 Uiso 0.760(5) 1 calc R U P A 1
H13B H 0.280063 -0.011351 0.491071 0.070 Uiso 0.760(5) 1 calc R U P A 1
H13C H 0.419680 0.101812 0.544532 0.070 Uiso 0.760(5) 1 calc R U P A 1
C14 C 0.1945(5) 0.0851(2) 0.64016(16) 0.0394(7) Uani 0.760(5) 1 d . U P A 1
H14A H 0.303720 0.113935 0.676814 0.059 Uiso 0.760(5) 1 calc R U P A 1
H14B H 0.180870 -0.010078 0.623135 0.059 Uiso 0.760(5) 1 calc R U P A 1
H14C H 0.106907 0.115558 0.670686 0.059 Uiso 0.760(5) 1 calc R U P A 1
N1A N 0.2184(15) 0.2751(12) 0.6095(6) 0.0356(19) Uani 0.240(5) 1 d . U P A 2
C9A C 0.0834(10) 0.2674(11) 0.5344(5) 0.0422(18) Uani 0.240(5) 1 d . U P A 2
H9A H 0.035956 0.174330 0.518943 0.051 Uiso 0.240(5) 1 calc R U P A 2
C10A C -0.0577(17) 0.3403(16) 0.5552(9) 0.057(3) Uani 0.240(5) 1 d . U P A 2
H10D H -0.104966 0.306098 0.597308 0.086 Uiso 0.240(5) 1 calc R U P A 2
H10E H -0.143187 0.330845 0.504187 0.086 Uiso 0.240(5) 1 calc R U P A 2
H10F H -0.018593 0.432526 0.577870 0.086 Uiso 0.240(5) 1 calc R U P A 2
C11A C 0.1301(19) 0.2902(18) 0.4539(9) 0.055(3) Uani 0.240(5) 1 d . U P A 2
H11D H 0.164804 0.382714 0.461228 0.083 Uiso 0.240(5) 1 calc R U P A 2
H11E H 0.033669 0.263760 0.407514 0.083 Uiso 0.240(5) 1 calc R U P A 2
H11F H 0.221928 0.238873 0.440891 0.083 Uiso 0.240(5) 1 calc R U P A 2
C12A C 0.2572(10) 0.1429(8) 0.6207(5) 0.0380(17) Uani 0.240(5) 1 d . U P A 2
H12A H 0.346944 0.160432 0.672355 0.046 Uiso 0.240(5) 1 calc R U P A 2
C13A C 0.3335(12) 0.0594(9) 0.5534(6) 0.046(2) Uani 0.240(5) 1 d . U P A 2
H13D H 0.374769 -0.015996 0.573056 0.068 Uiso 0.240(5) 1 calc R U P A 2
H13E H 0.426088 0.110673 0.541750 0.068 Uiso 0.240(5) 1 calc R U P A 2
H13F H 0.248954 0.029643 0.501733 0.068 Uiso 0.240(5) 1 calc R U P A 2
C14A C 0.1129(13) 0.0702(10) 0.6448(6) 0.040(2) Uani 0.240(5) 1 d . U P A 2
H14D H 0.089586 0.119696 0.697968 0.059 Uiso 0.240(5) 1 calc R U P A 2
H14E H 0.143461 -0.015844 0.651305 0.059 Uiso 0.240(5) 1 calc R U P A 2
H14F H 0.013506 0.060163 0.600354 0.059 Uiso 0.240(5) 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Ge Ge -1.0885 0.8855 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ge1 C1 90.53(5) . . ?
C21 O1 Ge1 123.80(9) . . ?
C8 N2 C15 111.64(10) . . ?
C8 N2 C18 109.07(10) . . ?
C18 N2 C15 110.83(10) . . ?
C2 C1 Ge1 119.53(10) . . ?
C2 C1 C6 119.17(12) . . ?
C6 C1 Ge1 121.27(10) . . ?
C1 C2 C3 120.80(13) . . ?
C1 C2 C8 118.49(12) . . ?
C3 C2 C8 120.70(12) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.45(14) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.25(14) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.39(14) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 119.83(12) . . ?
C5 C6 C1 119.86(13) . . ?
C5 C6 C7 120.31(13) . . ?
C6 C7 H7AA 109.5 . . ?
C6 C7 H7AB 109.5 . . ?
C6 C7 H7BC 108.8 . . ?
C6 C7 H7BD 108.8 . . ?
H7AA C7 H7AB 108.1 . . ?
H7BC C7 H7BD 107.7 . . ?
N1 C7 C6 110.68(15) . . ?
N1 C7 H7AA 109.5 . . ?
N1 C7 H7AB 109.5 . . ?
N1A C7 C6 113.6(5) . . ?
N1A C7 H7BC 108.8 . . ?
N1A C7 H7BD 108.8 . . ?
N2 C8 C2 111.72(11) . . ?
N2 C8 H8A 109.3 . . ?
N2 C8 H8B 109.3 . . ?
C2 C8 H8A 109.3 . . ?
C2 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N2 C15 H15 106.9 . . ?
N2 C15 C16 113.93(12) . . ?
N2 C15 C17 112.84(11) . . ?
C16 C15 H15 106.9 . . ?
C16 C15 C17 109.04(12) . . ?
C17 C15 H15 106.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18 107.6 . . ?
N2 C18 C19 112.53(11) . . ?
N2 C18 C20 112.01(11) . . ?
C19 C18 H18 107.6 . . ?
C20 C18 H18 107.6 . . ?
C20 C18 C19 109.40(12) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 C22 124.00(13) . . ?
O1 C21 C30 116.64(13) . . ?
C22 C21 C30 119.36(13) . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.29(13) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.3 . . ?
C24 C23 C22 121.42(14) . . ?
C24 C23 H23 119.3 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 119.92(13) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 121.78(14) . . ?
C24 C25 C30 119.59(14) . . ?
C26 C25 C30 118.63(15) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 C25 121.05(16) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.33(16) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.17(18) . . ?
C29 C28 H28 119.9 . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.70(16) . . ?
C30 C29 H29 119.6 . . ?
C25 C30 C21 119.42(14) . . ?
C29 C30 C21 121.46(13) . . ?
C29 C30 C25 119.10(14) . . ?
C7 N1 C12 114.1(2) . . ?
C9 N1 C7 113.16(19) . . ?
C9 N1 C12 113.5(2) . . ?
N1 C9 H9 106.3 . . ?
N1 C9 C10 111.2(2) . . ?
N1 C9 C11 116.0(2) . . ?
C10 C9 H9 106.3 . . ?
C10 C9 C11 110.1(2) . . ?
C11 C9 H9 106.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12 106.7 . . ?
N1 C12 C13 115.3(2) . . ?
N1 C12 C14 111.15(18) . . ?
C13 C12 H12 106.7 . . ?
C14 C12 H12 106.7 . . ?
C14 C12 C13 109.9(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 N1A C9A 110.6(8) . . ?
C7 N1A C12A 110.8(8) . . ?
C12A N1A C9A 111.5(9) . . ?
N1A C9A H9A 104.0 . . ?
N1A C9A C11A 119.0(9) . . ?
C10A C9A N1A 112.7(9) . . ?
C10A C9A H9A 104.0 . . ?
C10A C9A C11A 111.3(11) . . ?
C11A C9A H9A 104.0 . . ?
C9A C10A H10D 109.5 . . ?
C9A C10A H10E 109.5 . . ?
C9A C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C9A C11A H11D 109.5 . . ?
C9A C11A H11E 109.5 . . ?
C9A C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
N1A C12A H12A 104.1 . . ?
N1A C12A C13A 117.1(9) . . ?
N1A C12A C14A 112.2(8) . . ?
C13A C12A H12A 104.1 . . ?
C13A C12A C14A 113.4(7) . . ?
C14A C12A H12A 104.1 . . ?
C12A C13A H13D 109.5 . . ?
C12A C13A H13E 109.5 . . ?
C12A C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
C12A C14A H14D 109.5 . . ?
C12A C14A H14E 109.5 . . ?
C12A C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
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 1.9050(10) . ?
Ge1 C1 1.9968(13) . ?
O1 C21 1.3478(17) . ?
N2 C8 1.4846(17) . ?
N2 C15 1.5131(17) . ?
N2 C18 1.5120(16) . ?
C1 C2 1.3921(18) . ?
C1 C6 1.4019(18) . ?
C2 C3 1.394(2) . ?
C2 C8 1.5099(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C6 C7 1.5112(19) . ?
C7 H7AA 0.9900 . ?
C7 H7AB 0.9900 . ?
C7 H7BC 0.9900 . ?
C7 H7BD 0.9900 . ?
C7 N1 1.490(3) . ?
C7 N1A 1.438(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C15 H15 1.0000 . ?
C15 C16 1.529(2) . ?
C15 C17 1.5330(19) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 1.0000 . ?
C18 C19 1.5267(19) . ?
C18 C20 1.5250(19) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.380(2) . ?
C21 C30 1.4318(19) . ?
C22 H22 0.9500 . ?
C22 C23 1.416(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.366(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.412(2) . ?
C25 C26 1.417(2) . ?
C25 C30 1.424(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.362(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.415(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.369(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.415(2) . ?
N1 C9 1.488(3) . ?
N1 C12 1.491(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.526(3) . ?
C9 C11 1.535(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 1.0000 . ?
C12 C13 1.528(3) . ?
C12 C14 1.508(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N1A C9A 1.497(11) . ?
N1A C12A 1.493(15) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.475(16) . ?
C9A C11A 1.515(17) . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C12A H12A 1.0000 . ?
C12A C13A 1.517(11) . ?
C12A C14A 1.535(13) . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
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 O1 C21 C22 -30.38(17) . . . . ?
Ge1 O1 C21 C30 149.70(9) . . . . ?
Ge1 C1 C2 C3 175.86(10) . . . . ?
Ge1 C1 C2 C8 -5.63(15) . . . . ?
Ge1 C1 C6 C5 -174.89(10) . . . . ?
Ge1 C1 C6 C7 4.56(16) . . . . ?
O1 C21 C22 C23 179.82(12) . . . . ?
O1 C21 C30 C25 -179.45(12) . . . . ?
O1 C21 C30 C29 -1.25(19) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C1 C2 C8 N2 27.68(16) . . . . ?
C1 C6 C7 N1 42.44(19) . . . . ?
C1 C6 C7 N1A 23.8(5) . . . . ?
C2 C1 C6 C5 3.11(19) . . . . ?
C2 C1 C6 C7 -177.43(12) . . . . ?
C2 C3 C4 C5 2.1(2) . . . . ?
C3 C2 C8 N2 -153.81(12) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C4 C5 C6 C1 -1.5(2) . . . . ?
C4 C5 C6 C7 179.08(13) . . . . ?
C5 C6 C7 N1 -138.10(16) . . . . ?
C5 C6 C7 N1A -156.8(4) . . . . ?
C6 C1 C2 C3 -2.18(19) . . . . ?
C6 C1 C2 C8 176.33(11) . . . . ?
C6 C7 N1 C9 58.1(2) . . . . ?
C6 C7 N1 C12 -170.15(16) . . . . ?
C6 C7 N1A C9A 88.8(8) . . . . ?
C6 C7 N1A C12A -147.1(5) . . . . ?
C7 N1 C9 C10 -159.6(2) . . . . ?
C7 N1 C9 C11 73.6(3) . . . . ?
C7 N1 C12 C13 -36.0(3) . . . . ?
C7 N1 C12 C14 89.9(3) . . . . ?
C7 N1A C9A C10A -111.4(12) . . . . ?
C7 N1A C9A C11A 21.7(15) . . . . ?
C7 N1A C12A C13A -57.5(10) . . . . ?
C7 N1A C12A C14A 168.8(7) . . . . ?
C8 N2 C15 C16 -70.62(14) . . . . ?
C8 N2 C15 C17 54.42(15) . . . . ?
C8 N2 C18 C19 -56.45(14) . . . . ?
C8 N2 C18 C20 179.81(11) . . . . ?
C8 C2 C3 C4 -178.90(13) . . . . ?
C15 N2 C8 C2 -143.38(11) . . . . ?
C15 N2 C18 C19 -179.74(11) . . . . ?
C15 N2 C18 C20 56.51(14) . . . . ?
C18 N2 C8 C2 93.80(12) . . . . ?
C18 N2 C15 C16 51.18(15) . . . . ?
C18 N2 C15 C17 176.22(12) . . . . ?
C21 C22 C23 C24 0.2(2) . . . . ?
C22 C21 C30 C25 0.62(19) . . . . ?
C22 C21 C30 C29 178.82(13) . . . . ?
C22 C23 C24 C25 -0.5(2) . . . . ?
C23 C24 C25 C26 -177.96(14) . . . . ?
C23 C24 C25 C30 0.8(2) . . . . ?
C24 C25 C26 C27 177.93(17) . . . . ?
C24 C25 C30 C21 -0.9(2) . . . . ?
C24 C25 C30 C29 -179.15(13) . . . . ?
C25 C26 C27 C28 1.4(3) . . . . ?
C26 C25 C30 C21 177.92(13) . . . . ?
C26 C25 C30 C29 -0.3(2) . . . . ?
C26 C27 C28 C29 -0.7(3) . . . . ?
C27 C28 C29 C30 -0.5(3) . . . . ?
C28 C29 C30 C21 -177.22(15) . . . . ?
C28 C29 C30 C25 1.0(2) . . . . ?
C30 C21 C22 C23 -0.26(19) . . . . ?
C30 C25 C26 C27 -0.9(2) . . . . ?
C9 N1 C12 C13 95.6(3) . . . . ?
C9 N1 C12 C14 -138.5(2) . . . . ?
C12 N1 C9 C10 68.4(3) . . . . ?
C12 N1 C9 C11 -58.5(3) . . . . ?
C9A N1A C12A C13A 66.2(12) . . . . ?
C9A N1A C12A C14A -67.5(10) . . . . ?
C12A N1A C9A C10A 124.9(13) . . . . ?
C12A N1A C9A C11A -102.1(13) . . . . ?
