#------------------------------------------------------------------------------
#$Date: 2022-07-23 01:12:24 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276789 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/03/7130354.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_7130354
loop_
_publ_author_name
'Bischoff, Inga-Alexandra'
'Morgenstern, Bernd'
'Schäfer, André'
_publ_section_title
;
 Heavier N-heterocyclic half-sandwich tetrylenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03107H
_journal_year                    2022
_chemical_formula_moiety         'C20 H27 Ge N O5 Si W'
_chemical_formula_sum            'C20 H27 Ge N O5 Si W'
_chemical_formula_weight         645.95
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-07-04 deposited with the CCDC.	2022-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.750(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1997(4)
_cell_length_b                   26.2141(10)
_cell_length_c                   10.2037(4)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.38
_cell_volume                     2417.56(17)
_computing_cell_refinement       'SAINT  (Bruker, 2019)'
_computing_data_collection       'APEX 3 (Bruker, 2019)'
_computing_data_reduction        'SAINT  (Bruker, 2019)'
_computing_molecular_graphics    'DIAMOND, (Brandenburg, 2018)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement
;
SHELXL-2018/3 (Sheldrick, 2018),                                              
SHELXLe Rev 1000 (Huebschle et al., 2011)
;
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS D8 Venture, Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32787
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.902
_diffrn_reflns_theta_min         2.175
_diffrn_source                   'INCOATEC I\^A?S microfocus sealed tube'
_exptl_absorpt_coefficient_mu    6.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.991
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0220
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0116P)²+2.4981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0426
_refine_ls_wR_factor_ref         0.0453
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4998
_reflns_number_total             5770
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03107h3.cif
_cod_data_source_block           sh4900_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7130354
_shelx_shelxl_version_number     2018/3
_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_min   0.376
_shelx_estimated_absorpt_t_max   0.839
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
W1 W 0.58410(2) 0.30384(2) 0.41823(2) 0.02296(4) Uani 1 1 d . . . . .
Ge1 Ge 0.70092(3) 0.35822(2) 0.26120(3) 0.02372(7) Uani 1 1 d . . . . .
Si1 Si 0.84349(9) 0.41652(3) 0.10989(8) 0.03047(18) Uani 1 1 d . . . . .
O1 O 0.4477(3) 0.24254(10) 0.6321(3) 0.0493(6) Uani 1 1 d . . . . .
O2 O 0.8935(2) 0.30670(9) 0.6197(2) 0.0399(5) Uani 1 1 d . . . . .
O3 O 0.4781(3) 0.40458(9) 0.5463(3) 0.0475(6) Uani 1 1 d . . . . .
O4 O 0.2813(2) 0.29708(10) 0.2108(3) 0.0503(7) Uani 1 1 d . . . . .
O5 O 0.6911(3) 0.20165(10) 0.2970(3) 0.0572(8) Uani 1 1 d . . . . .
N1 N 0.7036(3) 0.36980(9) 0.0855(2) 0.0281(5) Uani 1 1 d . . . . .
C1 C 0.8447(3) 0.41699(10) 0.2951(3) 0.0261(6) Uani 1 1 d . . . . .
C2 C 0.7557(3) 0.45375(11) 0.3589(3) 0.0296(6) Uani 1 1 d . . . . .
C3 C 0.8198(3) 0.45796(11) 0.4906(3) 0.0306(6) Uani 1 1 d . . . . .
C4 C 0.9494(3) 0.42606(11) 0.5177(3) 0.0297(6) Uani 1 1 d . . . . .
C5 C 0.9671(3) 0.40189(11) 0.4038(3) 0.0273(6) Uani 1 1 d . . . . .
C6 C 1.0871(3) 0.36429(13) 0.3897(3) 0.0384(8) Uani 1 1 d . . . . .
H6A H 1.130186 0.350458 0.477626 0.058 Uiso 1 1 calc R U . . .
H6B H 1.164197 0.381542 0.351766 0.058 Uiso 1 1 calc R U . . .
H6C H 1.044910 0.336429 0.330643 0.058 Uiso 1 1 calc R U . . .
C7 C 1.0463(4) 0.42190(14) 0.6526(3) 0.0455(9) Uani 1 1 d . . . . .
H7A H 0.988502 0.408485 0.716496 0.068 Uiso 1 1 calc R U . . .
H7B H 1.084955 0.455694 0.681831 0.068 Uiso 1 1 calc R U . . .
H7C H 1.128922 0.398790 0.647876 0.068 Uiso 1 1 calc R U . . .
C8 C 0.7682(4) 0.49096(13) 0.5929(4) 0.0463(9) Uani 1 1 d . . . . .
H8A H 0.848656 0.513663 0.633612 0.070 Uiso 1 1 calc R U . . .
H8B H 0.738813 0.469385 0.661961 0.070 Uiso 1 1 calc R U . . .
H8C H 0.683324 0.511389 0.549974 0.070 Uiso 1 1 calc R U . . .
C9 C 0.6190(4) 0.48099(13) 0.2897(4) 0.0441(8) Uani 1 1 d . . . . .
H9A H 0.646644 0.514070 0.256879 0.066 Uiso 1 1 calc R U . . .
H9B H 0.551953 0.486312 0.352658 0.066 Uiso 1 1 calc R U . . .
H9C H 0.569282 0.460365 0.214437 0.066 Uiso 1 1 calc R U . . .
C10 C 0.7902(4) 0.47772(13) 0.0207(4) 0.0485(9) Uani 1 1 d . . . . .
H10A H 0.854967 0.505121 0.062901 0.073 Uiso 1 1 calc R U . . .
H10B H 0.687275 0.485876 0.025203 0.073 Uiso 1 1 calc R U . . .
H10C H 0.800331 0.474347 -0.072799 0.073 Uiso 1 1 calc R U . . .
C11 C 1.0215(4) 0.39528(14) 0.0649(3) 0.0429(8) Uani 1 1 d . . . . .
H11A H 1.041455 0.359881 0.093542 0.064 Uiso 1 1 calc R U . . .
H11B H 1.102038 0.417203 0.109379 0.064 Uiso 1 1 calc R U . . .
H11C H 1.014384 0.397598 -0.031983 0.064 Uiso 1 1 calc R U . . .
C12 C 0.6149(4) 0.34772(13) -0.0375(3) 0.0352(7) Uani 1 1 d . . . . .
C13 C 0.4796(4) 0.38112(16) -0.0817(4) 0.0614(12) Uani 1 1 d . . . . .
H13A H 0.418527 0.381077 -0.012632 0.092 Uiso 1 1 calc R U . . .
H13B H 0.421829 0.367753 -0.165106 0.092 Uiso 1 1 calc R U . . .
H13C H 0.511190 0.416063 -0.095956 0.092 Uiso 1 1 calc R U . . .
C14 C 0.5675(4) 0.29354(13) -0.0117(3) 0.0411(8) Uani 1 1 d . . . . .
H14A H 0.504524 0.294107 0.055861 0.062 Uiso 1 1 calc R U . . .
H14B H 0.655378 0.272676 0.020306 0.062 Uiso 1 1 calc R U . . .
H14C H 0.512222 0.278976 -0.094636 0.062 Uiso 1 1 calc R U . . .
C15 C 0.7106(5) 0.34600(18) -0.1452(3) 0.0584(11) Uani 1 1 d . . . . .
H15A H 0.797873 0.324720 -0.114478 0.088 Uiso 1 1 calc R U . . .
H15B H 0.742103 0.380644 -0.162796 0.088 Uiso 1 1 calc R U . . .
H15C H 0.653003 0.331535 -0.227300 0.088 Uiso 1 1 calc R U . . .
C16 C 0.4969(3) 0.26426(12) 0.5535(3) 0.0322(7) Uani 1 1 d . . . . .
C17 C 0.7834(3) 0.30675(11) 0.5470(3) 0.0274(6) Uani 1 1 d . . . . .
C18 C 0.5161(3) 0.36921(12) 0.4975(3) 0.0304(6) Uani 1 1 d . . . . .
C19 C 0.3893(3) 0.29993(11) 0.2851(3) 0.0318(7) Uani 1 1 d . . . . .
C20 C 0.6531(3) 0.23797(12) 0.3402(3) 0.0336(7) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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'
W W -0.8490 6.8722 '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
C16 W1 C19 91.01(12) . . ?
C16 W1 C18 88.30(12) . . ?
C19 W1 C18 90.58(12) . . ?
C16 W1 C17 90.17(12) . . ?
C19 W1 C17 178.03(12) . . ?
C18 W1 C17 91.04(12) . . ?
C16 W1 C20 91.36(13) . . ?
C19 W1 C20 89.80(11) . . ?
C18 W1 C20 179.50(12) . . ?
C17 W1 C20 88.59(11) . . ?
C16 W1 Ge1 175.86(9) . . ?
C19 W1 Ge1 91.77(9) . . ?
C18 W1 Ge1 88.61(9) . . ?
C17 W1 Ge1 87.14(8) . . ?
C20 W1 Ge1 91.71(9) . . ?
N1 Ge1 C1 84.99(11) . . ?
N1 Ge1 W1 143.34(8) . . ?
C1 Ge1 W1 131.62(8) . . ?
N1 Si1 C10 114.27(15) . . ?
N1 Si1 C11 114.18(14) . . ?
C10 Si1 C11 107.43(17) . . ?
N1 Si1 C1 90.79(12) . . ?
C10 Si1 C1 115.78(15) . . ?
C11 Si1 C1 113.99(15) . . ?
C12 N1 Si1 131.6(2) . . ?
C12 N1 Ge1 131.4(2) . . ?
Si1 N1 Ge1 96.93(11) . . ?
C5 C1 C2 104.4(2) . . ?
C5 C1 Si1 127.7(2) . . ?
C2 C1 Si1 122.7(2) . . ?
C5 C1 Ge1 107.88(19) . . ?
C2 C1 Ge1 99.90(18) . . ?
Si1 C1 Ge1 86.68(12) . . ?
C3 C2 C1 108.0(3) . . ?
C3 C2 C9 126.4(3) . . ?
C1 C2 C9 125.6(3) . . ?
C2 C3 C4 109.4(3) . . ?
C2 C3 C8 126.6(3) . . ?
C4 C3 C8 124.0(3) . . ?
C5 C4 C3 109.5(3) . . ?
C5 C4 C7 127.3(3) . . ?
C3 C4 C7 123.2(3) . . ?
C4 C5 C1 108.7(3) . . ?
C4 C5 C6 126.4(3) . . ?
C1 C5 C6 124.9(3) . . ?
N1 C12 C13 108.5(3) . . ?
N1 C12 C14 110.4(3) . . ?
C13 C12 C14 110.1(3) . . ?
N1 C12 C15 108.7(3) . . ?
C13 C12 C15 110.6(3) . . ?
C14 C12 C15 108.5(3) . . ?
O1 C16 W1 178.6(3) . . ?
O2 C17 W1 177.7(3) . . ?
O3 C18 W1 177.3(3) . . ?
O4 C19 W1 179.1(3) . . ?
O5 C20 W1 179.9(4) . . ?
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
W1 C16 2.009(3) . ?
W1 C19 2.039(3) . ?
W1 C18 2.042(3) . ?
W1 C17 2.048(3) . ?
W1 C20 2.051(3) . ?
W1 Ge1 2.5293(3) . ?
Ge1 N1 1.823(2) . ?
Ge1 C1 2.018(3) . ?
Si1 N1 1.760(3) . ?
Si1 C10 1.864(3) . ?
Si1 C11 1.866(3) . ?
Si1 C1 1.888(3) . ?
O1 C16 1.144(4) . ?
O2 C17 1.139(3) . ?
O3 C18 1.138(4) . ?
O4 C19 1.135(4) . ?
O5 C20 1.131(4) . ?
N1 C12 1.481(4) . ?
C1 C5 1.479(4) . ?
C1 C2 1.491(4) . ?
C2 C3 1.367(4) . ?
C2 C9 1.503(4) . ?
C3 C4 1.440(4) . ?
C3 C8 1.500(4) . ?
C4 C5 1.359(4) . ?
C4 C7 1.499(4) . ?
C5 C6 1.507(4) . ?
C12 C13 1.520(5) . ?
C12 C14 1.523(4) . ?
C12 C15 1.532(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
C10 Si1 N1 C12 53.7(3) . . . . ?
C11 Si1 N1 C12 -70.5(3) . . . . ?
C1 Si1 N1 C12 172.6(3) . . . . ?
C10 Si1 N1 Ge1 -125.31(16) . . . . ?
C11 Si1 N1 Ge1 110.45(15) . . . . ?
C1 Si1 N1 Ge1 -6.41(13) . . . . ?
C1 Ge1 N1 C12 -173.0(3) . . . . ?
W1 Ge1 N1 C12 4.3(4) . . . . ?
C1 Ge1 N1 Si1 6.02(12) . . . . ?
W1 Ge1 N1 Si1 -176.73(4) . . . . ?
N1 Si1 C1 C5 115.9(3) . . . . ?
C10 Si1 C1 C5 -126.6(3) . . . . ?
C11 Si1 C1 C5 -1.2(3) . . . . ?
N1 Si1 C1 C2 -93.9(2) . . . . ?
C10 Si1 C1 C2 23.7(3) . . . . ?
C11 Si1 C1 C2 149.1(2) . . . . ?
N1 Si1 C1 Ge1 5.75(11) . . . . ?
C10 Si1 C1 Ge1 123.34(15) . . . . ?
C11 Si1 C1 Ge1 -111.27(15) . . . . ?
C5 C1 C2 C3 -1.2(3) . . . . ?
Si1 C1 C2 C3 -157.2(2) . . . . ?
Ge1 C1 C2 C3 110.3(2) . . . . ?
C5 C1 C2 C9 179.1(3) . . . . ?
Si1 C1 C2 C9 23.0(4) . . . . ?
Ge1 C1 C2 C9 -69.4(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C9 C2 C3 C4 -179.6(3) . . . . ?
C1 C2 C3 C8 179.6(3) . . . . ?
C9 C2 C3 C8 -0.7(5) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C8 C3 C4 C5 -178.9(3) . . . . ?
C2 C3 C4 C7 179.7(3) . . . . ?
C8 C3 C4 C7 0.8(5) . . . . ?
C3 C4 C5 C1 -0.8(3) . . . . ?
C7 C4 C5 C1 179.5(3) . . . . ?
C3 C4 C5 C6 -178.6(3) . . . . ?
C7 C4 C5 C6 1.7(5) . . . . ?
C2 C1 C5 C4 1.2(3) . . . . ?
Si1 C1 C5 C4 155.7(2) . . . . ?
Ge1 C1 C5 C4 -104.4(2) . . . . ?
C2 C1 C5 C6 179.1(3) . . . . ?
Si1 C1 C5 C6 -26.5(4) . . . . ?
Ge1 C1 C5 C6 73.4(3) . . . . ?
Si1 N1 C12 C13 -87.3(3) . . . . ?
Ge1 N1 C12 C13 91.4(3) . . . . ?
Si1 N1 C12 C14 151.9(2) . . . . ?
Ge1 N1 C12 C14 -29.4(4) . . . . ?
Si1 N1 C12 C15 33.0(4) . . . . ?
Ge1 N1 C12 C15 -148.3(3) . . . . ?
