#------------------------------------------------------------------------------
#$Date: 2024-04-05 02:40:19 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290992 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/51/7715197.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_7715197
loop_
_publ_author_name
'Basu, Debayan'
'Ghosh, Barshali'
'Srivastava, Diship'
'Patra, Niladri'
'Nayek, Hari Pada'
_publ_section_title
;
 Mononuclear organogermanium(IV) catalysts for a [3 + 2] cycloaddition
 reaction.
;
_journal_issue                   12
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5648
_journal_page_last               5657
_journal_paper_doi               10.1039/d4dt00239c
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C25 H18 Ge N2 O4'
_chemical_formula_sum            'C25 H18 Ge N2 O4'
_chemical_formula_weight         483.00
_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             2023-08-14
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-01-25 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                78.913(7)
_cell_angle_beta                 89.952(8)
_cell_angle_gamma                73.801(8)
_cell_formula_units_Z            2
_cell_length_a                   7.9042(8)
_cell_length_b                   9.6253(9)
_cell_length_c                   14.8290(13)
_cell_measurement_reflns_used    5488
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4910
_cell_measurement_theta_min      2.6670
_cell_volume                     1061.51(18)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16290
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.249
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.479
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69404
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.054
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0535
_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)+(0.0850P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1522
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3548
_reflns_number_total             4609
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt00239c2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7715197--7715198.cif.'
_cod_database_code               7715197
_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.
;
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C2(H4), C3(H5), C4(H6), C5(H7), C7(H9), C9(H26), C11(H28), C12(H29), C15(H15),
  C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25)
;
_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
C1 C 1.0323(5) 0.4895(4) 0.8292(2) 0.0372(8) Uani 1 1 d . . . . .
C2 C 1.2077(5) 0.4048(4) 0.8418(3) 0.0456(9) Uani 1 1 d . . . . .
H4 H 1.247042 0.327609 0.810657 0.055 Uiso 1 1 calc R U . . .
C3 C 1.3237(5) 0.4338(5) 0.8997(3) 0.0494(10) Uani 1 1 d . . . . .
H5 H 1.440439 0.375598 0.907415 0.059 Uiso 1 1 calc R U . . .
C4 C 1.2690(5) 0.5483(4) 0.9465(3) 0.0468(10) Uani 1 1 d . . . . .
H6 H 1.348889 0.567148 0.985137 0.056 Uiso 1 1 calc R U . . .
C5 C 1.0982(5) 0.6335(4) 0.9360(3) 0.0400(8) Uani 1 1 d . . . . .
H7 H 1.061598 0.709929 0.967960 0.048 Uiso 1 1 calc R U . . .
C6 C 0.9760(5) 0.6066(4) 0.8766(2) 0.0343(8) Uani 1 1 d . . . . .
C7 C 0.7994(4) 0.6942(4) 0.8704(2) 0.0341(8) Uani 1 1 d . . . . .
H9 H 0.770904 0.762140 0.908899 0.041 Uiso 1 1 calc R U . . .
C8 C 0.4969(4) 0.7828(3) 0.8168(2) 0.0310(7) Uani 1 1 d . . . . .
C9 C 0.4297(5) 0.8639(4) 0.8819(2) 0.0357(8) Uani 1 1 d . . . . .
H26 H 0.499493 0.861796 0.932883 0.043 Uiso 1 1 calc R U . . .
C10 C 0.2552(5) 0.9491(4) 0.8698(3) 0.0384(8) Uani 1 1 d . . . . .
C11 C 0.1468(5) 0.9504(4) 0.7954(3) 0.0408(9) Uani 1 1 d . . . . .
H28 H 0.029701 1.007632 0.789242 0.049 Uiso 1 1 calc R U . . .
C12 C 0.2129(5) 0.8672(4) 0.7312(3) 0.0408(9) Uani 1 1 d . . . . .
H29 H 0.139792 0.865544 0.682519 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3903(5) 0.7847(4) 0.7390(2) 0.0343(8) Uani 1 1 d . . . . .
C14 C 0.8154(5) 0.6840(4) 0.6139(2) 0.0397(8) Uani 1 1 d . . . . .
C15 C 0.9785(6) 0.6160(5) 0.5869(3) 0.0553(11) Uani 1 1 d . . . . .
H15 H 1.037760 0.520451 0.616842 0.066 Uiso 1 1 calc R U . . .
C16 C 1.0571(7) 0.6880(6) 0.5152(3) 0.0688(14) Uani 1 1 d . . . . .
H16 H 1.167561 0.640363 0.497359 0.083 Uiso 1 1 calc R U . . .
C17 C 0.9706(7) 0.8289(6) 0.4712(3) 0.0672(13) Uani 1 1 d . . . . .
H17 H 1.021801 0.876706 0.422867 0.081 Uiso 1 1 calc R U . . .
C18 C 0.8093(7) 0.8995(5) 0.4981(4) 0.0678(13) Uani 1 1 d . . . . .
H18 H 0.751998 0.995789 0.468777 0.081 Uiso 1 1 calc R U . . .
C19 C 0.7311(6) 0.8283(4) 0.5687(3) 0.0521(10) Uani 1 1 d . . . . .
H19 H 0.620968 0.877077 0.586275 0.063 Uiso 1 1 calc R U . . .
C20 C 0.6270(5) 0.4103(4) 0.7018(2) 0.0364(8) Uani 1 1 d . . . . .
C21 C 0.6893(5) 0.2751(4) 0.7615(3) 0.0499(10) Uani 1 1 d . . . . .
H21 H 0.773934 0.263366 0.807998 0.060 Uiso 1 1 calc R U . . .
C22 C 0.6273(6) 0.1576(5) 0.7526(4) 0.0670(13) Uani 1 1 d . . . . .
H22 H 0.668019 0.068229 0.794160 0.080 Uiso 1 1 calc R U . . .
C23 C 0.5055(7) 0.1719(5) 0.6826(4) 0.0678(14) Uani 1 1 d . . . . .
H23 H 0.464707 0.092205 0.676547 0.081 Uiso 1 1 calc R U . . .
C24 C 0.4446(7) 0.3046(5) 0.6218(3) 0.0638(13) Uani 1 1 d . . . . .
H24 H 0.363672 0.314377 0.573794 0.077 Uiso 1 1 calc R U . . .
C25 C 0.5039(6) 0.4238(4) 0.6320(3) 0.0503(10) Uani 1 1 d . . . . .
H25 H 0.460403 0.513830 0.591393 0.060 Uiso 1 1 calc R U . . .
N1 N 0.6709(4) 0.6899(3) 0.81602(19) 0.0347(6) Uani 1 1 d . . . . .
N2 N 0.1847(4) 1.0371(4) 0.9368(2) 0.0479(8) Uani 1 1 d . . . . .
O1 O 0.9210(3) 0.4550(3) 0.77664(18) 0.0451(6) Uani 1 1 d . . . . .
O2 O 0.4645(3) 0.7120(3) 0.67744(18) 0.0435(6) Uani 1 1 d . . . . .
O31 O 0.2798(4) 1.0305(4) 1.0042(2) 0.0683(9) Uani 1 1 d . . . . .
O32 O 0.0317(4) 1.1158(3) 0.9246(2) 0.0621(8) Uani 1 1 d . . . . .
Ge1 Ge 0.70694(5) 0.58120(4) 0.71195(2) 0.03626(16) 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'
Ge Ge 0.1547 1.8001 '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
C2 C1 C6 118.6(3) . . ?
O1 C1 C2 119.7(3) . . ?
O1 C1 C6 121.7(3) . . ?
C1 C2 H4 119.6 . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H4 119.6 . . ?
C2 C3 H5 119.6 . . ?
C2 C3 C4 120.8(4) . . ?
C4 C3 H5 119.6 . . ?
C3 C4 H6 120.0 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H6 120.0 . . ?
C4 C5 H7 119.8 . . ?
C4 C5 C6 120.4(4) . . ?
C6 C5 H7 119.8 . . ?
C1 C6 C5 119.4(3) . . ?
C7 C6 C1 122.2(3) . . ?
C7 C6 C5 118.3(3) . . ?
C6 C7 H9 116.6 . . ?
N1 C7 C6 126.7(3) . . ?
N1 C7 H9 116.6 . . ?
C9 C8 C13 121.1(3) . . ?
C9 C8 N1 127.2(3) . . ?
N1 C8 C13 111.7(3) . . ?
C8 C9 H26 120.8 . . ?
C8 C9 C10 118.3(3) . . ?
C10 C9 H26 120.8 . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 N2 118.7(3) . . ?
C11 C10 N2 119.6(3) . . ?
C10 C11 H28 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H28 120.0 . . ?
C11 C12 H29 120.0 . . ?
C11 C12 C13 119.9(3) . . ?
C13 C12 H29 120.0 . . ?
C12 C13 C8 118.9(3) . . ?
O2 C13 C8 118.0(3) . . ?
O2 C13 C12 123.2(3) . . ?
C15 C14 C19 118.1(4) . . ?
C15 C14 Ge1 120.4(3) . . ?
C19 C14 Ge1 121.5(3) . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.0(4) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.7(5) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(5) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.3(5) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.8(4) . . ?
C18 C19 H19 119.6 . . ?
C21 C20 Ge1 122.7(3) . . ?
C25 C20 C21 118.5(3) . . ?
C25 C20 Ge1 118.9(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.7(4) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(4) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.7(4) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0(4) . . ?
C25 C24 H24 120.0 . . ?
C20 C25 C24 120.8(4) . . ?
C20 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C7 N1 C8 121.6(3) . . ?
C7 N1 Ge1 124.0(2) . . ?
C8 N1 Ge1 113.7(2) . . ?
O31 N2 C10 118.9(3) . . ?
O32 N2 C10 118.6(3) . . ?
O32 N2 O31 122.5(3) . . ?
C1 O1 Ge1 128.3(2) . . ?
C13 O2 Ge1 115.6(2) . . ?
C14 Ge1 C20 123.58(14) . . ?
C14 Ge1 N1 109.24(13) . . ?
C14 Ge1 O2 94.90(14) . . ?
C20 Ge1 N1 126.92(13) . . ?
C20 Ge1 O2 90.03(13) . . ?
O1 Ge1 C14 96.97(14) . . ?
O1 Ge1 C20 90.69(13) . . ?
O1 Ge1 N1 87.73(11) . . ?
O1 Ge1 O2 165.25(11) . . ?
O2 Ge1 N1 80.09(11) . . ?
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
C1 C2 1.390(5) . ?
C1 C6 1.408(5) . ?
C1 O1 1.326(4) . ?
C2 H4 0.9300 . ?
C2 C3 1.375(5) . ?
C3 H5 0.9300 . ?
C3 C4 1.383(6) . ?
C4 H6 0.9300 . ?
C4 C5 1.361(5) . ?
C5 H7 0.9300 . ?
C5 C6 1.416(5) . ?
C6 C7 1.408(5) . ?
C7 H9 0.9300 . ?
C7 N1 1.312(4) . ?
C8 C9 1.371(5) . ?
C8 C13 1.424(5) . ?
C8 N1 1.417(4) . ?
C9 H26 0.9300 . ?
C9 C10 1.386(5) . ?
C10 C11 1.394(5) . ?
C10 N2 1.441(5) . ?
C11 H28 0.9300 . ?
C11 C12 1.371(5) . ?
C12 H29 0.9300 . ?
C12 C13 1.398(5) . ?
C13 O2 1.297(4) . ?
C14 C15 1.371(5) . ?
C14 C19 1.396(5) . ?
C14 Ge1 1.936(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.398(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.370(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.366(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.385(5) . ?
C20 C25 1.384(5) . ?
C20 Ge1 1.950(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.379(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.377(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.376(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.388(5) . ?
C25 H25 0.9300 . ?
N1 Ge1 2.003(3) . ?
N2 O31 1.232(4) . ?
N2 O32 1.227(4) . ?
O1 Ge1 1.915(3) . ?
O2 Ge1 1.981(3) . ?
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
C1 C2 C3 C4 -0.3(6) . . . . ?
C1 C6 C7 N1 -6.7(5) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C2 C1 C6 C7 -177.6(3) . . . . ?
C2 C1 O1 Ge1 -155.4(3) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C4 C5 C6 C1 0.8(5) . . . . ?
C4 C5 C6 C7 177.8(3) . . . . ?
C5 C6 C7 N1 176.4(3) . . . . ?
C6 C1 C2 C3 0.5(6) . . . . ?
C6 C1 O1 Ge1 27.5(5) . . . . ?
C6 C7 N1 C8 179.1(3) . . . . ?
C6 C7 N1 Ge1 -11.6(5) . . . . ?
C8 C9 C10 C11 2.0(5) . . . . ?
C8 C9 C10 N2 -178.7(3) . . . . ?
C8 C13 O2 Ge1 10.0(4) . . . . ?
C9 C8 C13 C12 -2.2(5) . . . . ?
C9 C8 C13 O2 176.3(3) . . . . ?
C9 C8 N1 C7 -13.8(5) . . . . ?
C9 C8 N1 Ge1 175.9(3) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C9 C10 N2 O31 -2.2(5) . . . . ?
C9 C10 N2 O32 177.9(3) . . . . ?
C10 C11 C12 C13 -2.0(5) . . . . ?
C11 C10 N2 O31 177.2(4) . . . . ?
C11 C10 N2 O32 -2.8(5) . . . . ?
C11 C12 C13 C8 3.4(5) . . . . ?
C11 C12 C13 O2 -175.0(3) . . . . ?
C12 C13 O2 Ge1 -171.6(3) . . . . ?
C13 C8 C9 C10 -0.4(5) . . . . ?
C13 C8 N1 C7 166.3(3) . . . . ?
C13 C8 N1 Ge1 -4.0(3) . . . . ?
C14 C15 C16 C17 0.3(7) . . . . ?
C15 C14 C19 C18 0.7(6) . . . . ?
C15 C16 C17 C18 0.8(8) . . . . ?
C16 C17 C18 C19 -1.1(8) . . . . ?
C17 C18 C19 C14 0.4(7) . . . . ?
C19 C14 C15 C16 -1.0(6) . . . . ?
C20 C21 C22 C23 1.7(7) . . . . ?
C21 C20 C25 C24 -0.2(6) . . . . ?
C21 C22 C23 C24 -0.5(8) . . . . ?
C22 C23 C24 C25 -1.0(8) . . . . ?
C23 C24 C25 C20 1.3(7) . . . . ?
C25 C20 C21 C22 -1.3(6) . . . . ?
N1 C8 C9 C10 179.6(3) . . . . ?
N1 C8 C13 C12 177.8(3) . . . . ?
N1 C8 C13 O2 -3.8(4) . . . . ?
N2 C10 C11 C12 179.9(3) . . . . ?
O1 C1 C2 C3 -176.7(4) . . . . ?
O1 C1 C6 C5 176.4(3) . . . . ?
O1 C1 C6 C7 -0.4(5) . . . . ?
Ge1 C14 C15 C16 178.9(3) . . . . ?
Ge1 C14 C19 C18 -179.2(3) . . . . ?
Ge1 C20 C21 C22 179.1(3) . . . . ?
Ge1 C20 C25 C24 179.4(3) . . . . ?
