#------------------------------------------------------------------------------
#$Date: 2025-08-20 15:06:16 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301830 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/78/4077812.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_4077812
loop_
_publ_author_name
'Toltl, Nicholas P.'
'Stradiotto, Mark'
'Morkin, Tracy L.'
'Leigh, William J.'
_publ_section_title
;
 Homo- and Cross-[2+2]-Cycloaddition of 1,1-Diphenylsilene and
 1,1-Diphenylgermene. Absolute Rate Constants for Dimerization and the
 Molecular Structures and Photochemistry of the Resulting
 1,3-Dimetallacyclobutanes
;
_journal_issue                   26
_journal_name_full               Organometallics
_journal_page_first              5643
_journal_paper_doi               10.1021/om990447k
_journal_volume                  18
_journal_year                    1999
_chemical_formula_sum            'C26 H24 Ge2'
_chemical_formula_weight         481.63
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                103.4520(10)
_cell_angle_beta                 102.52
_cell_angle_gamma                93.0740(10)
_cell_formula_units_Z            2
_cell_length_a                   10.2432(2)
_cell_length_b                   10.54550(10)
_cell_length_c                   11.35420(10)
_cell_measurement_reflns_used    91
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      22.50
_cell_measurement_theta_min      1.90
_cell_volume                     1157.45(3)
_computing_structure_refinement  'SHELXL-V.5.03 (Sheldrick, 1994)'
_computing_structure_solution    'SHELXTL-V.5.03 (Sheldrick, 1994)'
_diffrn_ambient_temperature      300(2)
_diffrn_measurement_device_type  'Siemems Smart CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8478
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    2.605
_exptl_absorpt_correction_T_max  0.704
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_type   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.037
_refine_ls_goodness_of_fit_obs   1.070
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_restrained_S_obs      1.070
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_obs          0.0290
_refine_ls_shift/esd_max         -0.041
_refine_ls_shift/esd_mean        0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0400P)²+0.2236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0737
_refine_ls_wR_factor_obs         0.0693
_reflns_number_observed          2537
_reflns_number_total             2982
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            om990447k.cif
_cod_data_source_block           compound_3b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.2236P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.2236P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1157.42(3)
_cod_original_sg_symbol_H-M      P(-1)
_cod_database_code               4077812
loop_
_symmetry_equiv_pos_as_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
Ge1 Ge 0.62440(3) 0.55071(3) 0.49189(3) 0.04643(14) Uani 1 d .
Ge2 Ge 0.50397(3) 1.02016(3) 0.88326(3) 0.04836(14) Uani 1 d .
C1 C 0.5361(4) 0.3717(4) 0.4674(5) 0.0537(9) Uani 1 d .
C2 C 0.5608(5) 0.8846(4) 0.9724(4) 0.0540(9) Uani 1 d .
C3 C 0.6680(3) 0.5836(4) 0.3417(3) 0.0499(9) Uani 1 d .
C4 C 0.7391(4) 0.6989(4) 0.3451(4) 0.0650(10) Uani 1 d .
H4A H 0.7689(4) 0.7615(4) 0.4205(4) 0.078 Uiso 1 calc R
C5 C 0.7675(5) 0.7238(5) 0.2379(6) 0.093(2) Uani 1 d .
H5A H 0.8138(5) 0.8034(5) 0.2413(6) 0.112 Uiso 1 calc R
C6 C 0.7268(5) 0.6302(7) 0.1267(5) 0.096(2) Uani 1 d .
H6A H 0.7476(5) 0.6451(7) 0.0550(5) 0.116 Uiso 1 calc R
C7 C 0.6559(5) 0.5155(7) 0.1221(4) 0.096(2) Uani 1 d .
H7A H 0.6271(5) 0.4524(7) 0.0468(4) 0.115 Uiso 1 calc R
C8 C 0.6265(4) 0.4926(5) 0.2292(4) 0.0730(12) Uani 1 d .
H8A H 0.5777(4) 0.4140(5) 0.2248(4) 0.088 Uiso 1 calc R
C9 C 0.7829(3) 0.5957(3) 0.6298(3) 0.0480(8) Uani 1 d .
C10 C 0.7873(4) 0.6873(4) 0.7399(4) 0.0740(12) Uani 1 d .
H10A H 0.7131(4) 0.7329(4) 0.7478(4) 0.089 Uiso 1 calc R
C11 C 0.8988(4) 0.7128(5) 0.8384(4) 0.0861(14) Uani 1 d .
H11A H 0.8985(4) 0.7743(5) 0.9118(4) 0.103 Uiso 1 calc R
C12 C 1.0096(4) 0.6483(4) 0.8289(4) 0.0715(11) Uani 1 d .
H12A H 1.0855(4) 0.6668(4) 0.8948(4) 0.086 Uiso 1 calc R
C13 C 1.0077(4) 0.5558(4) 0.7211(4) 0.0706(11) Uani 1 d .
H13A H 1.0822(4) 0.5105(4) 0.7140(4) 0.085 Uiso 1 calc R
C14 C 0.8949(3) 0.5297(4) 0.6226(3) 0.0580(9) Uani 1 d .
H14A H 0.8947(3) 0.4665(4) 0.5502(3) 0.070 Uiso 1 calc R
C15 C 0.6538(3) 1.1188(3) 0.8520(3) 0.0478(8) Uani 1 d .
C16 C 0.6400(4) 1.2402(4) 0.8262(3) 0.0618(10) Uani 1 d .
H16A H 0.5574(4) 1.2738(4) 0.8208(3) 0.074 Uiso 1 calc R
C17 C 0.7487(5) 1.3124(4) 0.8081(4) 0.0730(11) Uani 1 d .
H17A H 0.7379(5) 1.3938(4) 0.7910(4) 0.088 Uiso 1 calc R
C18 C 0.8703(5) 1.2651(5) 0.8151(4) 0.0763(12) Uani 1 d .
H18A H 0.9426(5) 1.3145(5) 0.8041(4) 0.092 Uiso 1 calc R
C19 C 0.8860(4) 1.1442(5) 0.8384(4) 0.0725(12) Uani 1 d .
H19A H 0.9686(4) 1.1109(5) 0.8418(4) 0.087 Uiso 1 calc R
C20 C 0.7785(4) 1.0715(4) 0.8568(3) 0.0646(10) Uani 1 d .
H20A H 0.7902(4) 0.9897(4) 0.8727(3) 0.077 Uiso 1 calc R
C21 C 0.3604(4) 0.9579(3) 0.7333(3) 0.0547(9) Uani 1 d .
C22 C 0.2398(4) 0.8965(5) 0.7387(4) 0.0814(13) Uani 1 d .
H22A H 0.2294(4) 0.8821(5) 0.8140(4) 0.098 Uiso 1 calc R
C23 C 0.1341(5) 0.8560(5) 0.6342(5) 0.100(2) Uani 1 d .
H23A H 0.0535(5) 0.8158(5) 0.6399(5) 0.120 Uiso 1 calc R
C24 C 0.1487(5) 0.8754(5) 0.5225(5) 0.0905(14) Uani 1 d .
H24A H 0.0780(5) 0.8482(5) 0.4522(5) 0.109 Uiso 1 calc R
C25 C 0.2680(5) 0.9351(5) 0.5141(4) 0.0782(12) Uani 1 d .
H25A H 0.2781(5) 0.9477(5) 0.4380(4) 0.094 Uiso 1 calc R
C26 C 0.3723(4) 0.9761(4) 0.6186(3) 0.0616(10) Uani 1 d .
H26A H 0.4524(4) 1.0169(4) 0.6122(3) 0.074 Uiso 1 calc R
H1A H 0.5784(38) 0.3328(38) 0.5210(36) 0.072(13) Uiso 1 d .
H1B H 0.5231(33) 0.3222(35) 0.3878(34) 0.057(11) Uiso 1 d .
H2A H 0.6503(34) 0.8789(32) 0.9909(29) 0.051(11) Uiso 1 d .
H2B H 0.5158(35) 0.8092(38) 0.9292(34) 0.060(11) Uiso 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'
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
C9 Ge1 C3 110.18(14) . .
C9 Ge1 C1 113.7(2) . 2_666
C3 Ge1 C1 114.4(2) . 2_666
C9 Ge1 C1 112.8(2) . .
C3 Ge1 C1 113.7(2) . .
C1 Ge1 C1 90.94(15) 2_666 .
C9 Ge1 Ge1 124.22(9) . 2_666
C3 Ge1 Ge1 125.58(10) . 2_666
C1 Ge1 Ge1 45.62(11) 2_666 2_666
C1 Ge1 Ge1 45.32(10) . 2_666
C21 Ge2 C15 111.48(14) . .
C21 Ge2 C2 112.8(2) . 2_677
C15 Ge2 C2 113.1(2) . 2_677
C21 Ge2 C2 114.7(2) . .
C15 Ge2 C2 113.2(2) . .
C2 Ge2 C2 90.0(2) 2_677 .
C21 Ge2 Ge2 124.72(10) . 2_677
C15 Ge2 Ge2 123.78(10) . 2_677
C2 Ge2 Ge2 45.00(11) 2_677 2_677
C2 Ge2 Ge2 44.99(10) . 2_677
Ge1 C1 Ge1 89.06(15) 2_666 .
Ge2 C2 Ge2 90.0(2) 2_677 .
C8 C3 C4 118.0(4) . .
C8 C3 Ge1 120.9(3) . .
C4 C3 Ge1 121.1(3) . .
C3 C4 C5 121.2(4) . .
C6 C5 C4 119.7(5) . .
C7 C6 C5 119.6(5) . .
C6 C7 C8 120.1(5) . .
C3 C8 C7 121.3(5) . .
C10 C9 C14 117.1(3) . .
C10 C9 Ge1 122.9(3) . .
C14 C9 Ge1 119.9(3) . .
C9 C10 C11 121.7(4) . .
C12 C11 C10 120.4(4) . .
C11 C12 C13 119.2(4) . .
C12 C13 C14 120.1(3) . .
C13 C14 C9 121.4(3) . .
C16 C15 C20 117.6(3) . .
C16 C15 Ge2 120.9(3) . .
C20 C15 Ge2 121.5(3) . .
C15 C16 C17 120.7(4) . .
C18 C17 C16 120.7(4) . .
C17 C18 C19 119.8(4) . .
C18 C19 C20 120.0(4) . .
C19 C20 C15 121.2(4) . .
C22 C21 C26 117.5(4) . .
C22 C21 Ge2 120.4(3) . .
C26 C21 Ge2 122.2(3) . .
C23 C22 C21 121.4(4) . .
C24 C23 C22 119.8(4) . .
C23 C24 C25 120.1(4) . .
C24 C25 C26 119.8(4) . .
C25 C26 C21 121.4(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ge1 C9 1.945(3) .
Ge1 C3 1.954(3) .
Ge1 C1 1.970(3) 2_666
Ge1 C1 1.980(4) .
Ge1 Ge1 2.7704(6) 2_666
Ge2 C21 1.945(4) .
Ge2 C15 1.949(3) .
Ge2 C2 1.978(4) 2_677
Ge2 C2 1.978(4) .
Ge2 Ge2 2.7980(7) 2_677
C1 Ge1 1.970(3) 2_666
C2 Ge2 1.978(4) 2_677
C3 C8 1.373(5) .
C3 C4 1.372(5) .
C4 C5 1.388(6) .
C5 C6 1.375(7) .
C6 C7 1.362(7) .
C7 C8 1.383(6) .
C9 C10 1.381(5) .
C9 C14 1.381(4) .
C10 C11 1.379(5) .
C11 C12 1.366(5) .
C12 C13 1.373(5) .
C13 C14 1.387(5) .
C15 C16 1.386(5) .
C15 C20 1.391(5) .
C16 C17 1.393(5) .
C17 C18 1.360(6) .
C18 C19 1.372(6) .
C19 C20 1.388(5) .
C21 C22 1.384(5) .
C21 C26 1.390(5) .
C22 C23 1.385(6) .
C23 C24 1.368(6) .
C24 C25 1.376(6) .
C25 C26 1.378(5) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139106793
