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#$Date: 2023-08-06 08:09:12 +0300 (Sun, 06 Aug 2023) $
#$Revision: 285568 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/96/1569647.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_1569647
loop_
_publ_author_name
'Wagler, Jörg'
'Gericke, Robert'
_publ_section_title
;
 Ge-Cu-Complexes Ph(pyO)Ge(μ²-pyO)₂CuCl and
 PhGe(μ²-pyO)₄CuCl-Representatives of
 Cu(I)→Ge(IV) and Cu(II)→Ge(IV) Dative Bond Systems.
;
_journal_issue                   14
_journal_name_full               'Molecules (Basel, Switzerland)'
_journal_page_first              5442
_journal_paper_doi               10.3390/molecules28145442
_journal_volume                  28
_journal_year                    2023
_chemical_formula_moiety         'C21 H17 Cl Cu Ge N3 O3'
_chemical_formula_sum            'C21 H17 Cl Cu Ge N3 O3'
_chemical_formula_weight         530.96
_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     ShelXT
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 92.5550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4369(2)
_cell_length_b                   8.74990(10)
_cell_length_c                   16.2903(3)
_cell_measurement_reflns_used    48943
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.55
_cell_measurement_theta_min      1.25
_cell_volume                     2055.77(5)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            49966
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         1.844
_exptl_absorpt_coefficient_mu    2.655
_exptl_absorpt_correction_T_max  0.7752
_exptl_absorpt_correction_T_min  0.5031
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   XShape
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_description       piece
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0323P)²+1.7469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0671
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4507
_reflns_number_total             4971
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            compound2Ge'.cif
_cod_data_source_block           compound2Ge&#x00C2;&#x00B4;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1569647
_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   0.457
_shelx_estimated_absorpt_t_max   0.691
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
Ge1 Ge 0.48129(2) 0.28986(2) 0.62874(2) 0.01859(7) Uani 1 1 d . . . . .
Cu1 Cu 0.53394(2) 0.45678(3) 0.76900(2) 0.02341(7) Uani 1 1 d . . . . .
Cl1 Cl 0.52403(4) 0.64456(6) 0.86407(3) 0.02851(11) Uani 1 1 d . . . . .
O1 O 0.59887(10) 0.31958(18) 0.60162(10) 0.0298(3) Uani 1 1 d . . . . .
O2 O 0.48680(11) 0.13170(16) 0.69744(8) 0.0268(3) Uani 1 1 d . . . . .
O3 O 0.45698(10) 0.18879(17) 0.53474(8) 0.0247(3) Uani 1 1 d . . . . .
N1 N 0.63963(11) 0.50102(19) 0.69966(10) 0.0220(3) Uani 1 1 d . . . . .
N2 N 0.47979(11) 0.27128(18) 0.81706(10) 0.0203(3) Uani 1 1 d . . . . .
N3 N 0.31344(12) 0.1761(2) 0.58572(11) 0.0255(3) Uani 1 1 d . . . . .
C1 C 0.65799(13) 0.4258(2) 0.63085(12) 0.0245(4) Uani 1 1 d . . . . .
C2 C 0.73714(16) 0.4531(3) 0.58689(16) 0.0396(6) Uani 1 1 d . . . . .
H2 H 0.748135 0.397537 0.538177 0.048 Uiso 1 1 calc R U . . .
C3 C 0.79878(18) 0.5623(4) 0.61576(18) 0.0490(7) Uani 1 1 d . . . . .
H3 H 0.853961 0.581798 0.587858 0.059 Uiso 1 1 calc R U . . .
C4 C 0.77959(17) 0.6441(3) 0.68619(16) 0.0412(6) Uani 1 1 d . . . . .
H4 H 0.820855 0.721167 0.706547 0.049 Uiso 1 1 calc R U . . .
C5 C 0.70020(15) 0.6115(3) 0.72573(13) 0.0290(4) Uani 1 1 d . . . . .
H5 H 0.686908 0.668610 0.773397 0.035 Uiso 1 1 calc R U . . .
C6 C 0.47035(13) 0.1379(2) 0.77782(11) 0.0209(4) Uani 1 1 d . . . . .
C7 C 0.44638(15) 0.0026(2) 0.81686(13) 0.0280(4) Uani 1 1 d . . . . .
H7 H 0.442879 -0.091219 0.787576 0.034 Uiso 1 1 calc R U . . .
C8 C 0.42798(16) 0.0088(2) 0.89878(14) 0.0305(4) Uani 1 1 d . . . . .
H8 H 0.410966 -0.081303 0.926937 0.037 Uiso 1 1 calc R U . . .
C9 C 0.43436(15) 0.1473(3) 0.94033(13) 0.0285(4) Uani 1 1 d . . . . .
H9 H 0.420751 0.153934 0.996741 0.034 Uiso 1 1 calc R U . . .
C10 C 0.46080(14) 0.2745(2) 0.89787(12) 0.0249(4) Uani 1 1 d . . . . .
H10 H 0.466027 0.369075 0.926374 0.030 Uiso 1 1 calc R U . . .
C11 C 0.36752(13) 0.1435(2) 0.52431(12) 0.0226(4) Uani 1 1 d . . . . .
C12 C 0.33868(17) 0.0676(3) 0.45283(14) 0.0347(5) Uani 1 1 d . . . . .
H12 H 0.380435 0.044262 0.411155 0.042 Uiso 1 1 calc R U . . .
C13 C 0.2463(2) 0.0279(3) 0.44550(16) 0.0468(6) Uani 1 1 d . . . . .
H13 H 0.223074 -0.025346 0.398124 0.056 Uiso 1 1 calc R U . . .
C14 C 0.18735(17) 0.0657(3) 0.50714(16) 0.0419(6) Uani 1 1 d . . . . .
H14 H 0.123171 0.041826 0.501733 0.050 Uiso 1 1 calc R U . . .
C15 C 0.22329(15) 0.1381(3) 0.57613(14) 0.0322(5) Uani 1 1 d . . . . .
H15 H 0.182974 0.162396 0.618779 0.039 Uiso 1 1 calc R U . . .
C16 C 0.41569(12) 0.4781(2) 0.64404(11) 0.0196(3) Uani 1 1 d . . . . .
C17 C 0.33648(14) 0.4868(2) 0.68972(13) 0.0266(4) Uani 1 1 d . . . . .
H17 H 0.314199 0.398243 0.716237 0.032 Uiso 1 1 calc R U . . .
C18 C 0.29027(15) 0.6248(3) 0.69640(14) 0.0314(4) Uani 1 1 d . . . . .
H18 H 0.236866 0.631177 0.728257 0.038 Uiso 1 1 calc R U . . .
C19 C 0.32178(16) 0.7532(3) 0.65678(14) 0.0329(5) Uani 1 1 d . . . . .
H19 H 0.289338 0.847168 0.660946 0.040 Uiso 1 1 calc R U . . .
C20 C 0.40003(17) 0.7460(3) 0.61122(14) 0.0333(5) Uani 1 1 d . . . . .
H20 H 0.421435 0.834593 0.584228 0.040 Uiso 1 1 calc R U . . .
C21 C 0.44731(15) 0.6085(2) 0.60502(12) 0.0259(4) Uani 1 1 d . . . . .
H21 H 0.501444 0.603424 0.574043 0.031 Uiso 1 1 calc R U . . .
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O2 Ge1 O3 98.94(6) . . ?
O2 Ge1 O1 104.58(7) . . ?
O3 Ge1 O1 90.72(6) . . ?
O2 Ge1 C16 126.41(7) . . ?
O3 Ge1 C16 117.10(7) . . ?
O1 Ge1 C16 112.66(8) . . ?
O2 Ge1 Cu1 83.63(4) . . ?
O3 Ge1 Cu1 174.78(5) . . ?
O1 Ge1 Cu1 84.23(5) . . ?
C16 Ge1 Cu1 64.07(5) . . ?
N1 Cu1 N2 135.69(7) . . ?
N1 Cu1 Cl1 108.80(5) . . ?
N2 Cu1 Cl1 106.63(5) . . ?
N1 Cu1 Ge1 79.84(5) . . ?
N2 Cu1 Ge1 78.26(5) . . ?
Cl1 Cu1 Ge1 156.377(18) . . ?
C1 O1 Ge1 127.63(13) . . ?
C6 O2 Ge1 125.24(12) . . ?
C11 O3 Ge1 113.68(12) . . ?
C1 N1 C5 117.63(17) . . ?
C1 N1 Cu1 124.73(13) . . ?
C5 N1 Cu1 117.58(14) . . ?
C6 N2 C10 117.54(17) . . ?
C6 N2 Cu1 124.16(13) . . ?
C10 N2 Cu1 117.86(13) . . ?
C11 N3 C15 117.26(18) . . ?
O1 C1 N1 119.63(17) . . ?
O1 C1 C2 117.46(18) . . ?
N1 C1 C2 122.91(19) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 122.8(2) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
N2 C6 O2 118.96(17) . . ?
N2 C6 C7 123.08(18) . . ?
O2 C6 C7 117.94(17) . . ?
C8 C7 C6 118.19(19) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C7 C8 C9 119.75(19) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 118.39(19) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
N2 C10 C9 122.98(19) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
N3 C11 O3 115.61(17) . . ?
N3 C11 C12 124.79(19) . . ?
O3 C11 C12 119.60(19) . . ?
C13 C12 C11 116.5(2) . . ?
C13 C12 H12 121.8 . . ?
C11 C12 H12 121.8 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 118.8(2) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
N3 C15 C14 122.5(2) . . ?
N3 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C21 C16 C17 119.49(18) . . ?
C21 C16 Ge1 118.00(14) . . ?
C17 C16 Ge1 122.46(15) . . ?
C18 C17 C16 119.90(19) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 120.12(19) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.5(2) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 119.7(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 120.27(19) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
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 O2 1.7794(14) . ?
Ge1 O3 1.7894(14) . ?
Ge1 O1 1.7919(14) . ?
Ge1 C16 1.9217(19) . ?
Ge1 Cu1 2.7886(3) . ?
Cu1 N1 1.9767(16) . ?
Cu1 N2 1.9782(16) . ?
Cu1 Cl1 2.2669(5) . ?
O1 C1 1.335(2) . ?
O2 C6 1.342(2) . ?
O3 C11 1.355(2) . ?
N1 C1 1.337(3) . ?
N1 C5 1.359(3) . ?
N2 C6 1.334(2) . ?
N2 C10 1.357(2) . ?
N3 C11 1.327(3) . ?
N3 C15 1.346(3) . ?
C1 C2 1.396(3) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.395(3) . ?
C7 C8 1.373(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C12 C13 1.378(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.372(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.393(3) . ?
C16 C17 1.394(3) . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
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
O2 Ge1 O1 C1 -101.54(18) . . . . ?
O3 Ge1 O1 C1 159.02(18) . . . . ?
C16 Ge1 O1 C1 39.1(2) . . . . ?
Cu1 Ge1 O1 C1 -19.68(17) . . . . ?
O3 Ge1 O2 C6 -154.58(15) . . . . ?
O1 Ge1 O2 C6 112.32(16) . . . . ?
C16 Ge1 O2 C6 -21.03(19) . . . . ?
Cu1 Ge1 O2 C6 30.00(15) . . . . ?
O2 Ge1 O3 C11 77.52(14) . . . . ?
O1 Ge1 O3 C11 -177.61(14) . . . . ?
C16 Ge1 O3 C11 -61.55(15) . . . . ?
Ge1 O1 C1 N1 15.7(3) . . . . ?
Ge1 O1 C1 C2 -164.10(18) . . . . ?
C5 N1 C1 O1 -177.94(19) . . . . ?
Cu1 N1 C1 O1 5.0(3) . . . . ?
C5 N1 C1 C2 1.9(3) . . . . ?
Cu1 N1 C1 C2 -175.15(18) . . . . ?
O1 C1 C2 C3 179.8(3) . . . . ?
N1 C1 C2 C3 0.0(4) . . . . ?
C1 C2 C3 C4 -1.5(5) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C1 N1 C5 C4 -2.3(3) . . . . ?
Cu1 N1 C5 C4 174.9(2) . . . . ?
C3 C4 C5 N1 0.9(4) . . . . ?
C10 N2 C6 O2 178.66(17) . . . . ?
Cu1 N2 C6 O2 -9.1(2) . . . . ?
C10 N2 C6 C7 -3.1(3) . . . . ?
Cu1 N2 C6 C7 169.12(15) . . . . ?
Ge1 O2 C6 N2 -23.1(2) . . . . ?
Ge1 O2 C6 C7 158.55(15) . . . . ?
N2 C6 C7 C8 2.8(3) . . . . ?
O2 C6 C7 C8 -178.95(19) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C10 -1.2(3) . . . . ?
C6 N2 C10 C9 1.2(3) . . . . ?
Cu1 N2 C10 C9 -171.48(16) . . . . ?
C8 C9 C10 N2 0.9(3) . . . . ?
C15 N3 C11 O3 177.46(18) . . . . ?
C15 N3 C11 C12 -2.9(3) . . . . ?
Ge1 O3 C11 N3 -2.1(2) . . . . ?
Ge1 O3 C11 C12 178.18(16) . . . . ?
N3 C11 C12 C13 1.8(4) . . . . ?
O3 C11 C12 C13 -178.6(2) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 -2.1(4) . . . . ?
C11 N3 C15 C14 1.4(3) . . . . ?
C13 C14 C15 N3 1.0(4) . . . . ?
C21 C16 C17 C18 -0.4(3) . . . . ?
Ge1 C16 C17 C18 -177.87(16) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C17 C18 C19 C20 -0.9(4) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C16 0.5(3) . . . . ?
C17 C16 C21 C20 -0.3(3) . . . . ?
Ge1 C16 C21 C20 177.24(17) . . . . ?
