#------------------------------------------------------------------------------
#$Date: 2019-02-19 01:31:23 +0200 (Tue, 19 Feb 2019) $
#$Revision: 213691 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/06/1550600.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_1550600
loop_
_publ_author_name
'Sharma, Mahendra Kumar'
'Sinhababu, Soumen'
'Mahawar, Pritam'
'Mukherjee, Goutam'
'Pandey, Bhawana'
'Rajaraman, Gopalan'
'Selvarajan, Nagendran'
_publ_section_title
;
 Donor-Acceptor-Stabilized Germanium Analogues of Acid Chloride, Ester,
 and Acyl Pyrrole Compounds: Synthesis and Reactivity
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC05380D
_journal_year                    2019
_chemical_formula_moiety         'C30 H46 Cl2 Ge2 N4 O2'
_chemical_formula_sum            'C30 H46 Cl2 Ge2 N4 O2'
_chemical_formula_weight         710.83
_chemical_name_systematic
; 
 ? 
;
_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-97
_audit_update_record
;
2018-06-22 deposited with the CCDC.    2019-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                105.331(3)
_cell_angle_beta                 105.474(3)
_cell_angle_gamma                104.265(3)
_cell_formula_units_Z            1
_cell_length_a                   8.2234(14)
_cell_length_b                   10.4654(17)
_cell_length_c                   11.0901(19)
_cell_measurement_reflns_used    2003
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.15
_cell_volume                     833.9(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4407
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    1.995
_exptl_absorpt_correction_T_max  0.469
_exptl_absorpt_correction_T_min  0.449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368.0
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.413
_exptl_crystal_size_min          0.380
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0412P)²+0.0205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                2617
_reflns_number_total             2943
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8sc05380d2.cif
_cod_data_source_block           Compound_6__sharma2m
_cod_database_code               1550600
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ge1 Ge 0.60976(3) -0.02719(3) 0.59693(3) 0.03456(11) Uani 1 1 d .
Cl1 Cl 0.45602(10) -0.20966(8) 0.63120(8) 0.0578(2) Uani 1 1 d .
O1 O 0.4445(3) 0.0614(2) 0.57854(18) 0.0522(5) Uani 1 1 d .
N1 N 0.7559(3) 0.1025(2) 0.7735(2) 0.0365(5) Uani 1 1 d .
N2 N 0.8306(3) -0.0695(2) 0.6104(2) 0.0386(5) Uani 1 1 d .
C7 C 0.9617(3) -0.0069(3) 0.7296(3) 0.0370(6) Uani 1 1 d .
C1 C 0.9162(3) 0.0913(3) 0.8273(3) 0.0362(6) Uani 1 1 d .
C8 C 0.6851(3) 0.1936(3) 0.8544(3) 0.0406(6) Uani 1 1 d .
H8A H 0.6969 0.1740 0.9364 0.049 Uiso 1 1 calc R
H8B H 0.5581 0.1687 0.8059 0.049 Uiso 1 1 calc R
C2 C 1.0220(4) 0.1635(3) 0.9613(3) 0.0446(6) Uani 1 1 d .
H2 H 0.9696 0.2165 1.0097 0.054 Uiso 1 1 calc R
C9 C 0.8477(4) -0.1648(3) 0.4942(3) 0.0471(7) Uani 1 1 d .
H9A H 0.9741 -0.1428 0.5067 0.056 Uiso 1 1 calc R
H9B H 0.7904 -0.1463 0.4152 0.056 Uiso 1 1 calc R
C6 C 1.1266(4) -0.0295(3) 0.7570(3) 0.0483(7) Uani 1 1 d .
H6 H 1.1381 -0.0895 0.6837 0.058 Uiso 1 1 calc R
C10 C 0.7757(4) 0.3518(3) 0.8908(3) 0.0481(7) Uani 1 1 d .
H10 H 0.9036 0.3771 0.9412 0.058 Uiso 1 1 calc R
C3 C 1.1915(4) 0.1715(3) 1.0368(3) 0.0512(7) Uani 1 1 d .
H3 H 1.2329 0.2273 1.1267 0.061 Uiso 1 1 calc R
C4 C 1.3060(4) 0.1091(3) 0.9979(3) 0.0567(8) Uani 1 1 d .
H4 H 1.4161 0.1289 1.0631 0.068 Uiso 1 1 calc R
C5 C 1.2744(4) 0.0204(3) 0.8721(3) 0.0543(8) Uani 1 1 d .
H5 H 1.3683 -0.0112 0.8633 0.065 Uiso 1 1 calc R
C11 C 0.7676(5) -0.3200(3) 0.4689(3) 0.0653(9) Uani 1 1 d .
H11 H 0.6400 -0.3404 0.4561 0.078 Uiso 1 1 calc R
C12 C 0.7578(6) 0.3928(4) 0.7686(4) 0.0780(11) Uani 1 1 d .
H12A H 0.6330 0.3652 0.7160 0.117 Uiso 1 1 calc R
H12B H 0.8164 0.3464 0.7162 0.117 Uiso 1 1 calc R
H12C H 0.8126 0.4931 0.7957 0.117 Uiso 1 1 calc R
C13 C 0.6946(6) 0.4280(4) 0.9807(4) 0.0909(13) Uani 1 1 d .
H13A H 0.7504 0.5278 1.0060 0.136 Uiso 1 1 calc R
H13B H 0.7136 0.4030 1.0594 0.136 Uiso 1 1 calc R
H13C H 0.5681 0.4016 0.9340 0.136 Uiso 1 1 calc R
C15 C 0.7792(7) -0.4049(4) 0.3390(4) 0.0983(14) Uani 1 1 d .
H15A H 0.7277 -0.3734 0.2689 0.147 Uiso 1 1 calc R
H15B H 0.7145 -0.5030 0.3160 0.147 Uiso 1 1 calc R
H15C H 0.9027 -0.3919 0.3501 0.147 Uiso 1 1 calc R
C14 C 0.8481(7) -0.3659(4) 0.5795(4) 0.0998(15) Uani 1 1 d .
H14A H 0.9704 -0.3562 0.5886 0.150 Uiso 1 1 calc R
H14B H 0.7813 -0.4627 0.5599 0.150 Uiso 1 1 calc R
H14C H 0.8448 -0.3085 0.6615 0.150 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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
O1 Ge1 O1 83.27(8) 2_656 .
O1 Ge1 N1 145.99(10) 2_656 .
O1 Ge1 N1 93.71(8) . .
O1 Ge1 N2 91.39(8) 2_656 .
O1 Ge1 N2 162.00(10) . .
N1 Ge1 N2 81.12(9) . .
O1 Ge1 Cl1 110.38(8) 2_656 .
O1 Ge1 Cl1 98.72(7) . .
N1 Ge1 Cl1 103.58(7) . .
N2 Ge1 Cl1 99.26(7) . .
O1 Ge1 Ge1 42.08(6) 2_656 2_656
O1 Ge1 Ge1 41.18(6) . 2_656
N1 Ge1 Ge1 126.39(6) . 2_656
N2 Ge1 Ge1 131.14(7) . 2_656
Cl1 Ge1 Ge1 109.46(3) . 2_656
Ge1 O1 Ge1 96.73(8) 2_656 .
C1 N1 C8 121.1(2) . .
C1 N1 Ge1 116.70(17) . .
C8 N1 Ge1 121.48(16) . .
C7 N2 C9 123.2(2) . .
C7 N2 Ge1 115.90(17) . .
C9 N2 Ge1 120.94(17) . .
N2 C7 C6 123.0(2) . .
N2 C7 C1 112.8(2) . .
C6 C7 C1 124.1(2) . .
N1 C1 C2 122.1(2) . .
N1 C1 C7 112.6(2) . .
C2 C1 C7 125.3(2) . .
N1 C8 C10 115.4(2) . .
N1 C8 H8A 108.4 . .
C10 C8 H8A 108.4 . .
N1 C8 H8B 108.4 . .
C10 C8 H8B 108.4 . .
H8A C8 H8B 107.5 . .
C1 C2 C3 132.1(3) . .
C1 C2 H2 113.9 . .
C3 C2 H2 113.9 . .
N2 C9 C11 115.0(2) . .
N2 C9 H9A 108.5 . .
C11 C9 H9A 108.5 . .
N2 C9 H9B 108.5 . .
C11 C9 H9B 108.5 . .
H9A C9 H9B 107.5 . .
C5 C6 C7 131.9(3) . .
C5 C6 H6 114.0 . .
C7 C6 H6 114.0 . .
C13 C10 C12 111.7(3) . .
C13 C10 C8 107.8(3) . .
C12 C10 C8 112.1(3) . .
C13 C10 H10 108.4 . .
C12 C10 H10 108.4 . .
C8 C10 H10 108.4 . .
C4 C3 C2 129.3(3) . .
C4 C3 H3 115.3 . .
C2 C3 H3 115.3 . .
C3 C4 C5 126.4(3) . .
C3 C4 H4 116.8 . .
C5 C4 H4 116.8 . .
C4 C5 C6 130.5(3) . .
C4 C5 H5 114.7 . .
C6 C5 H5 114.7 . .
C14 C11 C9 114.8(3) . .
C14 C11 C15 110.5(3) . .
C9 C11 C15 109.0(3) . .
C14 C11 H11 107.4 . .
C9 C11 H11 107.4 . .
C15 C11 H11 107.4 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C10 C13 H13A 109.5 . .
C10 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C10 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C11 C15 H15A 109.5 . .
C11 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C11 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ge1 O1 1.7899(19) 2_656
Ge1 O1 1.8218(18) .
Ge1 N1 1.912(2) .
Ge1 N2 1.950(2) .
Ge1 Cl1 2.2000(8) .
Ge1 Ge1 2.6995(6) 2_656
O1 Ge1 1.7899(19) 2_656
N1 C1 1.342(3) .
N1 C8 1.467(3) .
N2 C7 1.331(3) .
N2 C9 1.470(3) .
C7 C6 1.402(4) .
C7 C1 1.479(4) .
C1 C2 1.389(4) .
C8 C10 1.529(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C2 C3 1.390(4) .
C2 H2 0.9300 .
C9 C11 1.512(4) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C6 C5 1.373(4) .
C6 H6 0.9300 .
C10 C13 1.506(4) .
C10 C12 1.509(4) .
C10 H10 0.9800 .
C3 C4 1.367(4) .
C3 H3 0.9300 .
C4 C5 1.370(4) .
C4 H4 0.9300 .
C5 H5 0.9300 .
C11 C14 1.487(5) .
C11 C15 1.520(5) .
C11 H11 0.9800 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
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_4
O1 Ge1 O1 Ge1 0.0 2_656 2_656
N1 Ge1 O1 Ge1 145.97(10) . 2_656
N2 Ge1 O1 Ge1 73.5(3) . 2_656
Cl1 Ge1 O1 Ge1 -109.67(8) . 2_656
O1 Ge1 N1 C1 -88.0(2) 2_656 .
O1 Ge1 N1 C1 -171.45(19) . .
N2 Ge1 N1 C1 -8.81(18) . .
Cl1 Ge1 N1 C1 88.65(18) . .
Ge1 Ge1 N1 C1 -144.21(15) 2_656 .
O1 Ge1 N1 C8 101.8(2) 2_656 .
O1 Ge1 N1 C8 18.4(2) . .
N2 Ge1 N1 C8 -179.0(2) . .
Cl1 Ge1 N1 C8 -81.53(19) . .
Ge1 Ge1 N1 C8 45.6(2) 2_656 .
O1 Ge1 N2 C7 153.41(19) 2_656 .
O1 Ge1 N2 C7 81.2(3) . .
N1 Ge1 N2 C7 6.75(18) . .
Cl1 Ge1 N2 C7 -95.68(18) . .
Ge1 Ge1 N2 C7 138.12(16) 2_656 .
O1 Ge1 N2 C9 -26.3(2) 2_656 .
O1 Ge1 N2 C9 -98.6(3) . .
N1 Ge1 N2 C9 -173.0(2) . .
Cl1 Ge1 N2 C9 84.57(19) . .
Ge1 Ge1 N2 C9 -41.6(2) 2_656 .
C9 N2 C7 C6 -2.3(4) . .
Ge1 N2 C7 C6 178.0(2) . .
C9 N2 C7 C1 176.0(2) . .
Ge1 N2 C7 C1 -3.7(3) . .
C8 N1 C1 C2 0.6(4) . .
Ge1 N1 C1 C2 -169.6(2) . .
C8 N1 C1 C7 179.3(2) . .
Ge1 N1 C1 C7 9.1(3) . .
N2 C7 C1 N1 -3.3(3) . .
C6 C7 C1 N1 175.0(2) . .
N2 C7 C1 C2 175.4(2) . .
C6 C7 C1 C2 -6.3(4) . .
C1 N1 C8 C10 73.3(3) . .
Ge1 N1 C8 C10 -116.9(2) . .
N1 C1 C2 C3 -177.8(3) . .
C7 C1 C2 C3 3.7(5) . .
C7 N2 C9 C11 98.1(3) . .
Ge1 N2 C9 C11 -82.2(3) . .
N2 C7 C6 C5 -177.7(3) . .
C1 C7 C6 C5 4.2(5) . .
N1 C8 C10 C13 -176.3(3) . .
N1 C8 C10 C12 60.3(3) . .
C1 C2 C3 C4 0.9(5) . .
C2 C3 C4 C5 -1.4(5) . .
C3 C4 C5 C6 -0.9(6) . .
C7 C6 C5 C4 0.2(6) . .
N2 C9 C11 C14 -60.8(4) . .
N2 C9 C11 C15 174.6(3) . .
