#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:07:34 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185164 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/32/1543299.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_1543299
loop_
_publ_author_name
'Xiong, Yun'
'Yao, Shenglai'
'Karni, Miriam'
'Kostenko, Arseni'
'Burchert, Alexander'
'Apeloig, Yitzhak'
'Driess, Matthias'
_publ_section_title
;
 Heavier congeners of CO and CO2as ligands: from zero-valent germanium
 (‘germylone’) to isolable monomeric GeX and GeX2complexes
 (X = S, Se, Te)
;
_journal_issue                   8
_journal_name_full               'Chem. Sci.'
_journal_page_first              5462
_journal_paper_doi               10.1039/C6SC01839D
_journal_volume                  7
_journal_year                    2016
_chemical_formula_sum            'C39 H56 Cl3 Ga Ge N4 O2 Se2'
_chemical_formula_weight         1019.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           8
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2y'
_symmetry_space_group_name_H-M   'C 1 m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_audit_update_record
;
2016-03-04 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.197(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.2434(7)
_cell_length_b                   21.8215(9)
_cell_length_c                   7.6828(3)
_cell_measurement_reflns_used    4979
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.7430
_cell_measurement_theta_min      3.5300
_cell_volume                     2555.76(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7876
_diffrn_reflns_theta_full        67.46
_diffrn_reflns_theta_max         67.46
_diffrn_reflns_theta_min         3.54
_exptl_absorpt_coefficient_mu    4.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.265
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3421
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0947P)²+0.9887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1245
_reflns_number_gt                3319
_reflns_number_total             3421
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6sc01839d2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 1543298--1543302.cif.'
_cod_original_cell_volume        2555.76(18)
_cod_original_sg_symbol_H-M      Cm
_cod_database_code               1543299
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, 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
Se1 Se 0.09375(5) 0.0000 0.15031(10) 0.0445(2) Uani 1 2 d S
Ge1 Ge 0.20095(5) 0.0000 0.03408(8) 0.0363(2) Uani 1 2 d S
Ga1 Ga 0.43631(7) 0.0000 0.07517(16) 0.0593(3) Uani 1 2 d S
Cl1 Cl 0.41567(12) 0.08135(8) -0.1059(2) 0.0694(4) Uani 1 1 d .
O1 O 0.1150(4) 0.30046(19) -0.3496(7) 0.0698(13) Uani 1 1 d .
C1 C 0.1878(3) 0.0654(2) -0.1537(7) 0.0392(10) Uani 1 1 d .
Cl2 Cl 0.57159(18) 0.0000 0.2655(5) 0.0854(8) Uani 1 2 d S
C2 C 0.1554(5) 0.1507(2) -0.3248(8) 0.0531(13) Uani 1 1 d .
H2 H 0.1393 0.1919 -0.3603 0.064 Uiso 1 1 calc R
C3 C 0.1763(4) 0.1073(2) -0.4298(7) 0.0498(12) Uani 1 1 d .
H3 H 0.1774 0.1120 -0.5518 0.060 Uiso 1 1 calc R
C4 C 0.2292(6) 0.0000 -0.3789(10) 0.0461(16) Uani 1 2 d S
H4A H 0.2131 0.0000 -0.5155 0.055 Uiso 1 2 calc SR
H4B H 0.2940 0.0000 -0.3236 0.055 Uiso 1 2 calc SR
C5 C 0.1389(4) 0.1557(2) -0.0162(7) 0.0450(11) Uani 1 1 d .
C6 C 0.2087(4) 0.1826(2) 0.1304(9) 0.0537(14) Uani 1 1 d .
C8 C 0.0973(6) 0.2216(3) 0.2442(9) 0.072(2) Uani 1 1 d .
H8 H 0.0823 0.2456 0.3318 0.086 Uiso 1 1 calc R
N9 N 0.1954(3) 0.05473(18) -0.3226(6) 0.0413(9) Uani 1 1 d .
C9 C 0.0320(6) 0.1924(3) 0.1032(11) 0.072(2) Uani 1 1 d .
H9 H -0.0270 0.1948 0.0992 0.086 Uiso 1 1 calc R
C10 C 0.0513(4) 0.1596(3) -0.0321(8) 0.0527(13) Uani 1 1 d .
C11 C -0.0200(5) 0.1319(3) -0.1941(11) 0.0656(16) Uani 1 1 d .
H11 H 0.0067 0.0999 -0.2514 0.079 Uiso 1 1 calc R
C12 C -0.0615(6) 0.1829(4) -0.3429(12) 0.081(2) Uani 1 1 d .
H12A H -0.0928 0.2126 -0.2928 0.122 Uiso 1 1 calc R
H12B H -0.1027 0.1641 -0.4550 0.122 Uiso 1 1 calc R
H12C H -0.0150 0.2039 -0.3736 0.122 Uiso 1 1 calc R
N13 N 0.1619(3) 0.12450(18) -0.1597(6) 0.0430(9) Uani 1 1 d .
C13 C -0.0934(6) 0.1020(5) -0.1399(17) 0.096(3) Uani 1 1 d .
H13A H -0.0708 0.0649 -0.0670 0.144 Uiso 1 1 calc R
H13B H -0.1423 0.0911 -0.2523 0.144 Uiso 1 1 calc R
H13C H -0.1138 0.1308 -0.0658 0.144 Uiso 1 1 calc R
C14 C 0.3012(5) 0.1780(3) 0.1402(12) 0.0695(18) Uani 1 1 d .
H14 H 0.3070 0.1386 0.0790 0.083 Uiso 1 1 calc R
C15 C 0.3246(8) 0.2285(4) 0.034(2) 0.110(4) Uani 1 1 d .
H15A H 0.2922 0.2232 -0.0986 0.166 Uiso 1 1 calc R
H15B H 0.3877 0.2273 0.0565 0.166 Uiso 1 1 calc R
H15C H 0.3093 0.2680 0.0751 0.166 Uiso 1 1 calc R
C16 C 0.3677(7) 0.1759(5) 0.3387(15) 0.104(3) Uani 1 1 d .
H16A H 0.3706 0.2162 0.3969 0.155 Uiso 1 1 calc R
H16B H 0.4256 0.1650 0.3353 0.155 Uiso 1 1 calc R
H16C H 0.3492 0.1452 0.4107 0.155 Uiso 1 1 calc R
C17 C 0.1521(8) 0.3511(3) -0.4148(15) 0.087(2) Uani 1 1 d .
H17A H 0.1185 0.3593 -0.5470 0.104 Uiso 1 1 calc R
H17B H 0.2138 0.3424 -0.4014 0.104 Uiso 1 1 calc R
C18 C 0.1469(10) 0.4053(4) -0.2962(18) 0.111(3) Uani 1 1 d .
H18A H 0.0937 0.4301 -0.3577 0.133 Uiso 1 1 calc R
H18B H 0.1993 0.4318 -0.2692 0.133 Uiso 1 1 calc R
C19 C 0.1430(8) 0.3751(4) -0.1183(17) 0.099(3) Uani 1 1 d .
H19A H 0.2020 0.3639 -0.0320 0.119 Uiso 1 1 calc R
H19B H 0.1132 0.4015 -0.0537 0.119 Uiso 1 1 calc R
C20 C 0.0891(7) 0.3193(4) -0.2022(14) 0.089(3) Uani 1 1 d .
H20A H 0.0997 0.2863 -0.1087 0.107 Uiso 1 1 calc R
H20B H 0.0258 0.3295 -0.2475 0.107 Uiso 1 1 calc R
Se2 Se 0.34206(5) 0.0000 0.25233(9) 0.0501(2) Uani 1 2 d S
C7 C 0.1820(6) 0.2164(3) 0.2587(8) 0.0647(18) Uani 1 1 d .
H7 H 0.2255 0.2361 0.3591 0.078 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga -1.2846 0.7763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge -1.0885 0.8855 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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
C1 Ge1 C1 91.8(3) 2 .
C1 Ge1 Se1 112.96(14) 2 .
C1 Ge1 Se1 112.96(14) . .
C1 Ge1 Se2 110.84(15) 2 .
C1 Ge1 Se2 110.84(15) . .
Se1 Ge1 Se2 115.19(4) . .
Cl2 Ga1 Cl1 108.74(7) . 2
Cl2 Ga1 Cl1 108.74(7) . .
Cl1 Ga1 Cl1 106.98(11) 2 .
Cl2 Ga1 Se2 108.41(10) . .
Cl1 Ga1 Se2 111.94(5) 2 .
Cl1 Ga1 Se2 111.94(5) . .
C20 O1 C17 109.7(6) . .
N13 C1 N9 105.0(4) . .
N13 C1 Ge1 131.6(3) . .
N9 C1 Ge1 123.0(3) . .
C3 C2 N13 107.7(5) . .
C2 C3 N9 106.0(4) . .
N9 C4 N9 111.9(6) 2 .
C10 C5 C6 124.0(5) . .
C10 C5 N13 119.1(5) . .
C6 C5 N13 116.8(5) . .
C7 C6 C5 114.5(6) . .
C7 C6 C14 123.4(6) . .
C5 C6 C14 122.1(5) . .
C7 C8 C9 120.8(6) . .
C1 N9 C3 110.4(4) . .
C1 N9 C4 126.5(4) . .
C3 N9 C4 122.6(4) . .
C8 C9 C10 120.9(7) . .
C9 C10 C5 117.1(6) . .
C9 C10 C11 121.3(7) . .
C5 C10 C11 121.5(5) . .
C10 C11 C13 113.2(7) . .
C10 C11 C12 109.4(6) . .
C13 C11 C12 108.6(7) . .
C1 N13 C2 110.9(4) . .
C1 N13 C5 125.5(4) . .
C2 N13 C5 123.6(4) . .
C6 C14 C15 111.5(7) . .
C6 C14 C16 113.9(8) . .
C15 C14 C16 109.8(8) . .
O1 C17 C18 106.1(8) . .
C17 C18 C19 103.1(7) . .
C20 C19 C18 99.4(8) . .
O1 C20 C19 106.8(7) . .
Ge1 Se2 Ga1 104.88(4) . .
C8 C7 C6 122.5(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 Ge1 2.2144(9) .
Ge1 C1 1.987(5) 2
Ge1 C1 1.987(5) .
Ge1 Se2 2.3263(10) .
Ga1 Cl2 2.179(3) .
Ga1 Cl1 2.2086(18) 2
Ga1 Cl1 2.2086(18) .
Ga1 Se2 2.3738(12) .
O1 C20 1.400(10) .
O1 C17 1.428(9) .
C1 N13 1.352(6) .
C1 N9 1.366(6) .
C2 C3 1.361(8) .
C2 N13 1.362(7) .
C3 N9 1.383(7) .
C4 N9 1.442(6) 2
C4 N9 1.442(6) .
C5 C10 1.387(9) .
C5 C6 1.420(9) .
C5 N13 1.452(6) .
C6 C7 1.413(8) .
C6 C14 1.481(10) .
C8 C7 1.346(11) .
C8 C9 1.383(12) .
C9 C10 1.385(9) .
C10 C11 1.503(10) .
C11 C13 1.538(12) .
C11 C12 1.571(10) .
C14 C15 1.495(12) .
C14 C16 1.535(13) .
C17 C18 1.513(14) .
C18 C19 1.539(17) .
C19 C20 1.508(12) .
