#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/14/7001449.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_7001449
loop_
_publ_author_name
'Lermontova, El'mira Kh.'
'Huan, MengMeng'
'Churakov, Andrei V.'
'Howard, Judith A. K.'
'Zabalov, Maxim V.'
'Karlov, Sergey S.'
'Zaitseva, Galina S.'
_publ_section_title
;
 Novel derivatives of hypervalent germanium: synthesis, structure, and
 stability
;
_journal_issue                   24
_journal_name_full               'Dalton Transactions'
_journal_page_first              4695
_journal_page_last               4702
_journal_paper_doi               10.1039/b901885a
_journal_year                    2009
_chemical_formula_moiety         'C17 H11 Cl2 F10 Ge N3, 1.5 (C7 H8)'
_chemical_formula_sum            'C27.5 H23 Cl2 F10 Ge N3'
_chemical_formula_weight         728.98
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.241(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4562(6)
_cell_length_b                   22.0794(17)
_cell_length_c                   17.7878(14)
_cell_measurement_reflns_used    5342
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.590
_cell_measurement_theta_min      2.470
_cell_volume                     2928.4(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19274
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.47
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.317
_exptl_absorpt_correction_T_max  0.8580
_exptl_absorpt_correction_T_min  0.7605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1460
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         6279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0338
_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)+(0.0451P)²+0.5303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                5240
_reflns_number_total             6279
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b901885a.txt
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C27.50 H23 Cl2 F10 Ge N3'
_cod_database_code               7001449
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge Ge 0.06171(3) 0.732786(9) 0.802903(11) 0.02010(7) Uani 1 1 d . . .
Cl1 Cl 0.28408(7) 0.66529(2) 0.81559(3) 0.02995(13) Uani 1 1 d . . .
Cl2 Cl 0.21666(9) 0.79084(3) 0.72902(3) 0.04323(17) Uani 1 1 d . . .
N3 N -0.1650(3) 0.79040(8) 0.79641(10) 0.0294(4) Uani 1 1 d . . .
C1 C -0.1947(4) 0.82306(13) 0.72470(15) 0.0499(7) Uani 1 1 d . . .
H1A H -0.3125 0.8427 0.7256 0.075 Uiso 1 1 calc R . .
H1B H -0.1902 0.7943 0.6828 0.075 Uiso 1 1 calc R . .
H1C H -0.1012 0.8538 0.7183 0.075 Uiso 1 1 calc R . .
N1 N -0.0943(2) 0.67824(8) 0.76077(10) 0.0249(4) Uani 1 1 d . . .
C11 C -0.3124(3) 0.74657(11) 0.80990(17) 0.0407(6) Uani 1 1 d . . .
H11A H -0.4300 0.7659 0.7999 0.049 Uiso 1 1 calc R . .
H11B H -0.3099 0.7326 0.8628 0.049 Uiso 1 1 calc R . .
C12 C -0.2841(3) 0.69331(11) 0.75686(16) 0.0422(7) Uani 1 1 d . . .
H12A H -0.3578 0.6583 0.7726 0.051 Uiso 1 1 calc R . .
H12B H -0.3183 0.7046 0.7049 0.051 Uiso 1 1 calc R . .
C13 C -0.0412(3) 0.62573(9) 0.72186(12) 0.0224(4) Uani 1 1 d . . .
C14 C 0.0111(3) 0.62804(9) 0.64727(12) 0.0255(5) Uani 1 1 d . . .
C15 C 0.0615(3) 0.57671(10) 0.60823(12) 0.0278(5) Uani 1 1 d . . .
C16 C 0.0626(3) 0.52175(9) 0.64374(12) 0.0282(5) Uani 1 1 d . . .
C17 C 0.0104(3) 0.51782(9) 0.71786(13) 0.0296(5) Uani 1 1 d . . .
C18 C -0.0426(3) 0.56910(10) 0.75556(12) 0.0279(5) Uani 1 1 d . . .
N2 N 0.0656(3) 0.75791(8) 0.90144(9) 0.0263(4) Uani 1 1 d . . .
C21 C -0.1434(3) 0.83393(10) 0.85932(13) 0.0328(5) Uani 1 1 d . . .
H21A H -0.2604 0.8527 0.8713 0.039 Uiso 1 1 calc R . .
H21B H -0.0590 0.8665 0.8448 0.039 Uiso 1 1 calc R . .
C22 C -0.0720(3) 0.80054(10) 0.92695(13) 0.0325(5) Uani 1 1 d . . .
H22A H -0.0196 0.8295 0.9634 0.039 Uiso 1 1 calc R . .
H22B H -0.1703 0.7784 0.9521 0.039 Uiso 1 1 calc R . .
C23 C 0.1591(3) 0.72620(9) 0.95814(11) 0.0255(5) Uani 1 1 d . . .
C24 C 0.0853(3) 0.67682(11) 0.99511(12) 0.0337(5) Uani 1 1 d . . .
C25 C 0.1789(4) 0.64399(11) 1.04819(13) 0.0393(6) Uani 1 1 d . . .
C26 C 0.3517(4) 0.66049(12) 1.06607(12) 0.0385(6) Uani 1 1 d . . .
C27 C 0.4280(3) 0.70997(12) 1.03211(13) 0.0357(6) Uani 1 1 d . . .
C28 C 0.3323(3) 0.74236(10) 0.97919(12) 0.0297(5) Uani 1 1 d . . .
F14 F 0.0136(2) 0.68151(5) 0.61104(7) 0.0390(3) Uani 1 1 d . . .
F15 F 0.1086(2) 0.58049(6) 0.53555(7) 0.0444(4) Uani 1 1 d . . .
F16 F 0.1128(2) 0.47199(6) 0.60591(8) 0.0406(4) Uani 1 1 d . . .
F17 F 0.0137(2) 0.46372(6) 0.75233(8) 0.0475(4) Uani 1 1 d . . .
F18 F -0.0935(2) 0.56414(6) 0.82701(7) 0.0448(4) Uani 1 1 d . . .
F24 F -0.0819(2) 0.65922(7) 0.97666(9) 0.0477(4) Uani 1 1 d . . .
F25 F 0.1028(3) 0.59687(7) 1.08274(9) 0.0590(5) Uani 1 1 d . . .
F26 F 0.4457(2) 0.62906(7) 1.11742(8) 0.0534(4) Uani 1 1 d . . .
F27 F 0.5955(2) 0.72687(8) 1.05085(9) 0.0526(4) Uani 1 1 d . . .
F28 F 0.4121(2) 0.78979(6) 0.94592(8) 0.0397(3) Uani 1 1 d . . .
C2 C 0.4831(4) 0.98903(15) 0.77020(16) 0.0530(8) Uani 1 1 d . . .
H2 H 0.5245 0.9860 0.7199 0.064 Uiso 1 1 calc R . .
C3 C 0.4072(4) 0.94014(13) 0.80427(17) 0.0488(7) Uani 1 1 d . . .
H3 H 0.3955 0.9030 0.7777 0.059 Uiso 1 1 calc R . .
C4 C 0.3480(4) 0.94442(11) 0.87647(15) 0.0408(6) Uani 1 1 d . . .
H4 H 0.2957 0.9101 0.9000 0.049 Uiso 1 1 calc R . .
C5 C 0.3635(3) 0.99809(11) 0.91560(14) 0.0355(6) Uani 1 1 d . . .
H5 H 0.3222 1.0003 0.9660 0.043 Uiso 1 1 calc R . .
C6 C 0.4384(3) 1.04873(11) 0.88260(15) 0.0366(6) Uani 1 1 d . . .
C7 C 0.4999(4) 1.04330(13) 0.80923(16) 0.0477(7) Uani 1 1 d . . .
H7 H 0.5542 1.0771 0.7854 0.057 Uiso 1 1 calc R . .
C8 C 0.4528(5) 1.10763(12) 0.9252(2) 0.0647(10) Uani 1 1 d . . .
H8A H 0.5041 1.1000 0.9751 0.097 Uiso 1 1 calc R . .
H8B H 0.3333 1.1255 0.9305 0.097 Uiso 1 1 calc R . .
H8C H 0.5304 1.1356 0.8976 0.097 Uiso 1 1 calc R . .
C31 C 0.3834(9) 0.5030(3) 0.9678(4) 0.0469(14) Uiso 0.50 1 d P A -1
C32 C 0.5453(10) 0.5355(2) 0.9543(4) 0.0371(12) Uiso 0.50 1 d P A -1
H32 H 0.5506 0.5646 0.9151 0.044 Uiso 0.50 1 calc PR A -1
C33 C 0.7009(13) 0.5241(4) 1.0006(5) 0.075(2) Uiso 0.50 1 d P A -1
H33 H 0.8127 0.5437 0.9929 0.090 Uiso 0.50 1 calc PR A -1
C34 C 0.6737(13) 0.4823(4) 1.0567(5) 0.0649(19) Uiso 0.50 1 d P A -1
H34 H 0.7713 0.4731 1.0893 0.078 Uiso 0.50 1 calc PR A -1
C35 C 0.5248(11) 0.4552(3) 1.0676(4) 0.0580(18) Uiso 0.50 1 d P A -1
H35 H 0.5195 0.4270 1.1079 0.070 Uiso 0.50 1 calc PR A -1
C36 C 0.3671(12) 0.4640(3) 1.0245(4) 0.0480(15) Uiso 0.50 1 d P A -1
H36 H 0.2579 0.4436 1.0352 0.058 Uiso 0.50 1 calc PR A -1
C37 C 0.2238(11) 0.5126(4) 0.9190(5) 0.077(2) Uiso 0.50 1 d P A -1
H37A H 0.1192 0.5213 0.9503 0.116 Uiso 0.50 1 calc PR A -1
H37B H 0.2012 0.4760 0.8893 0.116 Uiso 0.50 1 calc PR A -1
H37C H 0.2458 0.5468 0.8852 0.116 Uiso 0.50 1 calc PR A -1
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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
N1 Ge N2 126.55(8) . . ?
N1 Ge N3 82.37(8) . . ?
N2 Ge N3 83.11(8) . . ?
N1 Ge Cl2 118.60(6) . . ?
N2 Ge Cl2 113.11(6) . . ?
N3 Ge Cl2 92.24(6) . . ?
N1 Ge Cl1 94.15(6) . . ?
N2 Ge Cl1 95.52(6) . . ?
N3 Ge Cl1 174.35(6) . . ?
Cl2 Ge Cl1 93.34(3) . . ?
C1 N3 C21 110.46(18) . . ?
C1 N3 C11 110.4(2) . . ?
C21 N3 C11 112.24(19) . . ?
C1 N3 Ge 117.12(16) . . ?
C21 N3 Ge 105.29(14) . . ?
C11 N3 Ge 101.01(13) . . ?
N3 C1 H1A 109.5 . . ?
N3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 N1 C12 116.12(17) . . ?
C13 N1 Ge 124.25(14) . . ?
C12 N1 Ge 119.00(14) . . ?
N3 C11 C12 107.4(2) . . ?
N3 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
N3 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
N1 C12 C11 106.52(19) . . ?
N1 C12 H12A 110.4 . . ?
C11 C12 H12A 110.4 . . ?
N1 C12 H12B 110.4 . . ?
C11 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C14 C13 C18 116.73(18) . . ?
C14 C13 N1 121.42(19) . . ?
C18 C13 N1 121.83(19) . . ?
F14 C14 C15 118.34(19) . . ?
F14 C14 C13 119.71(18) . . ?
C15 C14 C13 121.96(19) . . ?
F15 C15 C16 119.89(18) . . ?
F15 C15 C14 120.35(19) . . ?
C16 C15 C14 119.76(19) . . ?
F16 C16 C15 119.71(19) . . ?
F16 C16 C17 120.53(19) . . ?
C15 C16 C17 119.76(19) . . ?
F17 C17 C18 121.0(2) . . ?
F17 C17 C16 119.21(19) . . ?
C18 C17 C16 119.82(19) . . ?
F18 C18 C17 118.8(2) . . ?
F18 C18 C13 119.28(19) . . ?
C17 C18 C13 121.94(19) . . ?
C23 N2 C22 116.24(17) . . ?
C23 N2 Ge 122.53(14) . . ?
C22 N2 Ge 118.74(14) . . ?
N3 C21 C22 108.80(17) . . ?
N3 C21 H21A 109.9 . . ?
C22 C21 H21A 109.9 . . ?
N3 C21 H21B 109.9 . . ?
C22 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
N2 C22 C21 108.20(18) . . ?
N2 C22 H22A 110.1 . . ?
C21 C22 H22A 110.1 . . ?
N2 C22 H22B 110.1 . . ?
C21 C22 H22B 110.1 . . ?
H22A C22 H22B 108.4 . . ?
C24 C23 C28 116.3(2) . . ?
C24 C23 N2 122.2(2) . . ?
C28 C23 N2 121.4(2) . . ?
F24 C24 C25 118.8(2) . . ?
F24 C24 C23 118.7(2) . . ?
C25 C24 C23 122.5(2) . . ?
F25 C25 C26 119.9(2) . . ?
F25 C25 C24 120.7(3) . . ?
C26 C25 C24 119.4(2) . . ?
F26 C26 C27 119.6(3) . . ?
F26 C26 C25 120.4(2) . . ?
C27 C26 C25 119.9(2) . . ?
F27 C27 C26 119.9(2) . . ?
F27 C27 C28 120.2(2) . . ?
C26 C27 C28 119.9(2) . . ?
F28 C28 C27 118.4(2) . . ?
F28 C28 C23 119.6(2) . . ?
C27 C28 C23 121.9(2) . . ?
C3 C2 C7 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C7 C2 H2 120.1 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 117.7(2) . . ?
C5 C6 C8 120.8(3) . . ?
C7 C6 C8 121.5(3) . . ?
C2 C7 C6 120.9(2) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C36 C31 C32 122.2(7) . . ?
C36 C31 C37 117.4(7) . . ?
C32 C31 C37 120.4(7) . . ?
C31 C32 C33 119.7(6) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C34 C33 C32 114.3(9) . . ?
C34 C33 H33 122.8 . . ?
C32 C33 H33 122.8 . . ?
C35 C34 C33 123.7(10) . . ?
C35 C34 H34 118.1 . . ?
C33 C34 H34 118.1 . . ?
C34 C35 C36 125.1(8) . . ?
C34 C35 H35 117.4 . . ?
C36 C35 H35 117.4 . . ?
C31 C36 C35 114.9(7) . . ?
C31 C36 H36 122.6 . . ?
C35 C36 H36 122.6 . . ?
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
Ge N1 1.8325(17) . ?
Ge N2 1.8385(17) . ?
Ge N3 2.1182(19) . ?
Ge Cl2 2.1719(6) . ?
Ge Cl1 2.2400(6) . ?
N3 C1 1.481(3) . ?
N3 C21 1.483(3) . ?
N3 C11 1.485(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N1 C13 1.408(2) . ?
N1 C12 1.455(3) . ?
C11 C12 1.523(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.385(3) . ?
C13 C18 1.387(3) . ?
C14 F14 1.345(2) . ?
C14 C15 1.382(3) . ?
C15 F15 1.344(2) . ?
C15 C16 1.368(3) . ?
C16 F16 1.343(2) . ?
C16 C17 1.379(3) . ?
C17 F17 1.343(2) . ?
C17 C18 1.375(3) . ?
C18 F18 1.332(2) . ?
N2 C23 1.410(3) . ?
N2 C22 1.465(3) . ?
C21 C22 1.506(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.388(3) . ?
C23 C28 1.389(3) . ?
C24 F24 1.346(3) . ?
C24 C25 1.378(3) . ?
C25 F25 1.336(3) . ?
C25 C26 1.375(4) . ?
C26 F26 1.342(3) . ?
C26 C27 1.373(4) . ?
C27 F27 1.344(3) . ?
C27 C28 1.379(3) . ?
C28 F28 1.343(3) . ?
C2 C3 1.362(4) . ?
C2 C7 1.390(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.363(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(4) . ?
C6 C8 1.509(4) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C31 C36 1.332(10) . ?
C31 C32 1.427(9) . ?
C31 C37 1.485(10) . ?
C32 C33 1.442(11) . ?
C32 H32 0.9500 . ?
C33 C34 1.375(12) . ?
C33 H33 0.9500 . ?
C34 C35 1.276(10) . ?
C34 H34 0.9500 . ?
C35 C36 1.414(10) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
