#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/90/2009081.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009081
loop_
_publ_author_name
'White, Jonathan M.'
_publ_section_title
;
 Trimethylgermylethyl p-nitrobenzoate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1660
_journal_page_last               1662
_journal_paper_doi               10.1107/S0108270199007258
_journal_volume                  55
_journal_year                    1999
_chemical_formula_iupac          '[Ge (C1 H3)3 (C9 H8 N1 O4)]'
_chemical_formula_sum            'C12 H17 Ge N O4'
_chemical_formula_weight         311.88
_chemical_melting_point          .59E-58
_chemical_name_systematic
;
2-trimethylgermylethyl p-nitrobenzoate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 96.920(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.670(2)
_cell_length_b                   7.3680(10)
_cell_length_c                   29.704(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    130.00(10)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      25
_cell_volume                     2752.7(7)
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'Process_data (Gable et al., 1994)'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      130.0(10)
_diffrn_measurement_device       'Enraf-Nonius CAD-4S'
_diffrn_measurement_method       θ2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_av_sigmaI/netI    0.0116
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3575
_diffrn_reflns_theta_max         63.98
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        insignificant
_diffrn_standards_interval_time  160
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.101
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_type   'Gaussian (Sheldrick, 1976)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.444
_refine_ls_extinction_coef       0.00006(3)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_all   0.977
_refine_ls_goodness_of_fit_obs   0.992
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_restrained_S_obs      0.992
_refine_ls_R_factor_all          0.032
_refine_ls_R_factor_obs          .030
_refine_ls_shift/esd_max         0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0605P)²+5.0898P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.085
_refine_ls_wR_factor_obs         .081
_reflns_number_observed          2113
_reflns_number_total             2251
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            ta1258.cif
_cod_data_source_block           jmwget
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0605P)^2^+5.0898P] 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^)+(0.0605P)^2^+5.0898P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2009081
_cod_database_fobs_code          2009081
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
Ge1 .81265(2) .03548(4) .193899(9) .01970(14) Uani d . 1 . Ge
O1 .67197(14) .0048(2) .09913(6) .0232(4) Uani d . 1 . O
O2 .55545(13) -.1626(2) .05348(6) .0270(4) Uani d . 1 . O
O3 .8539(2) .0172(3) -.12158(6) .0320(5) Uani d . 1 . O
O4 .97205(14) .1528(3) -.07471(6) .0321(4) Uani d . 1 . O
N1 .8871(2) .0718(3) -.08360(7) .0232(5) Uani d . 1 . N
C1 .6583(2) .0622(4) .17784(9) .0243(5) Uani d . 1 . C
H1A .642(2) .184(4) .1735(8) .019(6) Uiso d . 1 . H
H1B .622(2) .027(4) .2041(10) .025(7) Uiso d . 1 . H
C2 .6104(2) -.0394(4) .13627(9) .0241(6) Uani d . 1 . C
H2A .543(2) -.004(4) .1267(9) .016(6) Uiso d . 1 . H
H2B .613(2) -.156(5) .1412(9) .026(7) Uiso d . 1 . H
C3 .8413(3) .0482(4) .25968(10) .0324(6) Uani d . 1 . C
H3A .909(3) .020(5) .2688(13) .048(10) Uiso d . 1 . H
H3B .798(4) -.049(6) .2739(16) .083(15) Uiso d . 1 . H
H3C .829(3) .160(6) .2696(13) .064(12) Uiso d . 1 . H
C4 .8857(2) .2337(4) .16774(11) .0335(6) Uani d . 1 . C
H4A .881(3) .230(6) .1382(16) .073(13) Uiso d . 1 . H
H4B .943(4) .260(7) .1850(16) .092(16) Uiso d . 1 . H
H4C .860(4) .347(8) .1726(15) .083(15) Uiso d . 1 . H
C5 .8640(2) -.1941(4) .17262(11) .0345(6) Uani d . 1 . C
H5A .814(3) -.285(6) .1741(14) .072(13) Uiso d . 1 . H
H5B .929(4) -.219(6) .1876(14) .071(13) Uiso d . 1 . H
H5C .884(3) -.189(6) .1423(14) .069(12) Uiso d . 1 . H
C6 .6349(2) -.0694(3) .05909(8) .0201(5) Uani d . 1 . C
C7 .7019(2) -.0266(3) .02267(9) .0194(5) Uani d . 1 . C
C8 .8030(2) .0508(3) .03192(8) .0190(5) Uani d . 1 . C
H8 .826(2) .078(4) .0596(10) .021(7) Uiso d . 1 . H
C9 .8638(2) .0846(3) -.00253(8) .0199(5) Uani d . 1 . C
H9 .929(2) .127(4) .0022(8) .014(6) Uiso d . 1 . H
C10 .8222(2) .0407(3) -.04652(8) .0194(5) Uani d . 1 . C
C11 .7216(2) -.0347(3) -.05688(9) .0223(5) Uani d . 1 . C
H11 .697(2) -.064(4) -.0863(10) .024(7) Uiso d . 1 . H
C12 .6621(2) -.0676(3) -.02202(9) .0210(5) Uani d . 1 . C
H12 .596(2) -.116(4) -.0258(8) .018(6) Uiso d . 1 . H
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'
Ge Ge -1.0885 0.8855 '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_publ_flag
C4 Ge1 C5 109.27(14) y
C4 Ge1 C3 108.99(14) y
C5 Ge1 C3 109.79(14) y
C4 Ge1 C1 109.61(12) y
C5 Ge1 C1 111.74(12) y
C3 Ge1 C1 107.38(12) y
C6 O1 C2 114.6(2) ?
O3 N1 O4 123.5(2) ?
O3 N1 C10 118.6(2) ?
O4 N1 C10 117.9(2) ?
C2 C1 Ge1 116.1(2) y
C2 C1 H1A 107.9(16) ?
Ge1 C1 H1A 109.1(16) ?
C2 C1 H1B 109.6(17) ?
Ge1 C1 H1B 109.1(17) ?
H1A C1 H1B 104.(2) ?
O1 C2 C1 107.9(2) y
O1 C2 H2A 105.7(17) ?
C1 C2 H2A 112.7(17) ?
O1 C2 H2B 109.6(19) ?
C1 C2 H2B 110.5(19) ?
H2A C2 H2B 110.(3) ?
Ge1 C3 H3A 111.(2) ?
Ge1 C3 H3B 110.(3) ?
H3A C3 H3B 105.(3) ?
Ge1 C3 H3C 111.(3) ?
H3A C3 H3C 108.(3) ?
H3B C3 H3C 113.(4) ?
Ge1 C4 H4A 114.(3) ?
Ge1 C4 H4B 110.(3) ?
H4A C4 H4B 124.(4) ?
Ge1 C4 H4C 115.(3) ?
H4A C4 H4C 102.(4) ?
H4B C4 H4C 89.(4) ?
Ge1 C5 H5A 111.(3) ?
Ge1 C5 H5B 110.(3) ?
H5A C5 H5B 115.(4) ?
Ge1 C5 H5C 114.(3) ?
H5A C5 H5C 109.(4) ?
H5B C5 H5C 98.(3) ?
O2 C6 O1 123.2(2) ?
O2 C6 C7 123.8(2) ?
O1 C6 C7 112.9(2) ?
C12 C7 C8 119.5(2) ?
C12 C7 C6 118.3(2) ?
C8 C7 C6 122.2(2) ?
C9 C8 C7 120.6(2) ?
C9 C8 H8 120.5(19) ?
C7 C8 H8 118.9(19) ?
C8 C9 C10 118.4(2) ?
C8 C9 H9 123.2(16) ?
C10 C9 H9 118.4(16) ?
C9 C10 C11 122.4(2) ?
C9 C10 N1 119.1(2) ?
C11 C10 N1 118.5(2) ?
C12 C11 C10 118.4(2) ?
C12 C11 H11 121.1(18) ?
C10 C11 H11 120.5(18) ?
C11 C12 C7 120.7(2) ?
C11 C12 H12 124.0(16) ?
C7 C12 H12 115.3(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ge1 C4 . 1.941(3) y
Ge1 C5 . 1.945(3) y
Ge1 C3 . 1.946(3) y
Ge1 C1 . 1.966(3) y
O1 C6 . 1.341(3) ?
O1 C2 . 1.463(3) y
O2 C6 . 1.214(3) ?
O3 N1 . 1.224(3) ?
O4 N1 . 1.231(3) ?
N1 C10 . 1.470(3) ?
C1 C2 . 1.508(4) y
C1 H1A . .93(3) ?
C1 H1B . .99(3) ?
C2 H2A . .91(3) ?
C2 H2B . .87(3) ?
C3 H3A . .89(4) ?
C3 H3B . 1.02(5) ?
C3 H3C . .89(4) ?
C4 H4A . .87(4) ?
C4 H4B . .86(5) ?
C4 H4C . .91(5) ?
C5 H5A . .92(5) ?
C5 H5B . .90(4) ?
C5 H5C . .96(4) ?
C6 C7 . 1.487(4) ?
C7 C12 . 1.395(4) ?
C7 C8 . 1.399(3) ?
C8 C9 . 1.376(4) ?
C8 H8 . .86(3) ?
C9 C10 . 1.387(3) ?
C9 H9 . .88(3) ?
C10 C11 . 1.390(4) ?
C11 C12 . 1.374(4) ?
C11 H11 . .92(3) ?
C12 H12 . .91(3) ?
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_publ_flag
C4 Ge1 C1 C2 94.3(2) y
C5 Ge1 C1 C2 -27.0(2) y
C3 Ge1 C1 C2 -147.5(2) y
C6 O1 C2 C1 -176.8(2) y
Ge1 C1 C2 O1 -51.2(3) y
C2 O1 C6 O2 1.6(3) ?
C2 O1 C6 C7 -177.9(2) ?
O2 C6 C7 C12 11.9(3) ?
O1 C6 C7 C12 -168.6(2) ?
O2 C6 C7 C8 -167.4(2) ?
O1 C6 C7 C8 12.1(3) ?
C12 C7 C8 C9 -0.9(3) ?
C6 C7 C8 C9 178.4(2) ?
C7 C8 C9 C10 0.3(3) ?
C8 C9 C10 C11 0.4(3) ?
C8 C9 C10 N1 -178.5(2) ?
O3 N1 C10 C9 173.3(2) ?
O4 N1 C10 C9 -7.2(3) ?
O3 N1 C10 C11 -5.7(3) ?
O4 N1 C10 C11 173.8(2) ?
C9 C10 C11 C12 -0.5(3) ?
N1 C10 C11 C12 178.5(2) ?
C10 C11 C12 C7 -0.1(3) ?
C8 C7 C12 C11 0.8(3) ?
C6 C7 C12 C11 -178.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24729976
