#------------------------------------------------------------------------------
#$Date: 2017-07-11 14:26:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198632 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/02/79/7027941.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7027941
loop_
_publ_author_name
'Ghereg, Dumitru'
'Gornitzka, Heinz'
'Ranaivonjatovo, Henri'
'Escudié, Jean'
_publ_section_title
;
 Reactions of germenes with various naphthoquinones controlled by
 substituent effects
;
_journal_issue                   8
_journal_name_full               'Dalton Transactions'
_journal_page_first              2016
_journal_page_last               2022
_journal_paper_doi               10.1039/b921729k
_journal_volume                  39
_journal_year                    2010
_chemical_formula_sum            'C39 H46 Ge'
_chemical_formula_weight         587.35
_chemical_name_systematic
;
?
;
_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'
_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                 113.839(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.315(2)
_cell_length_b                   20.473(3)
_cell_length_c                   11.6852(16)
_cell_measurement_reflns_used    2544
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.517
_cell_measurement_theta_min      2.755
_cell_volume                     3351.2(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker CCD 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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8738
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         5.19
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.379405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0436
_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)+(0.0497P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                2204
_reflns_number_total             3053
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B921729Ksup1.cif
_cod_data_source_block           5
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7027941
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_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
Ge1 Ge 1.0000 0.43573(2) 0.2500 0.03327(17) Uani 1 2 d S . .
C1 C 1.0000 0.52393(19) 0.2500 0.0357(10) Uani 1 2 d S . .
C2 C 0.9179(2) 0.56745(13) 0.1920(2) 0.0347(6) Uani 1 1 d . . .
C3 C 0.8209(2) 0.55427(14) 0.1251(3) 0.0411(8) Uani 1 1 d . . .
H3 H 0.8002 0.5102 0.1092 0.049 Uiso 1 1 calc R . .
C4 C 0.7540(2) 0.60430(15) 0.0812(3) 0.0435(8) Uani 1 1 d . A .
C5 C 0.7871(3) 0.66870(15) 0.1090(3) 0.0507(9) Uani 1 1 d . . .
H5 H 0.7424 0.7036 0.0819 0.061 Uiso 1 1 calc R . .
C6 C 0.8818(3) 0.68282(15) 0.1739(3) 0.0496(9) Uani 1 1 d . . .
H6 H 0.9019 0.7270 0.1909 0.060 Uiso 1 1 calc R . .
C7 C 0.9484(2) 0.63304(13) 0.2147(3) 0.0380(7) Uani 1 1 d . . .
C8 C 0.6481(3) 0.58841(16) 0.0095(3) 0.0539(9) Uani 1 1 d DU . .
C9 C 0.5960(16) 0.5866(16) 0.0993(18) 0.103(7) Uani 0.44(3) 1 d PDU A 1
H9A H 0.6067 0.5441 0.1415 0.155 Uiso 0.44(3) 1 calc PR A 1
H9B H 0.5274 0.5932 0.0512 0.155 Uiso 0.44(3) 1 calc PR A 1
H9C H 0.6210 0.6213 0.1619 0.155 Uiso 0.44(3) 1 calc PR A 1
C10 C 0.6213(18) 0.5240(10) -0.062(3) 0.155(11) Uani 0.44(3) 1 d PDU A 1
H10A H 0.6595 0.5182 -0.1110 0.232 Uiso 0.44(3) 1 calc PR A 1
H10B H 0.5534 0.5246 -0.1177 0.232 Uiso 0.44(3) 1 calc PR A 1
H10C H 0.6338 0.4879 -0.0022 0.232 Uiso 0.44(3) 1 calc PR A 1
C11 C 0.5997(16) 0.6440(9) -0.0812(18) 0.096(6) Uani 0.44(3) 1 d PDU A 1
H11A H 0.6078 0.6849 -0.0344 0.144 Uiso 0.44(3) 1 calc PR A 1
H11B H 0.5315 0.6345 -0.1255 0.144 Uiso 0.44(3) 1 calc PR A 1
H11C H 0.6287 0.6483 -0.1417 0.144 Uiso 0.44(3) 1 calc PR A 1
C9' C 0.6154(17) 0.5593(14) 0.1042(16) 0.137(8) Uani 0.56(3) 1 d PDU A 2
H9'1 H 0.6522 0.5196 0.1398 0.205 Uiso 0.56(3) 1 calc PR A 2
H9'2 H 0.5474 0.5484 0.0631 0.205 Uiso 0.56(3) 1 calc PR A 2
H9'3 H 0.6253 0.5910 0.1711 0.205 Uiso 0.56(3) 1 calc PR A 2
C10' C 0.6424(11) 0.5387(9) -0.0903(14) 0.106(6) Uani 0.56(3) 1 d PDU A 2
H10D H 0.6825 0.5532 -0.1329 0.159 Uiso 0.56(3) 1 calc PR A 2
H10E H 0.5761 0.5348 -0.1513 0.159 Uiso 0.56(3) 1 calc PR A 2
H10F H 0.6649 0.4962 -0.0509 0.159 Uiso 0.56(3) 1 calc PR A 2
C11' C 0.5839(15) 0.6448(6) -0.0567(19) 0.109(6) Uani 0.56(3) 1 d PDU A 2
H11D H 0.5827 0.6767 0.0053 0.164 Uiso 0.56(3) 1 calc PR A 2
H11E H 0.5192 0.6286 -0.1049 0.164 Uiso 0.56(3) 1 calc PR A 2
H11F H 0.6083 0.6658 -0.1132 0.164 Uiso 0.56(3) 1 calc PR A 2
C12 C 1.1174(2) 0.38813(12) 0.3366(3) 0.0336(7) Uani 1 1 d . . .
C13 C 1.1551(2) 0.35032(14) 0.2659(3) 0.0403(7) Uani 1 1 d . . .
C14 C 1.2419(2) 0.31853(15) 0.3275(4) 0.0509(9) Uani 1 1 d . . .
H14 H 1.2673 0.2936 0.2796 0.061 Uiso 1 1 calc R . .
C15 C 1.2927(2) 0.32180(15) 0.4556(4) 0.0509(9) Uani 1 1 d . . .
C16 C 1.2534(2) 0.35856(16) 0.5227(3) 0.0486(8) Uani 1 1 d . . .
H16 H 1.2871 0.3614 0.6109 0.058 Uiso 1 1 calc R . .
C17 C 1.1675(2) 0.39115(13) 0.4670(3) 0.0385(7) Uani 1 1 d . . .
C18 C 1.1040(2) 0.34550(17) 0.1258(3) 0.0554(9) Uani 1 1 d . . .
H18A H 1.1387 0.3156 0.0937 0.083 Uiso 1 1 calc R . .
H18B H 1.1008 0.3888 0.0886 0.083 Uiso 1 1 calc R . .
H18C H 1.0392 0.3290 0.1039 0.083 Uiso 1 1 calc R . .
C19 C 1.3862(2) 0.28673(19) 0.5207(4) 0.0760(13) Uani 1 1 d . . .
H19A H 1.4036 0.2648 0.4584 0.114 Uiso 1 1 calc R . .
H19B H 1.3799 0.2543 0.5785 0.114 Uiso 1 1 calc R . .
H19C H 1.4359 0.3183 0.5675 0.114 Uiso 1 1 calc R . .
C20 C 1.1305(2) 0.43024(16) 0.5483(3) 0.0519(8) Uani 1 1 d . . .
H20A H 1.0831 0.4044 0.5649 0.078 Uiso 1 1 calc R . .
H20B H 1.1010 0.4706 0.5050 0.078 Uiso 1 1 calc R . .
H20C H 1.1837 0.4410 0.6276 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 0.0033 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'
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
C1 Ge1 C12 120.29(8) . .
C1 Ge1 C12 120.29(8) . 2_755
C12 Ge1 C12 119.43(15) . 2_755
C2 C1 C2 105.1(3) 2_755 .
C2 C1 Ge1 127.46(17) 2_755 .
C2 C1 Ge1 127.46(17) . .
C3 C2 C7 119.1(3) . .
C3 C2 C1 131.4(3) . .
C7 C2 C1 109.5(3) . .
C4 C3 C2 121.5(3) . .
C3 C4 C5 117.6(3) . .
C3 C4 C8 120.3(3) . .
C5 C4 C8 122.1(3) . .
C6 C5 C4 122.0(3) . .
C5 C6 C7 120.3(3) . .
C6 C7 C2 119.6(3) . .
C6 C7 C7 132.45(19) . 2_755
C2 C7 C7 107.92(17) . 2_755
C9' C8 C11' 109.7(10) . .
C9' C8 C10' 111.4(10) . .
C11' C8 C10' 107.1(8) . .
C9' C8 C10 87.9(16) . .
C11' C8 C10 113.9(14) . .
C10' C8 C10 23.8(16) . .
C9' C8 C11 126.2(14) . .
C11' C8 C11 16.8(15) . .
C10' C8 C11 96.0(11) . .
C10 C8 C11 108.5(12) . .
C9' C8 C4 106.0(9) . .
C11' C8 C4 116.4(9) . .
C10' C8 C4 106.4(7) . .
C10 C8 C4 118.4(10) . .
C11 C8 C4 109.4(9) . .
C9' C8 C9 23.5(15) . .
C11' C8 C9 87.6(12) . .
C10' C8 C9 127.9(15) . .
C10 C8 C9 104.5(13) . .
C11 C8 C9 104.4(10) . .
C4 C8 C9 110.8(10) . .
C17 C12 C13 119.0(3) . .
C17 C12 Ge1 122.1(2) . .
C13 C12 Ge1 118.9(2) . .
C14 C13 C12 119.0(3) . .
C14 C13 C18 120.0(3) . .
C12 C13 C18 121.0(3) . .
C15 C14 C13 122.7(3) . .
C14 C15 C16 117.1(3) . .
C14 C15 C19 121.9(4) . .
C16 C15 C19 121.0(4) . .
C17 C16 C15 123.0(3) . .
C16 C17 C12 119.3(3) . .
C16 C17 C20 119.1(3) . .
C12 C17 C20 121.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ge1 C1 1.806(4) .
Ge1 C12 1.932(3) .
Ge1 C12 1.932(3) 2_755
C1 C2 1.465(4) 2_755
C1 C2 1.465(4) .
C2 C3 1.397(4) .
C2 C7 1.412(4) .
C3 C4 1.392(4) .
C4 C5 1.403(4) .
C4 C8 1.529(5) .
C5 C6 1.369(5) .
C6 C7 1.383(4) .
C7 C7 1.457(6) 2_755
C8 C9' 1.509(11) .
C8 C11' 1.511(11) .
C8 C10' 1.523(9) .
C8 C10 1.524(13) .
C8 C11 1.528(11) .
C8 C9 1.555(12) .
C12 C17 1.404(4) .
C12 C13 1.415(4) .
C13 C14 1.391(4) .
C13 C18 1.506(4) .
C14 C15 1.381(5) .
C15 C16 1.387(5) .
C15 C19 1.504(5) .
C16 C17 1.381(4) .
C17 C20 1.516(4) .
