#------------------------------------------------------------------------------
#$Date: 2018-09-07 11:02:12 +0300 (Fri, 07 Sep 2018) $
#$Revision: 210513 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/37/7103758.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_7103758
loop_
_publ_author_name
'Ech-Cherif El Kettani, S.'
'Escudié, J.'
'Couret, C.'
'Ranaivonjatovo, H.'
'Lazraq, M.'
'Soufiaoui, M.'
'Gornitzka, H.'
'Cretiu Nemes, G.'
_publ_section_title
;
 The use of a germene for the synthesis of esters of α-germyl-substituted
 α-amino acid and α-aminophosphonic acid
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   14
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              1662
_journal_page_last               1663
_journal_paper_doi               10.1039/b303661h
_journal_year                    2003
_chemical_formula_sum            'C45 H51 Ge N O3'
_chemical_formula_weight         726.46
_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
_cell_angle_alpha                101.8250(10)
_cell_angle_beta                 95.7740(10)
_cell_angle_gamma                108.6110(10)
_cell_formula_units_Z            2
_cell_length_a                   11.9777(7)
_cell_length_b                   12.1155(7)
_cell_length_c                   14.5540(8)
_cell_measurement_reflns_used    9351
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29.339
_cell_measurement_theta_min      2.464
_cell_volume                     1927.47(19)
_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      193(2)
_diffrn_measured_fraction_theta_full 0.871
_diffrn_measured_fraction_theta_max 0.871
_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  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12972
_diffrn_reflns_theta_full        29.43
_diffrn_reflns_theta_max         29.43
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.760492
_exptl_absorpt_correction_type   SEMI-EMPIRICAL
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.7
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         9290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0450P)²+0.3714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0864
_reflns_number_gt                8168
_reflns_number_total             9290
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b303661h.txt
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7103758
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge1 Ge 0.832476(12) 0.737199(13) 0.255731(10) 0.02025(5) Uani 1 1 d . . .
C1 C 0.90153(12) 0.90834(13) 0.33822(10) 0.0228(3) Uani 1 1 d . . .
H1 H 0.9890 0.9421 0.3366 0.027 Uiso 1 1 calc R . .
C2 C 0.84081(13) 0.98909(13) 0.30746(11) 0.0265(3) Uani 1 1 d . . .
O1 O 0.76161(12) 1.01476(12) 0.34118(11) 0.0437(3) Uani 1 1 d . . .
O2 O 0.88766(11) 1.03178(11) 0.23691(8) 0.0342(3) Uani 1 1 d . . .
C3 C 0.8302(2) 1.09997(19) 0.19280(15) 0.0471(5) Uani 1 1 d . . .
H3A H 0.7476 1.0490 0.1634 0.071 Uiso 1 1 calc R . .
H3B H 0.8738 1.1282 0.1438 0.071 Uiso 1 1 calc R . .
H3C H 0.8299 1.1693 0.2412 0.071 Uiso 1 1 calc R . .
N1 N 0.88566(12) 0.89905(12) 0.43472(9) 0.0256(3) Uani 1 1 d . . .
H1N H 0.9300(18) 0.9427(19) 0.4686(15) 0.031 Uiso 1 1 d . . .
C4 C 0.87080(12) 0.77985(13) 0.45013(10) 0.0225(3) Uani 1 1 d . . .
H4 H 0.9477 0.7654 0.4438 0.027 Uiso 1 1 calc R . .
C5 C 0.84786(12) 0.77393(13) 0.54978(10) 0.0237(3) Uani 1 1 d . . .
C6 C 0.79047(14) 0.84351(14) 0.60071(11) 0.0285(3) Uani 1 1 d . . .
H6 H 0.7640 0.8971 0.5727 0.034 Uiso 1 1 calc R . .
C7 C 0.77185(16) 0.83493(16) 0.69217(12) 0.0340(3) Uani 1 1 d . . .
H7 H 0.7335 0.8834 0.7264 0.041 Uiso 1 1 calc R . .
C8 C 0.80853(16) 0.75655(17) 0.73373(12) 0.0361(4) Uani 1 1 d . . .
H8 H 0.7954 0.7510 0.7962 0.043 Uiso 1 1 calc R . .
C9 C 0.86472(16) 0.68606(17) 0.68359(12) 0.0361(4) Uani 1 1 d . . .
H9 H 0.8896 0.6314 0.7114 0.043 Uiso 1 1 calc R . .
C10 C 0.88456(14) 0.69545(16) 0.59292(11) 0.0306(3) Uani 1 1 d . . .
H10 H 0.9239 0.6475 0.5594 0.037 Uiso 1 1 calc R . .
C11 C 0.77068(12) 0.68131(13) 0.37008(10) 0.0210(3) Uani 1 1 d . . .
C12 C 0.64464(12) 0.67409(13) 0.38178(10) 0.0215(3) Uani 1 1 d . . .
C13 C 0.59264(13) 0.76209(14) 0.39144(11) 0.0264(3) Uani 1 1 d . . .
H13 H 0.6381 0.8426 0.3923 0.032 Uiso 1 1 calc R . .
C14 C 0.47177(14) 0.72981(16) 0.39988(12) 0.0312(3) Uani 1 1 d . . .
H14 H 0.4356 0.7896 0.4076 0.037 Uiso 1 1 calc R . .
C15 C 0.40360(14) 0.61218(16) 0.39721(12) 0.0325(3) Uani 1 1 d . . .
H15 H 0.3212 0.5922 0.4015 0.039 Uiso 1 1 calc R . .
C16 C 0.45487(13) 0.52380(15) 0.38837(12) 0.0295(3) Uani 1 1 d . . .
H16 H 0.4087 0.4434 0.3871 0.035 Uiso 1 1 calc R . .
C17 C 0.57549(13) 0.55544(13) 0.38135(10) 0.0233(3) Uani 1 1 d . . .
C18 C 0.65135(13) 0.48207(13) 0.37322(10) 0.0238(3) Uani 1 1 d . . .
C19 C 0.62529(15) 0.36146(15) 0.37224(12) 0.0324(3) Uani 1 1 d . . .
H19 H 0.5461 0.3119 0.3732 0.039 Uiso 1 1 calc R . .
C20 C 0.71723(17) 0.31469(16) 0.36982(14) 0.0374(4) Uani 1 1 d . . .
H20 H 0.7009 0.2323 0.3686 0.045 Uiso 1 1 calc R . .
C21 C 0.83296(16) 0.38801(16) 0.36920(13) 0.0352(4) Uani 1 1 d . . .
H21 H 0.8951 0.3551 0.3687 0.042 Uiso 1 1 calc R . .
C22 C 0.85963(14) 0.50815(15) 0.36934(11) 0.0280(3) Uani 1 1 d . . .
H22 H 0.9393 0.5573 0.3693 0.034 Uiso 1 1 calc R . .
C23 C 0.76771(13) 0.55575(13) 0.36960(10) 0.0227(3) Uani 1 1 d . . .
C24 C 0.73752(12) 0.73661(13) 0.13602(10) 0.0227(3) Uani 1 1 d . . .
C25 C 0.80292(13) 0.79931(14) 0.07522(11) 0.0252(3) Uani 1 1 d . . .
C26 C 0.74147(15) 0.81160(15) -0.00665(11) 0.0294(3) Uani 1 1 d . . .
H26 H 0.7858 0.8567 -0.0455 0.035 Uiso 1 1 calc R . .
C27 C 0.61790(15) 0.76031(16) -0.03323(12) 0.0323(3) Uani 1 1 d . . .
C28 C 0.55577(14) 0.69345(15) 0.02399(11) 0.0295(3) Uani 1 1 d . . .
H28 H 0.4714 0.6553 0.0058 0.035 Uiso 1 1 calc R . .
C29 C 0.61256(13) 0.67994(13) 0.10756(10) 0.0240(3) Uani 1 1 d . . .
C30 C 0.93807(14) 0.84886(16) 0.09069(12) 0.0317(3) Uani 1 1 d . . .
H30A H 0.9679 0.7841 0.0660 0.048 Uiso 1 1 calc R . .
H30B H 0.9701 0.8822 0.1591 0.048 Uiso 1 1 calc R . .
H30C H 0.9639 0.9124 0.0570 0.048 Uiso 1 1 calc R . .
C31 C 0.55352(19) 0.7717(2) -0.12394(15) 0.0498(5) Uani 1 1 d . . .
H31A H 0.6004 0.8458 -0.1396 0.075 Uiso 1 1 calc R . .
H31B H 0.4745 0.7744 -0.1146 0.075 Uiso 1 1 calc R . .
H31C H 0.5441 0.7023 -0.1763 0.075 Uiso 1 1 calc R . .
C32 C 0.53475(13) 0.60006(16) 0.16037(11) 0.0302(3) Uani 1 1 d . . .
H32A H 0.4992 0.6470 0.2034 0.045 Uiso 1 1 calc R . .
H32B H 0.5835 0.5675 0.1975 0.045 Uiso 1 1 calc R . .
H32C H 0.4710 0.5337 0.1145 0.045 Uiso 1 1 calc R . .
C33 C 0.94920(13) 0.65830(13) 0.21986(11) 0.0239(3) Uani 1 1 d . . .
C34 C 1.07454(13) 0.70820(15) 0.25223(11) 0.0275(3) Uani 1 1 d . . .
C35 C 1.14723(14) 0.64438(16) 0.21887(12) 0.0310(3) Uani 1 1 d . . .
H35 H 1.2312 0.6789 0.2414 0.037 Uiso 1 1 calc R . .
C36 C 1.10181(15) 0.53319(16) 0.15445(12) 0.0324(3) Uani 1 1 d . . .
C37 C 0.97830(15) 0.48280(15) 0.12491(12) 0.0314(3) Uani 1 1 d . . .
H37 H 0.9450 0.4057 0.0814 0.038 Uiso 1 1 calc R . .
C38 C 0.90168(13) 0.54239(14) 0.15741(11) 0.0262(3) Uani 1 1 d . . .
C39 C 1.13796(14) 0.82907(17) 0.32214(14) 0.0391(4) Uani 1 1 d . . .
H39A H 1.2187 0.8344 0.3482 0.059 Uiso 1 1 calc R . .
H39B H 1.0930 0.8381 0.3742 0.059 Uiso 1 1 calc R . .
H39C H 1.1433 0.8932 0.2894 0.059 Uiso 1 1 calc R . .
C40 C 1.18330(19) 0.4684(2) 0.11776(15) 0.0474(5) Uani 1 1 d . . .
H40A H 1.2252 0.5072 0.0720 0.071 Uiso 1 1 calc R . .
H40B H 1.1357 0.3842 0.0862 0.071 Uiso 1 1 calc R . .
H40C H 1.2420 0.4717 0.1713 0.071 Uiso 1 1 calc R . .
C41 C 0.76890(14) 0.47480(15) 0.12489(12) 0.0324(3) Uani 1 1 d . . .
H41A H 0.7558 0.3948 0.0846 0.049 Uiso 1 1 calc R . .
H41B H 0.7343 0.5192 0.0883 0.049 Uiso 1 1 calc R . .
H41C H 0.7304 0.4666 0.1807 0.049 Uiso 1 1 calc R . .
C42 C 0.48053(18) 1.03152(19) 0.36615(16) 0.0474(5) Uani 1 1 d . . .
H42A H 0.4619 1.1049 0.3677 0.071 Uiso 1 1 calc R . .
H42B H 0.5580 1.0517 0.4072 0.071 Uiso 1 1 calc R . .
H42C H 0.4180 0.9749 0.3892 0.071 Uiso 1 1 calc R . .
C43 C 0.48616(18) 0.9757(2) 0.26711(16) 0.0505(5) Uani 1 1 d . . .
H43A H 0.5506 1.0319 0.2442 0.061 Uiso 1 1 calc R . .
H43B H 0.5048 0.9014 0.2652 0.061 Uiso 1 1 calc R . .
O3 O 0.37427(12) 0.94756(13) 0.20673(10) 0.0429(3) Uani 1 1 d . . .
C44 C 0.3709(2) 0.8847(2) 0.11331(17) 0.0578(6) Uani 1 1 d . . .
H44A H 0.3847 0.8086 0.1143 0.069 Uiso 1 1 calc R . .
H44B H 0.4347 0.9338 0.0851 0.069 Uiso 1 1 calc R . .
C45 C 0.2509(2) 0.8582(2) 0.05458(19) 0.0649(7) Uani 1 1 d . . .
H45A H 0.1884 0.8071 0.0815 0.097 Uiso 1 1 calc R . .
H45B H 0.2488 0.8164 -0.0111 0.097 Uiso 1 1 calc R . .
H45C H 0.2371 0.9337 0.0550 0.097 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'
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
C24 Ge1 C33 107.39(6) . . ?
C24 Ge1 C1 108.42(6) . . ?
C33 Ge1 C1 116.49(6) . . ?
C24 Ge1 C11 127.84(6) . . ?
C33 Ge1 C11 107.23(6) . . ?
C1 Ge1 C11 89.16(6) . . ?
N1 C1 C2 110.46(12) . . ?
N1 C1 Ge1 105.46(9) . . ?
C2 C1 Ge1 112.95(10) . . ?
O1 C2 O2 123.36(15) . . ?
O1 C2 C1 126.03(15) . . ?
O2 C2 C1 110.61(13) . . ?
C2 O2 C3 117.07(14) . . ?
C1 N1 C4 113.97(12) . . ?
N1 C4 C5 111.46(12) . . ?
N1 C4 C11 109.66(12) . . ?
C5 C4 C11 112.97(11) . . ?
C10 C5 C6 118.13(14) . . ?
C10 C5 C4 119.16(14) . . ?
C6 C5 C4 122.71(13) . . ?
C7 C6 C5 120.45(15) . . ?
C8 C7 C6 120.65(16) . . ?
C7 C8 C9 119.51(16) . . ?
C10 C9 C8 119.93(16) . . ?
C9 C10 C5 121.32(16) . . ?
C23 C11 C12 102.54(11) . . ?
C23 C11 C4 112.41(12) . . ?
C12 C11 C4 114.21(11) . . ?
C23 C11 Ge1 112.95(9) . . ?
C12 C11 Ge1 117.63(9) . . ?
C4 C11 Ge1 97.63(9) . . ?
C13 C12 C17 119.64(13) . . ?
C13 C12 C11 130.55(13) . . ?
C17 C12 C11 109.81(12) . . ?
C12 C13 C14 118.61(14) . . ?
C15 C14 C13 121.37(15) . . ?
C16 C15 C14 120.48(15) . . ?
C15 C16 C17 118.54(15) . . ?
C16 C17 C12 121.33(14) . . ?
C16 C17 C18 129.86(14) . . ?
C12 C17 C18 108.81(12) . . ?
C19 C18 C23 121.16(14) . . ?
C19 C18 C17 130.36(14) . . ?
C23 C18 C17 108.44(13) . . ?
C18 C19 C20 118.77(15) . . ?
C21 C20 C19 120.25(16) . . ?
C22 C21 C20 121.40(16) . . ?
C21 C22 C23 119.01(15) . . ?
C22 C23 C18 119.35(14) . . ?
C22 C23 C11 130.37(13) . . ?
C18 C23 C11 110.24(12) . . ?
C29 C24 C25 118.52(13) . . ?
C29 C24 Ge1 125.51(11) . . ?
C25 C24 Ge1 115.97(10) . . ?
C26 C25 C24 119.45(14) . . ?
C26 C25 C30 116.94(14) . . ?
C24 C25 C30 123.53(14) . . ?
C27 C26 C25 122.32(15) . . ?
C28 C27 C26 117.55(14) . . ?
C28 C27 C31 121.00(16) . . ?
C26 C27 C31 121.38(16) . . ?
C27 C28 C29 122.47(14) . . ?
C28 C29 C24 119.49(14) . . ?
C28 C29 C32 116.79(13) . . ?
C24 C29 C32 123.69(13) . . ?
C38 C33 C34 118.02(14) . . ?
C38 C33 Ge1 116.42(10) . . ?
C34 C33 Ge1 125.55(12) . . ?
C35 C34 C33 119.71(15) . . ?
C35 C34 C39 116.13(14) . . ?
C33 C34 C39 124.16(14) . . ?
C36 C35 C34 122.53(15) . . ?
C35 C36 C37 117.62(14) . . ?
C35 C36 C40 121.11(16) . . ?
C37 C36 C40 121.27(17) . . ?
C36 C37 C38 121.93(16) . . ?
C37 C38 C33 120.08(14) . . ?
C37 C38 C41 116.78(14) . . ?
C33 C38 C41 123.12(13) . . ?
O3 C43 C42 109.79(17) . . ?
C44 O3 C43 112.28(16) . . ?
O3 C44 C45 109.09(19) . . ?
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
Ge1 C24 1.9800(14) . ?
Ge1 C33 1.9841(15) . ?
Ge1 C1 2.0274(14) . ?
Ge1 C11 2.0410(14) . ?
C1 N1 1.4581(19) . ?
C1 C2 1.501(2) . ?
C2 O1 1.207(2) . ?
C2 O2 1.3361(19) . ?
O2 C3 1.435(2) . ?
N1 C4 1.464(2) . ?
C4 C5 1.515(2) . ?
C4 C11 1.5670(19) . ?
C5 C10 1.396(2) . ?
C5 C6 1.396(2) . ?
C6 C7 1.391(2) . ?
C7 C8 1.382(3) . ?
C8 C9 1.387(3) . ?
C9 C10 1.385(2) . ?
C11 C23 1.509(2) . ?
C11 C12 1.5130(19) . ?
C12 C13 1.387(2) . ?
C12 C17 1.410(2) . ?
C13 C14 1.399(2) . ?
C14 C15 1.388(2) . ?
C15 C16 1.385(2) . ?
C16 C17 1.392(2) . ?
C17 C18 1.457(2) . ?
C18 C19 1.390(2) . ?
C18 C23 1.408(2) . ?
C19 C20 1.390(2) . ?
C20 C21 1.389(3) . ?
C21 C22 1.387(2) . ?
C22 C23 1.396(2) . ?
C24 C29 1.4093(19) . ?
C24 C25 1.417(2) . ?
C25 C26 1.396(2) . ?
C25 C30 1.511(2) . ?
C26 C27 1.388(2) . ?
C27 C28 1.386(2) . ?
C27 C31 1.515(2) . ?
C28 C29 1.398(2) . ?
C29 C32 1.506(2) . ?
C33 C38 1.409(2) . ?
C33 C34 1.415(2) . ?
C34 C35 1.397(2) . ?
C34 C39 1.510(2) . ?
C35 C36 1.379(3) . ?
C36 C37 1.391(2) . ?
C36 C40 1.509(2) . ?
C37 C38 1.399(2) . ?
C38 C41 1.511(2) . ?
C42 C43 1.479(3) . ?
C43 O3 1.426(2) . ?
O3 C44 1.405(3) . ?
C44 C45 1.498(3) . ?
