#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/30/2013018.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_2013018
loop_
_publ_author_name
'Hans, Karm'
'Parvez, Masood'
'Mahboob, Sumera'
Imtiaz-ud-Din
'Mazhar, Muhammad'
'Ali, Saqib'
_publ_section_title
;
 Derivatives of substituted 3-trichlorogermylpropionic acid
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m559
_journal_page_last               m562
_journal_paper_doi               10.1107/S010827010201795X
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          '[Ge (C6 H5)3 (C9 H8 F O2)]'
_chemical_formula_moiety         'C27 H23 F Ge O2'
_chemical_formula_sum            'C27 H23 F Ge O2'
_chemical_formula_weight         471.04
_chemical_name_systematic
;
3-(2-fluorophenyl)-3-(triphenylgermyl)propionic acid
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 110.907(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7278(10)
_cell_length_b                   17.907(3)
_cell_length_c                   13.541(2)
_cell_measurement_reflns_used    9816
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     2203.5(6)
_computing_cell_refinement       'HKL DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SAPI91 (Fan, 1991)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'ω and φ'
_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  0.017
_diffrn_reflns_av_sigmaI/netI    0.031
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9816
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.2
_diffrn_standards_decay_%        <0.1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.420
_exptl_absorpt_correction_T_max  0.820
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.035
_refine_ls_R_factor_gt           0.028
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0332P)²+0.8526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.067
_refine_ls_wR_factor_ref         0.070
_reflns_number_gt                4338
_reflns_number_total             5026
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1392.cif
_cod_data_source_block           I
_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:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013018
_cod_database_fobs_code          2013018
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Ge1 0.839925(17) 0.183673(9) 0.828679(12) 0.02017(6) Uani d . 1 . . Ge
F1 0.61906(12) 0.00707(6) 0.69416(9) 0.0392(3) Uani d . 1 . . F
O1 0.88991(12) 0.02038(6) 0.56415(9) 0.0279(3) Uani d . 1 . . O
O2 1.07267(14) 0.09183(7) 0.55351(10) 0.0341(3) Uani d . 1 . . O
H2 1.0824 0.0565 0.5158 0.051 Uiso calc R 1 . . H
C1 0.96590(17) 0.07620(9) 0.58850(12) 0.0231(3) Uani d . 1 . . C
C2 0.95146(18) 0.13483(9) 0.66445(13) 0.0260(3) Uani d . 1 . . C
H2A 0.9301 0.1836 0.6277 0.031 Uiso calc R 1 . . H
H2B 1.0465 0.1393 0.7241 0.031 Uiso calc R 1 . . H
C3 0.83045(16) 0.11711(9) 0.70813(12) 0.0225(3) Uani d . 1 . . C
H3 0.8481 0.0650 0.7365 0.027 Uiso calc R 1 . . H
C4 0.67724(17) 0.11887(9) 0.62599(12) 0.0220(3) Uani d . 1 . . C
C5 0.6257(2) 0.17702(10) 0.55313(14) 0.0304(4) Uani d . 1 . . C
H5 0.6911 0.2160 0.5513 0.036 Uiso calc R 1 . . H
C6 0.4808(2) 0.17886(11) 0.48336(15) 0.0392(5) Uani d . 1 . . C
H6 0.4479 0.2194 0.4354 0.047 Uiso calc R 1 . . H
C7 0.3844(2) 0.12260(12) 0.48314(14) 0.0401(5) Uani d . 1 . . C
H7 0.2860 0.1238 0.4343 0.048 Uiso calc R 1 . . H
C8 0.43100(19) 0.06432(11) 0.55400(14) 0.0348(4) Uani d . 1 . . C
H8 0.3656 0.0253 0.5553 0.042 Uiso calc R 1 . . H
C9 0.57508(18) 0.06432(9) 0.62294(13) 0.0269(3) Uani d . 1 . . C
C11 0.66775(17) 0.15948(9) 0.86442(12) 0.0224(3) Uani d . 1 . . C
C12 0.52581(18) 0.16953(10) 0.78972(13) 0.0267(4) Uani d . 1 . . C
H12 0.5136 0.1934 0.7245 0.032 Uiso calc R 1 . . H
C13 0.40272(19) 0.14504(11) 0.80971(15) 0.0348(4) Uani d . 1 . . C
H13 0.3074 0.1507 0.7575 0.042 Uiso calc R 1 . . H
C14 0.4194(2) 0.11243(12) 0.90557(15) 0.0401(5) Uani d . 1 . . C
H14 0.3354 0.0959 0.9196 0.048 Uiso calc R 1 . . H
C15 0.5585(2) 0.10372(12) 0.98131(15) 0.0386(4) Uani d . 1 . . C
H15 0.5694 0.0818 1.0476 0.046 Uiso calc R 1 . . H
C16 0.68217(19) 0.12679(10) 0.96110(13) 0.0294(4) Uani d . 1 . . C
H16 0.7772 0.1203 1.0134 0.035 Uiso calc R 1 . . H
C18 1.02127(17) 0.16128(9) 0.94756(12) 0.0231(3) Uani d . 1 . . C
C19 1.06854(18) 0.08792(9) 0.97522(13) 0.0270(3) Uani d . 1 . . C
H19 1.0147 0.0478 0.9330 0.032 Uiso calc R 1 . . H
C20 1.19301(19) 0.07254(11) 1.06353(14) 0.0335(4) Uani d . 1 . . C
H20 1.2228 0.0223 1.0813 0.040 Uiso calc R 1 . . H
C21 1.2733(2) 0.13015(12) 1.12541(15) 0.0395(4) Uani d . 1 . . C
H21 1.3577 0.1198 1.1861 0.047 Uiso calc R 1 . . H
C22 1.2295(2) 0.20313(12) 1.09784(16) 0.0433(5) Uani d . 1 . . C
H22 1.2854 0.2430 1.1394 0.052 Uiso calc R 1 . . H
C23 1.1049(2) 0.21889(10) 1.01034(14) 0.0335(4) Uani d . 1 . . C
H23 1.0761 0.2693 0.9930 0.040 Uiso calc R 1 . . H
C25 0.83946(18) 0.28931(9) 0.79274(12) 0.0246(3) Uani d . 1 . . C
C26 0.7291(2) 0.33745(10) 0.79790(14) 0.0318(4) Uani d . 1 . . C
H26 0.6522 0.3183 0.8185 0.038 Uiso calc R 1 . . H
C27 0.7298(2) 0.41287(11) 0.77340(15) 0.0402(5) Uani d . 1 . . C
H27 0.6538 0.4448 0.7771 0.048 Uiso calc R 1 . . H
C28 0.8411(2) 0.44124(11) 0.74363(15) 0.0414(5) Uani d . 1 . . C
H28 0.8410 0.4926 0.7261 0.050 Uiso calc R 1 . . H
C29 0.9525(2) 0.39507(11) 0.73934(15) 0.0379(4) Uani d . 1 . . C
H29 1.0295 0.4148 0.7194 0.045 Uiso calc R 1 . . H
C30 0.9521(2) 0.31984(9) 0.76410(14) 0.0302(4) Uani d . 1 . . C
H30 1.0297 0.2886 0.7615 0.036 Uiso calc R 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 0.0033 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'
O O 0.0106 0.0060 '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'
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_publ_flag
C11 Ge1 C25 110.55(7) y
C11 Ge1 C18 110.60(6) y
C25 Ge1 C18 108.93(7) y
C11 Ge1 C3 106.08(6) y
C25 Ge1 C3 112.29(7) y
C18 Ge1 C3 108.35(6) y
C1 O2 H2 109.5 n
O1 C1 O2 123.93(14) n
O1 C1 C2 124.07(14) n
O2 C1 C2 111.98(13) n
C1 C2 C3 113.01(13) n
C1 C2 H2A 109.0 n
C3 C2 H2A 109.0 n
C1 C2 H2B 109.0 n
C3 C2 H2B 109.0 n
H2A C2 H2B 107.8 n
C4 C3 C2 113.91(13) n
C4 C3 Ge1 109.60(10) n
C2 C3 Ge1 112.05(10) n
C4 C3 H3 107.0 n
C2 C3 H3 107.0 n
Ge1 C3 H3 107.0 n
C9 C4 C5 115.59(15) n
C9 C4 C3 121.16(14) n
C5 C4 C3 123.13(15) n
C6 C5 C4 121.23(17) n
C6 C5 H5 119.4 n
C4 C5 H5 119.4 n
C7 C6 C5 120.62(17) n
C7 C6 H6 119.7 n
C5 C6 H6 119.7 n
C6 C7 C8 119.87(17) n
C6 C7 H7 120.1 n
C8 C7 H7 120.1 n
C9 C8 C7 118.21(17) n
C9 C8 H8 120.9 n
C7 C8 H8 120.9 n
F1 C9 C8 117.64(15) n
F1 C9 C4 117.88(14) n
C8 C9 C4 124.47(16) n
C16 C11 C12 118.32(15) n
C16 C11 Ge1 121.22(12) n
C12 C11 Ge1 120.29(12) n
C13 C12 C11 120.96(16) n
C13 C12 H12 119.5 n
C11 C12 H12 119.5 n
C14 C13 C12 119.77(17) n
C14 C13 H13 120.1 n
C12 C13 H13 120.1 n
C13 C14 C15 120.06(17) n
C13 C14 H14 120.0 n
C15 C14 H14 120.0 n
C14 C15 C16 120.46(17) n
C14 C15 H15 119.8 n
C16 C15 H15 119.8 n
C15 C16 C11 120.39(16) n
C15 C16 H16 119.8 n
C11 C16 H16 119.8 n
C19 C18 C23 117.79(15) n
C19 C18 Ge1 121.75(12) n
C23 C18 Ge1 120.42(13) n
C20 C19 C18 121.21(16) n
C20 C19 H19 119.4 n
C18 C19 H19 119.4 n
C21 C20 C19 120.22(17) n
C21 C20 H20 119.9 n
C19 C20 H20 119.9 n
C20 C21 C22 119.22(17) n
C20 C21 H21 120.4 n
C22 C21 H21 120.4 n
C21 C22 C23 120.89(18) n
C21 C22 H22 119.6 n
C23 C22 H22 119.6 n
C22 C23 C18 120.66(18) n
C22 C23 H23 119.7 n
C18 C23 H23 119.7 n
C30 C25 C26 117.71(16) n
C30 C25 Ge1 121.05(13) n
C26 C25 Ge1 121.22(13) n
C27 C26 C25 121.15(18) n
C27 C26 H26 119.4 n
C25 C26 H26 119.4 n
C28 C27 C26 119.89(18) n
C28 C27 H27 120.1 n
C26 C27 H27 120.1 n
C27 C28 C29 120.09(18) n
C27 C28 H28 120.0 n
C29 C28 H28 120.0 n
C28 C29 C30 120.03(18) n
C28 C29 H29 120.0 n
C30 C29 H29 120.0 n
C29 C30 C25 121.12(17) n
C29 C30 H30 119.4 n
C25 C30 H30 119.4 n
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 C11 . 1.951(2) y
Ge1 C25 . 1.953(2) y
Ge1 C18 . 1.959(2) y
Ge1 C3 . 1.997(2) y
F1 C9 . 1.367(2) y
O1 C1 . 1.217(2) y
O2 C1 . 1.316(2) y
O2 H2 . 0.8400 n
C1 C2 . 1.511(2) n
C2 C3 . 1.527(2) n
C2 H2A . 0.9900 n
C2 H2B . 0.9900 n
C3 C4 . 1.509(2) n
C3 H3 . 1.0000 n
C4 C9 . 1.383(2) n
C4 C5 . 1.399(2) n
C5 C6 . 1.390(3) n
C5 H5 . 0.9500 n
C6 C7 . 1.375(3) n
C6 H6 . 0.9500 n
C7 C8 . 1.380(3) n
C7 H7 . 0.9500 n
C8 C9 . 1.379(2) n
C8 H8 . 0.9500 n
C11 C16 . 1.395(2) n
C11 C12 . 1.402(2) n
C12 C13 . 1.389(2) n
C12 H12 . 0.9500 n
C13 C14 . 1.379(3) n
C13 H13 . 0.9500 n
C14 C15 . 1.384(3) n
C14 H14 . 0.9500 n
C15 C16 . 1.388(2) n
C15 H15 . 0.9500 n
C16 H16 . 0.9500 n
C18 C19 . 1.398(2) n
C18 C23 . 1.398(2) n
C19 C20 . 1.392(2) n
C19 H19 . 0.9500 n
C20 C21 . 1.382(3) n
C20 H20 . 0.9500 n
C21 C22 . 1.384(3) n
C21 H21 . 0.9500 n
C22 C23 . 1.388(3) n
C22 H22 . 0.9500 n
C23 H23 . 0.9500 n
C25 C30 . 1.397(2) n
C25 C26 . 1.398(2) n
C26 C27 . 1.391(3) n
C26 H26 . 0.9500 n
C27 C28 . 1.380(3) n
C27 H27 . 0.9500 n
C28 C29 . 1.381(3) n
C28 H28 . 0.9500 n
C29 C30 . 1.389(3) n
C29 H29 . 0.9500 n
C30 H30 . 0.9500 n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2 O1 3_756 0.84 1.83 2.6689(16) 178
C8 H8 O1 3_656 0.95 2.57 3.323(2) 137
C3 H3 F1 . 1.00 2.34 2.805(2) 108
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
O1 C1 C2 C3 -0.1(2) n
O2 C1 C2 C3 -178.73(14) n
C1 C2 C3 C4 -66.29(18) n
C1 C2 C3 Ge1 168.58(11) n
C11 Ge1 C3 C4 47.19(12) n
C25 Ge1 C3 C4 -73.68(12) n
C18 Ge1 C3 C4 165.96(10) n
C11 Ge1 C3 C2 174.66(11) n
C25 Ge1 C3 C2 53.79(13) n
C18 Ge1 C3 C2 -66.56(13) n
C2 C3 C4 C9 136.78(15) n
Ge1 C3 C4 C9 -96.80(15) n
C2 C3 C4 C5 -47.4(2) n
Ge1 C3 C4 C5 78.99(16) n
C9 C4 C5 C6 0.3(2) n
C3 C4 C5 C6 -175.71(16) n
C4 C5 C6 C7 -1.0(3) n
C5 C6 C7 C8 1.2(3) n
C6 C7 C8 C9 -0.5(3) n
C7 C8 C9 F1 178.72(16) n
C7 C8 C9 C4 -0.2(3) n
C5 C4 C9 F1 -178.60(14) n
C3 C4 C9 F1 -2.5(2) n
C5 C4 C9 C8 0.3(2) n
C3 C4 C9 C8 176.41(15) n
C25 Ge1 C11 C16 -124.11(14) n
C18 Ge1 C11 C16 -3.38(16) n
C3 Ge1 C11 C16 113.91(14) n
C25 Ge1 C11 C12 60.74(15) n
C18 Ge1 C11 C12 -178.53(13) n
C3 Ge1 C11 C12 -61.24(14) n
C16 C11 C12 C13 -2.4(2) n
Ge1 C11 C12 C13 172.91(14) n
C11 C12 C13 C14 2.0(3) n
C12 C13 C14 C15 -0.4(3) n
C13 C14 C15 C16 -0.8(3) n
C14 C15 C16 C11 0.4(3) n
C12 C11 C16 C15 1.2(3) n
Ge1 C11 C16 C15 -174.07(14) n
C11 Ge1 C18 C19 73.15(14) n
C25 Ge1 C18 C19 -165.16(13) n
C3 Ge1 C18 C19 -42.73(14) n
C11 Ge1 C18 C23 -104.30(14) n
C25 Ge1 C18 C23 17.39(15) n
C3 Ge1 C18 C23 139.82(13) n
C23 C18 C19 C20 1.3(2) n
Ge1 C18 C19 C20 -176.26(13) n
C18 C19 C20 C21 -0.5(3) n
C19 C20 C21 C22 -0.7(3) n
C20 C21 C22 C23 1.2(3) n
C21 C22 C23 C18 -0.4(3) n
C19 C18 C23 C22 -0.8(3) n
Ge1 C18 C23 C22 176.77(15) n
C11 Ge1 C25 C30 -179.87(13) n
C18 Ge1 C25 C30 58.41(15) n
C3 Ge1 C25 C30 -61.61(15) n
C11 Ge1 C25 C26 2.13(15) n
C18 Ge1 C25 C26 -119.59(14) n
C3 Ge1 C25 C26 120.39(13) n
C30 C25 C26 C27 1.2(3) n
Ge1 C25 C26 C27 179.28(14) n
C25 C26 C27 C28 -0.2(3) n
C26 C27 C28 C29 -0.7(3) n
C27 C28 C29 C30 0.6(3) n
C28 C29 C30 C25 0.5(3) n
C26 C25 C30 C29 -1.4(3) n
Ge1 C25 C30 C29 -179.48(13) n
