#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:52:49 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179159 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/20/4312054.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_4312054
loop_
_publ_author_name
'Igor L. Fedushkin'
'Natalie M. Khvoinova'
'Andrey Yu. Baurin'
'Georgii K. Fukin'
'Vladimir K. Cherkasov'
'Mikhail P. Bubnov'
_publ_section_title
;
 Divalent Germanium Compound with a Radical-Anionic Ligand: Molecular
 Structures of (dpp-BIAN).-GeCl and Its Hydrochloration Products
 [(dpp-BIAN)(H)2].+[GeCl3]- and [{(dpp-BIAN)(H)2.+}2(Cl-)]+[GeCl3]-
 (dpp-BIAN = 1,2-Bis{(2,6-diisopropylphenyl)imino}acenaphthene)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7807
_journal_page_last               7815
_journal_paper_doi               10.1021/ic048801g
_journal_volume                  43
_journal_year                    2004
_chemical_formula_sum            'C36 H40 Cl Ge N2'
_chemical_formula_weight         608.74
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.369(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4153(12)
_cell_length_b                   19.789(2)
_cell_length_c                   15.8871(19)
_cell_measurement_reflns_used    950
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29
_cell_measurement_theta_min      2
_cell_volume                     3157.4(6)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area 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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16457
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    1.081
_exptl_absorpt_correction_T_max  0.9185
_exptl_absorpt_correction_T_min  0.8546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Sheldrick, 1998a)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1276
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.928
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         5564
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0416
_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)+(0.0638P)²+1.9937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                4570
_reflns_number_total             5564
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic048801gsi20040830_045626_1.cif
_cod_data_source_block           compound_1
_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 
;
_cod_database_code               4312054
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
Ge1 Ge 0.37225(2) 0.161144(14) 0.125340(18) 0.02814(8) Uani 1 1 d . . .
Cl1 Cl 0.42857(8) 0.26510(4) 0.18380(5) 0.0486(2) Uani 1 1 d . . .
N1 N 0.17469(18) 0.17599(9) 0.09032(13) 0.0219(4) Uani 1 1 d . . .
C1 C 0.1150(2) 0.14824(10) 0.14586(16) 0.0205(5) Uani 1 1 d . . .
C2 C 0.1986(2) 0.11594(11) 0.22032(15) 0.0210(5) Uani 1 1 d . . .
N2 N 0.32886(18) 0.11716(9) 0.22808(13) 0.0222(4) Uani 1 1 d . . .
C3 C 0.1149(2) 0.08446(11) 0.27043(16) 0.0212(5) Uani 1 1 d . . .
C4 C -0.0181(2) 0.10077(10) 0.22377(16) 0.0215(5) Uani 1 1 d . . .
C5 C -0.0240(2) 0.13871(11) 0.14719(16) 0.0219(5) Uani 1 1 d . . .
C6 C -0.1472(2) 0.15571(12) 0.09411(18) 0.0259(6) Uani 1 1 d . . .
H6 H -0.154(2) 0.1801(12) 0.0406(17) 0.022(6) Uiso 1 1 d . . .
C7 C -0.2621(2) 0.13602(13) 0.11990(19) 0.0312(6) Uani 1 1 d . . .
H7 H -0.342(3) 0.1486(13) 0.0865(18) 0.030(7) Uiso 1 1 d . . .
C8 C -0.2554(2) 0.09958(12) 0.19446(18) 0.0299(6) Uani 1 1 d . . .
H8 H -0.332(3) 0.0871(13) 0.2104(18) 0.031(7) Uiso 1 1 d . . .
C9 C -0.1298(2) 0.07974(11) 0.24928(16) 0.0247(5) Uani 1 1 d . . .
C10 C -0.1059(3) 0.03988(12) 0.32620(17) 0.0281(6) Uani 1 1 d . . .
H10 H -0.182(2) 0.0236(11) 0.3452(15) 0.015(6) Uiso 1 1 d . . .
C11 C 0.0224(3) 0.02363(12) 0.37038(17) 0.0281(6) Uani 1 1 d . . .
H11 H 0.037(3) -0.0015(14) 0.4209(19) 0.036(8) Uiso 1 1 d . . .
C12 C 0.1348(2) 0.04560(12) 0.34386(16) 0.0254(5) Uani 1 1 d . . .
H12 H 0.218(2) 0.0326(12) 0.3763(16) 0.021(6) Uiso 1 1 d . . .
C13 C 0.1003(2) 0.20432(11) 0.00890(15) 0.0219(5) Uani 1 1 d . . .
C14 C 0.0877(3) 0.16642(13) -0.06729(18) 0.0322(6) Uani 1 1 d . B .
C15 C 0.0166(3) 0.19494(14) -0.14559(17) 0.0355(7) Uani 1 1 d . . .
H15 H 0.005(3) 0.1715(13) -0.196(2) 0.033(7) Uiso 1 1 d . . .
C16 C -0.0420(3) 0.25746(13) -0.14855(17) 0.0337(6) Uani 1 1 d . . .
H16 H -0.090(3) 0.2748(13) -0.1967(18) 0.026(7) Uiso 1 1 d . . .
C17 C -0.0281(3) 0.29378(12) -0.07284(17) 0.0306(6) Uani 1 1 d . . .
H17 H -0.071(3) 0.3372(15) -0.076(2) 0.042(8) Uiso 1 1 d . . .
C18 C 0.0431(2) 0.26847(11) 0.00751(15) 0.0220(5) Uani 1 1 d . . .
C19 C 0.14411(12) 0.09569(10) -0.06530(12) 0.0576(10) Uani 1 1 d D . .
H19A H 0.2072 0.0845 -0.0077 0.069 Uiso 1 1 calc R A 1
C20 C 0.0337(3) 0.04294(13) -0.0937(3) 0.0706(11) Uani 1 1 d D B .
H20B H 0.081(4) -0.001(2) -0.085(2) 0.075(12) Uiso 1 1 d . . .
H20A H 0.006(6) 0.053(3) -0.160(4) 0.14(2) Uiso 1 1 d . . .
H20C H -0.034(3) 0.0452(17) -0.068(2) 0.057(10) Uiso 1 1 d . . .
C21 C 0.2113(3) 0.0935(4) -0.1401(2) 0.072(2) Uani 0.50 1 d PDU B 1
H21A H 0.2845 0.1263 -0.1288 0.108 Uiso 0.50 1 calc PR B 1
H21B H 0.1460 0.1049 -0.1951 0.108 Uiso 0.50 1 calc PR B 1
H21C H 0.2464 0.0481 -0.1443 0.108 Uiso 0.50 1 calc PR B 1
C21' C 0.2623(3) 0.0852(3) -0.1040(3) 0.0414(15) Uani 0.50 1 d PD B 2
H21D H 0.3410 0.0726 -0.0574 0.062 Uiso 0.50 1 calc PR B 2
H21E H 0.2801 0.1272 -0.1316 0.062 Uiso 0.50 1 calc PR B 2
H21F H 0.2414 0.0491 -0.1477 0.062 Uiso 0.50 1 calc PR B 2
C22 C 0.0607(3) 0.31200(12) 0.08879(16) 0.0261(6) Uani 1 1 d . . .
H22 H 0.098(2) 0.2868(12) 0.1335(16) 0.019(6) Uiso 1 1 d . . .
C23 C -0.0718(3) 0.33729(14) 0.10129(18) 0.0316(6) Uani 1 1 d . . .
H23C H -0.122(3) 0.3614(16) 0.051(2) 0.049(9) Uiso 1 1 d . . .
H23B H -0.127(3) 0.3059(15) 0.1089(18) 0.031(8) Uiso 1 1 d . . .
H23A H -0.063(3) 0.3647(14) 0.1517(19) 0.036(8) Uiso 1 1 d . . .
C24 C 0.1533(3) 0.37127(13) 0.08557(19) 0.0319(6) Uani 1 1 d . . .
H24C H 0.236(3) 0.3572(14) 0.0795(18) 0.031(7) Uiso 1 1 d . . .
H24B H 0.117(3) 0.3995(15) 0.037(2) 0.043(8) Uiso 1 1 d . . .
H24A H 0.168(3) 0.3959(13) 0.1370(18) 0.028(7) Uiso 1 1 d . . .
C25 C 0.4207(2) 0.07846(12) 0.29471(17) 0.0260(6) Uani 1 1 d . . .
C26 C 0.4920(2) 0.11117(13) 0.36973(16) 0.0272(6) Uani 1 1 d . . .
C27 C 0.5818(3) 0.07278(16) 0.43204(19) 0.0385(7) Uani 1 1 d . . .
H27 H 0.633(3) 0.0963(14) 0.488(2) 0.041(8) Uiso 1 1 d . . .
C28 C 0.5994(3) 0.00469(16) 0.4189(2) 0.0430(8) Uani 1 1 d . . .
H28 H 0.660(3) -0.0187(16) 0.465(2) 0.051(9) Uiso 1 1 d . . .
C29 C 0.5267(3) -0.02679(14) 0.3453(2) 0.0416(7) Uani 1 1 d . . .
H29 H 0.543(3) -0.0729(14) 0.3369(18) 0.034(7) Uiso 1 1 d . . .
C30 C 0.4349(2) 0.00868(13) 0.28107(19) 0.0328(6) Uani 1 1 d . . .
C31 C 0.4685(3) 0.18518(14) 0.38595(17) 0.0317(6) Uani 1 1 d . . .
H31 H 0.417(2) 0.2048(12) 0.3354(16) 0.019(6) Uiso 1 1 d . . .
C32 C 0.5962(4) 0.22575(19) 0.4171(3) 0.0609(11) Uani 1 1 d . . .
H32C H 0.636(4) 0.2115(18) 0.474(2) 0.065(11) Uiso 1 1 d . . .
H32B H 0.571(3) 0.2754(17) 0.421(2) 0.048(9) Uiso 1 1 d . . .
H32A H 0.655(4) 0.2148(18) 0.373(2) 0.067(11) Uiso 1 1 d . . .
C33 C 0.3804(4) 0.19157(19) 0.4489(3) 0.0576(9) Uani 1 1 d . . .
H33C H 0.356(3) 0.2366(19) 0.448(2) 0.060(10) Uiso 1 1 d . . .
H33B H 0.299(4) 0.1678(18) 0.427(3) 0.069(12) Uiso 1 1 d . . .
H33A H 0.430(4) 0.1733(19) 0.507(3) 0.079(13) Uiso 1 1 d . . .
C34 C 0.3542(3) -0.02780(13) 0.2006(2) 0.0426(8) Uani 1 1 d . . .
H34 H 0.278(3) 0.0005(13) 0.1745(17) 0.026(7) Uiso 1 1 d . . .
C35 C 0.2972(4) -0.09465(17) 0.2234(4) 0.0709(13) Uani 1 1 d . . .
H35C H 0.243(3) -0.1134(18) 0.172(2) 0.058(10) Uiso 1 1 d . . .
H35B H 0.370(4) -0.127(2) 0.243(3) 0.088(13) Uiso 1 1 d . . .
H35A H 0.242(4) -0.087(2) 0.262(3) 0.081(14) Uiso 1 1 d . . .
C36 C 0.4358(4) -0.0399(2) 0.1360(3) 0.0737(12) Uani 1 1 d . . .
H36C H 0.381(4) -0.0630(19) 0.077(2) 0.068(11) Uiso 1 1 d . . .
H36B H 0.455(4) 0.001(2) 0.107(3) 0.080(13) Uiso 1 1 d . . .
H36A H 0.508(4) -0.072(2) 0.162(3) 0.080(13) Uiso 1 1 d . . .
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'
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
N2 Ge1 N1 81.57(8) . . ?
N2 Ge1 Cl1 98.63(6) . . ?
N1 Ge1 Cl1 96.64(6) . . ?
C1 N1 C13 121.72(19) . . ?
C1 N1 Ge1 112.48(15) . . ?
C13 N1 Ge1 125.22(16) . . ?
N1 C1 C2 116.6(2) . . ?
N1 C1 C5 134.6(2) . . ?
C2 C1 C5 108.7(2) . . ?
N2 C2 C1 117.0(2) . . ?
N2 C2 C3 134.1(2) . . ?
C1 C2 C3 108.76(19) . . ?
C2 N2 C25 121.3(2) . . ?
C2 N2 Ge1 112.15(15) . . ?
C25 N2 Ge1 125.37(15) . . ?
C12 C3 C4 118.5(2) . . ?
C12 C3 C2 136.5(2) . . ?
C4 C3 C2 104.9(2) . . ?
C9 C4 C5 124.0(2) . . ?
C9 C4 C3 123.6(2) . . ?
C5 C4 C3 112.4(2) . . ?
C6 C5 C4 118.4(2) . . ?
C6 C5 C1 136.3(2) . . ?
C4 C5 C1 105.24(19) . . ?
C5 C6 C7 118.5(2) . . ?
C8 C7 C6 122.7(2) . . ?
C7 C8 C9 120.1(2) . . ?
C4 C9 C10 116.6(2) . . ?
C4 C9 C8 116.3(2) . . ?
C10 C9 C8 127.1(2) . . ?
C11 C10 C9 119.6(2) . . ?
C10 C11 C12 123.1(2) . . ?
C3 C12 C11 118.5(2) . . ?
C18 C13 C14 122.0(2) . . ?
C18 C13 N1 119.6(2) . . ?
C14 C13 N1 118.3(2) . . ?
C15 C14 C13 117.5(2) . . ?
C15 C14 C19 120.4(2) . . ?
C13 C14 C19 122.0(2) . . ?
C16 C15 C14 121.6(2) . . ?
C15 C16 C17 119.8(2) . . ?
C16 C17 C18 121.5(2) . . ?
C17 C18 C13 117.6(2) . . ?
C17 C18 C22 119.4(2) . . ?
C13 C18 C22 123.0(2) . . ?
C14 C19 C21' 117.8(3) . . ?
C14 C19 C20 111.56(17) . . ?
C21' C19 C20 114.2(3) . . ?
C14 C19 C21 105.3(3) . . ?
C21' C19 C21 26.1(2) . . ?
C20 C19 C21 102.4(3) . . ?
C18 C22 C24 109.9(2) . . ?
C18 C22 C23 112.7(2) . . ?
C24 C22 C23 110.7(2) . . ?
C26 C25 C30 122.3(2) . . ?
C26 C25 N2 118.8(2) . . ?
C30 C25 N2 118.8(2) . . ?
C25 C26 C27 117.5(2) . . ?
C25 C26 C31 121.5(2) . . ?
C27 C26 C31 120.9(2) . . ?
C28 C27 C26 121.0(3) . . ?
C29 C28 C27 120.6(3) . . ?
C28 C29 C30 121.1(3) . . ?
C29 C30 C25 117.4(3) . . ?
C29 C30 C34 119.9(2) . . ?
C25 C30 C34 122.6(2) . . ?
C26 C31 C32 113.5(2) . . ?
C26 C31 C33 110.0(2) . . ?
C32 C31 C33 111.6(3) . . ?
C36 C34 C30 111.3(3) . . ?
C36 C34 C35 110.2(3) . . ?
C30 C34 C35 112.0(3) . . ?
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 N2 2.004(2) . ?
Ge1 N1 2.0058(19) . ?
Ge1 Cl1 2.2693(8) . ?
N1 C1 1.326(3) . ?
N1 C13 1.434(3) . ?
C1 C2 1.421(3) . ?
C1 C5 1.465(3) . ?
C2 N2 1.329(3) . ?
C2 C3 1.466(3) . ?
N2 C25 1.444(3) . ?
C3 C12 1.366(3) . ?
C3 C4 1.425(3) . ?
C4 C9 1.393(3) . ?
C4 C5 1.417(3) . ?
C5 C6 1.377(3) . ?
C6 C7 1.419(4) . ?
C7 C8 1.373(4) . ?
C8 C9 1.422(3) . ?
C9 C10 1.420(4) . ?
C10 C11 1.373(4) . ?
C11 C12 1.413(4) . ?
C13 C18 1.400(3) . ?
C13 C14 1.400(3) . ?
C14 C15 1.388(4) . ?
C14 C19 1.515(3) . ?
C15 C16 1.375(4) . ?
C16 C17 1.375(4) . ?
C17 C18 1.389(3) . ?
C18 C22 1.522(3) . ?
C19 C21' 1.5285(10) . ?
C19 C20 1.5296(10) . ?
C19 C21 1.5311(11) . ?
C22 C24 1.528(4) . ?
C22 C23 1.529(4) . ?
C25 C26 1.386(3) . ?
C25 C30 1.412(4) . ?
C26 C27 1.393(4) . ?
C26 C31 1.518(4) . ?
C27 C28 1.383(4) . ?
C28 C29 1.364(4) . ?
C29 C30 1.390(4) . ?
C30 C34 1.514(4) . ?
C31 C32 1.519(4) . ?
C31 C33 1.531(5) . ?
C34 C36 1.514(5) . ?
C34 C35 1.532(5) . ?
