#------------------------------------------------------------------------------
#$Date: 2017-04-12 01:41:07 +0300 (Wed, 12 Apr 2017) $
#$Revision: 195331 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/56/4345666.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_4345666
loop_
_publ_author_name
'Glowacki, Britta'
'Lutter, Michael'
'Alnasr, Hazem'
'Seymen, Rana'
'Hiller, Wolf'
'Jurkschat, Klaus'
_publ_section_title
;
 Introducing Stereogenic Centers to Group XIV Metallatranes.
;
_journal_name_full               'Inorganic chemistry'
_journal_paper_doi               10.1021/acs.inorgchem.6b03126
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H20 Br Ge N O3'
_chemical_formula_weight         354.77
_chemical_melting_point          518
_chemical_name_systematic
;
1-Bromido-(2,8,9-trioxa-5-aza-3,3,6,6-tetramethyl-1-germatricyclo[3.3.3.01,5]undecane)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0471(3)
_cell_length_b                   11.6291(4)
_cell_length_c                   12.3359(5)
_cell_measurement_reflns_used    7906
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.1970
_cell_measurement_theta_min      2.3790
_cell_volume                     1297.86(8)
_computing_cell_refinement
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55''
_computing_data_collection
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55''
_computing_data_reduction
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55''
_computing_molecular_graphics    'ORTEP-III (1.0.3) (Farrugia, 2012)'
_computing_publication_material  'enCIFer Version 1.5.2'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0560
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω und ψ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1171
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23365
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         2.407
_exptl_absorpt_coefficient_mu    5.432
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.164
_refine_diff_density_max         2.338
_refine_diff_density_min         -1.125
_refine_diff_density_rms         0.248
_refine_ls_abs_structure_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.26(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0931P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1408
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2679
_reflns_number_total             2969
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b03126_si_002.cif
_cod_data_source_block           comp6
_cod_database_code               4345666
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.440
_shelx_estimated_absorpt_t_max   0.469
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Ge1 Ge 0.21995(8) 0.48183(7) 0.51857(6) 0.0204(2) Uani 1 1 d . .
Br1 Br -0.02931(8) 0.50330(7) 0.57523(6) 0.0292(3) Uani 1 1 d . .
O11 O 0.2857(6) 0.4406(5) 0.6479(4) 0.0229(11) Uani 1 1 d . .
C12 C 0.4132(9) 0.3663(7) 0.6491(6) 0.0247(16) Uani 1 1 d . .
C13 C 0.5128(9) 0.3848(7) 0.5464(6) 0.0248(17) Uani 1 1 d . .
H13A H 0.6092 0.4174 0.5689 0.030 Uiso 1 1 calc R U
H13B H 0.5317 0.3097 0.5112 0.030 Uiso 1 1 calc R U
N14 N 0.4407(7) 0.4640(5) 0.4672(5) 0.0214(13) Uani 1 1 d . .
C15 C 0.4990(9) 0.5863(6) 0.4625(6) 0.0243(17) Uani 1 1 d . .
C16 C 0.3678(9) 0.6571(6) 0.4220(7) 0.0303(18) Uani 1 1 d . .
H16A H 0.3894 0.7399 0.4318 0.036 Uiso 1 1 calc R U
H16B H 0.3534 0.6428 0.3436 0.036 Uiso 1 1 calc R U
O17 O 0.2356(6) 0.6286(5) 0.4788(5) 0.0280(12) Uani 1 1 d . .
C18 C 0.3541(9) 0.2413(7) 0.6523(6) 0.0278(17) Uani 1 1 d . .
H18A H 0.4375 0.1875 0.6532 0.042 Uiso 1 1 calc R U
H18B H 0.2943 0.2304 0.7177 0.042 Uiso 1 1 calc R U
H18C H 0.2933 0.2269 0.5880 0.042 Uiso 1 1 calc R U
C19 C 0.4995(9) 0.3909(7) 0.7517(7) 0.0289(17) Uani 1 1 d . .
H19A H 0.5870 0.3413 0.7544 0.043 Uiso 1 1 calc R U
H19B H 0.5304 0.4717 0.7522 0.043 Uiso 1 1 calc R U
H19C H 0.4369 0.3757 0.8149 0.043 Uiso 1 1 calc R U
C20 C 0.5388(9) 0.6285(7) 0.5756(6) 0.0285(17) Uani 1 1 d . .
H20A H 0.4537 0.6185 0.6239 0.043 Uiso 1 1 calc R U
H20B H 0.5656 0.7100 0.5724 0.043 Uiso 1 1 calc R U
H20C H 0.6226 0.5840 0.6034 0.043 Uiso 1 1 calc R U
C21 C 0.6325(9) 0.5983(8) 0.3879(7) 0.0318(19) Uani 1 1 d . .
H21A H 0.6028 0.5817 0.3131 0.048 Uiso 1 1 calc R U
H21B H 0.7094 0.5440 0.4103 0.048 Uiso 1 1 calc R U
H21C H 0.6710 0.6769 0.3924 0.048 Uiso 1 1 calc R U
O31 O 0.1767(6) 0.3734(5) 0.4204(4) 0.0268(12) Uani 1 1 d . .
C32 C 0.2976(10) 0.3250(7) 0.3630(6) 0.0293(18) Uani 1 1 d . .
H32A H 0.2661 0.3045 0.2886 0.035 Uiso 1 1 calc R U
H32B H 0.3310 0.2540 0.3998 0.035 Uiso 1 1 calc R U
C33 C 0.4246(9) 0.4112(7) 0.3580(6) 0.0248(17) Uani 1 1 d . .
H33A H 0.5173 0.3718 0.3371 0.030 Uiso 1 1 calc R U
H33B H 0.4032 0.4714 0.3034 0.030 Uiso 1 1 calc R U
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'
Br Br -0.2901 2.4595 '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
O11 Ge1 O17 118.8(3)
O11 Ge1 O31 119.5(3)
O17 Ge1 O31 120.4(3)
O11 Ge1 N14 85.8(2)
O17 Ge1 N14 86.3(3)
O31 Ge1 N14 86.2(2)
O11 Ge1 Br1 94.72(18)
O17 Ge1 Br1 93.19(18)
O31 Ge1 Br1 93.76(18)
N14 Ge1 Br1 179.44(18)
C12 O11 Ge1 116.2(4)
O11 C12 C19 108.0(6)
O11 C12 C18 106.6(6)
C19 C12 C18 109.5(7)
O11 C12 C13 111.6(6)
C19 C12 C13 110.7(6)
C18 C12 C13 110.3(6)
N14 C13 C12 111.2(6)
N14 C13 H13A 109.4
C12 C13 H13A 109.4
N14 C13 H13B 109.4
C12 C13 H13B 109.4
H13A C13 H13B 108.0
C33 N14 C13 112.4(6)
C33 N14 C15 112.7(6)
C13 N14 C15 116.8(6)
C33 N14 Ge1 102.8(5)
C13 N14 Ge1 106.1(4)
C15 N14 Ge1 104.4(5)
N14 C15 C20 110.4(6)
N14 C15 C21 112.6(6)
C20 C15 C21 109.7(7)
N14 C15 C16 104.3(6)
C20 C15 C16 108.0(7)
C21 C15 C16 111.6(7)
O17 C16 C15 111.4(6)
O17 C16 H16A 109.3
C15 C16 H16A 109.3
O17 C16 H16B 109.3
C15 C16 H16B 109.3
H16A C16 H16B 108.0
C16 O17 Ge1 115.1(5)
C12 C18 H18A 109.5
C12 C18 H18B 109.5
H18A C18 H18B 109.5
C12 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C12 C19 H19A 109.5
C12 C19 H19B 109.5
H19A C19 H19B 109.5
C12 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C15 C20 H20A 109.5
C15 C20 H20B 109.5
H20A C20 H20B 109.5
C15 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C15 C21 H21A 109.5
C15 C21 H21B 109.5
H21A C21 H21B 109.5
C15 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C32 O31 Ge1 116.6(5)
O31 C32 C33 109.9(6)
O31 C32 H32A 109.7
C33 C32 H32A 109.7
O31 C32 H32B 109.7
C33 C32 H32B 109.7
H32A C32 H32B 108.2
N14 C33 C32 107.9(6)
N14 C33 H33A 110.1
C32 C33 H33A 110.1
N14 C33 H33B 110.1
C32 C33 H33B 110.1
H33A C33 H33B 108.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ge1 O11 1.769(5)
Ge1 O17 1.782(5)
Ge1 O31 1.792(5)
Ge1 N14 2.105(7)
Ge1 Br1 2.3741(10)
O11 C12 1.442(9)
C12 C19 1.514(11)
C12 C18 1.550(11)
C12 C13 1.569(10)
C13 N14 1.494(9)
C13 H13A 0.9900
C13 H13B 0.9900
N14 C33 1.487(9)
N14 C15 1.518(9)
C15 C20 1.522(10)
C15 C21 1.524(11)
C15 C16 1.529(11)
C16 O17 1.426(10)
C16 H16A 0.9900
C16 H16B 0.9900
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
O31 C32 1.419(10)
C32 C33 1.527(11)
C32 H32A 0.9900
C32 H32B 0.9900
C33 H33A 0.9900
C33 H33B 0.9900
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
O17 Ge1 O11 C12 -112.5(5)
O31 Ge1 O11 C12 54.2(6)
N14 Ge1 O11 C12 -29.1(5)
Br1 Ge1 O11 C12 151.2(5)
Ge1 O11 C12 C19 150.1(5)
Ge1 O11 C12 C18 -92.3(6)
Ge1 O11 C12 C13 28.3(8)
O11 C12 C13 N14 -7.0(9)
C19 C12 C13 N14 -127.3(7)
C18 C12 C13 N14 111.4(7)
C12 C13 N14 C33 -123.9(7)
C12 C13 N14 C15 103.6(7)
C12 C13 N14 Ge1 -12.3(7)
C33 N14 C15 C20 -170.0(7)
C13 N14 C15 C20 -37.7(9)
Ge1 N14 C15 C20 79.2(7)
C33 N14 C15 C21 -47.1(9)
C13 N14 C15 C21 85.3(8)
Ge1 N14 C15 C21 -157.9(6)
C33 N14 C15 C16 74.1(7)
C13 N14 C15 C16 -153.5(6)
Ge1 N14 C15 C16 -36.7(6)
N14 C15 C16 O17 46.7(8)
C20 C15 C16 O17 -70.8(8)
C21 C15 C16 O17 168.5(6)
C15 C16 O17 Ge1 -33.9(8)
O11 Ge1 O17 C16 91.5(6)
O31 Ge1 O17 C16 -75.1(6)
N14 Ge1 O17 C16 8.3(5)
Br1 Ge1 O17 C16 -171.4(5)
O11 Ge1 O31 C32 -79.9(6)
O17 Ge1 O31 C32 86.6(6)
N14 Ge1 O31 C32 3.1(5)
Br1 Ge1 O31 C32 -177.5(5)
Ge1 O31 C32 C33 -26.6(8)
C13 N14 C33 C32 75.5(8)
C15 N14 C33 C32 -150.0(7)
Ge1 N14 C33 C32 -38.2(7)
O31 C32 C33 N14 43.8(9)
