 
data_shelxl
 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H21 Ge N O3' 
_chemical_formula_weight          323.91

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 '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'  -1.0885   0.8855
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0311   0.0180
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            61
_space_group_name_H-M_alt         'P b c a'
_space_group_name_Hall            '-P 2ac 2ab'
 
_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.
;
 
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'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    13.7717(2)
_cell_length_b                    11.15180(10)
_cell_length_c                    18.9206(2)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      2905.81(6)
_cell_formula_units_Z             8
_cell_measurement_temperature     150(1)
_cell_measurement_reflns_used     5000
_cell_measurement_theta_min       5.5990
_cell_measurement_theta_max       71.0820
 
_exptl_crystal_description        block 
_exptl_crystal_colour             ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.481          
_exptl_crystal_F_000              1344
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.240
_exptl_crystal_size_mid           0.220
_exptl_crystal_size_min           0.220
_exptl_absorpt_coefficient_mu     2.904
_shelx_estimated_absorpt_T_min    0.542
_shelx_estimated_absorpt_T_max    0.568
_exptl_absorpt_correction_T_min   0.56078
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
; 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(1)
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_type            CuK\a
_diffrn_source                    'micro-focus sealed X-ray tube'                       
_diffrn_measurement_device_type   'SuperNova, Dual, Cu at zero, AtlasS2' 
_diffrn_measurement_method        'ω scans' 
_diffrn_detector_area_resol_mean  5.2169
_diffrn_reflns_number             7116
_diffrn_reflns_av_unetI/netI      0.0206
_diffrn_reflns_av_R_equivalents   0.0215
_diffrn_reflns_limit_h_min        -16
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          4.674
_diffrn_reflns_theta_max          71.149
_diffrn_reflns_theta_full         67.684
_diffrn_measured_fraction_theta_max   0.976
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.976
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.976
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              2744
_reflns_number_gt                 2572
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement        'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction         'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution     'SHELXS-2013 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material   SHELXL-97
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0498P)²+1.3063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.00100(7)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2744
_refine_ls_number_parameters      181
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0306
_refine_ls_R_factor_gt            0.0288
_refine_ls_wR_factor_ref          0.0820
_refine_ls_wR_factor_gt           0.0803
_refine_ls_goodness_of_fit_ref    1.054
_refine_ls_restrained_S_all       1.054
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Ge1 Ge 0.40069(2) 0.55062(2) 0.34345(2) 0.01740(12) Uani 1 1 d . . . . .
O3 O 0.50132(9) 0.48651(11) 0.38962(7) 0.0213(3) Uani 1 1 d . . . . .
O2 O 0.28326(10) 0.55282(10) 0.38518(8) 0.0221(3) Uani 1 1 d . . . . .
O1 O 0.40149(10) 0.55263(11) 0.24601(8) 0.0252(3) Uani 1 1 d . . . . .
N2 N 0.36411(10) 0.35916(13) 0.32496(8) 0.0150(3) Uani 1 1 d . . . . .
C6 C 0.36852(13) 0.34380(16) 0.24888(9) 0.0179(4) Uani 1 1 d . . . . .
C11 C 0.43717(12) 0.28906(15) 0.36508(9) 0.0173(4) Uani 1 1 d . . . . .
H11A H 0.4538 0.2171 0.3390 0.021 Uiso 1 1 calc R U . . .
H11B H 0.4101 0.2650 0.4102 0.021 Uiso 1 1 calc R U . . .
C7 C 0.26277(13) 0.34629(16) 0.35142(9) 0.0176(4) Uani 1 1 d . . . . .
H7A H 0.2543 0.2672 0.3719 0.021 Uiso 1 1 calc R U . . .
H7B H 0.2177 0.3542 0.3123 0.021 Uiso 1 1 calc R U . . .
C12 C 0.52909(13) 0.36456(16) 0.37732(10) 0.0198(4) Uani 1 1 d . . . . .
C5 C 0.35321(13) 0.23507(17) 0.21512(10) 0.0236(4) Uani 1 1 d . . . . .
H5 H 0.3423 0.1658 0.2413 0.028 Uiso 1 1 calc R U . . .
C1 C 0.38492(14) 0.44870(16) 0.21120(11) 0.0218(4) Uani 1 1 d . . . . .
C8 C 0.24031(13) 0.44212(15) 0.40735(10) 0.0187(4) Uani 1 1 d . . . . .
C4 C 0.35437(15) 0.2309(2) 0.14172(11) 0.0301(5) Uani 1 1 d . . . . .
H4 H 0.3451 0.1585 0.1182 0.036 Uiso 1 1 calc R U . . .
C10 C 0.27754(14) 0.41004(18) 0.48098(10) 0.0244(4) Uani 1 1 d . . . . .
H10A H 0.3472 0.4077 0.4805 0.037 Uiso 1 1 calc R U . . .
H10B H 0.2528 0.3329 0.4945 0.037 Uiso 1 1 calc R U . . .
H10C H 0.2560 0.4694 0.5143 0.037 Uiso 1 1 calc R U . . .
C2 C 0.38461(16) 0.44417(19) 0.13735(12) 0.0279(5) Uani 1 1 d . . . . .
H2 H 0.3945 0.5136 0.1111 0.033 Uiso 1 1 calc R U . . .
C14 C 0.59748(13) 0.3597(2) 0.31393(12) 0.0268(5) Uani 1 1 d . . . . .
H14A H 0.5642 0.3881 0.2726 0.040 Uiso 1 1 calc R U . . .
H14B H 0.6183 0.2785 0.3064 0.040 Uiso 1 1 calc R U . . .
H14C H 0.6530 0.4095 0.3229 0.040 Uiso 1 1 calc R U . . .
C13 C 0.57969(15) 0.31923(19) 0.44378(11) 0.0292(5) Uani 1 1 d . . . . .
H13A H 0.6397 0.3617 0.4501 0.044 Uiso 1 1 calc R U . . .
H13B H 0.5927 0.2350 0.4391 0.044 Uiso 1 1 calc R U . . .
H13C H 0.5386 0.3324 0.4840 0.044 Uiso 1 1 calc R U . . .
C3 C 0.36957(15) 0.3358(2) 0.10378(11) 0.0308(5) Uani 1 1 d . . . . .
H3 H 0.3696 0.3330 0.0547 0.037 Uiso 1 1 calc R U . . .
C9 C 0.13038(14) 0.46028(18) 0.40966(12) 0.0267(5) Uani 1 1 d . . . . .
H9A H 0.1147 0.5194 0.4447 0.040 Uiso 1 1 calc R U . . .
H9B H 0.0993 0.3858 0.4214 0.040 Uiso 1 1 calc R U . . .
H9C H 0.1080 0.4870 0.3643 0.040 Uiso 1 1 calc R U . . .
H1 H 0.4227(17) 0.672(2) 0.3514(11) 0.021(6) Uiso 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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 O3 1.7873(13) . ?
Ge1 O2 1.7998(14) . ?
Ge1 O1 1.8439(16) . ?
Ge1 N2 2.2216(15) . ?
Ge1 H1 1.40(2) . ?
O3 C12 1.432(2) . ?
O2 C8 1.432(2) . ?
O1 C1 1.352(2) . ?
N2 C6 1.451(2) . ?
N2 C11 1.483(2) . ?
N2 C7 1.490(2) . ?
C6 C5 1.387(3) . ?
C6 C1 1.388(3) . ?
C11 C12 1.538(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C7 C8 1.535(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C12 C13 1.524(3) . ?
C12 C14 1.526(3) . ?
C5 C4 1.390(3) . ?
C5 H5 0.9300 . ?
C1 C2 1.398(3) . ?
C8 C10 1.527(3) . ?
C8 C9 1.528(3) . ?
C4 C3 1.389(3) . ?
C4 H4 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C3 H3 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
 
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
O3 Ge1 O2 119.19(6) . . ?
O3 Ge1 O1 119.27(6) . . ?
O2 Ge1 O1 116.35(6) . . ?
O3 Ge1 N2 82.44(5) . . ?
O2 Ge1 N2 83.02(5) . . ?
O1 Ge1 N2 81.69(6) . . ?
O3 Ge1 H1 99.7(9) . . ?
O2 Ge1 H1 97.7(9) . . ?
O1 Ge1 H1 95.4(9) . . ?
N2 Ge1 H1 177.0(9) . . ?
C12 O3 Ge1 120.51(11) . . ?
C8 O2 Ge1 119.21(11) . . ?
C1 O1 Ge1 118.39(12) . . ?
C6 N2 C11 114.66(14) . . ?
C6 N2 C7 111.18(13) . . ?
C11 N2 C7 114.38(14) . . ?
C6 N2 Ge1 105.08(11) . . ?
C11 N2 Ge1 105.79(10) . . ?
C7 N2 Ge1 104.60(10) . . ?
C5 C6 C1 121.67(17) . . ?
C5 C6 N2 123.64(17) . . ?
C1 C6 N2 114.63(16) . . ?
N2 C11 C12 110.31(14) . . ?
N2 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
N2 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
N2 C7 C8 110.69(14) . . ?
N2 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
O3 C12 C13 107.65(15) . . ?
O3 C12 C14 109.04(15) . . ?
C13 C12 C14 110.77(16) . . ?
O3 C12 C11 108.94(14) . . ?
C13 C12 C11 108.61(15) . . ?
C14 C12 C11 111.74(15) . . ?
C6 C5 C4 119.22(19) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
O1 C1 C6 119.97(18) . . ?
O1 C1 C2 121.20(18) . . ?
C6 C1 C2 118.82(18) . . ?
O2 C8 C10 109.30(15) . . ?
O2 C8 C9 107.66(15) . . ?
C10 C8 C9 109.73(17) . . ?
O2 C8 C7 108.36(15) . . ?
C10 C8 C7 113.46(15) . . ?
C9 C8 C7 108.15(16) . . ?
C3 C4 C5 119.34(19) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C2 C1 119.46(19) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C3 C4 121.48(19) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
 
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_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O2 Ge1 O3 C12 95.85(13) . . . . ?
O1 Ge1 O3 C12 -57.78(14) . . . . ?
N2 Ge1 O3 C12 18.25(13) . . . . ?
O3 Ge1 O2 C8 -57.82(15) . . . . ?
O1 Ge1 O2 C8 96.56(14) . . . . ?
N2 Ge1 O2 C8 19.45(13) . . . . ?
O3 Ge1 O1 C1 74.39(14) . . . . ?
O2 Ge1 O1 C1 -79.97(14) . . . . ?
N2 Ge1 O1 C1 -2.05(13) . . . . ?
C11 N2 C6 C5 62.2(2) . . . . ?
C7 N2 C6 C5 -69.5(2) . . . . ?
Ge1 N2 C6 C5 177.89(15) . . . . ?
C11 N2 C6 C1 -120.77(17) . . . . ?
C7 N2 C6 C1 107.55(18) . . . . ?
Ge1 N2 C6 C1 -5.06(18) . . . . ?
C6 N2 C11 C12 92.34(18) . . . . ?
C7 N2 C11 C12 -137.53(15) . . . . ?
Ge1 N2 C11 C12 -22.96(16) . . . . ?
C6 N2 C7 C8 -137.85(15) . . . . ?
C11 N2 C7 C8 90.33(18) . . . . ?
Ge1 N2 C7 C8 -24.94(15) . . . . ?
Ge1 O3 C12 C13 -153.79(13) . . . . ?
Ge1 O3 C12 C14 85.99(16) . . . . ?
Ge1 O3 C12 C11 -36.20(19) . . . . ?
N2 C11 C12 O3 36.7(2) . . . . ?
N2 C11 C12 C13 153.68(15) . . . . ?
N2 C11 C12 C14 -83.84(18) . . . . ?
C1 C6 C5 C4 0.0(3) . . . . ?
N2 C6 C5 C4 176.89(17) . . . . ?
Ge1 O1 C1 C6 -0.4(2) . . . . ?
Ge1 O1 C1 C2 -179.96(15) . . . . ?
C5 C6 C1 O1 -178.67(17) . . . . ?
N2 C6 C1 O1 4.2(3) . . . . ?
C5 C6 C1 C2 0.9(3) . . . . ?
N2 C6 C1 C2 -176.25(17) . . . . ?
Ge1 O2 C8 C10 85.40(16) . . . . ?
Ge1 O2 C8 C9 -155.46(13) . . . . ?
Ge1 O2 C8 C7 -38.70(19) . . . . ?
N2 C7 C8 O2 40.03(19) . . . . ?
N2 C7 C8 C10 -81.55(18) . . . . ?
N2 C7 C8 C9 156.47(15) . . . . ?
C6 C5 C4 C3 -0.8(3) . . . . ?
O1 C1 C2 C3 178.55(19) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C5 C4 C3 C2 0.7(3) . . . . ?
 
_refine_diff_density_max    0.601
_refine_diff_density_min   -0.478
_refine_diff_density_rms    0.083

_shelxl_version_number 2013-4



