# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_g594_new
_database_code_depnum_ccdc_archive 'CCDC 1518902'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;
_audit_creation_date             2016-10-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H22 Ge N2 O2'
_chemical_formula_sum            'C18 H22 Ge N2 O2'
_chemical_formula_weight         370.96
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Ge Ge 0.1547 1.8001 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+, y+, -z+'
'x+1/2, y+1/2, z+'
'-x+1/2, y+1/2, -z+'

_cell_length_a                   12.1559(11)
_cell_length_b                   7.3998(6)
_cell_length_c                   9.3532(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.252(6)
_cell_angle_gamma                90
_cell_volume                     818.93(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5151
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.882
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.4028
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'STOE X-AREA'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1085
_diffrn_reflns_av_unetI/netI     0.0781
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4713
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.711
_diffrn_reflns_theta_min         3.247
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                1700
_reflns_number_total             1717
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.427
_refine_diff_density_min         -1.118
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 
;
 Flack x determined using 733 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1717
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.064
_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)+(0.0489P)²+0.5015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0962
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.5000 0.27319(2) 0.5000 0.0252(2) Uani 1 2 d S T P . .
O1 O 0.5344(3) 0.4174(5) 0.3677(4) 0.0306(8) Uani 1 1 d . . . . .
C1 C 0.6884(4) 0.2339(6) 0.7197(5) 0.0270(12) Uani 1 1 d . . . . .
C6 C 0.8759(5) 0.3209(6) 0.8484(6) 0.0301(11) Uani 1 1 d . . . . .
H6 H 0.9538 0.3087 0.8630 0.036 Uiso 1 1 calc R . . . .
C7 C 0.8067(4) 0.2179(7) 0.7433(5) 0.0265(10) Uani 1 1 d . . . . .
H7 H 0.8379 0.1373 0.6874 0.032 Uiso 1 1 calc R . . . .
N1 N 0.6129(4) 0.1366(6) 0.6093(4) 0.0281(9) Uani 1 1 d . . . . .
C5 C 0.1677(5) 0.4433(7) 0.0661(6) 0.0332(12) Uani 1 1 d . . . . .
H5 H 0.1199 0.5139 -0.0040 0.040 Uiso 1 1 calc R . . . .
C2 C 0.3564(5) 0.3538(7) 0.1932(5) 0.0271(10) Uani 1 1 d . . . . .
C4 C 0.2852(5) 0.4575(7) 0.0880(5) 0.0308(11) Uani 1 1 d . . . . .
H4 H 0.3159 0.5377 0.0312 0.037 Uiso 1 1 calc R . . . .
C8 C 0.6522(5) -0.0270(7) 0.5465(6) 0.0295(11) Uani 1 1 d . . . . .
H8A H 0.7228 -0.0011 0.5191 0.035 Uiso 1 1 calc R . . . .
H8B H 0.5970 -0.0615 0.4584 0.035 Uiso 1 1 calc R . . . .
C9 C 0.6694(5) -0.1820(6) 0.6547(6) 0.0359(13) Uani 1 1 d . . . . .
H9A H 0.6947 -0.2866 0.6106 0.054 Uiso 1 1 calc GR . . . .
H9B H 0.5994 -0.2089 0.6810 0.054 Uiso 1 1 calc GR . . . .
H9C H 0.7252 -0.1490 0.7411 0.054 Uiso 1 1 calc GR . . . .
C3 C 0.4831(5) 0.3675(7) 0.2175(5) 0.0299(11) Uani 1 1 d . . . . .
H3A H 0.5133 0.2522 0.1953 0.036 Uiso 1 1 calc R . . . .
H3B H 0.5020 0.4572 0.1513 0.036 Uiso 1 1 calc R . . . .


_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 O1 1.756(4) . ?
Ge1 O1 1.756(4) 2_656 ?
Ge1 N1 1.818(4) 2_656 ?
Ge1 N1 1.818(4) . ?
O1 C3 1.448(6) . ?
C1 C7 1.409(7) . ?
C1 N1 1.411(6) . ?
C1 C2 1.397(7) 2_656 ?
C6 H6 0.9300 . ?
C6 C7 1.370(7) . ?
C6 C5 1.391(8) 2_656 ?
C7 H7 0.9300 . ?
N1 C8 1.472(7) . ?
C5 C6 1.391(8) 2_656 ?
C5 H5 0.9300 . ?
C5 C4 1.400(9) . ?
C2 C1 1.397(7) 2_656 ?
C2 C4 1.383(8) . ?
C2 C3 1.508(7) . ?
C4 H4 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.512(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

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
O1 Ge1 O1 105.1(2) . 2_656 ?
O1 Ge1 N1 102.26(18) 2_656 . ?
O1 Ge1 N1 102.26(18) . 2_656 ?
O1 Ge1 N1 117.60(19) . . ?
O1 Ge1 N1 117.60(19) 2_656 2_656 ?
N1 Ge1 N1 112.5(3) . 2_656 ?
C3 O1 Ge1 114.2(3) . . ?
C7 C1 N1 122.8(4) . . ?
C2 C1 C7 118.8(4) 2_656 . ?
C2 C1 N1 118.4(4) 2_656 . ?
C7 C6 H6 119.2 . . ?
C7 C6 C5 121.5(5) . 2_656 ?
C5 C6 H6 119.2 2_656 . ?
C1 C7 H7 119.9 . . ?
C6 C7 C1 120.2(5) . . ?
C6 C7 H7 119.9 . . ?
C1 N1 Ge1 114.1(3) . . ?
C1 N1 C8 119.7(4) . . ?
C8 N1 Ge1 120.3(3) . . ?
C6 C5 H5 120.8 2_656 . ?
C6 C5 C4 118.3(5) 2_656 . ?
C4 C5 H5 120.8 . . ?
C1 C2 C3 118.4(4) 2_656 . ?
C4 C2 C1 120.2(5) . 2_656 ?
C4 C2 C3 121.4(5) . . ?
C5 C4 H4 119.5 . . ?
C2 C4 C5 120.9(5) . . ?
C2 C4 H4 119.5 . . ?
N1 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
N1 C8 C9 111.4(4) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C3 C2 111.2(4) . . ?
O1 C3 H3A 109.4 . . ?
O1 C3 H3B 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?

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
Ge1 O1 C3 C2 55.5(5) . . . . ?
Ge1 N1 C8 C9 -136.7(4) . . . . ?
O1 Ge1 O1 C3 -134.1(4) 2_656 . . . ?
O1 Ge1 N1 C1 -39.1(4) 2_656 . . . ?
O1 Ge1 N1 C1 75.4(4) . . . . ?
O1 Ge1 N1 C8 -77.4(4) . . . . ?
O1 Ge1 N1 C8 168.1(4) 2_656 . . . ?
C1 N1 C8 C9 72.0(6) . . . . ?
C1 C2 C4 C5 -0.6(8) 2_656 . . . ?
C1 C2 C3 O1 -57.8(6) 2_656 . . . ?
C6 C5 C4 C2 -0.7(8) 2_656 . . . ?
C7 C1 N1 Ge1 -133.2(4) . . . . ?
C7 C1 N1 C8 19.8(7) . . . . ?
N1 Ge1 O1 C3 113.0(4) . . . . ?
N1 Ge1 O1 C3 -10.7(4) 2_656 . . . ?
N1 Ge1 N1 C1 -166.2(4) 2_656 . . . ?
N1 Ge1 N1 C8 41.0(4) 2_656 . . . ?
N1 C1 C7 C6 177.5(4) . . . . ?
C5 C6 C7 C1 -0.2(7) 2_656 . . . ?
C2 C1 C7 C6 -1.1(7) 2_656 . . . ?
C2 C1 N1 Ge1 45.4(5) 2_656 . . . ?
C2 C1 N1 C8 -161.6(5) 2_656 . . . ?
C4 C2 C3 O1 121.8(5) . . . . ?
C3 C2 C4 C5 179.8(5) . . . . ?

_shelx_SHELXL_version_number     2015/1

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p-1
_database_code_depnum_ccdc_archive 'CCDC 1518903'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;
_audit_creation_date             2015-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H11 Ge N O)'
_chemical_formula_sum            'C26 H22 Ge2 N2 O2'
_chemical_formula_weight         539.63
_chemical_melting_point          ?
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'
Ge Ge 0.1547 1.8001 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+, -y+, -z+'

_cell_length_a                   6.8500(3)
_cell_length_b                   6.8808(3)
_cell_length_c                   23.2208(9)
_cell_angle_alpha                90.720(3)
_cell_angle_beta                 90.263(3)
_cell_angle_gamma                104.661(3)
_cell_volume                     1058.72(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    35261
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.69
_cell_measurement_theta_min      1.75
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.867
_exptl_absorpt_correction_T_max  0.7745
_exptl_absorpt_correction_T_min  0.4331
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'STOE X-Area'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            47679
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.162
_diffrn_reflns_theta_min         2.632
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5257
_reflns_number_total             5680
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5680
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0291P)²+0.7017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0618
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.12453(2) 0.34035(3) 0.49142(2) 0.01927(5) Uani 1 1 d . . . . .
Ge2 Ge -0.16002(2) 1.12386(3) 1.00952(2) 0.01920(5) Uani 1 1 d . . . . .
O3 O -0.10147(18) 1.28337(18) 0.94533(5) 0.0220(2) Uani 1 1 d . . . . .
O4 O 0.28000(18) 0.39968(18) 0.55757(5) 0.0222(2) Uani 1 1 d . . . . .
C5 C 0.3146(2) 0.7755(3) 0.50720(7) 0.0208(3) Uani 1 1 d . . . . .
H5A H 0.4431 0.7536 0.4954 0.025 Uiso 1 1 calc R . . . .
H5B H 0.3157 0.9132 0.4984 0.025 Uiso 1 1 calc R . . . .
C6 C 0.2767(2) 1.3130(3) 0.99690(7) 0.0205(3) Uani 1 1 d . . . . .
H6A H 0.2552 1.4402 1.0101 0.025 Uiso 1 1 calc R . . . .
H6B H 0.4151 1.3132 1.0060 0.025 Uiso 1 1 calc R . . . .
N7 N 0.1480(2) 0.6359(2) 0.47305(6) 0.0189(3) Uani 1 1 d . . . . .
C8 C -0.3668(3) 0.8762(3) 0.89109(8) 0.0229(3) Uani 1 1 d . . . . .
H8 H -0.4469 0.9232 0.9173 0.028 Uiso 1 1 calc R . . . .
C9 C 0.2800(2) 0.5573(3) 0.59349(8) 0.0217(3) Uani 1 1 d . . . . .
N10 N -0.1368(2) 0.8548(2) 0.97101(6) 0.0191(3) Uani 1 1 d . . . . .
C11 C 0.2979(3) 0.9077(3) 0.60894(8) 0.0245(3) Uani 1 1 d . . . . .
H11 H 0.3082 1.0352 0.5944 0.029 Uiso 1 1 calc R . . . .
C12 C -0.1900(2) 0.8304(2) 0.90999(7) 0.0204(3) Uani 1 1 d . . . . .
C13 C 0.1762(2) 0.6875(3) 0.41246(7) 0.0207(3) Uani 1 1 d . . . . .
C14 C 0.2474(3) 1.2960(3) 0.93266(7) 0.0212(3) Uani 1 1 d . . . . .
C15 C 0.2706(3) 0.5279(3) 0.65285(8) 0.0245(3) Uani 1 1 d . . . . .
H15 H 0.2615 0.4009 0.6676 0.029 Uiso 1 1 calc R . . . .
C16 C 0.1276(3) 0.8608(3) 0.39287(8) 0.0234(3) Uani 1 1 d . . . . .
H16 H 0.0764 0.9403 0.4184 0.028 Uiso 1 1 calc R . . . .
C17 C 0.0564(3) 1.2868(2) 0.90975(7) 0.0210(3) Uani 1 1 d . . . . .
C18 C 0.2570(3) 0.5722(3) 0.37420(8) 0.0230(3) Uani 1 1 d . . . . .
H18 H 0.2930 0.4583 0.3869 0.028 Uiso 1 1 calc R . . . .
C19 C 0.4075(3) 1.3024(3) 0.89527(8) 0.0236(3) Uani 1 1 d . . . . .
H19 H 0.5353 1.3091 0.9102 0.028 Uiso 1 1 calc R . . . .
C20 C -0.0727(3) 0.7569(3) 0.87072(8) 0.0239(3) Uani 1 1 d . . . . .
H20 H 0.0439 0.7234 0.8830 0.029 Uiso 1 1 calc R . . . .
C21 C 0.2323(3) 0.7978(3) 0.29736(8) 0.0264(3) Uani 1 1 d . . . . .
H21 H 0.2493 0.8333 0.2588 0.032 Uiso 1 1 calc R . . . .
C22 C 0.0266(3) 1.2840(3) 0.85031(8) 0.0246(3) Uani 1 1 d . . . . .
H22 H -0.1008 1.2781 0.8352 0.030 Uiso 1 1 calc R . . . .
C23 C 0.2929(2) 0.7471(3) 0.57117(7) 0.0215(3) Uani 1 1 d . . . . .
C24 C 0.1875(3) 1.2901(3) 0.81372(8) 0.0267(4) Uani 1 1 d . . . . .
H24 H 0.1677 1.2882 0.7741 0.032 Uiso 1 1 calc R . . . .
C25 C 0.2748(3) 0.6887(3) 0.68971(8) 0.0263(4) Uani 1 1 d . . . . .
H25 H 0.2689 0.6694 0.7293 0.032 Uiso 1 1 calc R . . . .
C26 C -0.3042(3) 0.7821(3) 0.79427(8) 0.0254(3) Uani 1 1 d . . . . .
H26 H -0.3411 0.7677 0.7556 0.030 Uiso 1 1 calc R . . . .
C27 C 0.1549(3) 0.9150(3) 0.33582(8) 0.0254(3) Uani 1 1 d . . . . .
H27 H 0.1214 1.0301 0.3231 0.030 Uiso 1 1 calc R . . . .
C28 C 0.2876(3) 0.8786(3) 0.66796(8) 0.0273(4) Uani 1 1 d . . . . .
H28 H 0.2893 0.9859 0.6929 0.033 Uiso 1 1 calc R . . . .
C29 C -0.1304(3) 0.7337(3) 0.81295(8) 0.0266(4) Uani 1 1 d . . . . .
H29 H -0.0515 0.6853 0.7867 0.032 Uiso 1 1 calc R . . . .
C30 C 0.2839(3) 0.6280(3) 0.31677(8) 0.0259(3) Uani 1 1 d . . . . .
H30 H 0.3371 0.5503 0.2912 0.031 Uiso 1 1 calc R . . . .
C31 C -0.4234(3) 0.8522(3) 0.83368(8) 0.0247(3) Uani 1 1 d . . . . .
H31 H -0.5414 0.8831 0.8214 0.030 Uiso 1 1 calc R . . . .
C32 C 0.3784(3) 1.2990(3) 0.83606(8) 0.0265(4) Uani 1 1 d . . . . .
H32 H 0.4859 1.3026 0.8114 0.032 Uiso 1 1 calc R . . . .


_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 O4 1.8466(12) . ?
Ge1 N7 2.0494(14) . ?
Ge1 N7 2.0878(14) 2_566 ?
Ge2 O3 1.8469(13) . ?
Ge2 N10 2.0492(14) 2_577 ?
Ge2 N10 2.0884(14) . ?
O3 C17 1.360(2) . ?
O4 C9 1.360(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 N7 1.507(2) . ?
C5 C23 1.504(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N10 1.508(2) 2_577 ?
C6 C14 1.503(2) . ?
N7 Ge1 2.0878(14) 2_566 ?
N7 C13 1.457(2) . ?
C8 H8 0.9300 . ?
C8 C12 1.396(2) . ?
C8 C31 1.383(2) . ?
C9 C15 1.395(2) . ?
C9 C23 1.393(2) . ?
N10 Ge2 2.0492(14) 2_577 ?
N10 C6 1.508(2) 2_577 ?
N10 C12 1.458(2) . ?
C11 H11 0.9300 . ?
C11 C23 1.395(2) . ?
C11 C28 1.387(3) . ?
C12 C20 1.390(2) . ?
C13 C16 1.397(2) . ?
C13 C18 1.391(2) . ?
C14 C17 1.396(2) . ?
C14 C19 1.395(2) . ?
C15 H15 0.9300 . ?
C15 C25 1.385(3) . ?
C16 H16 0.9300 . ?
C16 C27 1.381(3) . ?
C17 C22 1.394(2) . ?
C18 H18 0.9300 . ?
C18 C30 1.393(2) . ?
C19 H19 0.9300 . ?
C19 C32 1.387(3) . ?
C20 H20 0.9300 . ?
C20 C29 1.393(2) . ?
C21 H21 0.9300 . ?
C21 C27 1.390(3) . ?
C21 C30 1.383(3) . ?
C22 H22 0.9300 . ?
C22 C24 1.387(3) . ?
C24 H24 0.9300 . ?
C24 C32 1.391(3) . ?
C25 H25 0.9300 . ?
C25 C28 1.389(3) . ?
C26 H26 0.9300 . ?
C26 C29 1.384(3) . ?
C26 C31 1.390(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?

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
O4 Ge1 N7 93.85(6) . . ?
O4 Ge1 N7 97.51(5) . 2_566 ?
N7 Ge1 N7 81.80(6) . 2_566 ?
O3 Ge2 N10 94.05(6) . 2_577 ?
O3 Ge2 N10 97.61(6) . . ?
N10 Ge2 N10 81.75(6) 2_577 . ?
C17 O3 Ge2 124.13(11) . . ?
C9 O4 Ge1 123.95(11) . . ?
H5A C5 H5B 107.8 . . ?
N7 C5 H5A 109.0 . . ?
N7 C5 H5B 109.0 . . ?
C23 C5 H5A 109.0 . . ?
C23 C5 H5B 109.0 . . ?
C23 C5 N7 113.13(13) . . ?
H6A C6 H6B 107.7 . . ?
N10 C6 H6A 108.9 2_577 . ?
N10 C6 H6B 108.9 2_577 . ?
C14 C6 H6A 108.9 . . ?
C14 C6 H6B 108.9 . . ?
C14 C6 N10 113.32(13) . 2_577 ?
Ge1 N7 Ge1 98.19(6) . 2_566 ?
C5 N7 Ge1 107.03(10) . 2_566 ?
C5 N7 Ge1 112.05(10) . . ?
C13 N7 Ge1 115.36(10) . . ?
C13 N7 Ge1 115.64(10) . 2_566 ?
C13 N7 C5 108.14(13) . . ?
C12 C8 H8 119.8 . . ?
C31 C8 H8 119.8 . . ?
C31 C8 C12 120.48(16) . . ?
O4 C9 C15 119.41(16) . . ?
O4 C9 C23 120.20(16) . . ?
C23 C9 C15 120.38(16) . . ?
Ge2 N10 Ge2 98.25(6) 2_577 . ?
C6 N10 Ge2 111.87(10) 2_577 2_577 ?
C6 N10 Ge2 106.90(10) 2_577 . ?
C12 N10 Ge2 115.71(10) . . ?
C12 N10 Ge2 115.55(10) . 2_577 ?
C12 N10 C6 108.11(13) . 2_577 ?
C23 C11 H11 119.7 . . ?
C28 C11 H11 119.7 . . ?
C28 C11 C23 120.53(17) . . ?
C8 C12 N10 118.88(15) . . ?
C20 C12 C8 119.43(16) . . ?
C20 C12 N10 121.66(15) . . ?
C16 C13 N7 119.17(15) . . ?
C18 C13 N7 121.48(15) . . ?
C18 C13 C16 119.31(16) . . ?
C17 C14 C6 118.79(15) . . ?
C19 C14 C6 121.98(15) . . ?
C19 C14 C17 119.10(16) . . ?
C9 C15 H15 120.2 . . ?
C25 C15 C9 119.69(17) . . ?
C25 C15 H15 120.2 . . ?
C13 C16 H16 119.7 . . ?
C27 C16 C13 120.50(17) . . ?
C27 C16 H16 119.7 . . ?
O3 C17 C14 120.18(15) . . ?
O3 C17 C22 119.44(16) . . ?
C22 C17 C14 120.37(16) . . ?
C13 C18 H18 120.1 . . ?
C13 C18 C30 119.72(17) . . ?
C30 C18 H18 120.1 . . ?
C14 C19 H19 119.6 . . ?
C32 C19 C14 120.76(17) . . ?
C32 C19 H19 119.6 . . ?
C12 C20 H20 120.1 . . ?
C12 C20 C29 119.76(17) . . ?
C29 C20 H20 120.1 . . ?
C27 C21 H21 120.2 . . ?
C30 C21 H21 120.2 . . ?
C30 C21 C27 119.53(17) . . ?
C17 C22 H22 120.1 . . ?
C24 C22 C17 119.79(17) . . ?
C24 C22 H22 120.1 . . ?
C9 C23 C5 118.87(15) . . ?
C9 C23 C11 119.19(16) . . ?
C11 C23 C5 121.83(16) . . ?
C22 C24 H24 119.8 . . ?
C22 C24 C32 120.36(17) . . ?
C32 C24 H24 119.8 . . ?
C15 C25 H25 119.8 . . ?
C15 C25 C28 120.44(17) . . ?
C28 C25 H25 119.8 . . ?
C29 C26 H26 120.2 . . ?
C29 C26 C31 119.67(17) . . ?
C31 C26 H26 120.2 . . ?
C16 C27 C21 120.17(17) . . ?
C16 C27 H27 119.9 . . ?
C21 C27 H27 119.9 . . ?
C11 C28 C25 119.77(17) . . ?
C11 C28 H28 120.1 . . ?
C25 C28 H28 120.1 . . ?
C20 C29 H29 119.7 . . ?
C26 C29 C20 120.60(17) . . ?
C26 C29 H29 119.7 . . ?
C18 C30 H30 119.6 . . ?
C21 C30 C18 120.74(17) . . ?
C21 C30 H30 119.6 . . ?
C8 C31 C26 120.04(17) . . ?
C8 C31 H31 120.0 . . ?
C26 C31 H31 120.0 . . ?
C19 C32 C24 119.63(17) . . ?
C19 C32 H32 120.2 . . ?
C24 C32 H32 120.2 . . ?

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
Ge1 O4 C9 C15 134.79(14) . . . . ?
Ge1 O4 C9 C23 -46.4(2) . . . . ?
Ge1 N7 C13 C16 158.87(13) . . . . ?
Ge1 N7 C13 C16 45.14(18) 2_566 . . . ?
Ge1 N7 C13 C18 -137.19(14) 2_566 . . . ?
Ge1 N7 C13 C18 -23.45(19) . . . . ?
Ge2 O3 C17 C14 -45.5(2) . . . . ?
Ge2 O3 C17 C22 135.49(14) . . . . ?
Ge2 N10 C12 C8 -160.39(13) 2_577 . . . ?
Ge2 N10 C12 C8 -46.40(18) . . . . ?
Ge2 N10 C12 C20 135.62(14) . . . . ?
Ge2 N10 C12 C20 21.6(2) 2_577 . . . ?
O3 C17 C22 C24 179.16(16) . . . . ?
O4 C9 C15 C25 178.64(15) . . . . ?
O4 C9 C23 C5 -2.2(2) . . . . ?
O4 C9 C23 C11 -178.36(15) . . . . ?
C5 N7 C13 C16 -74.80(18) . . . . ?
C5 N7 C13 C18 102.88(17) . . . . ?
C6 N10 C12 C8 73.40(19) 2_577 . . . ?
C6 N10 C12 C20 -104.59(18) 2_577 . . . ?
C6 C14 C17 O3 -3.2(2) . . . . ?
C6 C14 C17 C22 175.87(16) . . . . ?
C6 C14 C19 C32 -175.96(17) . . . . ?
N7 Ge1 O4 C9 -47.42(13) 2_566 . . . ?
N7 Ge1 O4 C9 34.80(13) . . . . ?
N7 C5 C23 C9 56.2(2) . . . . ?
N7 C5 C23 C11 -127.76(16) . . . . ?
N7 C13 C16 C27 179.22(15) . . . . ?
N7 C13 C18 C30 -179.19(15) . . . . ?
C8 C12 C20 C29 1.3(3) . . . . ?
C9 C15 C25 C28 0.2(3) . . . . ?
N10 Ge2 O3 C17 -47.61(13) . . . . ?
N10 Ge2 O3 C17 34.59(13) 2_577 . . . ?
N10 C6 C14 C17 56.7(2) 2_577 . . . ?
N10 C6 C14 C19 -127.52(17) 2_577 . . . ?
N10 C12 C20 C29 179.24(16) . . . . ?
C12 C8 C31 C26 0.0(3) . . . . ?
C12 C20 C29 C26 -0.4(3) . . . . ?
C13 C16 C27 C21 -0.4(3) . . . . ?
C13 C18 C30 C21 0.4(3) . . . . ?
C14 C17 C22 C24 0.1(3) . . . . ?
C14 C19 C32 C24 0.4(3) . . . . ?
C15 C9 C23 C5 176.59(15) . . . . ?
C15 C9 C23 C11 0.5(2) . . . . ?
C15 C25 C28 C11 -0.5(3) . . . . ?
C16 C13 C18 C30 -1.5(3) . . . . ?
C17 C14 C19 C32 -0.2(3) . . . . ?
C17 C22 C24 C32 0.0(3) . . . . ?
C18 C13 C16 C27 1.5(3) . . . . ?
C19 C14 C17 O3 -179.03(15) . . . . ?
C19 C14 C17 C22 0.0(3) . . . . ?
C22 C24 C32 C19 -0.2(3) . . . . ?
C23 C5 N7 Ge1 50.46(15) . . . 2_566 ?
C23 C5 N7 Ge1 -56.09(16) . . . . ?
C23 C5 N7 C13 175.67(14) . . . . ?
C23 C9 C15 C25 -0.2(2) . . . . ?
C23 C11 C28 C25 0.8(3) . . . . ?
C27 C21 C30 C18 0.7(3) . . . . ?
C28 C11 C23 C5 -176.77(16) . . . . ?
C28 C11 C23 C9 -0.8(3) . . . . ?
C29 C26 C31 C8 0.9(3) . . . . ?
C30 C21 C27 C16 -0.7(3) . . . . ?
C31 C8 C12 N10 -179.11(16) . . . . ?
C31 C8 C12 C20 -1.1(3) . . . . ?
C31 C26 C29 C20 -0.7(3) . . . . ?

_shelx_SHELXL_version_number     2015/1
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ed023x
_database_code_depnum_ccdc_archive 'CCDC 1518901'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 Ge N2 O2'
_chemical_formula_weight         370.97

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   12.1426(11)
_cell_length_b                   7.4037(5)
_cell_length_c                   9.3422(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.205(7)
_cell_angle_gamma                90.00
_cell_volume                     817.66(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6992
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.15

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    1.885
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.6085
_exptl_absorpt_correction_T_max  0.7970
_exptl_absorpt_process_details   'STOE X-AREA'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5407
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         26.74
_reflns_number_total             1684
_reflns_number_gt                1678
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0419P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(12)
_refine_ls_number_reflns         1684
_refine_ls_number_parameters     106
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4832(2) 0.2689(4) 0.2175(3) 0.0267(5) Uani 1 1 d . . .
H1A H 0.5022 0.1793 0.1512 0.032 Uiso 1 1 calc R . .
H1B H 0.5135 0.3842 0.1953 0.032 Uiso 1 1 calc R . .
C2 C 0.3564(2) 0.2827(4) 0.1928(3) 0.0236(5) Uani 1 1 d . . .
C3 C 0.2854(2) 0.1795(4) 0.0881(3) 0.0277(5) Uani 1 1 d . . .
H3 H 0.3161 0.0989 0.0316 0.033 Uiso 1 1 calc R . .
C4 C 0.1679(2) 0.1940(4) 0.0655(3) 0.0292(6) Uani 1 1 d . . .
H4 H 0.1202 0.1237 -0.0049 0.035 Uiso 1 1 calc R . .
C5 C 0.1243(2) 0.3158(3) 0.1508(3) 0.0264(6) Uani 1 1 d . . .
H5 H 0.0463 0.3279 0.1360 0.032 Uiso 1 1 calc R . .
C6 C 0.1935(2) 0.4194(4) 0.2570(3) 0.0232(5) Uani 1 1 d . . .
H6 H 0.1621 0.4998 0.3130 0.028 Uiso 1 1 calc R . .
C7 C 0.3118(2) 0.4035(3) 0.2806(3) 0.0217(6) Uani 1 1 d . . .
C8 C 0.3481(2) 0.6638(4) 0.4541(3) 0.0252(5) Uani 1 1 d . . .
H8A H 0.4036 0.6992 0.5417 0.030 Uiso 1 1 calc R . .
H8B H 0.2777 0.6380 0.4824 0.030 Uiso 1 1 calc R . .
C9 C 0.3300(3) 0.8176(4) 0.3454(4) 0.0339(7) Uani 1 1 d . . .
H9A H 0.4001 0.8455 0.3192 0.051 Uiso 1 1 calc R . .
H9B H 0.3039 0.9219 0.3889 0.051 Uiso 1 1 calc R . .
H9C H 0.2747 0.7833 0.2588 0.051 Uiso 1 1 calc R . .
N1 N 0.38741(18) 0.4999(3) 0.3920(2) 0.0233(4) Uani 1 1 d . . .
O2 O 0.53438(15) 0.2191(3) 0.3671(2) 0.0266(4) Uani 1 1 d . . .
Ge1 Ge 0.5000 0.363640(19) 0.5000 0.02085(12) Uani 1 2 d S . .


_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
C1 O2 1.442(3) . ?
C1 C2 1.507(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.377(4) . ?
C2 C7 1.403(4) . ?
C3 C4 1.398(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.407(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.414(3) . ?
C8 N1 1.470(3) . ?
C8 C9 1.508(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N1 Ge1 1.809(2) . ?
O2 Ge1 1.760(2) . ?
Ge1 O2 1.760(2) 2_656 ?
Ge1 N1 1.809(2) 2_656 ?

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
O2 C1 C2 111.4(2) . . ?
O2 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
O2 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C7 120.4(2) . . ?
C3 C2 C1 121.5(3) . . ?
C7 C2 C1 118.1(2) . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 118.6(2) . . ?
C2 C7 N1 118.7(2) . . ?
C6 C7 N1 122.7(2) . . ?
N1 C8 C9 111.6(2) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
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 . . ?
C7 N1 C8 119.5(2) . . ?
C7 N1 Ge1 114.19(16) . . ?
C8 N1 Ge1 120.81(17) . . ?
C1 O2 Ge1 114.16(16) . . ?
O2 Ge1 O2 105.09(13) 2_656 . ?
O2 Ge1 N1 102.51(9) 2_656 2_656 ?
O2 Ge1 N1 117.48(9) . 2_656 ?
O2 Ge1 N1 117.48(9) 2_656 . ?
O2 Ge1 N1 102.51(9) . . ?
N1 Ge1 N1 112.23(15) 2_656 . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.74
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.072
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_g459_new
_database_code_depnum_ccdc_archive 'CCDC 1518895'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;
_audit_creation_date             2016-10-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H26 N2 O2 Si'
_chemical_formula_sum            'C28 H26 N2 O2 Si'
_chemical_formula_weight         450.60
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+, -y+, z+'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x+, y+1/2, z+1/2'
'-x+, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y+, z+1/2'
'-x+1/2, -y+, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z+'
'-x+1/2, -y+1/2, z+'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   15.2934(11)
_cell_length_b                   32.451(3)
_cell_length_c                   9.2736(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4602.4(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8388
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.66
_cell_measurement_theta_min      1.25
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.8498
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'STOE X-AREA'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12368
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.688
_diffrn_reflns_theta_min         2.511
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2268
_reflns_number_total             2440
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 970 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2440
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0608
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C11(H11), C10(H10), C12(H12), C6(H6), C14(H14), C13(H13)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Si1 Si 0.5000 0.5000 0.46514(7) 0.02661(17) Uani 1 2 d S T P . .
O1 O 0.41502(8) 0.51041(4) 0.36298(13) 0.0299(3) Uani 1 1 d . . . . .
N1 N 0.51659(10) 0.54408(5) 0.56147(15) 0.0281(3) Uani 1 1 d . . . . .
C9 C 0.57024(12) 0.54595(6) 0.68540(18) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.41668(12) 0.54836(6) 0.29233(19) 0.0282(4) Uani 1 1 d . . . . .
C3 C 0.39897(13) 0.58800(6) 0.0778(2) 0.0318(4) Uani 1 1 d . . . . .
H3 H 0.3844 0.5895 -0.0194 0.038 Uiso 1 1 calc R . . . .
C8 C 0.46114(13) 0.58041(6) 0.52892(19) 0.0286(4) Uani 1 1 d . . . . .
H8A H 0.4914 0.6052 0.5590 0.034 Uiso 1 1 calc R . . . .
H8B H 0.4072 0.5785 0.5836 0.034 Uiso 1 1 calc R . . . .
C7 C 0.43982(12) 0.58340(6) 0.37005(19) 0.0281(4) Uani 1 1 d . . . . .
C4 C 0.42300(12) 0.62383(6) 0.1509(2) 0.0310(4) Uani 1 1 d . . . . .
C2 C 0.39631(13) 0.55007(6) 0.14727(19) 0.0312(4) Uani 1 1 d . . . . .
H2 H 0.3811 0.5263 0.0971 0.037 Uiso 1 1 calc R . . . .
C11 C 0.60975(14) 0.57530(7) 0.9160(2) 0.0348(4) Uani 1 1 d . . . . .
H11 H 0.5985 0.5940 0.9898 0.042 Uiso 1 1 calc R . . . .
C10 C 0.55498(13) 0.57397(6) 0.79644(19) 0.0318(4) Uani 1 1 d . . . . .
H10 H 0.5077 0.5919 0.7905 0.038 Uiso 1 1 calc R . . . .
C5 C 0.43049(16) 0.66454(6) 0.0725(2) 0.0384(5) Uani 1 1 d . . . . .
H5A H 0.4801 0.6638 0.0092 0.058 Uiso 1 1 calc GR . . . .
H5B H 0.4377 0.6864 0.1414 0.058 Uiso 1 1 calc GR . . . .
H5C H 0.3784 0.6693 0.0172 0.058 Uiso 1 1 calc GR . . . .
C12 C 0.68096(14) 0.54902(6) 0.9262(2) 0.0359(4) Uani 1 1 d . . . . .
H12 H 0.7179 0.5502 1.0058 0.043 Uiso 1 1 calc R . . . .
C6 C 0.44268(12) 0.62099(6) 0.2973(2) 0.0298(4) Uani 1 1 d . . . . .
H6 H 0.4581 0.6447 0.3476 0.036 Uiso 1 1 calc R . . . .
C14 C 0.64198(12) 0.51942(6) 0.6974(2) 0.0309(4) Uani 1 1 d . . . . .
H14 H 0.6533 0.5005 0.6244 0.037 Uiso 1 1 calc R . . . .
C13 C 0.69647(13) 0.52102(6) 0.8168(2) 0.0348(5) Uani 1 1 d . . . . .
H13 H 0.7438 0.5031 0.8233 0.042 Uiso 1 1 calc R . . . .


_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
Si1 O1 1.6433(13) 2_665 ?
Si1 O1 1.6434(13) . ?
Si1 N1 1.7055(15) . ?
Si1 N1 1.7055(15) 2_665 ?
O1 C1 1.395(2) . ?
N1 C9 1.413(2) . ?
N1 C8 1.483(2) . ?
C9 C10 1.393(3) . ?
C9 C14 1.399(3) . ?
C1 C7 1.392(3) . ?
C1 C2 1.382(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(3) . ?
C3 C2 1.390(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.512(3) . ?
C7 C6 1.394(3) . ?
C4 C5 1.512(3) . ?
C4 C6 1.394(3) . ?
C2 H2 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.391(3) . ?
C11 C12 1.386(3) . ?
C10 H10 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C13 1.383(3) . ?
C6 H6 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.387(3) . ?
C13 H13 0.9300 . ?

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
O1 Si1 O1 109.59(9) 2_665 . ?
O1 Si1 N1 104.32(7) 2_665 2_665 ?
O1 Si1 N1 110.90(7) . 2_665 ?
O1 Si1 N1 110.89(7) 2_665 . ?
O1 Si1 N1 104.32(7) . . ?
N1 Si1 N1 116.82(10) . 2_665 ?
C1 O1 Si1 115.95(11) . . ?
C9 N1 Si1 123.25(12) . . ?
C9 N1 C8 117.59(15) . . ?
C8 N1 Si1 118.36(12) . . ?
C10 C9 N1 122.12(16) . . ?
C10 C9 C14 118.31(16) . . ?
C14 C9 N1 119.57(16) . . ?
C7 C1 O1 118.86(15) . . ?
C2 C1 O1 119.23(17) . . ?
C2 C1 C7 121.91(18) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.39(17) . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
N1 C8 C7 111.88(15) . . ?
H8A C8 H8B 107.9 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C1 C7 C8 120.45(16) . . ?
C1 C7 C6 118.16(16) . . ?
C6 C7 C8 121.39(17) . . ?
C3 C4 C5 120.99(17) . . ?
C6 C4 C3 118.34(18) . . ?
C6 C4 C5 120.64(18) . . ?
C1 C2 C3 118.68(18) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C12 C11 C10 120.55(19) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.58(18) . . ?
C11 C10 H10 119.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.29(18) . . ?
C13 C12 H12 120.4 . . ?
C7 C6 H6 119.3 . . ?
C4 C6 C7 121.50(18) . . ?
C4 C6 H6 119.3 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.78(17) . . ?
C13 C14 H14 119.6 . . ?
C12 C13 C14 120.49(19) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?

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
Si1 O1 C1 C7 -46.43(19) . . . . ?
Si1 O1 C1 C2 132.88(15) . . . . ?
Si1 N1 C9 C10 -150.75(15) . . . . ?
Si1 N1 C9 C14 30.2(2) . . . . ?
Si1 N1 C8 C7 -35.4(2) . . . . ?
O1 Si1 O1 C1 -72.79(11) 2_665 . . . ?
O1 Si1 N1 C9 -76.90(16) 2_665 . . . ?
O1 Si1 N1 C9 165.20(14) . . . . ?
O1 Si1 N1 C8 -4.33(15) . . . . ?
O1 Si1 N1 C8 113.57(14) 2_665 . . . ?
O1 C1 C7 C8 -1.1(3) . . . . ?
O1 C1 C7 C6 178.88(16) . . . . ?
O1 C1 C2 C3 -179.43(16) . . . . ?
N1 Si1 O1 C1 45.99(13) . . . . ?
N1 Si1 O1 C1 172.57(12) 2_665 . . . ?
N1 Si1 N1 C9 42.41(13) 2_665 . . . ?
N1 Si1 N1 C8 -127.12(15) 2_665 . . . ?
N1 C9 C10 C11 -179.21(18) . . . . ?
N1 C9 C14 C13 179.02(17) . . . . ?
N1 C8 C7 C1 42.7(2) . . . . ?
N1 C8 C7 C6 -137.23(18) . . . . ?
C9 N1 C8 C7 154.47(16) . . . . ?
C9 C14 C13 C12 -0.2(3) . . . . ?
C1 C7 C6 C4 0.1(3) . . . . ?
C3 C4 C6 C7 0.8(3) . . . . ?
C8 N1 C9 C10 18.9(3) . . . . ?
C8 N1 C9 C14 -160.15(16) . . . . ?
C8 C7 C6 C4 -179.96(18) . . . . ?
C7 C1 C2 C3 -0.1(3) . . . . ?
C4 C3 C2 C1 1.1(3) . . . . ?
C2 C1 C7 C8 179.61(18) . . . . ?
C2 C1 C7 C6 -0.4(3) . . . . ?
C2 C3 C4 C5 176.61(19) . . . . ?
C2 C3 C4 C6 -1.4(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C10 C9 C14 C13 0.0(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C5 C4 C6 C7 -177.20(19) . . . . ?
C12 C11 C10 C9 0.6(3) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?

_shelx_SHELXL_version_number     2015/1

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_g450
_database_code_depnum_ccdc_archive 'CCDC 1518904'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_date             2014-06-14T15:26:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C26 H22 N2 O2 Si'
_chemical_formula_weight         422.54

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_Int_Tables_number      60
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.8114(6)
_cell_length_b                   8.5394(4)
_cell_length_c                   16.8172(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2127.05(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12599
_cell_measurement_theta_min      1.21
_cell_measurement_theta_max      27.36

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             888
_exptl_crystal_colour            colourless
_exptl_crystal_description       block
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.9420
_exptl_absorpt_process_details   'STOE X-AREA'


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.1172
_diffrn_reflns_number            20828
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.422
_diffrn_reflns_theta_max         26.716
_diffrn_reflns_theta_full        26
_diffrn_measurement_device_type  'STOE IPDS II/T'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             2254
_reflns_number_gt                2023
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0496P)²+0.6915P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2254
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.046
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.12

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0 0.06317(5) 0.75 0.01901(14) Uani 1 d . .
O1 O 0.09050(6) -0.04690(10) 0.74471(5) 0.0223(2) Uani 1 d . .
C2 C -0.07427(10) 0.56377(15) 0.59881(8) 0.0285(3) Uani 1 d . .
C3 C 0.10697(8) -0.02331(15) 0.60292(7) 0.0223(3) Uani 1 d . .
C4 C -0.01990(9) 0.43343(15) 0.61069(7) 0.0251(3) Uani 1 d . .
C5 C -0.19336(9) 0.44159(15) 0.67233(7) 0.0255(3) Uani 1 d . .
C6 C 0.11519(8) -0.11231(15) 0.67200(7) 0.0212(3) Uani 1 d . .
C7 C -0.13919(8) 0.31135(15) 0.68518(7) 0.0226(3) Uani 1 d . .
N8 N 0.00135(7) 0.16856(12) 0.66402(6) 0.0207(2) Uani 1 d . .
C9 C 0.14886(9) -0.26311(15) 0.67119(8) 0.0244(3) Uani 1 d . .
C10 C -0.16170(10) 0.56809(15) 0.62851(8) 0.0280(3) Uani 1 d . .
C11 C 0.16832(9) -0.24295(16) 0.52944(8) 0.0272(3) Uani 1 d . .
C12 C 0.07529(9) 0.14443(15) 0.60629(7) 0.0236(3) Uani 1 d . .
C13 C -0.05195(8) 0.30481(14) 0.65339(7) 0.0205(3) Uani 1 d . .
C14 C 0.17640(9) -0.32814(16) 0.59938(8) 0.0267(3) Uani 1 d . .
C15 C 0.13346(9) -0.09234(16) 0.53122(8) 0.0260(3) Uani 1 d . .
H12A H 0.0532(11) 0.1759(17) 0.5521(9) 0.030(4) Uiso 1 d . .
H10 H -0.2005(12) 0.659(2) 0.6192(10) 0.037(4) Uiso 1 d . .
H12B H 0.1283(12) 0.2157(19) 0.6191(9) 0.034(4) Uiso 1 d . .
H9 H 0.1527(11) -0.3209(19) 0.7198(10) 0.036(4) Uiso 1 d . .
H11 H 0.1875(10) -0.2886(18) 0.4798(10) 0.031(4) Uiso 1 d . .
H7 H -0.1630(10) 0.2217(18) 0.7153(9) 0.026(4) Uiso 1 d . .
H2 H -0.0473(11) 0.6566(19) 0.5712(9) 0.035(4) Uiso 1 d . .
H5 H -0.2541(12) 0.4419(17) 0.6924(9) 0.034(4) Uiso 1 d . .
H15 H 0.1289(11) -0.0309(18) 0.4829(9) 0.031(4) Uiso 1 d . .
H4 H 0.0413(12) 0.4341(18) 0.5880(9) 0.034(4) Uiso 1 d . .
H14 H 0.1998(11) -0.4388(19) 0.6000(9) 0.029(4) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Si1 O1 1.6396(9) . ?
Si1 O1 1.6396(9) 3_556 ?
Si1 N8 1.7033(10) 3_556 ?
Si1 N8 1.7033(10) . ?
O1 C6 1.3931(14) . ?
C2 C4 1.3883(19) . ?
C2 C10 1.388(2) . ?
C3 C6 1.3936(17) . ?
C3 C15 1.3982(17) . ?
C3 C12 1.5084(18) . ?
C4 C13 1.3956(17) . ?
C5 C7 1.3882(18) . ?
C5 C10 1.3892(19) . ?
C6 C9 1.3810(18) . ?
C7 C13 1.3995(17) . ?
N8 C13 1.4173(15) . ?
N8 C12 1.4780(15) . ?
C9 C14 1.3904(18) . ?
C11 C15 1.3863(19) . ?
C11 C14 1.3881(19) . ?

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
O1 Si1 O1 110.04(7) . 3_556 ?
O1 Si1 N8 111.01(4) . 3_556 ?
O1 Si1 N8 104.31(4) 3_556 3_556 ?
O1 Si1 N8 104.31(4) . . ?
O1 Si1 N8 111.01(4) 3_556 . ?
N8 Si1 N8 116.21(7) 3_556 . ?
C6 O1 Si1 119.48(7) . . ?
C4 C2 C10 120.70(13) . . ?
C6 C3 C15 117.67(11) . . ?
C6 C3 C12 120.91(10) . . ?
C15 C3 C12 121.34(11) . . ?
C2 C4 C13 120.51(12) . . ?
C7 C5 C10 120.69(12) . . ?
C9 C6 O1 118.51(11) . . ?
C9 C6 C3 122.13(11) . . ?
O1 C6 C3 119.35(11) . . ?
C5 C7 C13 120.41(12) . . ?
C13 N8 C12 116.38(10) . . ?
C13 N8 Si1 122.29(8) . . ?
C12 N8 Si1 119.51(8) . . ?
C6 C9 C14 119.14(12) . . ?
C2 C10 C5 119.02(12) . . ?
C15 C11 C14 120.00(12) . . ?
N8 C12 C3 112.81(10) . . ?
C4 C13 C7 118.64(12) . . ?
C4 C13 N8 121.43(11) . . ?
C7 C13 N8 119.93(11) . . ?
C11 C14 C9 120.09(12) . . ?
C11 C15 C3 120.95(12) . . ?

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
O1 Si1 O1 C6 80.41(8) 3_556 . . . ?
N8 Si1 O1 C6 -164.63(8) 3_556 . . . ?
N8 Si1 O1 C6 -38.74(10) . . . . ?
C10 C2 C4 C13 -0.6(2) . . . . ?
Si1 O1 C6 C9 -141.12(10) . . . . ?
Si1 O1 C6 C3 40.16(14) . . . . ?
C15 C3 C6 C9 0.56(18) . . . . ?
C12 C3 C6 C9 -176.24(11) . . . . ?
C15 C3 C6 O1 179.23(11) . . . . ?
C12 C3 C6 O1 2.43(17) . . . . ?
C10 C5 C7 C13 -0.67(19) . . . . ?
O1 Si1 N8 C13 -163.92(9) . . . . ?
O1 Si1 N8 C13 77.59(10) 3_556 . . . ?
N8 Si1 N8 C13 -41.37(8) 3_556 . . . ?
O1 Si1 N8 C12 0.20(10) . . . . ?
O1 Si1 N8 C12 -118.28(9) 3_556 . . . ?
N8 Si1 N8 C12 122.75(10) 3_556 . . . ?
O1 C6 C9 C14 -178.01(11) . . . . ?
C3 C6 C9 C14 0.67(19) . . . . ?
C4 C2 C10 C5 1.8(2) . . . . ?
C7 C5 C10 C2 -1.14(19) . . . . ?
C13 N8 C12 C3 -159.96(10) . . . . ?
Si1 N8 C12 C3 35.00(14) . . . . ?
C6 C3 C12 N8 -39.99(16) . . . . ?
C15 C3 C12 N8 143.33(12) . . . . ?
C2 C4 C13 C7 -1.23(18) . . . . ?
C2 C4 C13 N8 177.93(11) . . . . ?
C5 C7 C13 C4 1.84(18) . . . . ?
C5 C7 C13 N8 -177.32(11) . . . . ?
C12 N8 C13 C4 -21.32(16) . . . . ?
Si1 N8 C13 C4 143.27(10) . . . . ?
C12 N8 C13 C7 157.83(11) . . . . ?
Si1 N8 C13 C7 -37.58(15) . . . . ?
C15 C11 C14 C9 0.53(19) . . . . ?
C6 C9 C14 C11 -1.22(19) . . . . ?
C14 C11 C15 C3 0.73(19) . . . . ?
C6 C3 C15 C11 -1.26(19) . . . . ?
C12 C3 C15 C11 175.53(12) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_fdd2
_database_code_depnum_ccdc_archive 'CCDC 1518899'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;
_audit_creation_date             2015-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H20 Br2 Ge N2 O2'
_chemical_formula_sum            'C26 H20 Br2 Ge N2 O2'
_chemical_formula_weight         624.85
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z'
3 '-x+1/4, y+1/4, z+1/4'
4 'x+1/4, -y+1/4, z+1/4'
5 'x, y+1/2, z+1/2'
6 '-x, -y+1/2, z+1/2'
7 '-x+1/4, y+3/4, z+3/4'
8 'x+1/4, -y+3/4, z+3/4'
9 'x+1/2, y, z+1/2'
10 '-x+1/2, -y, z+1/2'
11 '-x+3/4, y+1/4, z+3/4'
12 'x+3/4, -y+1/4, z+3/4'
13 'x+1/2, y+1/2, z'
14 '-x+1/2, -y+1/2, z'
15 '-x+3/4, y+3/4, z+1/4'
16 'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   14.9416(7)
_cell_length_b                   33.2294(19)
_cell_length_c                   9.4680(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4700.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.16
_cell_measurement_theta_min      2.45
_exptl_absorpt_coefficient_mu    4.730
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1282 before and 0.0566 after correction.
The Ratio of minimum to maximum transmission is 0.6131.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2464
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.781
_exptl_crystal_size_min          0.414
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11322
_diffrn_reflns_theta_full        30.24
_diffrn_reflns_theta_max         30.24
_diffrn_reflns_theta_min         2.45
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3007
_reflns_number_total             3223
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.023(8)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.056
_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)+(0.0106P)²+3.9042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0532
_refine_ls_wR_factor_ref         0.0545
_refine_special_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C0AA C 0.92319(16) 0.88024(8) 0.4811(3) 0.0161(5) Uani 1 d . . 1 . . .
C1 C 0.95466(16) 0.91992(7) 0.1095(3) 0.0144(5) Uani 1 d . . 1 . . .
H1A H 0.9816 0.8942 0.0785 0.017 Uiso 1 calc . . 1 R . .
H1B H 0.8975 0.9234 0.0580 0.017 Uiso 1 calc . . 1 R . .
C1AA C 0.93256(15) 1.04886(7) -0.0506(2) 0.0134(5) Uani 1 d . . 1 . . .
C2 C 0.94158(14) 0.88149(7) 0.3381(3) 0.0141(5) Uani 1 d . . 1 . . .
H2 H 0.9581 0.8576 0.2893 0.017 Uiso 1 calc . . 1 R . .
C3 C 0.93573(15) 0.91783(7) 0.2661(3) 0.0142(5) Uani 1 d . . 1 . . .
C4 C 0.91230(15) 0.95234(7) 0.3420(3) 0.0125(5) Uani 1 d . . 1 . . .
C5 C 0.89319(16) 0.95070(8) 0.4854(3) 0.0168(5) Uani 1 d . . 1 . . .
H5 H 0.8768 0.9744 0.5350 0.020 Uiso 1 calc . . 1 R . .
C6 C 0.89817(16) 0.91431(8) 0.5556(3) 0.0171(5) Uani 1 d . . 1 . . .
H6 H 0.8846 0.9127 0.6535 0.021 Uiso 1 calc . . 1 R . .
C8 C 0.94809(16) 1.07750(7) -0.1559(3) 0.0167(5) Uani 1 d . . 1 . . .
H8 H 0.9957 1.0962 -0.1459 0.020 Uiso 1 calc . . 1 R . .
C9 C 0.89405(18) 1.07858(8) -0.2751(3) 0.0193(5) Uani 1 d . . 1 . . .
H9 H 0.9049 1.0982 -0.3461 0.023 Uiso 1 calc . . 1 R . .
C10 C 0.82417(17) 1.05136(8) -0.2919(3) 0.0206(6) Uani 1 d . . 1 . . .
H10 H 0.7871 1.0524 -0.3733 0.025 Uiso 1 calc . . 1 R . .
C11 C 0.80956(16) 1.02284(8) -0.1887(3) 0.0208(5) Uani 1 d . . 1 . . .
H11 H 0.7627 1.0038 -0.2004 0.025 Uiso 1 calc . . 1 R . .
C12 C 0.86175(15) 1.02152(7) -0.0691(3) 0.0170(5) Uani 1 d . . 1 . . .
H12 H 0.8498 1.0020 0.0016 0.020 Uiso 1 calc . . 1 R . .
N1 N 0.98447(13) 1.04681(6) 0.0727(2) 0.0141(4) Uani 1 d . . 1 . . .
O2 O 0.90671(11) 0.98919(5) 0.27514(19) 0.0156(4) Uani 1 d . . 1 . . .
Ge1 Ge 1.0000 1.0000 0.16542(4) 0.01162(8) Uani 1 d . . 2 S T P
Br1 Br 0.934884(17) 0.830584(8) 0.57895(3) 0.02341(7) Uani 1 d . . 1 . . .


_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
C0AA C2 1.382(4) . ?
C0AA C6 1.385(4) . ?
C0AA Br1 1.900(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C3 1.511(4) . ?
C1 N1 1.473(3) 2_775 ?
C1AA C8 1.398(3) . ?
C1AA C12 1.405(3) . ?
C1AA N1 1.404(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(3) . ?
C3 C4 1.398(3) . ?
C4 C5 1.388(3) . ?
C4 O2 1.381(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(3) . ?
C6 H6 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.388(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(4) . ?
C12 H12 0.9500 . ?
N1 C1 1.473(3) 2_775 ?
N1 Ge1 1.801(2) . ?
O2 Ge1 1.7752(17) . ?
Ge1 N1 1.801(2) 2_775 ?
Ge1 O2 1.7752(17) 2_775 ?

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
C2 C0AA C6 121.9(2) . . ?
C2 C0AA Br1 119.0(2) . . ?
C6 C0AA Br1 119.10(19) . . ?
H1A C1 H1B 107.8 . . ?
C3 C1 H1A 109.1 . . ?
C3 C1 H1B 109.1 . . ?
N1 C1 H1A 109.1 2_775 . ?
N1 C1 H1B 109.1 2_775 . ?
N1 C1 C3 112.4(2) 2_775 . ?
C8 C1AA C12 118.4(2) . . ?
C8 C1AA N1 122.3(2) . . ?
N1 C1AA C12 119.2(2) . . ?
C0AA C2 H2 120.2 . . ?
C0AA C2 C3 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C1 120.6(2) . . ?
C2 C3 C4 118.4(2) . . ?
C4 C3 C1 120.9(2) . . ?
C5 C4 C3 121.5(2) . . ?
O2 C4 C3 120.4(2) . . ?
O2 C4 C5 118.1(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C0AA C6 H6 120.5 . . ?
C5 C6 C0AA 119.0(2) . . ?
C5 C6 H6 120.5 . . ?
C1AA C8 H8 120.0 . . ?
C9 C8 C1AA 120.1(2) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C1AA C12 H12 119.7 . . ?
C11 C12 C1AA 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C1 N1 Ge1 116.98(16) 2_775 . ?
C1AA N1 C1 120.1(2) . 2_775 ?
C1AA N1 Ge1 121.23(16) . . ?
C4 O2 Ge1 113.59(14) . . ?
N1 Ge1 N1 121.68(14) . 2_775 ?
O2 Ge1 N1 111.02(8) 2_775 2_775 ?
O2 Ge1 N1 102.22(8) . 2_775 ?
O2 Ge1 N1 111.02(8) . . ?
O2 Ge1 N1 102.21(8) 2_775 . ?
O2 Ge1 O2 108.36(12) . 2_775 ?

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
C0AA C2 C3 C1 -179.4(2) . . . . ?
C0AA C2 C3 C4 0.8(3) . . . . ?
C1 C3 C4 C5 178.8(2) . . . . ?
C1 C3 C4 O2 -0.5(3) . . . . ?
C1 N1 Ge1 N1 -125.97(18) 2_775 . . 2_775 ?
C1 N1 Ge1 O2 -1.58(19) 2_775 . . 2_775 ?
C1 N1 Ge1 O2 113.80(17) 2_775 . . . ?
C1AA C8 C9 C10 -0.1(4) . . . . ?
C1AA N1 Ge1 N1 39.11(16) . . . 2_775 ?
C1AA N1 Ge1 O2 -81.12(19) . . . . ?
C1AA N1 Ge1 O2 163.50(17) . . . 2_775 ?
C2 C0AA C6 C5 -1.3(4) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C2 C3 C4 O2 179.2(2) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C3 C4 O2 Ge1 -47.4(2) . . . . ?
C4 C5 C6 C0AA 0.7(4) . . . . ?
C4 O2 Ge1 N1 44.87(17) . . . 2_775 ?
C4 O2 Ge1 N1 176.08(15) . . . . ?
C4 O2 Ge1 O2 -72.43(15) . . . 2_775 ?
C5 C4 O2 Ge1 133.18(19) . . . . ?
C6 C0AA C2 C3 0.5(4) . . . . ?
C8 C1AA C12 C11 0.5(4) . . . . ?
C8 C1AA N1 C1 12.8(3) . . . 2_775 ?
C8 C1AA N1 Ge1 -151.85(19) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 C12 1.3(4) . . . . ?
C10 C11 C12 C1AA -1.2(4) . . . . ?
C12 C1AA C8 C9 0.2(4) . . . . ?
C12 C1AA N1 C1 -166.6(2) . . . 2_775 ?
C12 C1AA N1 Ge1 28.8(3) . . . . ?
N1 C1 C3 C2 -132.2(2) 2_775 . . . ?
N1 C1 C3 C4 47.5(3) 2_775 . . . ?
N1 C1AA C8 C9 -179.2(2) . . . . ?
N1 C1AA C12 C11 179.9(2) . . . . ?
O2 C4 C5 C6 -180.0(2) . . . . ?
Br1 C0AA C2 C3 -178.21(17) . . . . ?
Br1 C0AA C6 C5 177.43(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_g319
_database_code_depnum_ccdc_archive 'CCDC 1518897'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 Ge N2 O2'
_chemical_formula_weight         467.05

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'
Ge Ge 0.1547 1.8001 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   14.8477(10)
_cell_length_b                   8.5189(4)
_cell_length_c                   17.0779(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2160.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9345
_cell_measurement_theta_min      1.19
_cell_measurement_theta_max      25.75

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.110
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    1.444
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7601
_exptl_absorpt_correction_T_max  0.8504
_exptl_absorpt_process_details   'Stoe X-Area V1.56, X-Shape V2.12.2'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23252
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_av_sigmaI/netI    0.0553
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         26.73
_reflns_number_total             2296
_reflns_number_gt                1557
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0251P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2296
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0609
_refine_ls_wR_factor_gt          0.0530
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_restrained_S_all      0.902
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge1 Ge 0.5000 0.06027(4) 0.2500 0.02728(9) Uani 1 2 d S . .
O1 O 0.40263(8) -0.05834(17) 0.25735(9) 0.0310(3) Uani 1 1 d . . .
N1 N 0.50112(14) 0.16497(18) 0.34179(9) 0.0296(3) Uani 1 1 d . . .
C9 C 0.51806(12) 0.4347(3) 0.39050(13) 0.0318(5) Uani 1 1 d . . .
C1 C 0.38137(14) -0.1181(3) 0.33110(12) 0.0293(5) Uani 1 1 d . . .
C6 C 0.39170(13) -0.0261(3) 0.39806(13) 0.0298(5) Uani 1 1 d . . .
C8 C 0.55099(14) 0.3055(3) 0.34933(12) 0.0285(5) Uani 1 1 d . . .
C13 C 0.63729(15) 0.3148(3) 0.31647(12) 0.0307(5) Uani 1 1 d . . .
C4 C 0.33273(15) -0.2433(3) 0.47417(15) 0.0355(5) Uani 1 1 d . . .
C2 C 0.34757(15) -0.2690(3) 0.33491(14) 0.0321(5) Uani 1 1 d . . .
C7 C 0.42185(15) 0.1427(3) 0.39353(13) 0.0312(5) Uani 1 1 d . . .
C12 C 0.68960(15) 0.4473(3) 0.32612(13) 0.0337(5) Uani 1 1 d . . .
C10 C 0.57075(16) 0.5677(3) 0.39945(13) 0.0368(5) Uani 1 1 d . . .
C3 C 0.32238(15) -0.3308(3) 0.40686(14) 0.0346(5) Uani 1 1 d . . .
C5 C 0.36748(15) -0.0933(3) 0.47008(14) 0.0335(6) Uani 1 1 d . . .
C11 C 0.65689(16) 0.5739(3) 0.36854(13) 0.0364(5) Uani 1 1 d . . .
H11 H 0.6590(14) 0.233(2) 0.2893(13) 0.027(6) Uiso 1 1 d . . .
H10 H 0.7506(16) 0.452(3) 0.3060(13) 0.032(6) Uiso 1 1 d . . .
H7 H 0.4587(14) 0.433(2) 0.4111(12) 0.024(5) Uiso 1 1 d . . .
H6 H 0.3703(14) 0.208(3) 0.3735(12) 0.027(6) Uiso 1 1 d . . .
H5 H 0.4413(15) 0.177(3) 0.4450(13) 0.028(6) Uiso 1 1 d . . .
H9 H 0.6891(15) 0.662(3) 0.3752(13) 0.029(6) Uiso 1 1 d . . .
H2 H 0.3000(15) -0.430(3) 0.4090(13) 0.036(6) Uiso 1 1 d . . .
H8 H 0.5470(16) 0.653(3) 0.4264(13) 0.033(6) Uiso 1 1 d . . .
H4 H 0.3756(15) -0.029(3) 0.5130(13) 0.036(6) Uiso 1 1 d . . .
H1 H 0.3418(16) -0.329(3) 0.2903(14) 0.039(7) Uiso 1 1 d . . .
H3 H 0.3156(15) -0.282(3) 0.5206(15) 0.040(7) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.7683(13) . ?
Ge1 O1 1.7683(13) 4_655 ?
Ge1 N1 1.8037(15) . ?
Ge1 N1 1.8037(15) 4_655 ?
O1 C1 1.395(2) . ?
N1 C8 1.414(3) . ?
N1 C7 1.484(3) . ?
C9 C10 1.385(3) . ?
C9 C8 1.395(3) . ?
C9 H7 0.95(2) . ?
C1 C2 1.382(3) . ?
C1 C6 1.395(3) . ?
C6 C5 1.403(3) . ?
C6 C7 1.508(3) . ?
C8 C13 1.401(3) . ?
C13 C12 1.380(3) . ?
C13 H11 0.90(2) . ?
C4 C3 1.379(3) . ?
C4 C5 1.380(3) . ?
C4 H3 0.90(2) . ?
C2 C3 1.388(3) . ?
C2 H1 0.92(2) . ?
C7 H6 1.01(2) . ?
C7 H5 0.97(2) . ?
C12 C11 1.387(3) . ?
C12 H10 0.97(2) . ?
C10 C11 1.385(3) . ?
C10 H8 0.93(2) . ?
C3 H2 0.91(3) . ?
C5 H4 0.92(2) . ?
C11 H9 0.90(2) . ?

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
O1 Ge1 O1 110.30(9) . 4_655 ?
O1 Ge1 N1 103.20(8) . . ?
O1 Ge1 N1 109.68(8) 4_655 . ?
O1 Ge1 N1 109.68(8) . 4_655 ?
O1 Ge1 N1 103.20(8) 4_655 4_655 ?
N1 Ge1 N1 120.73(10) . 4_655 ?
C1 O1 Ge1 117.24(13) . . ?
C8 N1 C7 117.99(16) . . ?
C8 N1 Ge1 120.19(13) . . ?
C7 N1 Ge1 116.56(14) . . ?
C10 C9 C8 120.20(19) . . ?
C10 C9 H7 119.7(14) . . ?
C8 C9 H7 120.1(14) . . ?
C2 C1 O1 117.7(2) . . ?
C2 C1 C6 121.6(2) . . ?
O1 C1 C6 120.68(19) . . ?
C1 C6 C5 117.5(2) . . ?
C1 C6 C7 121.8(2) . . ?
C5 C6 C7 120.7(2) . . ?
C9 C8 C13 118.6(2) . . ?
C9 C8 N1 122.06(19) . . ?
C13 C8 N1 119.3(2) . . ?
C12 C13 C8 120.9(2) . . ?
C12 C13 H11 119.7(14) . . ?
C8 C13 H11 119.4(14) . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H3 120.3(16) . . ?
C5 C4 H3 119.6(15) . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H1 120.6(15) . . ?
C3 C2 H1 119.9(15) . . ?
N1 C7 C6 112.81(18) . . ?
N1 C7 H6 109.3(12) . . ?
C6 C7 H6 108.7(12) . . ?
N1 C7 H5 105.4(13) . . ?
C6 C7 H5 109.0(13) . . ?
H6 C7 H5 111.7(17) . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H10 121.0(15) . . ?
C11 C12 H10 118.8(15) . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H8 120.5(15) . . ?
C9 C10 H8 118.7(15) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H2 120.6(15) . . ?
C2 C3 H2 119.1(15) . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H4 123.8(14) . . ?
C6 C5 H4 115.0(14) . . ?
C10 C11 C12 119.5(2) . . ?
C10 C11 H9 118.5(15) . . ?
C12 C11 H9 122.0(15) . . ?

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
O1 Ge1 O1 C1 81.84(14) 4_655 . . . ?
N1 Ge1 O1 C1 -35.26(15) . . . . ?
N1 Ge1 O1 C1 -165.14(14) 4_655 . . . ?
O1 Ge1 N1 C8 -160.01(16) . . . . ?
O1 Ge1 N1 C8 82.45(17) 4_655 . . . ?
N1 Ge1 N1 C8 -37.21(14) 4_655 . . . ?
O1 Ge1 N1 C7 -6.15(16) . . . . ?
O1 Ge1 N1 C7 -123.69(15) 4_655 . . . ?
N1 Ge1 N1 C7 116.65(16) 4_655 . . . ?
Ge1 O1 C1 C2 -141.88(17) . . . . ?
Ge1 O1 C1 C6 39.9(2) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
O1 C1 C6 C5 178.93(18) . . . . ?
C2 C1 C6 C7 -175.3(2) . . . . ?
O1 C1 C6 C7 2.9(3) . . . . ?
C10 C9 C8 C13 -1.1(3) . . . . ?
C10 C9 C8 N1 177.1(2) . . . . ?
C7 N1 C8 C9 -13.8(3) . . . . ?
Ge1 N1 C8 C9 139.65(18) . . . . ?
C7 N1 C8 C13 164.32(19) . . . . ?
Ge1 N1 C8 C13 -42.2(3) . . . . ?
C9 C8 C13 C12 1.5(3) . . . . ?
N1 C8 C13 C12 -176.70(19) . . . . ?
O1 C1 C2 C3 -177.59(19) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C8 N1 C7 C6 -162.55(19) . . . . ?
Ge1 N1 C7 C6 43.0(2) . . . . ?
C1 C6 C7 N1 -47.1(3) . . . . ?
C5 C6 C7 N1 137.0(2) . . . . ?
C8 C13 C12 C11 -0.2(3) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C5 C4 C3 C2 0.6(4) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C1 C6 C5 C4 -1.5(3) . . . . ?
C7 C6 C5 C4 174.6(2) . . . . ?
C9 C10 C11 C12 2.0(4) . . . . ?
C13 C12 C11 C10 -1.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.73
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.045

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_g592_0ma
_database_code_depnum_ccdc_archive 'CCDC 1518898'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;
_audit_creation_date             2015-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C28 H26 Ge N2 O2'
_chemical_formula_sum            'C28 H26 Ge N2 O2'
_chemical_formula_weight         495.10
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Ge Ge 0.1547 1.8001 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z'
3 '-x+1/4, y+1/4, z+1/4'
4 'x+1/4, -y+1/4, z+1/4'
5 'x, y+1/2, z+1/2'
6 '-x, -y+1/2, z+1/2'
7 '-x+1/4, y+3/4, z+3/4'
8 'x+1/4, -y+3/4, z+3/4'
9 'x+1/2, y, z+1/2'
10 '-x+1/2, -y, z+1/2'
11 '-x+3/4, y+1/4, z+3/4'
12 'x+3/4, -y+1/4, z+3/4'
13 'x+1/2, y+1/2, z'
14 '-x+1/2, -y+1/2, z'
15 '-x+3/4, y+3/4, z+1/4'
16 'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   15.2579(8)
_cell_length_b                   32.8165(17)
_cell_length_c                   9.2818(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4647.5(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.62
_cell_measurement_theta_min      2.64
_exptl_absorpt_coefficient_mu    1.347
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0926 before and 0.0757 after correction.
 The Ratio of minimum to maximum transmission is 0.65.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 26331 reflections, Rint = 0.1070
 (4984 with I > 3sig(I), Rint = 0.0551)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.409
_exptl_crystal_size_min          0.299
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10682
_diffrn_reflns_theta_full        30.62
_diffrn_reflns_theta_max         30.62
_diffrn_reflns_theta_min         2.48
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3040
_reflns_number_total             3209
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.034(8)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0272
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0157P)²+3.3250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0582
_refine_ls_wR_factor_ref         0.0596
_refine_special_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C3AA(H3AA), C4AA(H4AA), C2AA(H2AA), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Ge1 Ge 1.0000 0.0000 0.88792(4) 0.01161(6) Uani 1 d . . 2 S T P
O1 O 0.90841(8) -0.01172(4) 0.99818(14) 0.0152(3) Uani 1 d . . 1 . . .
N1 N 0.98162(10) 0.04708(4) 0.79233(17) 0.0142(3) Uani 1 d . . 1 . . .
C2 C 0.93056(11) 0.04805(5) 0.6662(2) 0.0131(4) Uani 1 d . . 1 . . .
C3 C 0.82228(13) 0.04946(6) 0.4220(2) 0.0223(4) Uani 1 d . . 1 . . .
H3 H 0.7856 0.0501 0.3393 0.027 Uiso 1 calc . . 1 R . .
C4 C 0.89230(13) 0.07610(6) 0.4340(2) 0.0216(4) Uani 1 d . . 1 . . .
H4 H 0.9036 0.0950 0.3588 0.026 Uiso 1 calc . . 1 R . .
C5 C 0.94627(12) 0.07549(5) 0.5546(2) 0.0169(4) Uani 1 d . . 1 . . .
H5 H 0.9942 0.0939 0.5610 0.020 Uiso 1 calc . . 1 R . .
C3AA C 0.85960(11) 0.02111(5) 0.6529(2) 0.0170(3) Uani 1 d . . 1 . . .
H3AA H 0.8480 0.0021 0.7278 0.020 Uiso 1 calc . . 1 R . .
C4AA C 0.80617(12) 0.02182(6) 0.5322(2) 0.0205(4) Uani 1 d . . 1 . . .
H4AA H 0.7584 0.0034 0.5248 0.025 Uiso 1 calc . . 1 R . .
C0AA C 1.04221(12) 0.08088(5) 0.82413(19) 0.0143(3) Uani 1 d . . 1 . . .
H0AA H 1.0158 0.1068 0.7910 0.017 Uiso 1 calc . . 1 R . .
H0AB H 1.0975 0.0767 0.7703 0.017 Uiso 1 calc . . 1 R . .
C1AA C 1.06233(11) 0.08391(5) 0.9836(2) 0.0138(3) Uani 1 d . . 1 . . .
C2AA C 1.05721(11) 0.12140(5) 1.0542(2) 0.0145(3) Uani 1 d . . 1 . . .
H2AA H 1.0402 0.1449 1.0014 0.017 Uiso 1 calc . . 1 R . .
C6 C 1.07651(11) 0.12514(5) 1.2006(2) 0.0168(4) Uani 1 d . . 1 . . .
C7 C 1.06755(13) 0.16574(6) 1.2759(2) 0.0230(4) Uani 1 d . . 1 . . .
H7A H 1.0586 0.1872 1.2041 0.034 Uiso 1 calc . . 1 GR . .
H7B H 1.1210 0.1714 1.3310 0.034 Uiso 1 calc . . 1 GR . .
H7C H 1.0172 0.1649 1.3415 0.034 Uiso 1 calc . . 1 GR . .
C8 C 0.89814(12) -0.09035(5) 1.2756(2) 0.0177(4) Uani 1 d . . 1 . . .
H8 H 0.8834 -0.0925 1.3748 0.021 Uiso 1 calc . . 1 R . .
C9 C 0.89385(12) -0.05271(6) 1.2093(2) 0.0175(4) Uani 1 d . . 1 . . .
H9 H 0.8777 -0.0292 1.2627 0.021 Uiso 1 calc . . 1 R . .
C10 C 0.91338(11) -0.04969(5) 1.0636(2) 0.0135(4) Uani 1 d . . 1 . . .


_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 O1 1.7743(12) 2_755 ?
Ge1 O1 1.7743(12) . ?
Ge1 N1 1.8035(15) . ?
Ge1 N1 1.8036(15) 2_755 ?
O1 C10 1.388(2) . ?
N1 C2 1.406(2) . ?
N1 C0AA 1.474(2) . ?
C2 C5 1.394(2) . ?
C2 C3AA 1.403(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C3 C4AA 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(3) . ?
C5 H5 0.9500 . ?
C3AA H3AA 0.9500 . ?
C3AA C4AA 1.386(3) . ?
C4AA H4AA 0.9500 . ?
C0AA H0AA 0.9900 . ?
C0AA H0AB 0.9900 . ?
C0AA C1AA 1.515(3) . ?
C1AA C2AA 1.397(2) . ?
C1AA C10 1.397(3) 2_755 ?
C2AA H2AA 0.9500 . ?
C2AA C6 1.396(3) . ?
C6 C7 1.511(2) . ?
C6 C8 1.392(3) 2_755 ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C6 1.392(3) 2_755 ?
C8 H8 0.9500 . ?
C8 C9 1.382(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(2) . ?
C10 C1AA 1.397(3) 2_755 ?

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
O1 Ge1 O1 109.55(9) 2_755 . ?
O1 Ge1 N1 110.30(6) 2_755 2_755 ?
O1 Ge1 N1 102.74(6) . 2_755 ?
O1 Ge1 N1 102.74(6) 2_755 . ?
O1 Ge1 N1 110.30(6) . . ?
N1 Ge1 N1 121.06(10) . 2_755 ?
C10 O1 Ge1 113.83(10) . . ?
C2 N1 Ge1 121.00(12) . . ?
C2 N1 C0AA 119.81(14) . . ?
C0AA N1 Ge1 116.65(11) . . ?
C5 C2 N1 122.55(16) . . ?
C5 C2 C3AA 118.32(17) . . ?
C3AA C2 N1 119.11(16) . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C4AA 119.32(18) . . ?
C4AA C3 H3 120.3 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.83(18) . . ?
C5 C4 H4 119.6 . . ?
C2 C5 H5 119.8 . . ?
C4 C5 C2 120.41(17) . . ?
C4 C5 H5 119.8 . . ?
C2 C3AA H3AA 119.5 . . ?
C4AA C3AA C2 120.97(17) . . ?
C4AA C3AA H3AA 119.5 . . ?
C3 C4AA H4AA 119.9 . . ?
C3AA C4AA C3 120.13(17) . . ?
C3AA C4AA H4AA 119.9 . . ?
N1 C0AA H0AA 109.2 . . ?
N1 C0AA H0AB 109.2 . . ?
N1 C0AA C1AA 111.85(14) . . ?
H0AA C0AA H0AB 107.9 . . ?
C1AA C0AA H0AA 109.2 . . ?
C1AA C0AA H0AB 109.2 . . ?
C2AA C1AA C0AA 120.35(16) . . ?
C2AA C1AA C10 118.26(17) . 2_755 ?
C10 C1AA C0AA 121.39(16) 2_755 . ?
C1AA C2AA H2AA 119.2 . . ?
C6 C2AA C1AA 121.51(17) . . ?
C6 C2AA H2AA 119.2 . . ?
C2AA C6 C7 120.57(18) . . ?
C8 C6 C2AA 118.26(17) 2_755 . ?
C8 C6 C7 121.15(18) 2_755 . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8 119.2 2_755 . ?
C9 C8 C6 121.56(18) . 2_755 ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.21(18) . . ?
C10 C9 H9 120.4 . . ?
O1 C10 C1AA 120.21(16) . 2_755 ?
C9 C10 O1 118.61(17) . . ?
C9 C10 C1AA 121.18(17) . 2_755 ?

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
Ge1 O1 C10 C1AA -46.42(19) . . . 2_755 ?
Ge1 O1 C10 C9 133.52(15) . . . . ?
Ge1 N1 C2 C5 -148.41(15) . . . . ?
Ge1 N1 C2 C3AA 33.2(2) . . . . ?
Ge1 N1 C0AA C1AA -41.33(19) . . . . ?
O1 Ge1 O1 C10 -74.11(11) 2_755 . . . ?
O1 Ge1 N1 C2 162.60(13) 2_755 . . . ?
O1 Ge1 N1 C2 -80.69(15) . . . . ?
O1 Ge1 N1 C0AA 117.42(13) . . . . ?
O1 Ge1 N1 C0AA 0.72(14) 2_755 . . . ?
N1 Ge1 O1 C10 173.51(12) . . . . ?
N1 Ge1 O1 C10 43.14(13) 2_755 . . . ?
N1 Ge1 N1 C2 39.13(12) 2_755 . . . ?
N1 Ge1 N1 C0AA -122.75(14) 2_755 . . . ?
N1 C2 C5 C4 -178.02(17) . . . . ?
N1 C2 C3AA C4AA 178.23(17) . . . . ?
N1 C0AA C1AA C2AA -131.81(16) . . . . ?
N1 C0AA C1AA C10 48.4(2) . . . 2_755 ?
C2 N1 C0AA C1AA 156.56(16) . . . . ?
C2 C3AA C4AA C3 -0.1(3) . . . . ?
C3 C4 C5 C2 -0.2(3) . . . . ?
C4 C3 C4AA C3AA 0.2(3) . . . . ?
C5 C2 C3AA C4AA -0.2(3) . . . . ?
C3AA C2 C5 C4 0.4(3) . . . . ?
C4AA C3 C4 C5 -0.1(3) . . . . ?
C0AA N1 C2 C5 12.9(3) . . . . ?
C0AA N1 C2 C3AA -165.50(16) . . . . ?
C0AA C1AA C2AA C6 -179.16(16) . . . . ?
C1AA C2AA C6 C7 -177.92(16) . . . . ?
C1AA C2AA C6 C8 0.4(3) . . . 2_755 ?
C6 C8 C9 C10 1.5(3) 2_755 . . . ?
C8 C9 C10 O1 179.71(15) . . . . ?
C8 C9 C10 C1AA -0.4(3) . . . 2_755 ?
C10 C1AA C2AA C6 0.6(3) 2_755 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

_vrf_PLAT029_g592_0ma            
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.976 Note 
RESPONSE: due to an unresolved second twin domain
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1518900'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 Ge N2 O2'
_chemical_formula_weight         399.02

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'
Ge Ge 0.1547 1.8001 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0089(2)
_cell_length_b                   10.1226(2)
_cell_length_c                   20.3118(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.923(2)
_cell_angle_gamma                90
_cell_volume                     1849.89(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    44969
_cell_measurement_theta_min      4.01
_cell_measurement_theta_max      59.45

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.672
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4943
_exptl_absorpt_correction_T_max  0.7688
_exptl_absorpt_process_details   'Stoe X-Area'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDSII'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52127
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.008
_diffrn_reflns_theta_max         29.193
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4955
_reflns_number_gt                4774
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0390P)²+0.5547P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4955
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0697
_refine_ls_wR_factor_gt          0.0684
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.002
_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 0.73662(2) 0.62978(2) 0.06534(2) 0.02323(5) Uani 1 1 d . . . . .
O1 O 0.72372(11) 0.45383(10) 0.07068(5) 0.0290(2) Uani 1 1 d . . . . .
O2 O 0.72249(11) 0.65126(10) -0.02180(5) 0.02840(19) Uani 1 1 d . . . . .
N1 N 0.57713(12) 0.68439(10) 0.10895(5) 0.0238(2) Uani 1 1 d . . . . .
N2 N 0.91736(12) 0.69928(12) 0.08768(6) 0.0263(2) Uani 1 1 d . . . . .
C8 C 0.99824(15) 0.66322(15) 0.14993(7) 0.0305(3) Uani 1 1 d . . . . .
H7 H 1.0831 0.7235 0.1554 0.037 Uiso 1 1 calc R U . . .
C9 C 1.06077(17) 0.52282(16) 0.15034(9) 0.0395(3) Uani 1 1 d . . . . .
H9A H 0.9804 0.4606 0.1462 0.059 Uiso 1 1 calc R U . . .
H9B H 1.1171 0.5075 0.1910 0.059 Uiso 1 1 calc R U . . .
H9C H 1.1240 0.5122 0.1141 0.059 Uiso 1 1 calc R U . . .
C10 C 0.90238(18) 0.6848(2) 0.20835(8) 0.0420(4) Uani 1 1 d . . . . .
H13A H 0.8630 0.7729 0.2069 0.063 Uiso 1 1 calc R U . . .
H13B H 0.9615 0.6727 0.2486 0.063 Uiso 1 1 calc R U . . .
H13C H 0.8220 0.6224 0.2065 0.063 Uiso 1 1 calc R U . . .
C19 C 0.43054(15) 0.82777(15) 0.02764(7) 0.0298(3) Uani 1 1 d . . . . .
H57A H 0.5020 0.8271 -0.0058 0.045 Uiso 1 1 calc R U . . .
H57B H 0.3757 0.9091 0.0253 0.045 Uiso 1 1 calc R U . . .
H57C H 0.3634 0.7548 0.0209 0.045 Uiso 1 1 calc R U . . .
C17 C 0.46502(14) 0.57909(13) 0.11518(7) 0.0253(2) Uani 1 1 d . . . . .
H60A H 0.4245 0.5548 0.0717 0.030 Uiso 1 1 calc R U . . .
H60B H 0.3841 0.6121 0.1403 0.030 Uiso 1 1 calc R U . . .
C5 C 1.01460(17) 0.89000(14) -0.05513(7) 0.0309(3) Uani 1 1 d . . . . .
H69 H 1.1101 0.9131 -0.0398 0.037 Uiso 1 1 calc R U . . .
C16 C 0.53149(14) 0.45890(13) 0.14885(6) 0.0249(2) Uani 1 1 d . . . . .
C6 C 0.94182(15) 0.78674(13) -0.02492(7) 0.0273(2) Uani 1 1 d . . . . .
C20 C 0.62748(16) 0.92289(14) 0.10595(7) 0.0309(3) Uani 1 1 d . . . . .
H96A H 0.6732 0.9152 0.1495 0.046 Uiso 1 1 calc R U . . .
H96B H 0.5812 1.0080 0.1010 0.046 Uiso 1 1 calc R U . . .
H96C H 0.7018 0.9133 0.0740 0.046 Uiso 1 1 calc R U . . .
C13 C 0.65339(16) 0.23021(14) 0.20635(7) 0.0312(3) Uani 1 1 d . . . . .
H108 H 0.6939 0.1540 0.2255 0.037 Uiso 1 1 calc R U . . .
C2 C 0.72911(16) 0.82408(15) -0.10083(7) 0.0303(3) Uani 1 1 d . . . . .
H120 H 0.6330 0.8022 -0.1158 0.036 Uiso 1 1 calc R U . . .
C15 C 0.46862(15) 0.40053(14) 0.20256(7) 0.0273(2) Uani 1 1 d . . . . .
H122 H 0.3852 0.4389 0.2198 0.033 Uiso 1 1 calc R U . . .
C11 C 0.65800(15) 0.40080(13) 0.12430(7) 0.0265(2) Uani 1 1 d . . . . .
C1 C 0.79814(15) 0.75484(13) -0.04891(7) 0.0268(2) Uani 1 1 d . . . . .
C18 C 0.51089(14) 0.81558(13) 0.09538(7) 0.0254(2) Uani 1 1 d . . . . .
H139 H 0.4364 0.8299 0.1282 0.031 Uiso 1 1 calc R U . . .
C3 C 0.80432(18) 0.92622(15) -0.13026(7) 0.0331(3) Uani 1 1 d . . . . .
H153 H 0.7587 0.9728 -0.1652 0.040 Uiso 1 1 calc R U . . .
C7 C 1.01418(15) 0.71004(15) 0.03137(7) 0.0295(3) Uani 1 1 d . . . . .
H15A H 1.0383 0.6221 0.0162 0.035 Uiso 1 1 calc R U . . .
H15B H 1.1063 0.7532 0.0458 0.035 Uiso 1 1 calc R U . . .
C12 C 0.71959(16) 0.28721(14) 0.15302(7) 0.0311(3) Uani 1 1 d . . . . .
H162 H 0.8044 0.2498 0.1366 0.037 Uiso 1 1 calc R U . . .
C4 C 0.94783(18) 0.95899(14) -0.10754(7) 0.0336(3) Uani 1 1 d . . . . .
H183 H 0.9987 1.0269 -0.1274 0.040 Uiso 1 1 calc R U . . .
C14 C 0.52737(16) 0.28598(14) 0.23133(7) 0.0296(3) Uani 1 1 d . . . . .
H196 H 0.4828 0.2473 0.2668 0.036 Uiso 1 1 calc R U . . .


_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 O2 1.7815(10) . ?
Ge1 O1 1.7885(10) . ?
Ge1 N2 1.8102(11) . ?
Ge1 N1 1.8124(11) . ?
O1 C11 1.3749(16) . ?
O2 C1 1.3803(16) . ?
N1 C18 1.4761(16) . ?
N1 C17 1.4782(16) . ?
N2 C8 1.4727(18) . ?
N2 C7 1.4774(17) . ?
C8 C10 1.519(2) . ?
C8 C9 1.529(2) . ?
C8 H7 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H13A 0.9600 . ?
C10 H13B 0.9600 . ?
C10 H13C 0.9600 . ?
C19 C18 1.5266(19) . ?
C19 H57A 0.9600 . ?
C19 H57B 0.9600 . ?
C19 H57C 0.9600 . ?
C17 C16 1.5049(18) . ?
C17 H60A 0.9700 . ?
C17 H60B 0.9700 . ?
C5 C4 1.385(2) . ?
C5 C6 1.3928(19) . ?
C5 H69 0.9300 . ?
C16 C15 1.3869(18) . ?
C16 C11 1.3969(18) . ?
C6 C1 1.3974(19) . ?
C6 C7 1.503(2) . ?
C20 C18 1.5187(19) . ?
C20 H96A 0.9600 . ?
C20 H96B 0.9600 . ?
C20 H96C 0.9600 . ?
C13 C14 1.387(2) . ?
C13 C12 1.388(2) . ?
C13 H108 0.9300 . ?
C2 C1 1.387(2) . ?
C2 C3 1.388(2) . ?
C2 H120 0.9300 . ?
C15 C14 1.391(2) . ?
C15 H122 0.9300 . ?
C11 C12 1.3918(19) . ?
C18 H139 0.9800 . ?
C3 C4 1.391(2) . ?
C3 H153 0.9300 . ?
C7 H15A 0.9700 . ?
C7 H15B 0.9700 . ?
C12 H162 0.9300 . ?
C4 H183 0.9300 . ?
C14 H196 0.9300 . ?

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
O2 Ge1 O1 100.39(4) . . ?
O2 Ge1 N2 102.68(5) . . ?
O1 Ge1 N2 115.61(5) . . ?
O2 Ge1 N1 115.48(5) . . ?
O1 Ge1 N1 102.62(5) . . ?
N2 Ge1 N1 118.97(5) . . ?
C11 O1 Ge1 117.96(8) . . ?
C1 O2 Ge1 118.51(8) . . ?
C18 N1 C17 113.16(10) . . ?
C18 N1 Ge1 120.41(8) . . ?
C17 N1 Ge1 112.58(8) . . ?
C8 N2 C7 113.40(11) . . ?
C8 N2 Ge1 121.22(9) . . ?
C7 N2 Ge1 113.18(9) . . ?
N2 C8 C10 111.04(12) . . ?
N2 C8 C9 113.65(13) . . ?
C10 C8 C9 110.70(14) . . ?
N2 C8 H7 107.0 . . ?
C10 C8 H7 107.0 . . ?
C9 C8 H7 107.0 . . ?
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 . . ?
C8 C10 H13A 109.5 . . ?
C8 C10 H13B 109.5 . . ?
H13A C10 H13B 109.5 . . ?
C8 C10 H13C 109.5 . . ?
H13A C10 H13C 109.5 . . ?
H13B C10 H13C 109.5 . . ?
C18 C19 H57A 109.5 . . ?
C18 C19 H57B 109.5 . . ?
H57A C19 H57B 109.5 . . ?
C18 C19 H57C 109.5 . . ?
H57A C19 H57C 109.5 . . ?
H57B C19 H57C 109.5 . . ?
N1 C17 C16 111.35(10) . . ?
N1 C17 H60A 109.4 . . ?
C16 C17 H60A 109.4 . . ?
N1 C17 H60B 109.4 . . ?
C16 C17 H60B 109.4 . . ?
H60A C17 H60B 108.0 . . ?
C4 C5 C6 121.43(14) . . ?
C4 C5 H69 119.3 . . ?
C6 C5 H69 119.3 . . ?
C15 C16 C11 118.34(12) . . ?
C15 C16 C17 122.20(12) . . ?
C11 C16 C17 119.42(12) . . ?
C5 C6 C1 117.92(13) . . ?
C5 C6 C7 121.81(13) . . ?
C1 C6 C7 120.26(12) . . ?
C18 C20 H96A 109.5 . . ?
C18 C20 H96B 109.5 . . ?
H96A C20 H96B 109.5 . . ?
C18 C20 H96C 109.5 . . ?
H96A C20 H96C 109.5 . . ?
H96B C20 H96C 109.5 . . ?
C14 C13 C12 120.55(13) . . ?
C14 C13 H108 119.7 . . ?
C12 C13 H108 119.7 . . ?
C1 C2 C3 119.61(14) . . ?
C1 C2 H120 120.2 . . ?
C3 C2 H120 120.2 . . ?
C16 C15 C14 121.59(13) . . ?
C16 C15 H122 119.2 . . ?
C14 C15 H122 119.2 . . ?
O1 C11 C12 118.42(12) . . ?
O1 C11 C16 120.69(12) . . ?
C12 C11 C16 120.88(12) . . ?
O2 C1 C2 118.41(12) . . ?
O2 C1 C6 120.26(12) . . ?
C2 C1 C6 121.32(13) . . ?
N1 C18 C20 110.30(11) . . ?
N1 C18 C19 114.19(11) . . ?
C20 C18 C19 111.24(11) . . ?
N1 C18 H139 106.9 . . ?
C20 C18 H139 106.9 . . ?
C19 C18 H139 106.9 . . ?
C2 C3 C4 120.06(14) . . ?
C2 C3 H153 120.0 . . ?
C4 C3 H153 120.0 . . ?
N2 C7 C6 112.14(11) . . ?
N2 C7 H15A 109.2 . . ?
C6 C7 H15A 109.2 . . ?
N2 C7 H15B 109.2 . . ?
C6 C7 H15B 109.2 . . ?
H15A C7 H15B 107.9 . . ?
C13 C12 C11 119.50(13) . . ?
C13 C12 H162 120.3 . . ?
C11 C12 H162 120.3 . . ?
C5 C4 C3 119.66(13) . . ?
C5 C4 H183 120.2 . . ?
C3 C4 H183 120.2 . . ?
C13 C14 C15 119.13(13) . . ?
C13 C14 H196 120.4 . . ?
C15 C14 H196 120.4 . . ?

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 O1 C11 -148.19(10) . . . . ?
N2 Ge1 O1 C11 102.23(10) . . . . ?
N1 Ge1 O1 C11 -28.90(10) . . . . ?
O1 Ge1 O2 C1 -147.57(10) . . . . ?
N2 Ge1 O2 C1 -28.12(11) . . . . ?
N1 Ge1 O2 C1 102.96(10) . . . . ?
O2 Ge1 N1 C18 -48.01(11) . . . . ?
O1 Ge1 N1 C18 -156.15(9) . . . . ?
N2 Ge1 N1 C18 74.79(11) . . . . ?
O2 Ge1 N1 C17 89.54(9) . . . . ?
O1 Ge1 N1 C17 -18.60(10) . . . . ?
N2 Ge1 N1 C17 -147.67(8) . . . . ?
O2 Ge1 N2 C8 -158.58(10) . . . . ?
O1 Ge1 N2 C8 -50.35(12) . . . . ?
N1 Ge1 N2 C8 72.48(12) . . . . ?
O2 Ge1 N2 C7 -18.70(10) . . . . ?
O1 Ge1 N2 C7 89.52(10) . . . . ?
N1 Ge1 N2 C7 -147.64(9) . . . . ?
C7 N2 C8 C10 166.68(13) . . . . ?
Ge1 N2 C8 C10 -53.52(16) . . . . ?
C7 N2 C8 C9 -67.74(15) . . . . ?
Ge1 N2 C8 C9 72.06(14) . . . . ?
C18 N1 C17 C16 -162.51(11) . . . . ?
Ge1 N1 C17 C16 56.77(12) . . . . ?
N1 C17 C16 C15 128.33(13) . . . . ?
N1 C17 C16 C11 -53.80(16) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C5 C6 C7 179.13(13) . . . . ?
C11 C16 C15 C14 -0.9(2) . . . . ?
C17 C16 C15 C14 177.03(12) . . . . ?
Ge1 O1 C11 C12 -140.47(11) . . . . ?
Ge1 O1 C11 C16 40.20(16) . . . . ?
C15 C16 C11 O1 179.26(12) . . . . ?
C17 C16 C11 O1 1.30(19) . . . . ?
C15 C16 C11 C12 0.0(2) . . . . ?
C17 C16 C11 C12 -178.01(12) . . . . ?
Ge1 O2 C1 C2 -140.54(11) . . . . ?
Ge1 O2 C1 C6 40.55(16) . . . . ?
C3 C2 C1 O2 -178.14(12) . . . . ?
C3 C2 C1 C6 0.8(2) . . . . ?
C5 C6 C1 O2 178.41(12) . . . . ?
C7 C6 C1 O2 -1.06(19) . . . . ?
C5 C6 C1 C2 -0.5(2) . . . . ?
C7 C6 C1 C2 -179.94(13) . . . . ?
C17 N1 C18 C20 166.32(11) . . . . ?
Ge1 N1 C18 C20 -56.35(14) . . . . ?
C17 N1 C18 C19 -67.55(14) . . . . ?
Ge1 N1 C18 C19 69.78(13) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C8 N2 C7 C6 -161.87(12) . . . . ?
Ge1 N2 C7 C6 55.04(14) . . . . ?
C5 C6 C7 N2 130.15(14) . . . . ?
C1 C6 C7 N2 -50.41(17) . . . . ?
C14 C13 C12 C11 -0.4(2) . . . . ?
O1 C11 C12 C13 -178.65(12) . . . . ?
C16 C11 C12 C13 0.7(2) . . . . ?
C6 C5 C4 C3 0.8(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C16 C15 C14 C13 1.1(2) . . . . ?

_refine_diff_density_max         0.384
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.050

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_g455_new
_database_code_depnum_ccdc_archive 'CCDC 1518896'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;
_audit_creation_date             2016-10-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 Br2 N2 O2 Si'
_chemical_formula_sum            'C26 H20 Br2 N2 O2 Si'
_chemical_formula_weight         580.35
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+, -y+, z+'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x+, y+1/2, z+1/2'
'-x+, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y+, z+1/2'
'-x+1/2, -y+, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z+'
'-x+1/2, -y+1/2, z+'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   14.9435(6)
_cell_length_b                   32.8797(14)
_cell_length_c                   9.4404(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4638.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    20803
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      1.24
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.575
_exptl_absorpt_correction_T_max  0.7319
_exptl_absorpt_correction_T_min  0.4372
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'STOE X-Area'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26568
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.693
_diffrn_reflns_theta_min         2.478
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2435
_reflns_number_total             2450
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Flack x determined using 1112 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0224
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+3.8197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0563
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C07(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C09(H005), C06(H009), C02(H00C), C11(H00D), C12(H00E), C03(H00F),
 C05(H00G), C04(H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br01 Br 0.43375(2) 0.66748(2) 0.06287(4) 0.02885(11) Uani 1 1 d . . . . .
Si01 Si 0.5000 0.5000 0.48354(12) 0.0182(2) Uani 1 2 d S T P . .
O01 O 0.41306(14) 0.50948(6) 0.3826(2) 0.0214(4) Uani 1 1 d . . . . .
N01 N 0.51449(16) 0.54390(7) 0.5768(3) 0.0201(5) Uani 1 1 d . . . . .
C09 C 0.44274(17) 0.61787(9) 0.3087(4) 0.0208(5) Uani 1 1 d . . . . .
H005 H 0.4583 0.6419 0.3546 0.025 Uiso 1 1 calc R . . . .
C01 C 0.56870(18) 0.54664(9) 0.6990(3) 0.0196(6) Uani 1 1 d . . . . .
C07 C 0.4589(2) 0.57955(8) 0.5399(3) 0.0209(6) Uani 1 1 d . . . . .
H00A H 0.4901 0.6042 0.5676 0.025 Uiso 1 1 calc R . . . .
H00B H 0.4033 0.5784 0.5926 0.025 Uiso 1 1 calc R . . . .
C13 C 0.41541(18) 0.54612(8) 0.3093(4) 0.0195(5) Uani 1 1 d . . . . .
C06 C 0.5540(2) 0.57583(8) 0.8038(4) 0.0228(6) Uani 1 1 d . . . . .
H009 H 0.5069 0.5941 0.7947 0.027 Uiso 1 1 calc R . . . .
C08 C 0.43842(19) 0.58132(9) 0.3835(3) 0.0197(6) Uani 1 1 d . . . . .
C02 C 0.63974(19) 0.51921(8) 0.7165(4) 0.0233(6) Uani 1 1 d . . . . .
H00C H 0.6505 0.4995 0.6479 0.028 Uiso 1 1 calc R . . . .
C11 C 0.3992(2) 0.58296(8) 0.0925(4) 0.0233(6) Uani 1 1 d . . . . .
H00D H 0.3855 0.5840 -0.0035 0.028 Uiso 1 1 calc R . . . .
C12 C 0.39566(19) 0.54639(9) 0.1661(3) 0.0226(6) Uani 1 1 d . . . . .
H00E H 0.3803 0.5224 0.1198 0.027 Uiso 1 1 calc R . . . .
C03 C 0.6942(2) 0.52128(9) 0.8359(4) 0.0253(6) Uani 1 1 d . . . . .
H00F H 0.7406 0.5027 0.8470 0.030 Uiso 1 1 calc R . . . .
C05 C 0.6097(2) 0.57766(9) 0.9221(3) 0.0251(6) Uani 1 1 d . . . . .
H00G H 0.5994 0.5973 0.9912 0.030 Uiso 1 1 calc R . . . .
C10 C 0.4235(2) 0.61789(10) 0.1653(4) 0.0231(6) Uani 1 1 d . . . . .
C04 C 0.6800(2) 0.55071(11) 0.9381(3) 0.0262(6) Uani 1 1 d . . . . .
H00H H 0.7173 0.5524 1.0168 0.031 Uiso 1 1 calc R . . . .


_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
Br01 C10 1.902(3) . ?
Si01 O01 1.641(2) . ?
Si01 O01 1.641(2) 2_665 ?
Si01 N01 1.705(2) 2_665 ?
Si01 N01 1.705(2) . ?
O01 C13 1.390(3) . ?
N01 C01 1.412(4) . ?
N01 C07 1.478(3) . ?
C09 H005 0.9300 . ?
C09 C08 1.396(4) . ?
C09 C10 1.384(5) . ?
C01 C06 1.396(4) . ?
C01 C02 1.403(4) . ?
C07 H00A 0.9700 . ?
C07 H00B 0.9700 . ?
C07 C08 1.509(4) . ?
C13 C08 1.396(4) . ?
C13 C12 1.384(4) . ?
C06 H009 0.9300 . ?
C06 C05 1.393(5) . ?
C02 H00C 0.9300 . ?
C02 C03 1.392(5) . ?
C11 H00D 0.9300 . ?
C11 C12 1.390(4) . ?
C11 C10 1.387(5) . ?
C12 H00E 0.9300 . ?
C03 H00F 0.9300 . ?
C03 C04 1.383(5) . ?
C05 H00G 0.9300 . ?
C05 C04 1.383(5) . ?
C04 H00H 0.9300 . ?

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
O01 Si01 O01 109.00(17) . 2_665 ?
O01 Si01 N01 103.88(11) 2_665 2_665 ?
O01 Si01 N01 103.88(11) . . ?
O01 Si01 N01 111.12(10) . 2_665 ?
O01 Si01 N01 111.11(10) 2_665 . ?
N01 Si01 N01 117.77(19) 2_665 . ?
C13 O01 Si01 115.69(18) . . ?
C01 N01 Si01 123.3(2) . . ?
C01 N01 C07 117.6(2) . . ?
C07 N01 Si01 118.6(2) . . ?
C08 C09 H005 120.5 . . ?
C10 C09 H005 120.5 . . ?
C10 C09 C08 119.1(3) . . ?
C06 C01 N01 122.2(3) . . ?
C06 C01 C02 118.5(3) . . ?
C02 C01 N01 119.3(3) . . ?
N01 C07 H00A 109.2 . . ?
N01 C07 H00B 109.2 . . ?
N01 C07 C08 112.0(2) . . ?
H00A C07 H00B 107.9 . . ?
C08 C07 H00A 109.2 . . ?
C08 C07 H00B 109.2 . . ?
O01 C13 C08 118.4(3) . . ?
C12 C13 O01 119.1(3) . . ?
C12 C13 C08 122.5(3) . . ?
C01 C06 H009 119.9 . . ?
C05 C06 C01 120.3(3) . . ?
C05 C06 H009 119.9 . . ?
C09 C08 C07 121.3(3) . . ?
C09 C08 C13 118.1(3) . . ?
C13 C08 C07 120.6(3) . . ?
C01 C02 H00C 119.8 . . ?
C03 C02 C01 120.4(3) . . ?
C03 C02 H00C 119.8 . . ?
C12 C11 H00D 120.7 . . ?
C10 C11 H00D 120.7 . . ?
C10 C11 C12 118.6(3) . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H00E 120.5 . . ?
C11 C12 H00E 120.5 . . ?
C02 C03 H00F 119.7 . . ?
C04 C03 C02 120.6(3) . . ?
C04 C03 H00F 119.7 . . ?
C06 C05 H00G 119.6 . . ?
C04 C05 C06 120.9(3) . . ?
C04 C05 H00G 119.6 . . ?
C09 C10 Br01 118.8(2) . . ?
C09 C10 C11 122.6(3) . . ?
C11 C10 Br01 118.6(2) . . ?
C03 C04 C05 119.3(3) . . ?
C03 C04 H00H 120.4 . . ?
C05 C04 H00H 120.4 . . ?

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
Si01 O01 C13 C08 -47.6(3) . . . . ?
Si01 O01 C13 C12 132.0(2) . . . . ?
Si01 N01 C01 C06 -154.1(2) . . . . ?
Si01 N01 C01 C02 25.9(4) . . . . ?
Si01 N01 C07 C08 -33.6(3) . . . . ?
O01 Si01 O01 C13 -70.42(19) 2_665 . . . ?
O01 Si01 N01 C01 -77.7(3) 2_665 . . . ?
O01 Si01 N01 C01 165.2(2) . . . . ?
O01 Si01 N01 C07 110.4(2) 2_665 . . . ?
O01 Si01 N01 C07 -6.6(2) . . . . ?
O01 C13 C08 C09 178.5(2) . . . . ?
O01 C13 C08 C07 -0.8(4) . . . . ?
O01 C13 C12 C11 -179.2(3) . . . . ?
N01 Si01 O01 C13 175.7(2) 2_665 . . . ?
N01 Si01 O01 C13 48.1(2) . . . . ?
N01 Si01 N01 C01 41.9(2) 2_665 . . . ?
N01 Si01 N01 C07 -130.0(2) 2_665 . . . ?
N01 C01 C06 C05 -179.5(3) . . . . ?
N01 C01 C02 C03 179.9(3) . . . . ?
N01 C07 C08 C09 -137.2(3) . . . . ?
N01 C07 C08 C13 42.1(4) . . . . ?
C01 N01 C07 C08 154.1(2) . . . . ?
C01 C06 C05 C04 -0.1(5) . . . . ?
C01 C02 C03 C04 -0.9(5) . . . . ?
C07 N01 C01 C06 17.8(4) . . . . ?
C07 N01 C01 C02 -162.2(3) . . . . ?
C06 C01 C02 C03 -0.1(4) . . . . ?
C06 C05 C04 C03 -0.8(5) . . . . ?
C08 C09 C10 Br01 -177.8(2) . . . . ?
C08 C09 C10 C11 0.6(4) . . . . ?
C08 C13 C12 C11 0.3(5) . . . . ?
C02 C01 C06 C05 0.6(4) . . . . ?
C02 C03 C04 C05 1.3(5) . . . . ?
C12 C13 C08 C09 -1.0(4) . . . . ?
C12 C13 C08 C07 179.7(3) . . . . ?
C12 C11 C10 Br01 177.1(2) . . . . ?
C12 C11 C10 C09 -1.3(5) . . . . ?
C10 C09 C08 C07 179.8(3) . . . . ?
C10 C09 C08 C13 0.5(4) . . . . ?
C10 C11 C12 C13 0.8(5) . . . . ?

_shelx_SHELXL_version_number     2015/1

_olex2_submission_special_instructions 'No special instructions were received'
