# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_snr138m
_database_code_depnum_ccdc_archive 'CCDC 1858164'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H23 F3 Ge N2 O3 S'
_chemical_formula_sum            'C16 H23 F3 Ge N2 O3 S'
_chemical_formula_weight         453.04

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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   'P 21/c'
_symmetry_space_group_name_hall  '-P 2ybc'

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

_cell_length_a                   15.057(3)
_cell_length_b                   16.433(3)
_cell_length_c                   16.648(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.621(4)
_cell_angle_gamma                90.00
_cell_volume                     4111.0(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3276
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      22.00

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1856.0
_exptl_absorpt_coefficient_mu    1.635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.582
_exptl_absorpt_correction_T_max  0.816
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21356
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7243
_reflns_number_gt                5131
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0453P)²+0.3702P] 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         7233
_refine_ls_number_parameters     477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_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 0.22319(3) 0.83778(2) 0.08784(2) 0.04171(13) Uani 1 1 d . . .
Ge2 Ge 0.71045(3) 0.54675(2) 0.20420(2) 0.04161(13) Uani 1 1 d . . .
O1 O 0.12292(17) 0.76424(15) 0.01717(15) 0.0477(7) Uani 1 1 d . . .
O2 O 0.0120(2) 0.7520(2) -0.09273(17) 0.0863(11) Uani 1 1 d . . .
O3 O -0.0089(2) 0.84843(16) 0.01445(19) 0.0680(9) Uani 1 1 d . . .
O4 O 0.59365(17) 0.48497(15) 0.25157(15) 0.0473(7) Uani 1 1 d . . .
O5 O 0.4728(2) 0.51270(19) 0.15151(17) 0.0638(8) Uani 1 1 d . . .
O6 O 0.4725(2) 0.39019(17) 0.23176(19) 0.0689(9) Uani 1 1 d . . .
N1 N 0.16122(19) 0.93884(17) 0.08158(16) 0.0357(7) Uani 1 1 d . . .
N2 N 0.1619(2) 0.82901(17) 0.18417(17) 0.0379(7) Uani 1 1 d . . .
N3 N 0.65999(19) 0.54970(17) 0.09627(16) 0.0362(7) Uani 1 1 d . . .
N4 N 0.6605(2) 0.65330(17) 0.20599(17) 0.0383(7) Uani 1 1 d . . .
S1 S 0.02964(7) 0.77427(6) -0.01080(6) 0.0445(3) Uani 1 1 d . . .
S2 S 0.50051(7) 0.47200(6) 0.22503(6) 0.0434(3) Uani 1 1 d . . .
C1 C 0.1072(2) 0.9551(2) 0.1407(2) 0.0340(8) Uani 1 1 d . . .
C2 C 0.0571(2) 1.0267(2) 0.1412(2) 0.0421(9) Uani 1 1 d . . .
H2 H 0.0633 1.0605 0.0971 0.051 Uiso 1 1 calc R . .
C3 C -0.0002(3) 1.0557(2) 0.1964(3) 0.0528(11) Uani 1 1 d . . .
H3 H -0.0240 1.1070 0.1849 0.063 Uiso 1 1 calc R . .
C4 C -0.0274(3) 1.0206(3) 0.2656(3) 0.0616(12) Uani 1 1 d . . .
H4 H -0.0675 1.0501 0.2943 0.074 Uiso 1 1 calc R . .
C5 C -0.0014(3) 0.9459(3) 0.2969(2) 0.0522(11) Uani 1 1 d . . .
H5 H -0.0271 0.9313 0.3441 0.063 Uiso 1 1 calc R . .
C6 C 0.0567(2) 0.8901(2) 0.2688(2) 0.0419(9) Uani 1 1 d . . .
H6 H 0.0639 0.8437 0.3004 0.050 Uiso 1 1 calc R . .
C7 C 0.1070(2) 0.8904(2) 0.2012(2) 0.0357(8) Uani 1 1 d . . .
C8 C 0.1666(3) 0.9911(2) 0.0093(2) 0.0433(10) Uani 1 1 d . . .
H8A H 0.1076 1.0121 -0.0055 0.052 Uiso 1 1 calc R . .
H8B H 0.1843 0.9575 -0.0348 0.052 Uiso 1 1 calc R . .
C9 C 0.1698(3) 0.7550(2) 0.2332(2) 0.0402(9) Uani 1 1 d . . .
H9A H 0.1862 0.7103 0.1991 0.048 Uiso 1 1 calc R . .
H9B H 0.1120 0.7425 0.2526 0.048 Uiso 1 1 calc R . .
C10 C 0.2304(3) 1.0623(2) 0.0189(2) 0.0549(11) Uani 1 1 d . . .
H10 H 0.2100 1.0983 0.0609 0.066 Uiso 1 1 calc R . .
C11 C 0.2374(3) 0.7600(2) 0.3051(2) 0.0481(10) Uani 1 1 d . . .
H11 H 0.2191 0.8036 0.3407 0.058 Uiso 1 1 calc R . .
C12 C 0.3249(3) 1.0352(3) 0.0434(3) 0.0718(14) Uani 1 1 d . . .
H12A H 0.3254 1.0060 0.0933 0.108 Uiso 1 1 calc R . .
H12B H 0.3627 1.0821 0.0498 0.108 Uiso 1 1 calc R . .
H12C H 0.3462 1.0004 0.0024 0.108 Uiso 1 1 calc R . .
C13 C 0.2271(4) 1.1092(3) -0.0602(3) 0.0811(16) Uani 1 1 d . . .
H13A H 0.2529 1.0768 -0.1007 0.122 Uiso 1 1 calc R . .
H13B H 0.2599 1.1590 -0.0529 0.122 Uiso 1 1 calc R . .
H13C H 0.1663 1.1213 -0.0769 0.122 Uiso 1 1 calc R . .
C14 C 0.2374(3) 0.6804(3) 0.3512(3) 0.0617(12) Uani 1 1 d . . .
H14A H 0.1787 0.6699 0.3681 0.093 Uiso 1 1 calc R . .
H14B H 0.2784 0.6840 0.3976 0.093 Uiso 1 1 calc R . .
H14C H 0.2550 0.6370 0.3171 0.093 Uiso 1 1 calc R . .
C15 C 0.3302(3) 0.7798(3) 0.2791(3) 0.0807(16) Uani 1 1 d . . .
H15A H 0.3716 0.7801 0.3254 0.121 Uiso 1 1 calc R . .
H15B H 0.3297 0.8324 0.2540 0.121 Uiso 1 1 calc R . .
H15C H 0.3479 0.7394 0.2416 0.121 Uiso 1 1 calc R . .
C16 C -0.0250(3) 0.6975(3) 0.0451(3) 0.0590(12) Uani 1 1 d . . .
C17 C 0.6135(2) 0.6167(2) 0.0744(2) 0.0345(8) Uani 1 1 d . . .
C18 C 0.5719(3) 0.6255(2) -0.0028(2) 0.0426(9) Uani 1 1 d . . .
H18 H 0.5803 0.5819 -0.0371 0.051 Uiso 1 1 calc R . .
C19 C 0.5202(3) 0.6881(3) -0.0370(2) 0.0526(11) Uani 1 1 d . . .
H19 H 0.5019 0.6810 -0.0909 0.063 Uiso 1 1 calc R . .
C20 C 0.4923(3) 0.7590(3) -0.0028(3) 0.0641(13) Uani 1 1 d . . .
H20 H 0.4567 0.7931 -0.0359 0.077 Uiso 1 1 calc R . .
C21 C 0.5112(3) 0.7853(3) 0.0754(3) 0.0598(12) Uani 1 1 d . . .
H21 H 0.4850 0.8343 0.0886 0.072 Uiso 1 1 calc R . .
C22 C 0.5635(3) 0.7492(2) 0.1367(2) 0.0467(10) Uani 1 1 d . . .
H22 H 0.5677 0.7786 0.1845 0.056 Uiso 1 1 calc R . .
C23 C 0.6110(2) 0.6765(2) 0.1394(2) 0.0358(8) Uani 1 1 d . . .
C24 C 0.6647(3) 0.4784(2) 0.0438(2) 0.0438(10) Uani 1 1 d . . .
H24A H 0.6072 0.4713 0.0150 0.053 Uiso 1 1 calc R . .
H24B H 0.6755 0.4307 0.0774 0.053 Uiso 1 1 calc R . .
C25 C 0.6744(3) 0.7050(2) 0.2775(2) 0.0464(10) Uani 1 1 d . . .
H25A H 0.6942 0.6712 0.3229 0.056 Uiso 1 1 calc R . .
H25B H 0.6180 0.7291 0.2895 0.056 Uiso 1 1 calc R . .
C26 C 0.7351(3) 0.4818(2) -0.0169(2) 0.0560(12) Uani 1 1 d . . .
H26 H 0.7236 0.5297 -0.0511 0.067 Uiso 1 1 calc R . .
C27 C 0.7424(3) 0.7733(2) 0.2687(3) 0.0538(11) Uani 1 1 d . . .
H27 H 0.7211 0.8077 0.2234 0.065 Uiso 1 1 calc R . .
C28 C 0.7279(4) 0.4062(3) -0.0700(3) 0.0920(19) Uani 1 1 d . . .
H28A H 0.7387 0.3586 -0.0374 0.138 Uiso 1 1 calc R . .
H28B H 0.7712 0.4092 -0.1098 0.138 Uiso 1 1 calc R . .
H28C H 0.6694 0.4033 -0.0961 0.138 Uiso 1 1 calc R . .
C29 C 0.8274(3) 0.4895(3) 0.0232(3) 0.0868(17) Uani 1 1 d . . .
H29A H 0.8402 0.4426 0.0563 0.130 Uiso 1 1 calc R . .
H29B H 0.8307 0.5376 0.0560 0.130 Uiso 1 1 calc R . .
H29C H 0.8700 0.4932 -0.0172 0.130 Uiso 1 1 calc R . .
C30 C 0.8321(3) 0.7396(3) 0.2501(3) 0.0879(17) Uani 1 1 d . . .
H30A H 0.8713 0.7836 0.2387 0.132 Uiso 1 1 calc R . .
H30B H 0.8253 0.7043 0.2042 0.132 Uiso 1 1 calc R . .
H30C H 0.8567 0.7094 0.2956 0.132 Uiso 1 1 calc R . .
C31 C 0.7483(3) 0.8249(3) 0.3433(3) 0.0838(16) Uani 1 1 d . . .
H31A H 0.7659 0.7916 0.3890 0.126 Uiso 1 1 calc R . .
H31B H 0.6913 0.8488 0.3508 0.126 Uiso 1 1 calc R . .
H31C H 0.7915 0.8671 0.3377 0.126 Uiso 1 1 calc R . .
C32 C 0.4435(4) 0.5250(3) 0.3021(4) 0.0784(16) Uani 1 1 d . . .
F1 F 0.0033(2) 0.62356(17) 0.0266(2) 0.1129(12) Uani 1 1 d . . .
F2 F -0.11224(17) 0.69884(16) 0.03097(17) 0.0786(8) Uani 1 1 d . . .
F3 F -0.0086(2) 0.7066(2) 0.12336(18) 0.1040(11) Uani 1 1 d . . .
F4 F 0.4644(3) 0.60222(19) 0.3048(2) 0.1180(12) Uani 1 1 d . . .
F5 F 0.3555(2) 0.5182(2) 0.2867(2) 0.1172(12) Uani 1 1 d . . .
F6 F 0.4634(3) 0.4933(2) 0.37417(19) 0.1118(12) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ge1 N1 1.905(3) . ?
Ge1 N2 1.906(3) . ?
Ge1 O1 2.213(3) . ?
Ge2 N3 1.907(3) . ?
Ge2 N4 1.907(3) . ?
Ge2 O4 2.218(3) . ?
O1 S1 1.461(3) . ?
O2 S1 1.421(3) . ?
O3 S1 1.425(3) . ?
O4 S2 1.459(3) . ?
O5 S2 1.433(3) . ?
O6 S2 1.415(3) . ?
N1 C1 1.342(4) . ?
N1 C8 1.484(4) . ?
N2 C7 1.345(4) . ?
N2 C9 1.465(4) . ?
N3 C17 1.343(4) . ?
N3 C24 1.466(4) . ?
N4 C23 1.351(4) . ?
N4 C25 1.466(4) . ?
S1 C16 1.798(5) . ?
S2 C32 1.811(5) . ?
C1 C2 1.399(5) . ?
C1 C7 1.465(5) . ?
C2 C3 1.385(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(5) . ?
C6 H6 0.9300 . ?
C8 C10 1.516(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.523(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12 1.522(6) . ?
C10 C13 1.525(5) . ?
C10 H10 0.9800 . ?
C11 C14 1.516(5) . ?
C11 C15 1.524(6) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 F3 1.319(5) . ?
C16 F2 1.319(5) . ?
C16 F1 1.330(5) . ?
C17 C18 1.401(5) . ?
C17 C23 1.463(5) . ?
C18 C19 1.390(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.373(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.391(5) . ?
C22 H22 0.9300 . ?
C24 C26 1.511(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C27 1.531(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C29 1.508(7) . ?
C26 C28 1.524(6) . ?
C26 H26 0.9800 . ?
C27 C31 1.502(5) . ?
C27 C30 1.510(6) . ?
C27 H27 0.9800 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 F4 1.308(6) . ?
C32 F6 1.325(6) . ?
C32 F5 1.339(6) . ?

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
N1 Ge1 N2 81.39(12) . . ?
N1 Ge1 O1 97.56(11) . . ?
N2 Ge1 O1 93.19(11) . . ?
N3 Ge2 N4 81.79(12) . . ?
N3 Ge2 O4 93.96(11) . . ?
N4 Ge2 O4 95.28(11) . . ?
S1 O1 Ge1 135.86(15) . . ?
S2 O4 Ge2 136.68(15) . . ?
C1 N1 C8 123.1(3) . . ?
C1 N1 Ge1 116.8(2) . . ?
C8 N1 Ge1 119.8(2) . . ?
C7 N2 C9 122.3(3) . . ?
C7 N2 Ge1 117.2(2) . . ?
C9 N2 Ge1 120.3(2) . . ?
C17 N3 C24 122.5(3) . . ?
C17 N3 Ge2 116.5(2) . . ?
C24 N3 Ge2 120.6(2) . . ?
C23 N4 C25 123.1(3) . . ?
C23 N4 Ge2 116.4(2) . . ?
C25 N4 Ge2 120.5(2) . . ?
O2 S1 O3 116.7(2) . . ?
O2 S1 O1 113.24(18) . . ?
O3 S1 O1 113.83(17) . . ?
O2 S1 C16 104.6(2) . . ?
O3 S1 C16 103.8(2) . . ?
O1 S1 C16 102.61(19) . . ?
O6 S2 O5 116.03(19) . . ?
O6 S2 O4 113.57(18) . . ?
O5 S2 O4 114.37(16) . . ?
O6 S2 C32 104.1(2) . . ?
O5 S2 C32 104.8(2) . . ?
O4 S2 C32 101.8(2) . . ?
N1 C1 C2 121.6(3) . . ?
N1 C1 C7 112.9(3) . . ?
C2 C1 C7 125.5(3) . . ?
C3 C2 C1 130.8(4) . . ?
C3 C2 H2 114.6 . . ?
C1 C2 H2 114.6 . . ?
C4 C3 C2 130.0(4) . . ?
C4 C3 H3 115.0 . . ?
C2 C3 H3 115.0 . . ?
C3 C4 C5 126.7(4) . . ?
C3 C4 H4 116.6 . . ?
C5 C4 H4 116.6 . . ?
C6 C5 C4 129.6(4) . . ?
C6 C5 H5 115.2 . . ?
C4 C5 H5 115.2 . . ?
C5 C6 C7 131.6(4) . . ?
C5 C6 H6 114.2 . . ?
C7 C6 H6 114.2 . . ?
N2 C7 C6 122.7(3) . . ?
N2 C7 C1 111.7(3) . . ?
C6 C7 C1 125.6(3) . . ?
N1 C8 C10 115.3(3) . . ?
N1 C8 H8A 108.4 . . ?
C10 C8 H8A 108.4 . . ?
N1 C8 H8B 108.4 . . ?
C10 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
N2 C9 C11 114.8(3) . . ?
N2 C9 H9A 108.6 . . ?
C11 C9 H9A 108.6 . . ?
N2 C9 H9B 108.6 . . ?
C11 C9 H9B 108.6 . . ?
H9A C9 H9B 107.5 . . ?
C8 C10 C12 112.2(3) . . ?
C8 C10 C13 108.2(4) . . ?
C12 C10 C13 111.0(4) . . ?
C8 C10 H10 108.4 . . ?
C12 C10 H10 108.4 . . ?
C13 C10 H10 108.4 . . ?
C14 C11 C9 109.2(3) . . ?
C14 C11 C15 110.9(3) . . ?
C9 C11 C15 111.6(3) . . ?
C14 C11 H11 108.3 . . ?
C9 C11 H11 108.3 . . ?
C15 C11 H11 108.3 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F3 C16 F2 107.2(4) . . ?
F3 C16 F1 106.8(4) . . ?
F2 C16 F1 107.7(4) . . ?
F3 C16 S1 111.6(3) . . ?
F2 C16 S1 112.3(3) . . ?
F1 C16 S1 110.9(3) . . ?
N3 C17 C18 121.9(3) . . ?
N3 C17 C23 112.8(3) . . ?
C18 C17 C23 125.3(3) . . ?
C19 C18 C17 131.2(4) . . ?
C19 C18 H18 114.4 . . ?
C17 C18 H18 114.4 . . ?
C20 C19 C18 129.5(4) . . ?
C20 C19 H19 115.2 . . ?
C18 C19 H19 115.2 . . ?
C19 C20 C21 127.1(4) . . ?
C19 C20 H20 116.5 . . ?
C21 C20 H20 116.5 . . ?
C22 C21 C20 129.4(4) . . ?
C22 C21 H21 115.3 . . ?
C20 C21 H21 115.3 . . ?
C21 C22 C23 131.3(4) . . ?
C21 C22 H22 114.4 . . ?
C23 C22 H22 114.4 . . ?
N4 C23 C22 121.6(3) . . ?
N4 C23 C17 112.3(3) . . ?
C22 C23 C17 126.1(3) . . ?
N3 C24 C26 115.5(3) . . ?
N3 C24 H24A 108.4 . . ?
C26 C24 H24A 108.4 . . ?
N3 C24 H24B 108.4 . . ?
C26 C24 H24B 108.4 . . ?
H24A C24 H24B 107.5 . . ?
N4 C25 C27 114.2(3) . . ?
N4 C25 H25A 108.7 . . ?
C27 C25 H25A 108.7 . . ?
N4 C25 H25B 108.7 . . ?
C27 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
C29 C26 C24 111.9(4) . . ?
C29 C26 C28 110.7(4) . . ?
C24 C26 C28 109.3(4) . . ?
C29 C26 H26 108.3 . . ?
C24 C26 H26 108.3 . . ?
C28 C26 H26 108.3 . . ?
C31 C27 C30 111.7(4) . . ?
C31 C27 C25 109.9(4) . . ?
C30 C27 C25 111.3(4) . . ?
C31 C27 H27 108.0 . . ?
C30 C27 H27 108.0 . . ?
C25 C27 H27 108.0 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C27 C31 H31A 109.5 . . ?
C27 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C27 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
F4 C32 F6 108.1(5) . . ?
F4 C32 F5 108.7(5) . . ?
F6 C32 F5 107.7(5) . . ?
F4 C32 S2 111.6(4) . . ?
F6 C32 S2 111.2(4) . . ?
F5 C32 S2 109.5(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
N1 Ge1 O1 S1 -14.6(2) . . . . ?
N2 Ge1 O1 S1 67.1(2) . . . . ?
N3 Ge2 O4 S2 -18.2(2) . . . . ?
N4 Ge2 O4 S2 63.9(2) . . . . ?
N2 Ge1 N1 C1 -1.2(3) . . . . ?
O1 Ge1 N1 C1 90.9(3) . . . . ?
N2 Ge1 N1 C8 -174.7(3) . . . . ?
O1 Ge1 N1 C8 -82.6(3) . . . . ?
N1 Ge1 N2 C7 1.5(3) . . . . ?
O1 Ge1 N2 C7 -95.7(3) . . . . ?
N1 Ge1 N2 C9 176.7(3) . . . . ?
O1 Ge1 N2 C9 79.6(3) . . . . ?
N4 Ge2 N3 C17 -2.9(2) . . . . ?
O4 Ge2 N3 C17 91.9(2) . . . . ?
N4 Ge2 N3 C24 -176.7(3) . . . . ?
O4 Ge2 N3 C24 -81.9(3) . . . . ?
N3 Ge2 N4 C23 5.1(3) . . . . ?
O4 Ge2 N4 C23 -88.2(3) . . . . ?
N3 Ge2 N4 C25 -176.3(3) . . . . ?
O4 Ge2 N4 C25 90.4(3) . . . . ?
Ge1 O1 S1 O2 134.4(2) . . . . ?
Ge1 O1 S1 O3 -2.0(3) . . . . ?
Ge1 O1 S1 C16 -113.5(3) . . . . ?
Ge2 O4 S2 O6 131.7(2) . . . . ?
Ge2 O4 S2 O5 -4.6(3) . . . . ?
Ge2 O4 S2 C32 -117.0(3) . . . . ?
C8 N1 C1 C2 -5.3(5) . . . . ?
Ge1 N1 C1 C2 -178.7(3) . . . . ?
C8 N1 C1 C7 174.0(3) . . . . ?
Ge1 N1 C1 C7 0.7(4) . . . . ?
N1 C1 C2 C3 -178.4(4) . . . . ?
C7 C1 C2 C3 2.3(7) . . . . ?
C1 C2 C3 C4 -3.0(8) . . . . ?
C2 C3 C4 C5 1.0(8) . . . . ?
C3 C4 C5 C6 0.7(8) . . . . ?
C4 C5 C6 C7 -0.1(8) . . . . ?
C9 N2 C7 C6 3.2(5) . . . . ?
Ge1 N2 C7 C6 178.3(3) . . . . ?
C9 N2 C7 C1 -176.6(3) . . . . ?
Ge1 N2 C7 C1 -1.5(4) . . . . ?
C5 C6 C7 N2 179.2(4) . . . . ?
C5 C6 C7 C1 -1.0(7) . . . . ?
N1 C1 C7 N2 0.5(4) . . . . ?
C2 C1 C7 N2 179.8(3) . . . . ?
N1 C1 C7 C6 -179.3(3) . . . . ?
C2 C1 C7 C6 0.0(6) . . . . ?
C1 N1 C8 C10 85.9(4) . . . . ?
Ge1 N1 C8 C10 -101.0(3) . . . . ?
C7 N2 C9 C11 -86.9(4) . . . . ?
Ge1 N2 C9 C11 98.1(3) . . . . ?
N1 C8 C10 C12 57.5(4) . . . . ?
N1 C8 C10 C13 -179.7(3) . . . . ?
N2 C9 C11 C14 178.8(3) . . . . ?
N2 C9 C11 C15 -58.1(4) . . . . ?
O2 S1 C16 F3 175.1(3) . . . . ?
O3 S1 C16 F3 -62.1(4) . . . . ?
O1 S1 C16 F3 56.6(3) . . . . ?
O2 S1 C16 F2 -64.5(4) . . . . ?
O3 S1 C16 F2 58.3(4) . . . . ?
O1 S1 C16 F2 177.1(3) . . . . ?
O2 S1 C16 F1 56.1(4) . . . . ?
O3 S1 C16 F1 178.9(3) . . . . ?
O1 S1 C16 F1 -62.3(4) . . . . ?
C24 N3 C17 C18 -5.2(5) . . . . ?
Ge2 N3 C17 C18 -178.8(3) . . . . ?
C24 N3 C17 C23 174.1(3) . . . . ?
Ge2 N3 C17 C23 0.4(4) . . . . ?
N3 C17 C18 C19 178.9(4) . . . . ?
C23 C17 C18 C19 -0.3(7) . . . . ?
C17 C18 C19 C20 -2.8(8) . . . . ?
C18 C19 C20 C21 1.2(8) . . . . ?
C19 C20 C21 C22 1.9(9) . . . . ?
C20 C21 C22 C23 -1.2(8) . . . . ?
C25 N4 C23 C22 -5.4(5) . . . . ?
Ge2 N4 C23 C22 173.2(3) . . . . ?
C25 N4 C23 C17 175.4(3) . . . . ?
Ge2 N4 C23 C17 -6.1(4) . . . . ?
C21 C22 C23 N4 178.2(4) . . . . ?
C21 C22 C23 C17 -2.6(7) . . . . ?
N3 C17 C23 N4 3.6(4) . . . . ?
C18 C17 C23 N4 -177.2(3) . . . . ?
N3 C17 C23 C22 -175.6(3) . . . . ?
C18 C17 C23 C22 3.6(6) . . . . ?
C17 N3 C24 C26 84.9(4) . . . . ?
Ge2 N3 C24 C26 -101.6(3) . . . . ?
C23 N4 C25 C27 -77.0(5) . . . . ?
Ge2 N4 C25 C27 104.5(3) . . . . ?
N3 C24 C26 C29 60.4(5) . . . . ?
N3 C24 C26 C28 -176.6(3) . . . . ?
N4 C25 C27 C31 177.2(4) . . . . ?
N4 C25 C27 C30 -58.6(5) . . . . ?
O6 S2 C32 F4 178.5(4) . . . . ?
O5 S2 C32 F4 -59.2(5) . . . . ?
O4 S2 C32 F4 60.3(5) . . . . ?
O6 S2 C32 F6 57.8(5) . . . . ?
O5 S2 C32 F6 -179.9(4) . . . . ?
O4 S2 C32 F6 -60.5(4) . . . . ?
O6 S2 C32 F5 -61.1(4) . . . . ?
O5 S2 C32 F5 61.1(4) . . . . ?
O4 S2 C32 F5 -179.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_ssb51m
_database_code_depnum_ccdc_archive 'CCDC 1858166'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H23 Ge N2, I'
_chemical_formula_sum            'C15 H23 Ge I N2'
_chemical_formula_weight         430.86

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'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_hall  '-P 2yn'

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

_cell_length_a                   8.7656(7)
_cell_length_b                   17.3579(15)
_cell_length_c                   11.8312(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.5640(10)
_cell_angle_gamma                90.00
_cell_volume                     1716.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3623
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.18

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848.0
_exptl_absorpt_coefficient_mu    3.574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.263
_exptl_absorpt_correction_T_max  0.364
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8839
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3022
_reflns_number_gt                2590
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0773P)²+2.1387P] 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         3015
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1350
_refine_ls_wR_factor_gt          0.1226
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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 0.65059(7) 0.26034(3) 0.06127(5) 0.0520(2) Uani 1 1 d . . .
I1 I 0.92263(5) 0.19032(2) 0.31057(4) 0.0707(2) Uani 1 1 d . . .
N1 N 0.6714(4) 0.3629(2) 0.1284(3) 0.0408(9) Uani 1 1 d . . .
N2 N 0.4800(5) 0.2538(2) 0.1336(3) 0.0419(9) Uani 1 1 d . . .
C1 C 0.5691(5) 0.3801(3) 0.1895(4) 0.0376(10) Uani 1 1 d . . .
C2 C 0.5619(6) 0.4531(3) 0.2382(5) 0.0500(12) Uani 1 1 d . . .
H2 H 0.6249 0.4898 0.2161 0.060 Uiso 1 1 calc R . .
C3 C 0.4799(7) 0.4819(3) 0.3128(5) 0.0582(14) Uani 1 1 d . . .
H3 H 0.4988 0.5335 0.3333 0.070 Uiso 1 1 calc R . .
C4 C 0.3741(7) 0.4450(4) 0.3610(5) 0.0594(14) Uani 1 1 d . . .
H4 H 0.3365 0.4730 0.4141 0.071 Uiso 1 1 calc R . .
C5 C 0.3207(7) 0.3720(3) 0.3377(5) 0.0576(14) Uani 1 1 d . . .
H5 H 0.2501 0.3559 0.3779 0.069 Uiso 1 1 calc R . .
C6 C 0.3546(6) 0.3176(3) 0.2636(5) 0.0528(13) Uani 1 1 d . . .
H6 H 0.2935 0.2730 0.2568 0.063 Uiso 1 1 calc R . .
C7 C 0.4625(5) 0.3155(3) 0.1962(4) 0.0394(10) Uani 1 1 d . . .
C8 C 0.7987(6) 0.4156(3) 0.1132(5) 0.0501(12) Uani 1 1 d . . .
C9 C 0.3839(7) 0.1806(3) 0.1207(5) 0.0550(13) Uani 1 1 d . . .
C10 C 0.9116(7) 0.4402(4) 0.2311(6) 0.0721(17) Uani 1 1 d . . .
H10A H 0.8595 0.4774 0.2671 0.108 Uiso 1 1 calc R . .
H10B H 1.0055 0.4628 0.2193 0.108 Uiso 1 1 calc R . .
H10C H 0.9415 0.3961 0.2820 0.108 Uiso 1 1 calc R . .
C11 C 0.7279(8) 0.4835(4) 0.0327(6) 0.0731(18) Uani 1 1 d . . .
H11A H 0.6657 0.4647 -0.0436 0.110 Uiso 1 1 calc R . .
H11B H 0.8128 0.5156 0.0239 0.110 Uiso 1 1 calc R . .
H11C H 0.6606 0.5130 0.0672 0.110 Uiso 1 1 calc R . .
C12 C 0.8975(8) 0.3675(5) 0.0509(7) 0.083(2) Uani 1 1 d . . .
H12A H 0.9494 0.3261 0.1019 0.125 Uiso 1 1 calc R . .
H12B H 0.9767 0.3997 0.0337 0.125 Uiso 1 1 calc R . .
H12C H 0.8279 0.3468 -0.0216 0.125 Uiso 1 1 calc R . .
C13 C 0.4076(9) 0.1406(4) 0.2389(6) 0.0745(18) Uani 1 1 d . . .
H13A H 0.5190 0.1415 0.2836 0.112 Uiso 1 1 calc R . .
H13B H 0.3719 0.0882 0.2255 0.112 Uiso 1 1 calc R . .
H13C H 0.3470 0.1669 0.2825 0.112 Uiso 1 1 calc R . .
C14 C 0.2076(8) 0.1971(5) 0.0553(7) 0.087(2) Uani 1 1 d . . .
H14A H 0.1611 0.2255 0.1063 0.131 Uiso 1 1 calc R . .
H14B H 0.1513 0.1493 0.0331 0.131 Uiso 1 1 calc R . .
H14C H 0.2000 0.2269 -0.0146 0.131 Uiso 1 1 calc R . .
C15 C 0.4434(11) 0.1268(4) 0.0428(7) 0.092(2) Uani 1 1 d . . .
H15A H 0.4311 0.1510 -0.0324 0.139 Uiso 1 1 calc R . .
H15B H 0.3825 0.0799 0.0310 0.139 Uiso 1 1 calc R . .
H15C H 0.5543 0.1154 0.0803 0.139 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 N1 1.936(4) . ?
Ge1 N2 1.937(4) . ?
N1 C1 1.344(6) . ?
N1 C8 1.495(6) . ?
N2 C7 1.337(6) . ?
N2 C9 1.507(6) . ?
C1 C2 1.402(7) . ?
C1 C7 1.477(6) . ?
C2 C3 1.388(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.349(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.410(7) . ?
C6 H6 0.9300 . ?
C8 C10 1.508(8) . ?
C8 C11 1.524(8) . ?
C8 C12 1.541(8) . ?
C9 C15 1.511(9) . ?
C9 C13 1.518(8) . ?
C9 C14 1.532(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ge1 N2 82.09(16) . . ?
C1 N1 C8 124.9(4) . . ?
C1 N1 Ge1 115.4(3) . . ?
C8 N1 Ge1 119.6(3) . . ?
C7 N2 C9 125.3(4) . . ?
C7 N2 Ge1 115.5(3) . . ?
C9 N2 Ge1 119.2(3) . . ?
N1 C1 C2 122.8(4) . . ?
N1 C1 C7 113.3(4) . . ?
C2 C1 C7 123.8(4) . . ?
C3 C2 C1 133.1(5) . . ?
C3 C2 H2 113.5 . . ?
C1 C2 H2 113.5 . . ?
C4 C3 C2 129.5(5) . . ?
C4 C3 H3 115.3 . . ?
C2 C3 H3 115.3 . . ?
C5 C4 C3 125.8(5) . . ?
C5 C4 H4 117.1 . . ?
C3 C4 H4 117.1 . . ?
C4 C5 C6 130.1(5) . . ?
C4 C5 H5 115.0 . . ?
C6 C5 H5 115.0 . . ?
C5 C6 C7 133.3(5) . . ?
C5 C6 H6 113.3 . . ?
C7 C6 H6 113.3 . . ?
N2 C7 C6 122.8(4) . . ?
N2 C7 C1 113.5(4) . . ?
C6 C7 C1 123.7(4) . . ?
N1 C8 C10 111.5(4) . . ?
N1 C8 C11 111.7(4) . . ?
C10 C8 C11 112.9(5) . . ?
N1 C8 C12 105.9(4) . . ?
C10 C8 C12 106.8(5) . . ?
C11 C8 C12 107.6(5) . . ?
N2 C9 C15 107.3(5) . . ?
N2 C9 C13 112.1(5) . . ?
C15 C9 C13 107.7(5) . . ?
N2 C9 C14 109.9(5) . . ?
C15 C9 C14 106.7(6) . . ?
C13 C9 C14 112.9(6) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Ge1 N1 C1 0.7(3) . . . . ?
N2 Ge1 N1 C8 179.0(4) . . . . ?
N1 Ge1 N2 C7 -3.3(3) . . . . ?
N1 Ge1 N2 C9 179.4(4) . . . . ?
C8 N1 C1 C2 5.5(7) . . . . ?
Ge1 N1 C1 C2 -176.4(3) . . . . ?
C8 N1 C1 C7 -176.4(4) . . . . ?
Ge1 N1 C1 C7 1.7(5) . . . . ?
N1 C1 C2 C3 -172.6(5) . . . . ?
C7 C1 C2 C3 9.5(9) . . . . ?
C1 C2 C3 C4 -1.4(11) . . . . ?
C2 C3 C4 C5 -4.6(10) . . . . ?
C3 C4 C5 C6 -0.2(10) . . . . ?
C4 C5 C6 C7 6.3(11) . . . . ?
C9 N2 C7 C6 3.2(7) . . . . ?
Ge1 N2 C7 C6 -173.9(4) . . . . ?
C9 N2 C7 C1 -177.9(4) . . . . ?
Ge1 N2 C7 C1 5.0(5) . . . . ?
C5 C6 C7 N2 176.9(6) . . . . ?
C5 C6 C7 C1 -1.9(9) . . . . ?
N1 C1 C7 N2 -4.3(5) . . . . ?
C2 C1 C7 N2 173.7(4) . . . . ?
N1 C1 C7 C6 174.5(4) . . . . ?
C2 C1 C7 C6 -7.5(7) . . . . ?
C1 N1 C8 C10 57.3(6) . . . . ?
Ge1 N1 C8 C10 -120.7(5) . . . . ?
C1 N1 C8 C11 -70.0(6) . . . . ?
Ge1 N1 C8 C11 111.9(5) . . . . ?
C1 N1 C8 C12 173.1(5) . . . . ?
Ge1 N1 C8 C12 -4.9(6) . . . . ?
C7 N2 C9 C15 180.0(5) . . . . ?
Ge1 N2 C9 C15 -3.0(6) . . . . ?
C7 N2 C9 C13 -62.1(7) . . . . ?
Ge1 N2 C9 C13 114.9(5) . . . . ?
C7 N2 C9 C14 64.3(7) . . . . ?
Ge1 N2 C9 C14 -118.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.547
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.130
####################################################################### 
# 
# 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_ssb41m
_database_code_depnum_ccdc_archive 'CCDC 1858167'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H23 Ge I N2'
_chemical_formula_sum            'C15 H23 Ge I N2'
_chemical_formula_weight         430.86

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'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_hall  '-P 2ybc'

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

_cell_length_a                   13.175(3)
_cell_length_b                   16.047(4)
_cell_length_c                   8.182(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.806(5)
_cell_angle_gamma                90.00
_cell_volume                     1729.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    175(2)
_cell_measurement_reflns_used    2292
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      23.72

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848.0
_exptl_absorpt_coefficient_mu    3.547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.301
_exptl_absorpt_correction_T_max  0.473
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      175(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8911
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3053
_reflns_number_gt                2670
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0421P)²+4.1500P] 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         3050
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.001
_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 0.21164(5) 1.04425(5) 0.34847(8) 0.0309(2) Uani 1 1 d . . .
I1 I 0.37654(4) 1.11730(3) 0.51250(5) 0.03780(18) Uani 1 1 d . . .
N1 N 0.2662(4) 1.0516(3) 0.1301(6) 0.0274(12) Uani 1 1 d . . .
N2 N 0.2707(4) 0.9333(3) 0.3319(6) 0.0256(12) Uani 1 1 d . . .
C1 C 0.3226(4) 0.9871(4) 0.0787(7) 0.0246(14) Uani 1 1 d . . .
C2 C 0.3670(5) 0.9867(4) -0.0756(7) 0.0329(16) Uani 1 1 d . . .
H2 H 0.3493 1.0318 -0.1414 0.039 Uiso 1 1 calc R . .
C3 C 0.4327(5) 0.9306(4) -0.1471(8) 0.0323(16) Uani 1 1 d . . .
H3 H 0.4534 0.9446 -0.2518 0.039 Uiso 1 1 calc R . .
C4 C 0.4721(5) 0.8572(5) -0.0863(8) 0.0341(16) Uani 1 1 d . . .
H4 H 0.5157 0.8280 -0.1539 0.041 Uiso 1 1 calc R . .
C5 C 0.4537(5) 0.8227(5) 0.0642(8) 0.0384(17) Uani 1 1 d . . .
H5 H 0.4884 0.7734 0.0857 0.046 Uiso 1 1 calc R . .
C6 C 0.3917(5) 0.8498(4) 0.1893(8) 0.0319(15) Uani 1 1 d . . .
H6 H 0.3916 0.8154 0.2809 0.038 Uiso 1 1 calc R . .
C7 C 0.3295(5) 0.9198(4) 0.2009(7) 0.0259(14) Uani 1 1 d . . .
C8 C 0.2472(5) 1.1271(4) 0.0341(8) 0.0324(16) Uani 1 1 d . . .
H8A H 0.3060 1.1383 -0.0323 0.039 Uiso 1 1 calc R . .
H8B H 0.2391 1.1737 0.1084 0.039 Uiso 1 1 calc R . .
C9 C 0.2678(5) 0.8740(5) 0.4684(7) 0.0331(16) Uani 1 1 d . . .
H9A H 0.3298 0.8797 0.5330 0.040 Uiso 1 1 calc R . .
H9B H 0.2661 0.8178 0.4247 0.040 Uiso 1 1 calc R . .
C10 C 0.1535(7) 1.1220(6) -0.0773(13) 0.067(3) Uani 1 1 d . . .
H10 H 0.1688 1.0786 -0.1576 0.081 Uiso 1 1 calc R . .
C11 C 0.1781(5) 0.8859(5) 0.5786(8) 0.0347(16) Uani 1 1 d . . .
H11 H 0.1798 0.9432 0.6200 0.042 Uiso 1 1 calc R . .
C12 C 0.1452(7) 1.2027(6) -0.1748(13) 0.077(3) Uani 1 1 d . . .
H12A H 0.0949 1.1963 -0.2599 0.116 Uiso 1 1 calc R . .
H12B H 0.2096 1.2152 -0.2223 0.116 Uiso 1 1 calc R . .
H12C H 0.1258 1.2473 -0.1035 0.116 Uiso 1 1 calc R . .
C13 C 0.0623(10) 1.0995(11) -0.012(2) 0.169(9) Uani 1 1 d . . .
H13A H 0.0741 1.0641 0.0814 0.253 Uiso 1 1 calc R . .
H13B H 0.0224 1.0701 -0.0920 0.253 Uiso 1 1 calc R . .
H13C H 0.0265 1.1486 0.0221 0.253 Uiso 1 1 calc R . .
C14 C 0.1862(6) 0.8279(5) 0.7220(9) 0.050(2) Uani 1 1 d . . .
H14A H 0.1850 0.7713 0.6841 0.076 Uiso 1 1 calc R . .
H14B H 0.1302 0.8372 0.7935 0.076 Uiso 1 1 calc R . .
H14C H 0.2487 0.8382 0.7803 0.076 Uiso 1 1 calc R . .
C15 C 0.0775(6) 0.8732(6) 0.4876(10) 0.053(2) Uani 1 1 d . . .
H15A H 0.0729 0.8165 0.4503 0.080 Uiso 1 1 calc R . .
H15B H 0.0740 0.9102 0.3955 0.080 Uiso 1 1 calc R . .
H15C H 0.0224 0.8848 0.5597 0.080 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 N1 1.939(5) . ?
Ge1 N2 1.948(5) . ?
Ge1 I1 2.7951(10) . ?
N1 C1 1.346(8) . ?
N1 C8 1.464(8) . ?
N2 C7 1.349(8) . ?
N2 C9 1.469(8) . ?
C1 C2 1.399(9) . ?
C1 C7 1.473(9) . ?
C2 C3 1.384(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(9) . ?
C6 H6 0.9300 . ?
C8 C10 1.527(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.509(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C13 1.372(16) . ?
C10 C12 1.523(11) . ?
C10 H10 0.9800 . ?
C11 C14 1.500(10) . ?
C11 C15 1.524(10) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ge1 N2 80.7(2) . . ?
N1 Ge1 I1 96.97(16) . . ?
N2 Ge1 I1 96.20(16) . . ?
C1 N1 C8 124.1(5) . . ?
C1 N1 Ge1 117.1(4) . . ?
C8 N1 Ge1 118.8(4) . . ?
C7 N2 C9 121.4(5) . . ?
C7 N2 Ge1 115.9(4) . . ?
C9 N2 Ge1 121.6(4) . . ?
N1 C1 C2 121.7(6) . . ?
N1 C1 C7 112.4(5) . . ?
C2 C1 C7 125.9(6) . . ?
C3 C2 C1 131.0(7) . . ?
C3 C2 H2 114.5 . . ?
C1 C2 H2 114.5 . . ?
C4 C3 C2 129.6(6) . . ?
C4 C3 H3 115.2 . . ?
C2 C3 H3 115.2 . . ?
C5 C4 C3 126.7(7) . . ?
C5 C4 H4 116.7 . . ?
C3 C4 H4 116.7 . . ?
C4 C5 C6 130.4(7) . . ?
C4 C5 H5 114.8 . . ?
C6 C5 H5 114.8 . . ?
C5 C6 C7 130.9(6) . . ?
C5 C6 H6 114.6 . . ?
C7 C6 H6 114.6 . . ?
N2 C7 C6 121.9(6) . . ?
N2 C7 C1 113.0(6) . . ?
C6 C7 C1 125.1(6) . . ?
N1 C8 C10 114.0(6) . . ?
N1 C8 H8A 108.8 . . ?
C10 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C10 C8 H8B 108.8 . . ?
H8A C8 H8B 107.6 . . ?
N2 C9 C11 113.7(6) . . ?
N2 C9 H9A 108.8 . . ?
C11 C9 H9A 108.8 . . ?
N2 C9 H9B 108.8 . . ?
C11 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C13 C10 C12 111.8(9) . . ?
C13 C10 C8 119.0(10) . . ?
C12 C10 C8 108.5(7) . . ?
C13 C10 H10 105.4 . . ?
C12 C10 H10 105.4 . . ?
C8 C10 H10 105.4 . . ?
C14 C11 C9 109.9(6) . . ?
C14 C11 C15 110.6(6) . . ?
C9 C11 C15 112.0(6) . . ?
C14 C11 H11 108.1 . . ?
C9 C11 H11 108.1 . . ?
C15 C11 H11 108.1 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Ge1 N1 C1 -5.9(4) . . . . ?
I1 Ge1 N1 C1 89.3(4) . . . . ?
N2 Ge1 N1 C8 176.3(5) . . . . ?
I1 Ge1 N1 C8 -88.5(4) . . . . ?
N1 Ge1 N2 C7 9.2(4) . . . . ?
I1 Ge1 N2 C7 -86.9(4) . . . . ?
N1 Ge1 N2 C9 177.8(5) . . . . ?
I1 Ge1 N2 C9 81.7(5) . . . . ?
C8 N1 C1 C2 -1.2(9) . . . . ?
Ge1 N1 C1 C2 -178.9(5) . . . . ?
C8 N1 C1 C7 179.6(5) . . . . ?
Ge1 N1 C1 C7 1.9(7) . . . . ?
N1 C1 C2 C3 174.7(7) . . . . ?
C7 C1 C2 C3 -6.2(12) . . . . ?
C1 C2 C3 C4 1.4(13) . . . . ?
C2 C3 C4 C5 0.0(12) . . . . ?
C3 C4 C5 C6 1.6(13) . . . . ?
C4 C5 C6 C7 -0.1(13) . . . . ?
C9 N2 C7 C6 -1.1(9) . . . . ?
Ge1 N2 C7 C6 167.5(5) . . . . ?
C9 N2 C7 C1 -179.2(5) . . . . ?
Ge1 N2 C7 C1 -10.6(7) . . . . ?
C5 C6 C7 N2 176.9(7) . . . . ?
C5 C6 C7 C1 -5.2(12) . . . . ?
N1 C1 C7 N2 5.6(8) . . . . ?
C2 C1 C7 N2 -173.6(6) . . . . ?
N1 C1 C7 C6 -172.4(6) . . . . ?
C2 C1 C7 C6 8.4(10) . . . . ?
C1 N1 C8 C10 89.2(8) . . . . ?
Ge1 N1 C8 C10 -93.2(7) . . . . ?
C7 N2 C9 C11 -163.4(6) . . . . ?
Ge1 N2 C9 C11 28.6(7) . . . . ?
N1 C8 C10 C13 53.0(14) . . . . ?
N1 C8 C10 C12 -177.6(7) . . . . ?
N2 C9 C11 C14 -175.0(6) . . . . ?
N2 C9 C11 C15 61.6(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.158
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.128
####################################################################### 
# 
# 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_dhy110m
_database_code_depnum_ccdc_archive 'CCDC 1858165'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H23 Ge N2, Cl4 Ga'
_chemical_formula_sum            'C15 H23 Cl4 Ga Ge N2'
_chemical_formula_weight         515.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga 0.2307 1.6083 '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   'P 21/n'
_symmetry_space_group_name_hall  '-P 2yn'

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

_cell_length_a                   10.6849(16)
_cell_length_b                   19.510(3)
_cell_length_c                   10.8848(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.004(3)
_cell_angle_gamma                90.00
_cell_volume                     2145.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3542
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      25.71

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032.0
_exptl_absorpt_coefficient_mu    3.154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.370
_exptl_absorpt_correction_T_max  0.619
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11126
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3779
_reflns_number_gt                3269
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0437P)²+0.0286P] 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         3769
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge1 Ge 0.67517(3) 0.854602(17) 0.24395(3) 0.02777(11) Uani 1 1 d . . .
Ga1 Ga 0.95950(3) 0.196192(17) 0.53772(3) 0.02437(11) Uani 1 1 d . . .
Cl1 Cl 1.09849(8) 0.13247(5) 0.47859(8) 0.0385(2) Uani 1 1 d . . .
Cl4 Cl 1.02363(9) 0.30254(4) 0.55307(8) 0.0396(2) Uani 1 1 d . . .
Cl2 Cl 0.76909(8) 0.18632(4) 0.38875(8) 0.0383(2) Uani 1 1 d . . .
Cl3 Cl 0.95305(9) 0.15802(5) 0.72301(8) 0.0401(2) Uani 1 1 d . . .
N1 N 0.6720(2) 0.95116(12) 0.2626(2) 0.0236(6) Uani 1 1 d . . .
N2 N 0.5097(2) 0.86197(13) 0.2734(2) 0.0259(6) Uani 1 1 d . . .
C1 C 0.5643(3) 0.97825(15) 0.2837(3) 0.0231(7) Uani 1 1 d . . .
C2 C 0.5467(3) 1.04931(16) 0.2906(3) 0.0286(7) Uani 1 1 d . . .
H2 H 0.6123 1.0758 0.2750 0.034 Uiso 1 1 calc R . .
C3 C 0.4488(3) 1.08635(17) 0.3166(3) 0.0334(8) Uani 1 1 d . . .
H3 H 0.4582 1.1337 0.3151 0.040 Uiso 1 1 calc R . .
C4 C 0.3388(3) 1.06389(18) 0.3445(3) 0.0357(8) Uani 1 1 d . . .
H4 H 0.2854 1.0976 0.3619 0.043 Uiso 1 1 calc R . .
C5 C 0.2994(3) 0.99729(19) 0.3495(3) 0.0352(8) Uani 1 1 d . . .
H5 H 0.2227 0.9920 0.3713 0.042 Uiso 1 1 calc R . .
C6 C 0.3559(3) 0.93676(17) 0.3271(3) 0.0320(8) Uani 1 1 d . . .
H6 H 0.3099 0.8973 0.3340 0.038 Uiso 1 1 calc R . .
C7 C 0.4713(3) 0.92546(15) 0.2957(3) 0.0239(7) Uani 1 1 d . . .
C8 C 0.7827(3) 0.99343(16) 0.2529(3) 0.0276(7) Uani 1 1 d . . .
H8A H 0.8627 0.9659 0.2790 0.033 Uiso 1 1 calc R . .
H8B H 0.7960 1.0313 0.3136 0.033 Uiso 1 1 calc R . .
C9 C 0.4300(3) 0.79985(16) 0.2715(3) 0.0310(8) Uani 1 1 d . . .
H9A H 0.4539 0.7652 0.2193 0.037 Uiso 1 1 calc R . .
H9B H 0.3373 0.8109 0.2295 0.037 Uiso 1 1 calc R . .
C10 C 0.7624(3) 1.02235(17) 0.1170(3) 0.0349(8) Uani 1 1 d . . .
H10 H 0.6860 1.0533 0.0936 0.042 Uiso 1 1 calc R . .
C11 C 0.4464(3) 0.76964(16) 0.4051(3) 0.0310(7) Uani 1 1 d . . .
H11 H 0.4164 0.8039 0.4553 0.037 Uiso 1 1 calc R . .
C12 C 0.7378(4) 0.9665(2) 0.0161(3) 0.0533(11) Uani 1 1 d . . .
H12A H 0.7361 0.9861 -0.0654 0.080 Uiso 1 1 calc R . .
H12B H 0.6544 0.9449 0.0063 0.080 Uiso 1 1 calc R . .
H12C H 0.8074 0.9331 0.0432 0.080 Uiso 1 1 calc R . .
C13 C 0.8852(4) 1.0631(2) 0.1214(4) 0.0657(13) Uani 1 1 d . . .
H13A H 0.9607 1.0332 0.1449 0.099 Uiso 1 1 calc R . .
H13B H 0.8989 1.0991 0.1845 0.099 Uiso 1 1 calc R . .
H13C H 0.8734 1.0826 0.0374 0.099 Uiso 1 1 calc R . .
C14 C 0.5897(3) 0.75226(18) 0.4796(4) 0.0426(9) Uani 1 1 d . . .
H14A H 0.6230 0.7211 0.4294 0.064 Uiso 1 1 calc R . .
H14B H 0.5949 0.7313 0.5609 0.064 Uiso 1 1 calc R . .
H14C H 0.6417 0.7934 0.4956 0.064 Uiso 1 1 calc R . .
C15 C 0.3568(3) 0.70675(17) 0.3875(4) 0.0408(9) Uani 1 1 d . . .
H15A H 0.3824 0.6732 0.3357 0.061 Uiso 1 1 calc R . .
H15B H 0.2665 0.7200 0.3448 0.061 Uiso 1 1 calc R . .
H15C H 0.3652 0.6875 0.4710 0.061 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 N1 1.896(2) . ?
Ge1 N2 1.902(2) . ?
Ga1 Cl2 2.1580(9) . ?
Ga1 Cl3 2.1720(9) . ?
Ga1 Cl4 2.1744(9) . ?
Ga1 Cl1 2.1881(9) . ?
N1 C1 1.352(4) . ?
N1 C8 1.474(4) . ?
N2 C7 1.351(4) . ?
N2 C9 1.478(4) . ?
C1 C2 1.404(4) . ?
C1 C7 1.466(4) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.400(4) . ?
C6 H6 0.9300 . ?
C8 C10 1.531(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.525(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12 1.508(5) . ?
C10 C13 1.521(5) . ?
C10 H10 0.9800 . ?
C11 C14 1.519(5) . ?
C11 C15 1.530(4) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ge1 N2 81.76(10) . . ?
Cl2 Ga1 Cl3 111.10(4) . . ?
Cl2 Ga1 Cl4 109.83(3) . . ?
Cl3 Ga1 Cl4 111.12(4) . . ?
Cl2 Ga1 Cl1 107.00(4) . . ?
Cl3 Ga1 Cl1 107.95(4) . . ?
Cl4 Ga1 Cl1 109.73(4) . . ?
C1 N1 C8 122.7(2) . . ?
C1 N1 Ge1 116.90(19) . . ?
C8 N1 Ge1 120.36(18) . . ?
C7 N2 C9 123.1(3) . . ?
C7 N2 Ge1 116.9(2) . . ?
C9 N2 Ge1 119.9(2) . . ?
N1 C1 C2 122.1(3) . . ?
N1 C1 C7 112.3(3) . . ?
C2 C1 C7 125.6(3) . . ?
C3 C2 C1 130.8(3) . . ?
C3 C2 H2 114.6 . . ?
C1 C2 H2 114.6 . . ?
C2 C3 C4 129.7(3) . . ?
C2 C3 H3 115.1 . . ?
C4 C3 H3 115.1 . . ?
C5 C4 C3 127.2(3) . . ?
C5 C4 H4 116.4 . . ?
C3 C4 H4 116.4 . . ?
C4 C5 C6 130.0(3) . . ?
C4 C5 H5 115.0 . . ?
C6 C5 H5 115.0 . . ?
C5 C6 C7 130.3(3) . . ?
C5 C6 H6 114.8 . . ?
C7 C6 H6 114.8 . . ?
N2 C7 C6 122.1(3) . . ?
N2 C7 C1 112.0(3) . . ?
C6 C7 C1 126.0(3) . . ?
N1 C8 C10 114.2(2) . . ?
N1 C8 H8A 108.7 . . ?
C10 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
C10 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N2 C9 C11 114.7(2) . . ?
N2 C9 H9A 108.6 . . ?
C11 C9 H9A 108.6 . . ?
N2 C9 H9B 108.6 . . ?
C11 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C12 C10 C13 110.1(3) . . ?
C12 C10 C8 112.0(3) . . ?
C13 C10 C8 108.2(3) . . ?
C12 C10 H10 108.8 . . ?
C13 C10 H10 108.8 . . ?
C8 C10 H10 108.8 . . ?
C14 C11 C9 112.2(3) . . ?
C14 C11 C15 111.6(3) . . ?
C9 C11 C15 108.5(3) . . ?
C14 C11 H11 108.1 . . ?
C9 C11 H11 108.1 . . ?
C15 C11 H11 108.1 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Ge1 N1 C1 -1.0(2) . . . . ?
N2 Ge1 N1 C8 179.5(2) . . . . ?
N1 Ge1 N2 C7 -1.8(2) . . . . ?
N1 Ge1 N2 C9 178.4(2) . . . . ?
C8 N1 C1 C2 3.7(4) . . . . ?
Ge1 N1 C1 C2 -175.8(2) . . . . ?
C8 N1 C1 C7 -177.2(2) . . . . ?
Ge1 N1 C1 C7 3.3(3) . . . . ?
N1 C1 C2 C3 -176.8(3) . . . . ?
C7 C1 C2 C3 4.3(5) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C2 C3 C4 C5 -1.9(6) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C4 C5 C6 C7 1.6(6) . . . . ?
C9 N2 C7 C6 4.1(4) . . . . ?
Ge1 N2 C7 C6 -175.7(2) . . . . ?
C9 N2 C7 C1 -176.3(2) . . . . ?
Ge1 N2 C7 C1 4.0(3) . . . . ?
C5 C6 C7 N2 -178.0(3) . . . . ?
C5 C6 C7 C1 2.4(5) . . . . ?
N1 C1 C7 N2 -4.6(3) . . . . ?
C2 C1 C7 N2 174.5(3) . . . . ?
N1 C1 C7 C6 175.1(3) . . . . ?
C2 C1 C7 C6 -5.9(5) . . . . ?
C1 N1 C8 C10 -85.3(3) . . . . ?
Ge1 N1 C8 C10 94.2(3) . . . . ?
C7 N2 C9 C11 -82.6(4) . . . . ?
Ge1 N2 C9 C11 97.2(3) . . . . ?
N1 C8 C10 C12 -57.1(4) . . . . ?
N1 C8 C10 C13 -178.6(3) . . . . ?
N2 C9 C11 C14 -57.0(4) . . . . ?
N2 C9 C11 C15 179.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.081



####################################################################### 
# 
# 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_snr33m
_database_code_depnum_ccdc_archive 'CCDC 1893692'
_audit_update_record             
;
2019-01-31 deposited with the CCDC.
2019-02-06 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         'C15 H26 B Ge N2'
_chemical_formula_sum            'C15 H26 B Ge N2'
_chemical_formula_weight         317.80

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'
B B 0.0013 0.0007 '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'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.538(4)
_cell_length_b                   10.012(4)
_cell_length_c                   17.299(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1652.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2726
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      24.99

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.562
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.844
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7791
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.350
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2893
_reflns_number_gt                2726
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.987

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0297P)²] 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_abs_structure_details 
;
 Flack x determined using 1082 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2893
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge1 Ge 0.64891(4) 0.43063(4) 0.94230(2) 0.02435(14) Uani 1 1 d . . . . .
N1 N 0.7371(4) 0.5079(3) 0.85181(19) 0.0230(8) Uani 1 1 d . . . . .
N2 N 0.5202(3) 0.5776(3) 0.93134(16) 0.0235(7) Uani 1 1 d . . . . .
C1 C 0.6745(4) 0.6190(4) 0.8277(2) 0.0213(9) Uani 1 1 d . . . . .
C2 C 0.6953(4) 0.6763(4) 0.7529(2) 0.0255(10) Uani 1 1 d . . . . .
H2 H 0.7341 0.6180 0.7170 0.031 Uiso 1 1 calc R U . . .
C3 C 0.6686(5) 0.8016(4) 0.7244(2) 0.0307(10) Uani 1 1 d . . . . .
H3 H 0.6936 0.8150 0.6731 0.037 Uiso 1 1 calc R U . . .
C4 C 0.6100(4) 0.9109(4) 0.7610(2) 0.0318(10) Uani 1 1 d . . . . .
H4 H 0.6131 0.9919 0.7347 0.038 Uiso 1 1 calc R U . . .
C5 C 0.5481(4) 0.9112(4) 0.8321(2) 0.0297(10) Uani 1 1 d . . . . .
H5 H 0.5184 0.9943 0.8497 0.036 Uiso 1 1 calc R U . . .
C6 C 0.5227(4) 0.8042(4) 0.8825(2) 0.0255(9) Uani 1 1 d . . . . .
H6 H 0.4674 0.8259 0.9250 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5658(4) 0.6703(4) 0.8804(2) 0.0219(9) Uani 1 1 d . . . . .
C8 C 0.8542(4) 0.4366(4) 0.8110(2) 0.0279(9) Uani 1 1 d . . . . .
C9 C 0.3945(4) 0.5917(4) 0.9830(2) 0.0280(10) Uani 1 1 d . . . . .
C10 C 0.9702(5) 0.5322(5) 0.7845(3) 0.0394(12) Uani 1 1 d . . . . .
H10A H 0.9895 0.5955 0.8248 0.059 Uiso 1 1 calc R U . . .
H10B H 0.9402 0.5788 0.7389 0.059 Uiso 1 1 calc R U . . .
H10C H 1.0536 0.4822 0.7732 0.059 Uiso 1 1 calc R U . . .
C11 C 0.7965(5) 0.3534(5) 0.7439(3) 0.0400(12) Uani 1 1 d . . . . .
H11A H 0.7550 0.4116 0.7062 0.060 Uiso 1 1 calc R U . . .
H11B H 0.7268 0.2927 0.7631 0.060 Uiso 1 1 calc R U . . .
H11C H 0.8714 0.3039 0.7205 0.060 Uiso 1 1 calc R U . . .
C12 C 0.9201(5) 0.3410(5) 0.8703(3) 0.0443(13) Uani 1 1 d . . . . .
H12A H 0.8520 0.2755 0.8856 0.067 Uiso 1 1 calc R U . . .
H12B H 0.9499 0.3907 0.9148 0.067 Uiso 1 1 calc R U . . .
H12C H 0.9994 0.2970 0.8475 0.067 Uiso 1 1 calc R U . . .
C13 C 0.2661(4) 0.6365(5) 0.9380(3) 0.0401(11) Uani 1 1 d . . . . .
H13A H 0.2565 0.5827 0.8924 0.060 Uiso 1 1 calc R U . . .
H13B H 0.2766 0.7285 0.9235 0.060 Uiso 1 1 calc R U . . .
H13C H 0.1842 0.6265 0.9697 0.060 Uiso 1 1 calc R U . . .
C14 C 0.4249(5) 0.6836(5) 1.0524(3) 0.0369(11) Uani 1 1 d . . . . .
H14A H 0.4316 0.7744 1.0349 0.055 Uiso 1 1 calc R U . . .
H14B H 0.5118 0.6576 1.0760 0.055 Uiso 1 1 calc R U . . .
H14C H 0.3504 0.6761 1.0894 0.055 Uiso 1 1 calc R U . . .
C15 C 0.3632(5) 0.4529(4) 1.0145(3) 0.0413(12) Uani 1 1 d . . . . .
H15A H 0.4393 0.4242 1.0468 0.062 Uiso 1 1 calc R U . . .
H15B H 0.3523 0.3915 0.9723 0.062 Uiso 1 1 calc R U . . .
H15C H 0.2783 0.4554 1.0442 0.062 Uiso 1 1 calc R U . . .
B1 B 0.7522(5) 0.4292(5) 1.0463(3) 0.0339(11) Uani 1 1 d . . . . .
H1A H 0.6955 0.3849 1.0843 0.051 Uiso 1 1 calc R U . . .
H1B H 0.7698 0.5193 1.0624 0.051 Uiso 1 1 calc R U . . .
H1C H 0.8396 0.3826 1.0407 0.051 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 N2 1.925(3) . ?
Ge1 N1 1.938(3) . ?
Ge1 B1 2.050(4) . ?
N1 C1 1.330(5) . ?
N1 C8 1.502(5) . ?
N2 C7 1.352(5) . ?
N2 C9 1.502(5) . ?
C1 C2 1.429(5) . ?
C1 C7 1.473(5) . ?
C2 C3 1.371(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.403(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.402(6) . ?
C6 H6 0.9300 . ?
C8 C11 1.530(6) . ?
C8 C10 1.533(6) . ?
C8 C12 1.537(6) . ?
C9 C13 1.518(6) . ?
C9 C15 1.523(6) . ?
C9 C14 1.540(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
B1 H1A 0.9600 . ?
B1 H1B 0.9600 . ?
B1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ge1 N1 83.82(13) . . ?
N2 Ge1 B1 113.45(17) . . ?
N1 Ge1 B1 120.17(19) . . ?
C1 N1 C8 125.8(3) . . ?
C1 N1 Ge1 113.1(3) . . ?
C8 N1 Ge1 120.9(2) . . ?
C7 N2 C9 125.4(3) . . ?
C7 N2 Ge1 112.6(3) . . ?
C9 N2 Ge1 121.5(2) . . ?
N1 C1 C2 123.8(4) . . ?
N1 C1 C7 114.5(3) . . ?
C2 C1 C7 121.2(3) . . ?
C3 C2 C1 131.8(4) . . ?
C3 C2 H2 114.1 . . ?
C1 C2 H2 114.1 . . ?
C2 C3 C4 129.5(4) . . ?
C2 C3 H3 115.3 . . ?
C4 C3 H3 115.3 . . ?
C5 C4 C3 126.1(4) . . ?
C5 C4 H4 117.0 . . ?
C3 C4 H4 117.0 . . ?
C4 C5 C6 129.3(4) . . ?
C4 C5 H5 115.3 . . ?
C6 C5 H5 115.3 . . ?
C7 C6 C5 131.5(4) . . ?
C7 C6 H6 114.2 . . ?
C5 C6 H6 114.2 . . ?
N2 C7 C6 123.0(4) . . ?
N2 C7 C1 113.0(3) . . ?
C6 C7 C1 123.8(4) . . ?
N1 C8 C11 110.3(3) . . ?
N1 C8 C10 112.4(3) . . ?
C11 C8 C10 111.9(3) . . ?
N1 C8 C12 106.6(3) . . ?
C11 C8 C12 108.3(4) . . ?
C10 C8 C12 107.1(4) . . ?
N2 C9 C13 111.5(3) . . ?
N2 C9 C15 106.4(3) . . ?
C13 C9 C15 107.1(4) . . ?
N2 C9 C14 111.7(3) . . ?
C13 C9 C14 112.0(4) . . ?
C15 C9 C14 107.7(3) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Ge1 B1 H1A 109.5 . . ?
Ge1 B1 H1B 109.5 . . ?
H1A B1 H1B 109.5 . . ?
Ge1 B1 H1C 109.5 . . ?
H1A B1 H1C 109.5 . . ?
H1B B1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 9.9(6) . . . . ?
Ge1 N1 C1 C2 -163.7(3) . . . . ?
C8 N1 C1 C7 -178.0(4) . . . . ?
Ge1 N1 C1 C7 8.4(4) . . . . ?
N1 C1 C2 C3 -162.3(4) . . . . ?
C7 C1 C2 C3 26.1(7) . . . . ?
C1 C2 C3 C4 -1.1(8) . . . . ?
C2 C3 C4 C5 -9.5(8) . . . . ?
C3 C4 C5 C6 -3.4(8) . . . . ?
C4 C5 C6 C7 8.4(8) . . . . ?
C9 N2 C7 C6 16.3(6) . . . . ?
Ge1 N2 C7 C6 -155.6(3) . . . . ?
C9 N2 C7 C1 -169.1(3) . . . . ?
Ge1 N2 C7 C1 18.9(4) . . . . ?
C5 C6 C7 N2 -173.9(4) . . . . ?
C5 C6 C7 C1 12.1(7) . . . . ?
N1 C1 C7 N2 -18.2(5) . . . . ?
C2 C1 C7 N2 154.1(3) . . . . ?
N1 C1 C7 C6 156.3(4) . . . . ?
C2 C1 C7 C6 -31.4(6) . . . . ?
C1 N1 C8 C11 -78.9(5) . . . . ?
Ge1 N1 C8 C11 94.3(4) . . . . ?
C1 N1 C8 C10 46.7(5) . . . . ?
Ge1 N1 C8 C10 -140.1(3) . . . . ?
C1 N1 C8 C12 163.7(4) . . . . ?
Ge1 N1 C8 C12 -23.1(4) . . . . ?
C7 N2 C9 C13 49.7(5) . . . . ?
Ge1 N2 C9 C13 -139.0(3) . . . . ?
C7 N2 C9 C15 166.3(4) . . . . ?
Ge1 N2 C9 C15 -22.4(4) . . . . ?
C7 N2 C9 C14 -76.5(5) . . . . ?
Ge1 N2 C9 C14 94.8(4) . . . . ?

_refine_diff_density_max         0.552
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.060


