# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1457869'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;

_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H52 Cl3 Ga Ge N8'
_chemical_formula_weight         881.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga -1.2846 0.7763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge -1.0885 0.8855 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.8149(4)
_cell_length_b                   13.6703(4)
_cell_length_c                   14.6341(4)
_cell_angle_alpha                109.690(3)
_cell_angle_beta                 90.728(2)
_cell_angle_gamma                112.290(3)
_cell_volume                     2204.15(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11030
_cell_measurement_theta_min      3.2300
_cell_measurement_theta_max      73.6050

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    3.541
_exptl_absorpt_correction_T_min  0.15591
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_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            14861
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         67.49
_reflns_number_total             7940
_reflns_number_gt                7328
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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)+(0.0672P)²+2.9264P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7940
_refine_ls_number_parameters     481
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.006
_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 0.64630(3) 0.77307(3) 0.82039(2) 0.02011(11) Uani 1 1 d . . .
Ga1 Ga 0.59421(3) 0.77035(3) 0.65264(3) 0.02103(11) Uani 1 1 d . . .
Cl1 Cl 0.62632(7) 0.94461(6) 0.65498(6) 0.03200(18) Uani 1 1 d . . .
N1 N 0.8273(2) 0.6743(2) 0.77519(19) 0.0222(5) Uani 1 1 d . . .
C1 C 0.7172(2) 0.6594(2) 0.7611(2) 0.0198(5) Uani 1 1 d . . .
Cl2 Cl 0.68612(6) 0.70211(6) 0.53326(5) 0.02876(17) Uani 1 1 d . . .
N2 N 0.6612(2) 0.5496(2) 0.69973(18) 0.0206(5) Uani 1 1 d . . .
C2 C 0.4985(2) 0.6341(2) 0.7973(2) 0.0209(6) Uani 1 1 d . . .
Cl3 Cl 0.41297(6) 0.66194(6) 0.57464(5) 0.02763(17) Uani 1 1 d . . .
N3 N 0.4725(2) 0.5269(2) 0.73205(18) 0.0211(5) Uani 1 1 d . . .
C3 C 0.8399(3) 0.5760(3) 0.7210(2) 0.0278(6) Uani 1 1 d . . .
H3 H 0.9093 0.5658 0.7184 0.033 Uiso 1 1 calc R . .
N4 N 0.4071(2) 0.6265(2) 0.84372(19) 0.0253(5) Uani 1 1 d . . .
C4 C 0.7359(3) 0.4972(3) 0.6726(2) 0.0259(6) Uani 1 1 d . . .
H4 H 0.7174 0.4214 0.6289 0.031 Uiso 1 1 calc R . .
N5 N 0.9011(3) 0.3760(4) 0.5521(3) 0.0574(10) Uani 1 1 d . . .
C5 C 0.5406(2) 0.4983(2) 0.6569(2) 0.0226(6) Uani 1 1 d . . .
H5A H 0.5305 0.5263 0.6046 0.027 Uiso 1 1 calc R . .
H5B H 0.5141 0.4147 0.6267 0.027 Uiso 1 1 calc R . .
N6 N 0.9238(7) 0.8302(6) 0.3884(6) 0.122(3) Uani 1 1 d . . .
C6 C 0.3644(3) 0.4536(3) 0.7363(2) 0.0282(7) Uani 1 1 d . . .
H6 H 0.3265 0.3748 0.6974 0.034 Uiso 1 1 calc R . .
N7 N 0.4714(5) 0.7796(4) 0.3596(3) 0.0710(12) Uani 1 1 d . . .
C7 C 0.3236(3) 0.5160(3) 0.8064(3) 0.0303(7) Uani 1 1 d . . .
H7 H 0.2513 0.4893 0.8266 0.036 Uiso 1 1 calc R . .
N8 N 0.0401(3) 0.4134(3) 0.7917(3) 0.0579(10) Uani 1 1 d . . .
C8 C 0.9221(3) 0.7762(2) 0.8421(2) 0.0245(6) Uani 1 1 d . . .
C9 C 0.9794(3) 0.8631(3) 0.8087(2) 0.0254(6) Uani 1 1 d . . .
C10 C 1.0741(3) 0.9564(3) 0.8726(3) 0.0305(7) Uani 1 1 d . . .
H10 H 1.1150 1.0181 0.8529 0.037 Uiso 1 1 calc R . .
C11 C 1.1087(3) 0.9598(3) 0.9632(3) 0.0326(7) Uani 1 1 d . . .
H11 H 1.1731 1.0237 1.0056 0.039 Uiso 1 1 calc R . .
C12 C 1.0507(3) 0.8712(3) 0.9930(3) 0.0324(7) Uani 1 1 d . . .
H12 H 1.0764 0.8746 1.0556 0.039 Uiso 1 1 calc R . .
C13 C 0.9549(3) 0.7763(3) 0.9337(2) 0.0288(7) Uani 1 1 d . . .
C14 C 0.8934(4) 0.6795(3) 0.9683(3) 0.0395(8) Uani 1 1 d . . .
H14 H 0.8215 0.6264 0.9205 0.047 Uiso 1 1 calc R . .
C15 C 0.8603(4) 0.7218(4) 1.0687(4) 0.0567(12) Uani 1 1 d . . .
H15A H 0.8141 0.6567 1.0859 0.085 Uiso 1 1 calc R . .
H15B H 0.8160 0.7662 1.0672 0.085 Uiso 1 1 calc R . .
H15C H 0.9296 0.7700 1.1180 0.085 Uiso 1 1 calc R . .
C16 C 0.9648(5) 0.6131(4) 0.9697(4) 0.0642(14) Uani 1 1 d . . .
H16A H 0.9812 0.5821 0.9035 0.096 Uiso 1 1 calc R . .
H16B H 0.9225 0.5506 0.9915 0.096 Uiso 1 1 calc R . .
H16C H 1.0366 0.6637 1.0152 0.096 Uiso 1 1 calc R . .
C17 C 0.9457(3) 0.8599(3) 0.7078(2) 0.0310(7) Uani 1 1 d . . .
H17 H 0.8747 0.7894 0.6748 0.037 Uiso 1 1 calc R . .
C18 C 1.0392(4) 0.8536(4) 0.6454(3) 0.0496(10) Uani 1 1 d . . .
H18A H 1.1106 0.9206 0.6776 0.074 Uiso 1 1 calc R . .
H18B H 1.0164 0.8515 0.5804 0.074 Uiso 1 1 calc R . .
H18C H 1.0508 0.7846 0.6381 0.074 Uiso 1 1 calc R . .
C19 C 0.9195(4) 0.9624(3) 0.7153(3) 0.0442(9) Uani 1 1 d . . .
H19A H 0.8565 0.9621 0.7527 0.066 Uiso 1 1 calc R . .
H19B H 0.8976 0.9580 0.6491 0.066 Uiso 1 1 calc R . .
H19C H 0.9875 1.0327 0.7489 0.066 Uiso 1 1 calc R . .
C20 C 0.3969(3) 0.7195(3) 0.9234(2) 0.0282(7) Uani 1 1 d . . .
C21 C 0.3500(3) 0.7865(3) 0.8986(2) 0.0288(7) Uani 1 1 d . . .
C22 C 0.3395(3) 0.8735(3) 0.9767(3) 0.0396(8) Uani 1 1 d . . .
H22 H 0.3098 0.9220 0.9631 0.048 Uiso 1 1 calc R . .
C23 C 0.3710(3) 0.8908(4) 1.0725(3) 0.0454(9) Uani 1 1 d . . .
H23 H 0.3623 0.9503 1.1242 0.054 Uiso 1 1 calc R . .
C24 C 0.4155(4) 0.8220(4) 1.0944(3) 0.0466(10) Uani 1 1 d . . .
H24 H 0.4366 0.8346 1.1612 0.056 Uiso 1 1 calc R . .
C25 C 0.4298(3) 0.7348(4) 1.0202(3) 0.0387(8) Uani 1 1 d . . .
C26 C 0.4802(5) 0.6621(5) 1.0469(3) 0.0574(12) Uani 1 1 d . . .
H26 H 0.4982 0.6150 0.9857 0.069 Uiso 1 1 calc R . .
C27 C 0.5916(5) 0.7359(7) 1.1211(6) 0.094(2) Uani 1 1 d . . .
H27A H 0.6417 0.7948 1.0986 0.140 Uiso 1 1 calc R . .
H27B H 0.6303 0.6879 1.1265 0.140 Uiso 1 1 calc R . .
H27C H 0.5739 0.7719 1.1856 0.140 Uiso 1 1 calc R . .
C28 C 0.3971(6) 0.5830(5) 1.0887(4) 0.0739(16) Uani 1 1 d . . .
H28A H 0.3789 0.6276 1.1492 0.111 Uiso 1 1 calc R . .
H28B H 0.4314 0.5359 1.1035 0.111 Uiso 1 1 calc R . .
H28C H 0.3270 0.5340 1.0407 0.111 Uiso 1 1 calc R . .
C29 C 0.3053(3) 0.7624(3) 0.7939(3) 0.0343(7) Uani 1 1 d . . .
H29 H 0.3380 0.7119 0.7493 0.041 Uiso 1 1 calc R . .
C30 C 0.1750(3) 0.6987(3) 0.7731(3) 0.0392(8) Uani 1 1 d . . .
H30A H 0.1535 0.6287 0.7867 0.059 Uiso 1 1 calc R . .
H30B H 0.1473 0.6796 0.7040 0.059 Uiso 1 1 calc R . .
H30C H 0.1410 0.7471 0.8154 0.059 Uiso 1 1 calc R . .
C31 C 0.3395(4) 0.8700(4) 0.7699(3) 0.0494(10) Uani 1 1 d . . .
H31A H 0.3055 0.9193 0.8107 0.074 Uiso 1 1 calc R . .
H31B H 0.3120 0.8490 0.7003 0.074 Uiso 1 1 calc R . .
H31C H 0.4229 0.9106 0.7832 0.074 Uiso 1 1 calc R . .
C32 C 1.1180(4) 0.4276(4) 0.5582(3) 0.0489(10) Uani 1 1 d . . .
H32A H 1.1509 0.4364 0.6228 0.073 Uiso 1 1 calc R . .
H32B H 1.1552 0.4990 0.5472 0.073 Uiso 1 1 calc R . .
H32C H 1.1298 0.3665 0.5070 0.073 Uiso 1 1 calc R . .
C33 C 0.9962(4) 0.3992(3) 0.5548(3) 0.0403(8) Uani 1 1 d . . .
C34 C 0.7765(6) 0.9203(5) 0.4347(5) 0.0795(17) Uani 1 1 d . . .
H34A H 0.7282 0.8863 0.4766 0.119 Uiso 1 1 calc R . .
H34B H 0.7287 0.9068 0.3752 0.119 Uiso 1 1 calc R . .
H34C H 0.8180 1.0023 0.4706 0.119 Uiso 1 1 calc R . .
C35 C 0.8576(6) 0.8690(5) 0.4074(4) 0.0704(15) Uani 1 1 d . . .
C36 C 0.3701(4) 0.8700(4) 0.4918(4) 0.0508(10) Uani 1 1 d . . .
H36A H 0.3003 0.8099 0.4964 0.076 Uiso 1 1 calc R . .
H36B H 0.3502 0.9245 0.4739 0.076 Uiso 1 1 calc R . .
H36C H 0.4208 0.9094 0.5554 0.076 Uiso 1 1 calc R . .
C37 C 0.4270(4) 0.8206(3) 0.4181(3) 0.0508(11) Uani 1 1 d . . .
C38 C -0.1464(5) 0.2306(5) 0.7317(5) 0.087(2) Uani 1 1 d . . .
H38A H -0.1467 0.1837 0.7698 0.131 Uiso 1 1 calc R . .
H38B H -0.1510 0.1877 0.6619 0.131 Uiso 1 1 calc R . .
H38C H -0.2122 0.2508 0.7410 0.131 Uiso 1 1 calc R . .
C39 C -0.0411(3) 0.3340(4) 0.7653(3) 0.0441(9) 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 C2 2.033(3) . ?
Ge1 C1 2.043(3) . ?
Ge1 Ga1 2.5202(5) . ?
Ga1 Cl1 2.2464(8) . ?
Ga1 Cl3 2.2529(8) . ?
Ga1 Cl2 2.2576(8) . ?
N1 C1 1.349(4) . ?
N1 C3 1.382(4) . ?
N1 C8 1.463(4) . ?
C1 N2 1.354(4) . ?
N2 C4 1.386(4) . ?
N2 C5 1.461(4) . ?
C2 N4 1.349(4) . ?
C2 N3 1.360(4) . ?
N3 C6 1.385(4) . ?
N3 C5 1.454(4) . ?
C3 C4 1.346(5) . ?
N4 C7 1.389(4) . ?
N4 C20 1.457(4) . ?
N5 C33 1.133(5) . ?
N6 C35 1.152(8) . ?
C6 C7 1.348(5) . ?
N7 C37 1.140(7) . ?
N8 C39 1.123(6) . ?
C8 C9 1.388(5) . ?
C8 C13 1.399(5) . ?
C9 C10 1.403(4) . ?
C9 C17 1.515(5) . ?
C10 C11 1.373(5) . ?
C11 C12 1.376(5) . ?
C12 C13 1.396(5) . ?
C13 C14 1.517(5) . ?
C14 C15 1.518(6) . ?
C14 C16 1.518(6) . ?
C17 C18 1.527(5) . ?
C17 C19 1.531(5) . ?
C20 C25 1.394(5) . ?
C20 C21 1.403(5) . ?
C21 C22 1.396(5) . ?
C21 C29 1.510(5) . ?
C22 C23 1.369(6) . ?
C23 C24 1.385(6) . ?
C24 C25 1.391(5) . ?
C25 C26 1.517(6) . ?
C26 C28 1.506(8) . ?
C26 C27 1.538(9) . ?
C29 C31 1.531(6) . ?
C29 C30 1.531(5) . ?
C32 C33 1.454(6) . ?
C34 C35 1.450(9) . ?
C36 C37 1.433(7) . ?
C38 C39 1.459(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
C2 Ge1 C1 85.67(12) . . ?
C2 Ge1 Ga1 89.78(8) . . ?
C1 Ge1 Ga1 90.83(8) . . ?
Cl1 Ga1 Cl3 104.36(3) . . ?
Cl1 Ga1 Cl2 104.79(3) . . ?
Cl3 Ga1 Cl2 98.87(3) . . ?
Cl1 Ga1 Ge1 112.27(3) . . ?
Cl3 Ga1 Ge1 118.14(3) . . ?
Cl2 Ga1 Ge1 116.58(2) . . ?
C1 N1 C3 110.7(2) . . ?
C1 N1 C8 126.5(2) . . ?
C3 N1 C8 122.7(2) . . ?
N1 C1 N2 104.6(2) . . ?
N1 C1 Ge1 128.8(2) . . ?
N2 C1 Ge1 126.6(2) . . ?
C1 N2 C4 111.4(2) . . ?
C1 N2 C5 123.8(2) . . ?
C4 N2 C5 124.3(2) . . ?
N4 C2 N3 105.2(3) . . ?
N4 C2 Ge1 128.3(2) . . ?
N3 C2 Ge1 126.4(2) . . ?
C2 N3 C6 110.7(3) . . ?
C2 N3 C5 124.0(2) . . ?
C6 N3 C5 124.5(2) . . ?
C4 C3 N1 107.5(3) . . ?
C2 N4 C7 110.4(3) . . ?
C2 N4 C20 125.5(3) . . ?
C7 N4 C20 124.0(3) . . ?
C3 C4 N2 105.8(3) . . ?
N3 C5 N2 110.4(2) . . ?
C7 C6 N3 106.5(3) . . ?
C6 C7 N4 107.2(3) . . ?
C9 C8 C13 123.8(3) . . ?
C9 C8 N1 118.5(3) . . ?
C13 C8 N1 117.5(3) . . ?
C8 C9 C10 116.9(3) . . ?
C8 C9 C17 123.2(3) . . ?
C10 C9 C17 119.8(3) . . ?
C11 C10 C9 121.0(3) . . ?
C10 C11 C12 120.3(3) . . ?
C11 C12 C13 121.8(3) . . ?
C12 C13 C8 116.2(3) . . ?
C12 C13 C14 120.4(3) . . ?
C8 C13 C14 123.3(3) . . ?
C13 C14 C15 111.6(3) . . ?
C13 C14 C16 111.3(4) . . ?
C15 C14 C16 110.3(3) . . ?
C9 C17 C18 110.3(3) . . ?
C9 C17 C19 111.2(3) . . ?
C18 C17 C19 111.1(3) . . ?
C25 C20 C21 123.3(3) . . ?
C25 C20 N4 118.7(3) . . ?
C21 C20 N4 118.0(3) . . ?
C22 C21 C20 116.5(3) . . ?
C22 C21 C29 120.8(3) . . ?
C20 C21 C29 122.6(3) . . ?
C23 C22 C21 121.7(4) . . ?
C22 C23 C24 120.3(3) . . ?
C23 C24 C25 121.0(4) . . ?
C24 C25 C20 117.2(3) . . ?
C24 C25 C26 119.6(3) . . ?
C20 C25 C26 123.2(3) . . ?
C28 C26 C25 111.5(4) . . ?
C28 C26 C27 109.2(4) . . ?
C25 C26 C27 111.4(5) . . ?
C21 C29 C31 113.0(3) . . ?
C21 C29 C30 110.1(3) . . ?
C31 C29 C30 109.6(3) . . ?
N5 C33 C32 179.3(5) . . ?
N6 C35 C34 178.1(8) . . ?
N7 C37 C36 178.8(5) . . ?
N8 C39 C38 179.6(5) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        67.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.685
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.093
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1457870'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;

_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H56 Cl3 Ga Ge N4 O2 Se2'
_chemical_formula_weight         1019.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga -1.2846 0.7763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge -1.0885 0.8855 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Cm

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                   16.2434(7)
_cell_length_b                   21.8215(9)
_cell_length_c                   7.6828(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.197(4)
_cell_angle_gamma                90.00
_cell_volume                     2555.76(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4979
_cell_measurement_theta_min      3.5300
_cell_measurement_theta_max      73.7430

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    4.691
_exptl_absorpt_correction_T_min  0.58147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_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            7876
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         67.46
_reflns_number_total             3421
_reflns_number_gt                3319
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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)+(0.0947P)²+0.9887P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_number_reflns         3421
_refine_ls_number_parameters     248
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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
Se1 Se 0.09375(5) 0.0000 0.15031(10) 0.0445(2) Uani 1 2 d S . .
Ge1 Ge 0.20095(5) 0.0000 0.03408(8) 0.0363(2) Uani 1 2 d S . .
Ga1 Ga 0.43631(7) 0.0000 0.07517(16) 0.0593(3) Uani 1 2 d S . .
Cl1 Cl 0.41567(12) 0.08135(8) -0.1059(2) 0.0694(4) Uani 1 1 d . . .
O1 O 0.1150(4) 0.30046(19) -0.3496(7) 0.0698(13) Uani 1 1 d . . .
C1 C 0.1878(3) 0.0654(2) -0.1537(7) 0.0392(10) Uani 1 1 d . . .
Cl2 Cl 0.57159(18) 0.0000 0.2655(5) 0.0854(8) Uani 1 2 d S . .
C2 C 0.1554(5) 0.1507(2) -0.3248(8) 0.0531(13) Uani 1 1 d . . .
H2 H 0.1393 0.1919 -0.3603 0.064 Uiso 1 1 calc R . .
C3 C 0.1763(4) 0.1073(2) -0.4298(7) 0.0498(12) Uani 1 1 d . . .
H3 H 0.1774 0.1120 -0.5518 0.060 Uiso 1 1 calc R . .
C4 C 0.2292(6) 0.0000 -0.3789(10) 0.0461(16) Uani 1 2 d S . .
H4A H 0.2131 0.0000 -0.5155 0.055 Uiso 1 2 calc SR . .
H4B H 0.2940 0.0000 -0.3236 0.055 Uiso 1 2 calc SR . .
C5 C 0.1389(4) 0.1557(2) -0.0162(7) 0.0450(11) Uani 1 1 d . . .
C6 C 0.2087(4) 0.1826(2) 0.1304(9) 0.0537(14) Uani 1 1 d . . .
C8 C 0.0973(6) 0.2216(3) 0.2442(9) 0.072(2) Uani 1 1 d . . .
H8 H 0.0823 0.2456 0.3318 0.086 Uiso 1 1 calc R . .
N9 N 0.1954(3) 0.05473(18) -0.3226(6) 0.0413(9) Uani 1 1 d . . .
C9 C 0.0320(6) 0.1924(3) 0.1032(11) 0.072(2) Uani 1 1 d . . .
H9 H -0.0270 0.1948 0.0992 0.086 Uiso 1 1 calc R . .
C10 C 0.0513(4) 0.1596(3) -0.0321(8) 0.0527(13) Uani 1 1 d . . .
C11 C -0.0200(5) 0.1319(3) -0.1941(11) 0.0656(16) Uani 1 1 d . . .
H11 H 0.0067 0.0999 -0.2514 0.079 Uiso 1 1 calc R . .
C12 C -0.0615(6) 0.1829(4) -0.3429(12) 0.081(2) Uani 1 1 d . . .
H12A H -0.0928 0.2126 -0.2928 0.122 Uiso 1 1 calc R . .
H12B H -0.1027 0.1641 -0.4550 0.122 Uiso 1 1 calc R . .
H12C H -0.0150 0.2039 -0.3736 0.122 Uiso 1 1 calc R . .
N13 N 0.1619(3) 0.12450(18) -0.1597(6) 0.0430(9) Uani 1 1 d . . .
C13 C -0.0934(6) 0.1020(5) -0.1399(17) 0.096(3) Uani 1 1 d . . .
H13A H -0.0708 0.0649 -0.0670 0.144 Uiso 1 1 calc R . .
H13B H -0.1423 0.0911 -0.2523 0.144 Uiso 1 1 calc R . .
H13C H -0.1138 0.1308 -0.0658 0.144 Uiso 1 1 calc R . .
C14 C 0.3012(5) 0.1780(3) 0.1402(12) 0.0695(18) Uani 1 1 d . . .
H14 H 0.3070 0.1386 0.0790 0.083 Uiso 1 1 calc R . .
C15 C 0.3246(8) 0.2285(4) 0.034(2) 0.110(4) Uani 1 1 d . . .
H15A H 0.2922 0.2232 -0.0986 0.166 Uiso 1 1 calc R . .
H15B H 0.3877 0.2273 0.0565 0.166 Uiso 1 1 calc R . .
H15C H 0.3093 0.2680 0.0751 0.166 Uiso 1 1 calc R . .
C16 C 0.3677(7) 0.1759(5) 0.3387(15) 0.104(3) Uani 1 1 d . . .
H16A H 0.3706 0.2162 0.3969 0.155 Uiso 1 1 calc R . .
H16B H 0.4256 0.1650 0.3353 0.155 Uiso 1 1 calc R . .
H16C H 0.3492 0.1452 0.4107 0.155 Uiso 1 1 calc R . .
C17 C 0.1521(8) 0.3511(3) -0.4148(15) 0.087(2) Uani 1 1 d . . .
H17A H 0.1185 0.3593 -0.5470 0.104 Uiso 1 1 calc R . .
H17B H 0.2138 0.3424 -0.4014 0.104 Uiso 1 1 calc R . .
C18 C 0.1469(10) 0.4053(4) -0.2962(18) 0.111(3) Uani 1 1 d . . .
H18A H 0.0937 0.4301 -0.3577 0.133 Uiso 1 1 calc R . .
H18B H 0.1993 0.4318 -0.2692 0.133 Uiso 1 1 calc R . .
C19 C 0.1430(8) 0.3751(4) -0.1183(17) 0.099(3) Uani 1 1 d . . .
H19A H 0.2020 0.3639 -0.0320 0.119 Uiso 1 1 calc R . .
H19B H 0.1132 0.4015 -0.0537 0.119 Uiso 1 1 calc R . .
C20 C 0.0891(7) 0.3193(4) -0.2022(14) 0.089(3) Uani 1 1 d . . .
H20A H 0.0997 0.2863 -0.1087 0.107 Uiso 1 1 calc R . .
H20B H 0.0258 0.3295 -0.2475 0.107 Uiso 1 1 calc R . .
Se2 Se 0.34206(5) 0.0000 0.25233(9) 0.0501(2) Uani 1 2 d S . .
C7 C 0.1820(6) 0.2164(3) 0.2587(8) 0.0647(18) Uani 1 1 d . . .
H7 H 0.2255 0.2361 0.3591 0.078 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
Se1 Ge1 2.2144(9) . ?
Ge1 C1 1.987(5) 2 ?
Ge1 C1 1.987(5) . ?
Ge1 Se2 2.3263(10) . ?
Ga1 Cl2 2.179(3) . ?
Ga1 Cl1 2.2086(18) 2 ?
Ga1 Cl1 2.2086(18) . ?
Ga1 Se2 2.3738(12) . ?
O1 C20 1.400(10) . ?
O1 C17 1.428(9) . ?
C1 N13 1.352(6) . ?
C1 N9 1.366(6) . ?
C2 C3 1.361(8) . ?
C2 N13 1.362(7) . ?
C3 N9 1.383(7) . ?
C4 N9 1.442(6) 2 ?
C4 N9 1.442(6) . ?
C5 C10 1.387(9) . ?
C5 C6 1.420(9) . ?
C5 N13 1.452(6) . ?
C6 C7 1.413(8) . ?
C6 C14 1.481(10) . ?
C8 C7 1.346(11) . ?
C8 C9 1.383(12) . ?
C9 C10 1.385(9) . ?
C10 C11 1.503(10) . ?
C11 C13 1.538(12) . ?
C11 C12 1.571(10) . ?
C14 C15 1.495(12) . ?
C14 C16 1.535(13) . ?
C17 C18 1.513(14) . ?
C18 C19 1.539(17) . ?
C19 C20 1.508(12) . ?

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
C1 Ge1 C1 91.8(3) 2 . ?
C1 Ge1 Se1 112.96(14) 2 . ?
C1 Ge1 Se1 112.96(14) . . ?
C1 Ge1 Se2 110.84(15) 2 . ?
C1 Ge1 Se2 110.84(15) . . ?
Se1 Ge1 Se2 115.19(4) . . ?
Cl2 Ga1 Cl1 108.74(7) . 2 ?
Cl2 Ga1 Cl1 108.74(7) . . ?
Cl1 Ga1 Cl1 106.98(11) 2 . ?
Cl2 Ga1 Se2 108.41(10) . . ?
Cl1 Ga1 Se2 111.94(5) 2 . ?
Cl1 Ga1 Se2 111.94(5) . . ?
C20 O1 C17 109.7(6) . . ?
N13 C1 N9 105.0(4) . . ?
N13 C1 Ge1 131.6(3) . . ?
N9 C1 Ge1 123.0(3) . . ?
C3 C2 N13 107.7(5) . . ?
C2 C3 N9 106.0(4) . . ?
N9 C4 N9 111.9(6) 2 . ?
C10 C5 C6 124.0(5) . . ?
C10 C5 N13 119.1(5) . . ?
C6 C5 N13 116.8(5) . . ?
C7 C6 C5 114.5(6) . . ?
C7 C6 C14 123.4(6) . . ?
C5 C6 C14 122.1(5) . . ?
C7 C8 C9 120.8(6) . . ?
C1 N9 C3 110.4(4) . . ?
C1 N9 C4 126.5(4) . . ?
C3 N9 C4 122.6(4) . . ?
C8 C9 C10 120.9(7) . . ?
C9 C10 C5 117.1(6) . . ?
C9 C10 C11 121.3(7) . . ?
C5 C10 C11 121.5(5) . . ?
C10 C11 C13 113.2(7) . . ?
C10 C11 C12 109.4(6) . . ?
C13 C11 C12 108.6(7) . . ?
C1 N13 C2 110.9(4) . . ?
C1 N13 C5 125.5(4) . . ?
C2 N13 C5 123.6(4) . . ?
C6 C14 C15 111.5(7) . . ?
C6 C14 C16 113.9(8) . . ?
C15 C14 C16 109.8(8) . . ?
O1 C17 C18 106.1(8) . . ?
C17 C18 C19 103.1(7) . . ?
C20 C19 C18 99.4(8) . . ?
O1 C20 C19 106.8(7) . . ?
Ge1 Se2 Ga1 104.88(4) . . ?
C8 C7 C6 122.5(7) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        67.46
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.265
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.120
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1457871'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;
_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H64 Cl3 Ga Ge N4 O3 Te'
_chemical_formula_weight         1061.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga -1.2846 0.7763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge -1.0885 0.8855 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Te Te -0.1759 6.3531 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   p-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.3788(3)
_cell_length_b                   13.0772(3)
_cell_length_c                   17.5125(4)
_cell_angle_alpha                69.253(2)
_cell_angle_beta                 83.744(2)
_cell_angle_gamma                84.543(2)
_cell_volume                     2417.94(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9024
_cell_measurement_theta_min      2.7140
_cell_measurement_theta_max      71.6050

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    7.950
_exptl_absorpt_correction_T_min  0.31666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_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            14971
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         67.49
_reflns_number_total             8672
_reflns_number_gt                7814
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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)+(0.0966P)²+3.3777P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8672
_refine_ls_number_parameters     559
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1475
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.084
_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
Te1 Te 0.13763(3) 0.29284(2) 0.314004(17) 0.03357(12) Uani 1 1 d . . .
Ge1 Ge -0.08706(5) 0.36495(4) 0.32677(3) 0.02733(15) Uani 1 1 d . . .
Ga1 Ga 0.20744(6) 0.34144(5) 0.16415(4) 0.03524(17) Uani 1 1 d . . .
Cl1 Cl 0.10794(13) 0.25990(11) 0.10050(8) 0.0454(3) Uani 1 1 d . . .
O1 O -0.3479(10) 0.5863(11) 0.1328(12) 0.092(5) Uani 0.485(17) 1 d PDU A 1
N1 N -0.2233(3) 0.2282(3) 0.2635(2) 0.0271(8) Uani 1 1 d . . .
C1 C -0.1590(4) 0.3168(4) 0.2441(3) 0.0255(8) Uani 1 1 d . . .
N2 N -0.1752(3) 0.3753(3) 0.1644(2) 0.0283(8) Uani 1 1 d . . .
Cl2 Cl 0.39617(13) 0.29330(14) 0.14539(11) 0.0595(4) Uani 1 1 d . . .
O2 O 0.0899(5) 0.9003(4) 0.0674(3) 0.0660(13) Uani 1 1 d . . .
C2 C -0.0744(4) 0.5138(4) 0.2364(3) 0.0281(9) Uani 1 1 d . . .
Cl3 Cl 0.18876(12) 0.51910(10) 0.08891(7) 0.0419(3) Uani 1 1 d . . .
O3 O 0.5674(4) 0.0200(4) 0.2208(3) 0.0603(12) Uani 1 1 d . . .
N3 N -0.0966(4) 0.5441(3) 0.1568(2) 0.0312(8) Uani 1 1 d . . .
C3 C -0.2763(4) 0.2293(4) 0.1953(3) 0.0328(10) Uani 1 1 d . . .
H3 H -0.3243 0.1753 0.1926 0.039 Uiso 1 1 calc R . .
N4 N -0.0533(4) 0.6077(3) 0.2467(2) 0.0303(8) Uani 1 1 d . . .
C4 C -0.2464(4) 0.3217(4) 0.1337(3) 0.0344(10) Uani 1 1 d . . .
H4 H -0.2699 0.3456 0.0794 0.041 Uiso 1 1 calc R . .
C5 C -0.1136(5) 0.4713(4) 0.1127(3) 0.0340(10) Uani 1 1 d . . .
H5A H -0.1596 0.5118 0.0651 0.041 Uiso 1 1 calc R . .
H5B H -0.0354 0.4475 0.0917 0.041 Uiso 1 1 calc R . .
C6 C -0.0873(5) 0.6552(4) 0.1168(3) 0.0411(12) Uani 1 1 d . . .
H6 H -0.0980 0.6954 0.0608 0.049 Uiso 1 1 calc R . .
C7 C -0.0596(5) 0.6953(4) 0.1741(3) 0.0387(11) Uani 1 1 d . . .
H7 H -0.0470 0.7694 0.1657 0.046 Uiso 1 1 calc R . .
C8 C -0.2315(4) 0.1399(4) 0.3419(3) 0.0278(9) Uani 1 1 d . . .
C9 C -0.1565(4) 0.0457(4) 0.3510(4) 0.0376(11) Uani 1 1 d . . .
C10 C -0.1712(5) -0.0412(5) 0.4243(4) 0.0547(16) Uani 1 1 d . . .
H10 H -0.1225 -0.1068 0.4326 0.066 Uiso 1 1 calc R . .
C11 C -0.2565(6) -0.0339(5) 0.4860(4) 0.0576(17) Uani 1 1 d . . .
H11 H -0.2653 -0.0943 0.5358 0.069 Uiso 1 1 calc R . .
C12 C -0.3277(5) 0.0600(5) 0.4752(4) 0.0506(14) Uani 1 1 d . . .
H12 H -0.3857 0.0632 0.5177 0.061 Uiso 1 1 calc R . .
C13 C -0.3172(4) 0.1510(4) 0.4032(3) 0.0339(10) Uani 1 1 d . . .
C14 C -0.3964(5) 0.2544(5) 0.3928(4) 0.0437(13) Uani 1 1 d . . .
H14 H -0.3509 0.3178 0.3562 0.052 Uiso 1 1 calc R . .
C15 C -0.4293(10) 0.2720(7) 0.4743(5) 0.087(3) Uani 1 1 d . . .
H15A H -0.4725 0.3434 0.4645 0.130 Uiso 1 1 calc R . .
H15B H -0.3571 0.2700 0.5007 0.130 Uiso 1 1 calc R . .
H15C H -0.4795 0.2140 0.5100 0.130 Uiso 1 1 calc R . .
C16 C -0.5067(6) 0.2545(7) 0.3525(6) 0.077(2) Uani 1 1 d . . .
H16A H -0.4846 0.2469 0.2990 0.116 Uiso 1 1 calc R . .
H16B H -0.5539 0.3235 0.3451 0.116 Uiso 1 1 calc R . .
H16C H -0.5534 0.1931 0.3872 0.116 Uiso 1 1 calc R . .
C17 C -0.0641(5) 0.0340(4) 0.2846(4) 0.0478(14) Uani 1 1 d . . .
H17 H -0.0543 0.1085 0.2423 0.057 Uiso 1 1 calc R . .
C18 C 0.0556(5) -0.0100(5) 0.3167(6) 0.065(2) Uani 1 1 d . . .
H18A H 0.0506 -0.0862 0.3535 0.098 Uiso 1 1 calc R . .
H18B H 0.0793 0.0342 0.3468 0.098 Uiso 1 1 calc R . .
H18C H 0.1144 -0.0064 0.2707 0.098 Uiso 1 1 calc R . .
C19 C -0.1056(6) -0.0382(6) 0.2432(5) 0.0618(17) Uani 1 1 d . . .
H19A H -0.1094 -0.1134 0.2822 0.093 Uiso 1 1 calc R . .
H19B H -0.0500 -0.0373 0.1961 0.093 Uiso 1 1 calc R . .
H19C H -0.1844 -0.0108 0.2244 0.093 Uiso 1 1 calc R . .
C20 C -0.0440(5) 0.6196(4) 0.3247(3) 0.0305(10) Uani 1 1 d . . .
C21 C -0.1511(5) 0.6322(4) 0.3708(3) 0.0370(11) Uani 1 1 d . . .
C22 C -0.1416(5) 0.6493(5) 0.4431(3) 0.0437(12) Uani 1 1 d . . .
H22 H -0.2115 0.6577 0.4758 0.052 Uiso 1 1 calc R . .
C23 C -0.0325(6) 0.6544(5) 0.4688(3) 0.0487(14) Uani 1 1 d . . .
H23 H -0.0283 0.6668 0.5187 0.058 Uiso 1 1 calc R . .
C24 C 0.0693(6) 0.6419(4) 0.4233(4) 0.0436(13) Uani 1 1 d . . .
H24 H 0.1436 0.6450 0.4421 0.052 Uiso 1 1 calc R . .
C25 C 0.0656(5) 0.6243(4) 0.3484(3) 0.0343(10) Uani 1 1 d . . .
C26 C 0.1798(5) 0.6174(4) 0.2965(4) 0.0407(12) Uani 1 1 d . . .
H26 H 0.1621 0.5839 0.2561 0.049 Uiso 1 1 calc R . .
C27 C 0.2202(6) 0.7322(5) 0.2477(5) 0.0624(18) Uani 1 1 d . . .
H27A H 0.2371 0.7680 0.2856 0.094 Uiso 1 1 calc R . .
H27B H 0.1574 0.7753 0.2138 0.094 Uiso 1 1 calc R . .
H27C H 0.2919 0.7270 0.2125 0.094 Uiso 1 1 calc R . .
C28 C 0.2763(5) 0.5487(5) 0.3432(4) 0.0506(14) Uani 1 1 d . . .
H28A H 0.2970 0.5800 0.3829 0.076 Uiso 1 1 calc R . .
H28B H 0.3458 0.5458 0.3055 0.076 Uiso 1 1 calc R . .
H28C H 0.2504 0.4744 0.3724 0.076 Uiso 1 1 calc R . .
C29 C -0.2718(5) 0.6277(5) 0.3428(4) 0.0463(13) Uani 1 1 d . . .
H29 H -0.2592 0.6030 0.2944 0.056 Uiso 1 1 calc R . .
C30 C -0.3491(7) 0.5467(8) 0.4093(6) 0.080(2) Uani 1 1 d . . .
H30A H -0.3069 0.4743 0.4271 0.119 Uiso 1 1 calc R . .
H30B H -0.4232 0.5419 0.3873 0.119 Uiso 1 1 calc R . .
H30C H -0.3667 0.5718 0.4560 0.119 Uiso 1 1 calc R . .
C31 C -0.3367(8) 0.7408(7) 0.3160(8) 0.095(3) Uani 1 1 d . . .
H31A H -0.3299 0.7757 0.3564 0.143 Uiso 1 1 calc R . .
H31B H -0.4204 0.7334 0.3119 0.143 Uiso 1 1 calc R . .
H31C H -0.3013 0.7861 0.2625 0.143 Uiso 1 1 calc R . .
C32B C -0.479(2) 0.5304(19) 0.1657(11) 0.106(6) Uani 0.515(17) 1 d PDU A 2
H32A H -0.5592 0.5277 0.1942 0.127 Uiso 0.515(17) 1 calc PR A 2
H32B H -0.4459 0.4544 0.1757 0.127 Uiso 0.515(17) 1 calc PR A 2
C33B C -0.485(3) 0.592(2) 0.0729(12) 0.122(9) Uani 0.515(17) 1 d PDU A 2
H33A H -0.4319 0.5556 0.0405 0.146 Uiso 0.515(17) 1 calc PR A 2
H33B H -0.5669 0.5981 0.0568 0.146 Uiso 0.515(17) 1 calc PR A 2
C34B C -0.443(3) 0.705(2) 0.0615(13) 0.115(9) Uani 0.515(17) 1 d PDU A 2
H34A H -0.3717 0.7223 0.0228 0.138 Uiso 0.515(17) 1 calc PR A 2
H34B H -0.5063 0.7635 0.0428 0.138 Uiso 0.515(17) 1 calc PR A 2
C35B C -0.4164(17) 0.6851(16) 0.1491(10) 0.081(5) Uani 0.515(17) 1 d PDU A 2
H35A H -0.3393 0.7147 0.1487 0.097 Uiso 0.515(17) 1 calc PR A 2
H35B H -0.4783 0.7242 0.1745 0.097 Uiso 0.515(17) 1 calc PR A 2
C36 C 0.1435(9) 1.0026(6) 0.0484(6) 0.080(2) Uani 1 1 d . . .
H36A H 0.1640 1.0112 0.0992 0.095 Uiso 1 1 calc R . .
H36B H 0.0880 1.0645 0.0209 0.095 Uiso 1 1 calc R . .
C37 C 0.2491(18) 1.0010(16) -0.0052(11) 0.197(10) Uani 1 1 d . . .
H37A H 0.3200 1.0040 0.0219 0.236 Uiso 1 1 calc R . .
H37B H 0.2459 1.0653 -0.0564 0.236 Uiso 1 1 calc R . .
C38 C 0.2560(10) 0.9010(10) -0.0236(8) 0.107(4) Uani 1 1 d . . .
H38A H 0.3280 0.8551 -0.0028 0.129 Uiso 1 1 calc R . .
H38B H 0.2589 0.9179 -0.0835 0.129 Uiso 1 1 calc R . .
C39 C 0.1507(9) 0.8447(7) 0.0166(6) 0.087(3) Uani 1 1 d . . .
H39A H 0.0986 0.8436 -0.0248 0.105 Uiso 1 1 calc R . .
H39B H 0.1727 0.7681 0.0502 0.105 Uiso 1 1 calc R . .
C40 C 0.5027(6) -0.0018(6) 0.3006(5) 0.0621(17) Uani 1 1 d . . .
H40A H 0.5477 -0.0575 0.3433 0.075 Uiso 1 1 calc R . .
H40B H 0.4905 0.0660 0.3141 0.075 Uiso 1 1 calc R . .
C41 C 0.3917(8) -0.0408(15) 0.2973(6) 0.135(6) Uani 1 1 d . . .
H41A H 0.3282 -0.0089 0.3269 0.162 Uiso 1 1 calc R . .
H41B H 0.3938 -0.1216 0.3230 0.162 Uiso 1 1 calc R . .
C42 C 0.3694(6) -0.0072(7) 0.2100(5) 0.0633(18) Uani 1 1 d . . .
H42A H 0.3194 0.0620 0.1926 0.076 Uiso 1 1 calc R . .
H42B H 0.3304 -0.0647 0.1992 0.076 Uiso 1 1 calc R . .
C43 C 0.4919(6) 0.0079(7) 0.1667(5) 0.0666(19) Uani 1 1 d . . .
H43A H 0.5196 -0.0565 0.1510 0.080 Uiso 1 1 calc R . .
H43B H 0.4912 0.0738 0.1164 0.080 Uiso 1 1 calc R . .
C32 C -0.449(2) 0.552(2) 0.111(3) 0.138(10) Uani 0.485(17) 1 d PDU A 1
H32C H -0.4855 0.4953 0.1588 0.166 Uiso 0.485(17) 1 calc PR A 1
H32D H -0.4246 0.5195 0.0678 0.166 Uiso 0.485(17) 1 calc PR A 1
O1B O -0.413(2) 0.5813(14) 0.1921(11) 0.130(7) Uani 0.515(17) 1 d PDU A 2
C35 C -0.3595(17) 0.6975(16) 0.0861(19) 0.101(7) Uani 0.485(17) 1 d PDU A 1
H35C H -0.3255 0.7096 0.0293 0.121 Uiso 0.485(17) 1 calc PR A 1
H35D H -0.3156 0.7398 0.1095 0.121 Uiso 0.485(17) 1 calc PR A 1
C33 C -0.5338(19) 0.6422(18) 0.080(2) 0.125(9) Uani 0.485(17) 1 d PDU A 1
H33C H -0.5478 0.6540 0.0228 0.150 Uiso 0.485(17) 1 calc PR A 1
H33D H -0.6101 0.6287 0.1142 0.150 Uiso 0.485(17) 1 calc PR A 1
C34 C -0.4820(17) 0.735(2) 0.086(2) 0.111(9) Uani 0.485(17) 1 d PDU A 1
H1 H -0.5113 0.7485 0.1365 0.134 Uiso 0.485(17) 1 calc PR A 1
H2 H -0.4968 0.8014 0.0377 0.134 Uiso 0.485(17) 1 calc PR A 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
Te1 Ga1 2.5262(7) . ?
Te1 Ge1 2.6538(6) . ?
Ge1 C2 2.034(5) . ?
Ge1 C1 2.040(4) . ?
Ga1 Cl2 2.2027(16) . ?
Ga1 Cl3 2.2310(13) . ?
Ga1 Cl1 2.2379(14) . ?
O1 C35 1.39(2) . ?
O1 C32 1.41(2) . ?
N1 C1 1.350(6) . ?
N1 C3 1.391(6) . ?
N1 C8 1.448(6) . ?
C1 N2 1.357(6) . ?
N2 C4 1.380(6) . ?
N2 C5 1.453(6) . ?
O2 C39 1.424(10) . ?
O2 C36 1.437(9) . ?
C2 N4 1.348(6) . ?
C2 N3 1.353(6) . ?
O3 C43 1.404(9) . ?
O3 C40 1.452(9) . ?
N3 C6 1.381(6) . ?
N3 C5 1.459(6) . ?
C3 C4 1.347(7) . ?
N4 C7 1.380(6) . ?
N4 C20 1.445(6) . ?
C6 C7 1.361(8) . ?
C8 C9 1.401(7) . ?
C8 C13 1.407(7) . ?
C9 C10 1.386(8) . ?
C9 C17 1.521(7) . ?
C10 C11 1.395(10) . ?
C11 C12 1.370(10) . ?
C12 C13 1.397(8) . ?
C13 C14 1.518(7) . ?
C14 C16 1.505(10) . ?
C14 C15 1.526(9) . ?
C17 C19 1.512(10) . ?
C17 C18 1.514(9) . ?
C20 C25 1.370(7) . ?
C20 C21 1.416(7) . ?
C21 C22 1.377(8) . ?
C21 C29 1.521(8) . ?
C22 C23 1.383(9) . ?
C23 C24 1.363(9) . ?
C24 C25 1.416(7) . ?
C25 C26 1.517(8) . ?
C26 C28 1.473(8) . ?
C26 C27 1.527(8) . ?
C29 C31 1.526(9) . ?
C29 C30 1.527(10) . ?
C32B O1B 1.27(2) . ?
C32B C33B 1.54(2) . ?
C33B C34B 1.53(2) . ?
C34B C35B 1.52(2) . ?
C35B O1B 1.297(19) . ?
C36 C37 1.445(18) . ?
C37 C38 1.447(19) . ?
C38 C39 1.447(12) . ?
C40 C41 1.420(11) . ?
C41 C42 1.478(12) . ?
C42 C43 1.507(10) . ?
C32 C33 1.43(2) . ?
C35 C34 1.43(2) . ?
C33 C34 1.43(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
Ga1 Te1 Ge1 108.95(2) . . ?
C2 Ge1 C1 86.40(18) . . ?
C2 Ge1 Te1 97.69(13) . . ?
C1 Ge1 Te1 101.76(12) . . ?
Cl2 Ga1 Cl3 105.05(6) . . ?
Cl2 Ga1 Cl1 106.40(7) . . ?
Cl3 Ga1 Cl1 104.24(5) . . ?
Cl2 Ga1 Te1 112.38(5) . . ?
Cl3 Ga1 Te1 115.41(4) . . ?
Cl1 Ga1 Te1 112.54(4) . . ?
C35 O1 C32 98.6(19) . . ?
C1 N1 C3 110.2(4) . . ?
C1 N1 C8 125.9(4) . . ?
C3 N1 C8 123.7(4) . . ?
N1 C1 N2 105.4(4) . . ?
N1 C1 Ge1 124.9(3) . . ?
N2 C1 Ge1 128.3(3) . . ?
C1 N2 C4 110.4(4) . . ?
C1 N2 C5 126.3(4) . . ?
C4 N2 C5 122.5(4) . . ?
C39 O2 C36 107.9(6) . . ?
N4 C2 N3 104.9(4) . . ?
N4 C2 Ge1 125.6(3) . . ?
N3 C2 Ge1 129.1(3) . . ?
C43 O3 C40 108.5(5) . . ?
C2 N3 C6 111.4(4) . . ?
C2 N3 C5 126.6(4) . . ?
C6 N3 C5 121.6(4) . . ?
C4 C3 N1 106.8(4) . . ?
C2 N4 C7 110.9(4) . . ?
C2 N4 C20 125.1(4) . . ?
C7 N4 C20 123.3(4) . . ?
C3 C4 N2 107.0(4) . . ?
N2 C5 N3 112.0(4) . . ?
C7 C6 N3 105.9(4) . . ?
C6 C7 N4 106.9(4) . . ?
C9 C8 C13 123.6(4) . . ?
C9 C8 N1 117.6(4) . . ?
C13 C8 N1 118.7(4) . . ?
C10 C9 C8 117.0(5) . . ?
C10 C9 C17 119.6(5) . . ?
C8 C9 C17 123.4(5) . . ?
C9 C10 C11 121.0(5) . . ?
C12 C11 C10 120.3(5) . . ?
C11 C12 C13 121.8(5) . . ?
C12 C13 C8 116.2(5) . . ?
C12 C13 C14 120.8(5) . . ?
C8 C13 C14 122.9(4) . . ?
C16 C14 C13 112.0(5) . . ?
C16 C14 C15 110.1(7) . . ?
C13 C14 C15 111.7(6) . . ?
C19 C17 C18 110.0(5) . . ?
C19 C17 C9 110.6(5) . . ?
C18 C17 C9 112.6(6) . . ?
C25 C20 C21 123.3(5) . . ?
C25 C20 N4 119.4(4) . . ?
C21 C20 N4 117.2(4) . . ?
C22 C21 C20 116.9(5) . . ?
C22 C21 C29 120.8(5) . . ?
C20 C21 C29 122.3(5) . . ?
C21 C22 C23 121.3(5) . . ?
C24 C23 C22 120.6(5) . . ?
C23 C24 C25 120.8(5) . . ?
C20 C25 C24 117.1(5) . . ?
C20 C25 C26 123.2(5) . . ?
C24 C25 C26 119.7(5) . . ?
C28 C26 C25 114.1(5) . . ?
C28 C26 C27 110.3(5) . . ?
C25 C26 C27 110.2(5) . . ?
C21 C29 C31 110.9(5) . . ?
C21 C29 C30 112.1(6) . . ?
C31 C29 C30 109.5(7) . . ?
O1B C32B C33B 107.8(15) . . ?
C34B C33B C32B 102.8(15) . . ?
C35B C34B C33B 99.5(15) . . ?
O1B C35B C34B 110.8(16) . . ?
O2 C36 C37 107.4(9) . . ?
C36 C37 C38 108.5(9) . . ?
C37 C38 C39 106.4(10) . . ?
O2 C39 C38 108.9(8) . . ?
C41 C40 O3 107.8(7) . . ?
C40 C41 C42 107.3(7) . . ?
C41 C42 C43 103.2(6) . . ?
O3 C43 C42 107.8(6) . . ?
O1 C32 C33 111.3(17) . . ?
C32B O1B C35B 111.4(17) . . ?
O1 C35 C34 109.8(17) . . ?
C34 C33 C32 104.8(18) . . ?
C33 C34 C35 100.6(18) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        67.49
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         2.197
_refine_diff_density_min         -1.761
_refine_diff_density_rms         0.139
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1457872'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;

_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H43 Cl3 Ga Ge N5 Se'
_chemical_formula_weight         837.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga -1.2846 0.7763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge -1.0885 0.8855 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   12.53200(10)
_cell_length_b                   18.88550(10)
_cell_length_c                   16.07690(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.0910(10)
_cell_angle_gamma                90.00
_cell_volume                     3804.96(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    18336
_cell_measurement_theta_min      2.3270
_cell_measurement_theta_max      73.6070

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    5.094
_exptl_absorpt_correction_T_min  0.44228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_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            24155
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         67.50
_reflns_number_total             6855
_reflns_number_gt                6665
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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)+(0.0593P)²+4.3987P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6855
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1002
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
Se1 Se 0.13391(2) 0.160545(15) 0.913590(17) 0.02513(10) Uani 1 1 d . . .
Ge1 Ge 0.24189(2) 0.137087(15) 0.790592(18) 0.02145(10) Uani 1 1 d . . .
Ga1 Ga -0.01154(2) 0.232674(17) 0.88030(2) 0.02243(10) Uani 1 1 d . . .
Cl1 Cl 0.03672(5) 0.34337(3) 0.85615(4) 0.02894(15) Uani 1 1 d . . .
N1 N 0.08047(17) 0.05629(11) 0.68868(13) 0.0212(4) Uani 1 1 d . . .
C1 C 0.12305(19) 0.12005(13) 0.70538(15) 0.0197(5) Uani 1 1 d . . .
Cl2 Cl -0.11948(5) 0.23298(4) 0.98970(4) 0.02957(15) Uani 1 1 d . . .
N2 N 0.08548(16) 0.16357(11) 0.64539(13) 0.0203(4) Uani 1 1 d . . .
C2 C 0.0160(2) 0.05995(15) 0.61868(17) 0.0265(6) Uani 1 1 d . . .
H2 H -0.0226 0.0219 0.5943 0.032 Uiso 1 1 calc R . .
Cl3 Cl -0.11314(5) 0.20128(3) 0.77452(4) 0.02598(14) Uani 1 1 d . . .
N3 N 0.20460(16) 0.26155(11) 0.67051(13) 0.0199(4) Uani 1 1 d . . .
C3 C 0.0183(2) 0.12710(15) 0.59184(17) 0.0253(5) Uani 1 1 d . . .
H3 H -0.0189 0.1460 0.5453 0.030 Uiso 1 1 calc R . .
N4 N 0.34556(17) 0.27616(12) 0.74357(13) 0.0222(4) Uani 1 1 d . . .
C4 C 0.0978(2) 0.23997(14) 0.64396(17) 0.0233(5) Uani 1 1 d . . .
H4A H 0.0442 0.2617 0.6812 0.028 Uiso 1 1 calc R . .
H4B H 0.0845 0.2575 0.5869 0.028 Uiso 1 1 calc R . .
N5 N 0.4990(5) -0.0411(4) 0.8751(4) 0.127(2) Uani 1 1 d . . .
C5 C 0.25858(19) 0.23481(13) 0.73634(16) 0.0206(5) Uani 1 1 d . . .
C6 C 0.3458(2) 0.32868(15) 0.68331(17) 0.0265(6) Uani 1 1 d . . .
H6 H 0.3984 0.3643 0.6758 0.032 Uiso 1 1 calc R . .
C7 C 0.2572(2) 0.31941(14) 0.63762(17) 0.0247(5) Uani 1 1 d . . .
H7 H 0.2349 0.3473 0.5916 0.030 Uiso 1 1 calc R . .
C8 C 0.1040(2) -0.00747(13) 0.73563(16) 0.0226(5) Uani 1 1 d . . .
C9 C 0.0370(2) -0.02465(14) 0.80222(17) 0.0248(5) Uani 1 1 d . . .
C10 C 0.0634(2) -0.08545(15) 0.84724(18) 0.0300(6) Uani 1 1 d . . .
H10 H 0.0217 -0.0985 0.8941 0.036 Uiso 1 1 calc R . .
C11 C 0.1495(3) -0.12698(15) 0.8244(2) 0.0339(6) Uani 1 1 d . . .
H11 H 0.1656 -0.1685 0.8554 0.041 Uiso 1 1 calc R . .
C12 C 0.2124(2) -0.10889(15) 0.7574(2) 0.0326(6) Uani 1 1 d . . .
H12 H 0.2708 -0.1384 0.7425 0.039 Uiso 1 1 calc R . .
C13 C 0.1917(2) -0.04809(15) 0.71111(18) 0.0273(6) Uani 1 1 d . . .
C14 C 0.2579(2) -0.02925(16) 0.6352(2) 0.0342(6) Uani 1 1 d . . .
H14 H 0.2463 0.0221 0.6228 0.041 Uiso 1 1 calc R . .
C15 C 0.2210(3) -0.0719(2) 0.5596(2) 0.0511(9) Uani 1 1 d . . .
H15A H 0.2306 -0.1225 0.5706 0.077 Uiso 1 1 calc R . .
H15B H 0.2633 -0.0583 0.5110 0.077 Uiso 1 1 calc R . .
H15C H 0.1454 -0.0621 0.5488 0.077 Uiso 1 1 calc R . .
C16 C 0.3774(3) -0.0404(2) 0.6503(3) 0.0565(10) Uani 1 1 d . . .
H16A H 0.3994 -0.0141 0.7000 0.085 Uiso 1 1 calc R . .
H16B H 0.4176 -0.0233 0.6021 0.085 Uiso 1 1 calc R . .
H16C H 0.3916 -0.0909 0.6585 0.085 Uiso 1 1 calc R . .
C17 C -0.0618(2) 0.01859(15) 0.82085(19) 0.0303(6) Uani 1 1 d . . .
H17 H -0.0471 0.0683 0.8026 0.036 Uiso 1 1 calc R . .
C18 C -0.0910(3) 0.02137(19) 0.9127(2) 0.0423(8) Uani 1 1 d . . .
H18A H -0.1147 -0.0255 0.9310 0.063 Uiso 1 1 calc R . .
H18B H -0.1486 0.0557 0.9210 0.063 Uiso 1 1 calc R . .
H18C H -0.0284 0.0357 0.9452 0.063 Uiso 1 1 calc R . .
C19 C -0.1568(2) -0.00846(19) 0.7694(2) 0.0414(7) Uani 1 1 d . . .
H19A H -0.1386 -0.0071 0.7102 0.062 Uiso 1 1 calc R . .
H19B H -0.2191 0.0217 0.7796 0.062 Uiso 1 1 calc R . .
H19C H -0.1733 -0.0573 0.7856 0.062 Uiso 1 1 calc R . .
C20 C 0.4294(2) 0.26587(14) 0.80474(16) 0.0232(5) Uani 1 1 d . . .
C21 C 0.4169(2) 0.29724(16) 0.88297(17) 0.0272(6) Uani 1 1 d . . .
C22 C 0.4990(2) 0.2867(2) 0.94025(19) 0.0373(7) Uani 1 1 d . . .
H22 H 0.4930 0.3064 0.9944 0.045 Uiso 1 1 calc R . .
C23 C 0.5892(2) 0.2481(2) 0.9198(2) 0.0422(8) Uani 1 1 d . . .
H23 H 0.6444 0.2419 0.9597 0.051 Uiso 1 1 calc R . .
C24 C 0.5992(2) 0.21827(19) 0.8413(2) 0.0384(7) Uani 1 1 d . . .
H24 H 0.6614 0.1919 0.8280 0.046 Uiso 1 1 calc R . .
C25 C 0.5194(2) 0.22652(16) 0.78170(19) 0.0298(6) Uani 1 1 d . . .
C26 C 0.5347(2) 0.19473(18) 0.6963(2) 0.0347(7) Uani 1 1 d . . .
H26 H 0.4663 0.1999 0.6648 0.042 Uiso 1 1 calc R . .
C27 C 0.6216(3) 0.2350(2) 0.6493(2) 0.0457(8) Uani 1 1 d . . .
H27A H 0.5982 0.2837 0.6394 0.068 Uiso 1 1 calc R . .
H27B H 0.6352 0.2116 0.5960 0.068 Uiso 1 1 calc R . .
H27C H 0.6873 0.2354 0.6825 0.068 Uiso 1 1 calc R . .
C28 C 0.5617(4) 0.1164(2) 0.7014(3) 0.0624(11) Uani 1 1 d . . .
H28A H 0.6336 0.1106 0.7246 0.094 Uiso 1 1 calc R . .
H28B H 0.5592 0.0957 0.6455 0.094 Uiso 1 1 calc R . .
H28C H 0.5099 0.0924 0.7372 0.094 Uiso 1 1 calc R . .
C29 C 0.3216(2) 0.34313(17) 0.90450(18) 0.0300(6) Uani 1 1 d . . .
H29 H 0.2607 0.3276 0.8686 0.036 Uiso 1 1 calc R . .
C30 C 0.3439(3) 0.42081(19) 0.8847(2) 0.0440(8) Uani 1 1 d . . .
H30A H 0.4000 0.4386 0.9218 0.066 Uiso 1 1 calc R . .
H30B H 0.2787 0.4486 0.8928 0.066 Uiso 1 1 calc R . .
H30C H 0.3675 0.4251 0.8268 0.066 Uiso 1 1 calc R . .
C31 C 0.2864(3) 0.33569(19) 0.9946(2) 0.0413(8) Uani 1 1 d . . .
H31A H 0.2754 0.2855 1.0075 0.062 Uiso 1 1 calc R . .
H31B H 0.2196 0.3616 1.0029 0.062 Uiso 1 1 calc R . .
H31C H 0.3416 0.3551 1.0313 0.062 Uiso 1 1 calc R . .
C32 C 0.3264(4) -0.0126(4) 0.9533(4) 0.096(2) Uani 1 1 d . . .
H32A H 0.2927 -0.0566 0.9723 0.145 Uiso 1 1 calc R . .
H32B H 0.2770 0.0130 0.9167 0.145 Uiso 1 1 calc R . .
H32C H 0.3440 0.0170 1.0014 0.145 Uiso 1 1 calc R . .
C33 C 0.4187(5) -0.0286(3) 0.9100(4) 0.0867(16) 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
Se1 Ga1 2.3370(4) . ?
Se1 Ge1 2.4385(4) . ?
Ge1 C1 2.047(2) . ?
Ge1 C5 2.052(3) . ?
Ga1 Cl3 2.2041(7) . ?
Ga1 Cl1 2.2108(7) . ?
Ga1 Cl2 2.2205(7) . ?
N1 C1 1.344(3) . ?
N1 C2 1.386(3) . ?
N1 C8 1.451(3) . ?
C1 N2 1.351(3) . ?
N2 C3 1.387(3) . ?
N2 C4 1.451(3) . ?
C2 C3 1.340(4) . ?
N3 C5 1.353(3) . ?
N3 C7 1.381(3) . ?
N3 C4 1.462(3) . ?
N4 C5 1.346(3) . ?
N4 C6 1.387(3) . ?
N4 C20 1.451(3) . ?
N5 C33 1.176(7) . ?
C6 C7 1.342(4) . ?
C8 C13 1.398(4) . ?
C8 C9 1.400(4) . ?
C9 C10 1.397(4) . ?
C9 C17 1.513(4) . ?
C10 C11 1.384(4) . ?
C11 C12 1.380(5) . ?
C12 C13 1.392(4) . ?
C13 C14 1.519(4) . ?
C14 C15 1.529(5) . ?
C14 C16 1.530(5) . ?
C17 C18 1.523(4) . ?
C17 C19 1.536(4) . ?
C20 C21 1.399(4) . ?
C20 C25 1.401(4) . ?
C21 C22 1.394(4) . ?
C21 C29 1.516(4) . ?
C22 C23 1.385(5) . ?
C23 C24 1.388(5) . ?
C24 C25 1.392(4) . ?
C25 C26 1.510(4) . ?
C26 C28 1.520(5) . ?
C26 C27 1.530(5) . ?
C29 C31 1.521(4) . ?
C29 C30 1.527(5) . ?
C32 C33 1.384(7) . ?

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
Ga1 Se1 Ge1 110.724(15) . . ?
C1 Ge1 C5 86.07(10) . . ?
C1 Ge1 Se1 99.62(7) . . ?
C5 Ge1 Se1 103.79(7) . . ?
Cl3 Ga1 Cl1 106.06(3) . . ?
Cl3 Ga1 Cl2 105.07(3) . . ?
Cl1 Ga1 Cl2 107.69(3) . . ?
Cl3 Ga1 Se1 117.99(2) . . ?
Cl1 Ga1 Se1 112.20(2) . . ?
Cl2 Ga1 Se1 107.22(2) . . ?
C1 N1 C2 110.4(2) . . ?
C1 N1 C8 124.0(2) . . ?
C2 N1 C8 125.5(2) . . ?
N1 C1 N2 105.3(2) . . ?
N1 C1 Ge1 124.23(18) . . ?
N2 C1 Ge1 129.37(18) . . ?
C1 N2 C3 110.6(2) . . ?
C1 N2 C4 125.4(2) . . ?
C3 N2 C4 123.3(2) . . ?
C3 C2 N1 107.2(2) . . ?
C5 N3 C7 110.9(2) . . ?
C5 N3 C4 125.5(2) . . ?
C7 N3 C4 123.1(2) . . ?
C2 C3 N2 106.4(2) . . ?
C5 N4 C6 110.9(2) . . ?
C5 N4 C20 124.5(2) . . ?
C6 N4 C20 124.6(2) . . ?
N2 C4 N3 111.7(2) . . ?
N4 C5 N3 104.8(2) . . ?
N4 C5 Ge1 124.62(18) . . ?
N3 C5 Ge1 128.10(18) . . ?
C7 C6 N4 106.7(2) . . ?
C6 C7 N3 106.7(2) . . ?
C13 C8 C9 124.2(2) . . ?
C13 C8 N1 117.9(2) . . ?
C9 C8 N1 118.0(2) . . ?
C10 C9 C8 116.4(3) . . ?
C10 C9 C17 122.3(3) . . ?
C8 C9 C17 121.2(2) . . ?
C11 C10 C9 120.9(3) . . ?
C12 C11 C10 120.9(3) . . ?
C11 C12 C13 121.0(3) . . ?
C12 C13 C8 116.6(3) . . ?
C12 C13 C14 121.4(3) . . ?
C8 C13 C14 121.9(3) . . ?
C13 C14 C15 110.5(2) . . ?
C13 C14 C16 112.1(3) . . ?
C15 C14 C16 110.4(3) . . ?
C9 C17 C18 114.1(3) . . ?
C9 C17 C19 110.3(2) . . ?
C18 C17 C19 110.3(3) . . ?
C21 C20 C25 123.6(2) . . ?
C21 C20 N4 118.1(2) . . ?
C25 C20 N4 118.3(2) . . ?
C22 C21 C20 116.7(3) . . ?
C22 C21 C29 120.8(3) . . ?
C20 C21 C29 122.4(2) . . ?
C23 C22 C21 121.4(3) . . ?
C22 C23 C24 120.2(3) . . ?
C23 C24 C25 121.0(3) . . ?
C24 C25 C20 117.1(3) . . ?
C24 C25 C26 119.3(3) . . ?
C20 C25 C26 123.7(3) . . ?
C25 C26 C28 111.6(3) . . ?
C25 C26 C27 110.1(3) . . ?
C28 C26 C27 110.5(3) . . ?
C21 C29 C31 113.2(3) . . ?
C21 C29 C30 110.9(2) . . ?
C31 C29 C30 109.9(3) . . ?
N5 C33 C32 178.0(8) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.436
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.097
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1457873'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;
_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H56 Cl3 Ga Ge N4 O2 S2'
_chemical_formula_weight         925.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga -1.2846 0.7763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge -1.0885 0.8855 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Cm

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                   16.3230(2)
_cell_length_b                   21.5944(3)
_cell_length_c                   7.62520(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.7720(10)
_cell_angle_gamma                90.00
_cell_volume                     2529.32(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6148
_cell_measurement_theta_min      3.5310
_cell_measurement_theta_max      73.4140

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    3.865
_exptl_absorpt_correction_T_min  0.61062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_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            8297
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         67.50
_reflns_number_total             3656
_reflns_number_gt                3577
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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)+(0.0939P)²+0.3597P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_number_reflns         3656
_refine_ls_number_parameters     248
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.122
_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 0.13458(3) 0.5000 0.45108(4) 0.03184(16) Uani 1 2 d S . .
Ga1 Ga -0.09170(5) 0.5000 0.40818(9) 0.0563(2) Uani 1 2 d S . .
Cl1 Cl -0.07421(9) 0.58163(7) 0.59043(18) 0.0711(3) Uani 1 1 d . . .
S1 S 0.23383(8) 0.5000 0.33598(15) 0.0387(3) Uani 1 2 d S . .
O1 O 0.2213(3) 0.19797(16) 0.8300(5) 0.0693(9) Uani 1 1 d . . .
N1 N 0.1427(2) 0.44455(14) 0.8127(4) 0.0388(6) Uani 1 1 d . . .
C1 C 0.1489(2) 0.43383(16) 0.6422(5) 0.0355(7) Uani 1 1 d . . .
Cl2 Cl -0.22422(12) 0.5000 0.2095(3) 0.0844(6) Uani 1 2 d S . .
S2 S 0.00159(9) 0.5000 0.24837(17) 0.0453(3) Uani 1 2 d S . .
N2 N 0.1745(2) 0.37528(14) 0.6449(4) 0.0414(7) Uani 1 1 d . . .
C2 C 0.1829(3) 0.34776(18) 0.8146(6) 0.0518(10) Uani 1 1 d . . .
H2 H 0.1998 0.3063 0.8506 0.062 Uiso 1 1 calc R . .
C3 C 0.1620(3) 0.39180(19) 0.9186(5) 0.0491(9) Uani 1 1 d . . .
H3 H 0.1610 0.3870 1.0417 0.059 Uiso 1 1 calc R . .
C4 C 0.1084(4) 0.5000 0.8696(7) 0.0399(10) Uani 1 2 d S . .
H4A H 0.0441 0.5000 0.8136 0.048 Uiso 1 2 calc SR . .
H4B H 0.1238 0.5000 1.0068 0.048 Uiso 1 2 calc SR . .
C5 C 0.1976(3) 0.34369(16) 0.4993(5) 0.0429(8) Uani 1 1 d . . .
C6 C 0.1311(4) 0.31534(18) 0.3548(6) 0.0537(10) Uani 1 1 d . . .
C7 C 0.2404(5) 0.2764(2) 0.2382(7) 0.0781(18) Uani 1 1 d . . .
H7 H 0.2554 0.2516 0.1507 0.094 Uiso 1 1 calc R . .
C20 C 0.1565(5) 0.2818(2) 0.2263(6) 0.0664(14) Uani 1 1 d . . .
H20 H 0.1130 0.2620 0.1262 0.080 Uiso 1 1 calc R . .
C8 C 0.3058(5) 0.3075(3) 0.3803(8) 0.0729(16) Uani 1 1 d . . .
H8 H 0.3645 0.3061 0.3837 0.087 Uiso 1 1 calc R . .
C9 C 0.2842(3) 0.34034(19) 0.5163(6) 0.0512(9) Uani 1 1 d . . .
C10 C 0.3567(3) 0.3699(2) 0.6770(8) 0.0673(13) Uani 1 1 d . . .
H10 H 0.3295 0.4010 0.7373 0.081 Uiso 1 1 calc R . .
C11 C 0.4012(4) 0.3195(3) 0.8252(8) 0.0772(15) Uani 1 1 d . . .
H11A H 0.3567 0.2974 0.8604 0.116 Uiso 1 1 calc R . .
H11B H 0.4423 0.3394 0.9356 0.116 Uiso 1 1 calc R . .
H11C H 0.4324 0.2902 0.7726 0.116 Uiso 1 1 calc R . .
C12 C 0.4235(4) 0.4033(4) 0.6145(13) 0.099(2) Uani 1 1 d . . .
H12A H 0.4586 0.3729 0.5757 0.149 Uiso 1 1 calc R . .
H12B H 0.4614 0.4280 0.7178 0.149 Uiso 1 1 calc R . .
H12C H 0.3937 0.4305 0.5094 0.149 Uiso 1 1 calc R . .
C13 C 0.0355(4) 0.3204(3) 0.3450(8) 0.0705(13) Uani 1 1 d . . .
H13 H 0.0296 0.3603 0.4060 0.085 Uiso 1 1 calc R . .
C14 C -0.0274(5) 0.3233(4) 0.1438(11) 0.099(2) Uani 1 1 d . . .
H14A H -0.0281 0.2832 0.0832 0.148 Uiso 1 1 calc R . .
H14B H -0.0082 0.3555 0.0758 0.148 Uiso 1 1 calc R . .
H14C H -0.0860 0.3330 0.1435 0.148 Uiso 1 1 calc R . .
C15 C 0.0132(6) 0.2686(4) 0.4569(14) 0.109(3) Uani 1 1 d . . .
H15A H -0.0466 0.2739 0.4554 0.164 Uiso 1 1 calc R . .
H15B H 0.0534 0.2701 0.5859 0.164 Uiso 1 1 calc R . .
H15C H 0.0187 0.2286 0.4016 0.164 Uiso 1 1 calc R . .
C16 C 0.2531(6) 0.1766(3) 0.6891(10) 0.0866(18) Uani 1 1 d . . .
H16A H 0.3152 0.1650 0.7442 0.104 Uiso 1 1 calc R . .
H16B H 0.2475 0.2094 0.5953 0.104 Uiso 1 1 calc R . .
C17 C 0.2019(6) 0.1236(4) 0.6039(14) 0.107(2) Uani 1 1 d . . .
H17A H 0.2352 0.0952 0.5515 0.128 Uiso 1 1 calc R . .
H17B H 0.1478 0.1362 0.5038 0.128 Uiso 1 1 calc R . .
C18 C 0.1825(9) 0.0946(3) 0.7613(13) 0.127(3) Uani 1 1 d . . .
H18A H 0.2285 0.0645 0.8265 0.152 Uiso 1 1 calc R . .
H18B H 0.1259 0.0728 0.7165 0.152 Uiso 1 1 calc R . .
C19 C 0.1797(6) 0.1482(2) 0.8922(11) 0.0867(17) Uani 1 1 d . . .
H19A H 0.1189 0.1589 0.8792 0.104 Uiso 1 1 calc R . .
H19B H 0.2119 0.1375 1.0238 0.104 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 C1 1.998(3) 2_565 ?
Ge1 C1 1.998(3) . ?
Ge1 S1 2.0873(12) . ?
Ge1 S2 2.1981(13) . ?
Ga1 Cl2 2.1810(18) . ?
Ga1 Cl1 2.2027(14) . ?
Ga1 Cl1 2.2027(14) 2_565 ?
Ga1 S2 2.2493(15) . ?
O1 C16 1.420(7) . ?
O1 C19 1.435(7) . ?
N1 C1 1.358(4) . ?
N1 C3 1.370(5) . ?
N1 C4 1.449(4) . ?
C1 N2 1.329(5) . ?
N2 C2 1.388(5) . ?
N2 C5 1.457(5) . ?
C2 C3 1.353(6) . ?
C4 N1 1.449(4) 2_565 ?
C5 C9 1.377(7) . ?
C5 C6 1.400(6) . ?
C6 C20 1.389(7) . ?
C6 C13 1.541(8) . ?
C7 C20 1.347(9) . ?
C7 C8 1.408(10) . ?
C8 C9 1.397(7) . ?
C9 C10 1.526(7) . ?
C10 C12 1.511(9) . ?
C10 C11 1.559(7) . ?
C13 C15 1.523(9) . ?
C13 C14 1.532(9) . ?
C16 C17 1.435(10) . ?
C17 C18 1.480(13) . ?
C18 C19 1.538(10) . ?

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
C1 Ge1 C1 91.35(19) 2_565 . ?
C1 Ge1 S1 112.99(11) 2_565 . ?
C1 Ge1 S1 112.99(11) . . ?
C1 Ge1 S2 110.94(11) 2_565 . ?
C1 Ge1 S2 110.94(11) . . ?
S1 Ge1 S2 115.26(5) . . ?
Cl2 Ga1 Cl1 108.95(5) . . ?
Cl2 Ga1 Cl1 108.95(5) . 2_565 ?
Cl1 Ga1 Cl1 106.32(8) . 2_565 ?
Cl2 Ga1 S2 108.53(8) . . ?
Cl1 Ga1 S2 112.01(4) . . ?
Cl1 Ga1 S2 112.01(4) 2_565 . ?
C16 O1 C19 109.9(5) . . ?
C1 N1 C3 110.2(3) . . ?
C1 N1 C4 126.1(3) . . ?
C3 N1 C4 123.1(3) . . ?
N2 C1 N1 105.8(3) . . ?
N2 C1 Ge1 130.6(2) . . ?
N1 C1 Ge1 123.2(2) . . ?
Ge1 S2 Ga1 107.91(6) . . ?
C1 N2 C2 110.7(3) . . ?
C1 N2 C5 126.5(3) . . ?
C2 N2 C5 122.7(3) . . ?
C3 C2 N2 106.3(3) . . ?
C2 C3 N1 107.0(3) . . ?
N1 C4 N1 111.4(4) 2_565 . ?
C9 C5 C6 123.3(4) . . ?
C9 C5 N2 118.3(4) . . ?
C6 C5 N2 118.2(4) . . ?
C20 C6 C5 116.5(5) . . ?
C20 C6 C13 122.8(5) . . ?
C5 C6 C13 120.7(4) . . ?
C20 C7 C8 120.0(4) . . ?
C7 C20 C6 122.5(5) . . ?
C9 C8 C7 119.8(6) . . ?
C5 C9 C8 117.8(5) . . ?
C5 C9 C10 123.2(4) . . ?
C8 C9 C10 119.1(5) . . ?
C12 C10 C9 113.1(5) . . ?
C12 C10 C11 110.6(5) . . ?
C9 C10 C11 109.5(4) . . ?
C15 C13 C14 112.7(6) . . ?
C15 C13 C6 110.5(6) . . ?
C14 C13 C6 112.0(5) . . ?
O1 C16 C17 107.2(6) . . ?
C16 C17 C18 102.8(7) . . ?
C17 C18 C19 105.6(6) . . ?
O1 C19 C18 103.1(6) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.188
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.110

