# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_Compound_1
_database_code_depnum_ccdc_archive 'CCDC 1402721'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-09-30 downloaded from the CCDC.
;
_audit_creation_date             2015-05-24T18:06:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C28 H36 Cl Ge N2 P'
_chemical_formula_sum            'C28 H36 Cl Ge N2 P'
_chemical_formula_weight         539.6
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_Int_Tables_number      9
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   16.954(10)
_cell_length_b                   9.058(5)
_cell_length_c                   35.25(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.174(8)
_cell_angle_gamma                90
_cell_volume                     5399(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9310
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.84

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2256
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0701 before and 0.0543 after correction.
        The Ratio of minimum to maximum transmission is 0.8040.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.5998
_exptl_absorpt_correction_T_max  0.746

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

_diffrn_source                   'sealed tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 8
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_number            25911
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             9725
_reflns_number_gt                8694
_reflns_threshold_expression     >2sigma(I)

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

_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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)+(0.0417P)²+2.1224P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9725
_refine_ls_number_parameters     609
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.078
_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
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.288(8)
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.057

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0993(2) 0.7526(4) 0.86725(10) 0.0153(8) Uani 1 d . .
C2 C 0.1161(2) 0.8022(4) 0.83077(11) 0.0166(8) Uani 1 d . .
C3 C 0.1657(2) 0.9234(4) 0.82817(12) 0.0196(9) Uani 1 d . .
H3 H 0.1771 0.958 0.8037 0.023 Uiso 1 calc . .
C4 C 0.1988(2) 0.9946(5) 0.85985(12) 0.0212(9) Uani 1 d . .
H4 H 0.2332 1.0762 0.8572 0.025 Uiso 1 calc . .
C5 C 0.1816(2) 0.9465(4) 0.89566(11) 0.0200(8) Uani 1 d . .
H5 H 0.205 0.9954 0.9175 0.024 Uiso 1 calc . .
C6 C 0.1306(2) 0.8273(4) 0.90035(11) 0.0166(8) Uani 1 d . .
C7 C 0.0799(2) 0.7337(4) 0.79416(11) 0.0206(8) Uani 1 d . .
H7 H 0.053 0.6402 0.801 0.025 Uiso 1 calc . .
C8 C 0.0167(3) 0.8369(5) 0.77518(11) 0.0290(10) Uani 1 d . .
H8A H -0.023 0.8595 0.7932 0.044 Uiso 1 calc . .
H8B H -0.009 0.7883 0.7527 0.044 Uiso 1 calc . .
H8C H 0.0417 0.9286 0.7675 0.044 Uiso 1 calc . .
C9 C 0.1430(3) 0.6941(5) 0.76640(11) 0.0277(10) Uani 1 d . .
H9A H 0.1701 0.7842 0.7591 0.042 Uiso 1 calc . .
H9B H 0.1174 0.6473 0.7437 0.042 Uiso 1 calc . .
H9C H 0.1815 0.6258 0.7788 0.042 Uiso 1 calc . .
C10 C 0.1092(2) 0.7855(4) 0.93970(11) 0.0225(9) Uani 1 d . .
H10 H 0.0722 0.6995 0.937 0.027 Uiso 1 calc . .
C11 C 0.1829(3) 0.7351(6) 0.96469(13) 0.0335(12) Uani 1 d . .
H11A H 0.2078 0.6517 0.9525 0.05 Uiso 1 calc . .
H11B H 0.1671 0.7048 0.9897 0.05 Uiso 1 calc . .
H11C H 0.2206 0.817 0.9677 0.05 Uiso 1 calc . .
C12 C 0.0658(3) 0.9106(6) 0.95894(14) 0.0315(12) Uani 1 d . .
H12A H 0.0994 0.9988 0.9606 0.047 Uiso 1 calc . .
H12B H 0.054 0.8798 0.9846 0.047 Uiso 1 calc . .
H12C H 0.0163 0.9331 0.9439 0.047 Uiso 1 calc . .
C13 C 0.1014(2) 0.3945(4) 0.92159(10) 0.0162(8) Uani 1 d . .
C14 C 0.1708(2) 0.3120(4) 0.92856(10) 0.0153(8) Uani 1 d . .
H14 H 0.2019 0.2867 0.9082 0.018 Uiso 1 calc . .
C15 C 0.1942(3) 0.2673(5) 0.96552(12) 0.0194(9) Uani 1 d . .
H15 H 0.241 0.2106 0.9703 0.023 Uiso 1 calc . .
C16 C 0.1489(2) 0.3055(4) 0.99546(11) 0.0214(9) Uani 1 d . .
H16 H 0.1652 0.2752 1.0206 0.026 Uiso 1 calc . .
C17 C 0.0804(2) 0.3875(5) 0.98877(11) 0.0215(9) Uani 1 d . .
H17 H 0.05 0.4145 1.0093 0.026 Uiso 1 calc . .
C18 C 0.0560(3) 0.4304(5) 0.95179(11) 0.0162(9) Uani 1 d . .
H18 H 0.0082 0.4843 0.9471 0.019 Uiso 1 calc . .
C19 C 0.1368(2) 0.4004(4) 0.84241(11) 0.0146(8) Uani 1 d . .
C20 C 0.1129(2) 0.3249(4) 0.80919(11) 0.0183(8) Uani 1 d . .
H20 H 0.0585 0.3044 0.8033 0.022 Uiso 1 calc . .
C21 C 0.1685(3) 0.2794(4) 0.78453(11) 0.0238(9) Uani 1 d . .
H21 H 0.1521 0.2286 0.7617 0.029 Uiso 1 calc . .
C22 C 0.2478(3) 0.3084(4) 0.79329(12) 0.0268(10) Uani 1 d . .
H22 H 0.286 0.2736 0.777 0.032 Uiso 1 calc . .
C23 C 0.2721(2) 0.3874(5) 0.82555(12) 0.0253(9) Uani 1 d . .
H23 H 0.3265 0.4088 0.8311 0.03 Uiso 1 calc . .
C24 C 0.2167(2) 0.4352(4) 0.84972(11) 0.0186(9) Uani 1 d . .
H24 H 0.2331 0.4922 0.8715 0.022 Uiso 1 calc . .
C25 C -0.0691(2) 0.2656(4) 0.86473(11) 0.0190(9) Uani 1 d . .
C26 C -0.0119(3) 0.1353(4) 0.86750(15) 0.0284(11) Uani 1 d . .
H26A H 0.0184 0.133 0.8449 0.043 Uiso 1 calc . .
H26B H -0.0418 0.0432 0.8691 0.043 Uiso 1 calc . .
H26C H 0.0244 0.1461 0.8903 0.043 Uiso 1 calc . .
C27 C -0.1188(3) 0.2647(5) 0.89950(13) 0.0298(10) Uani 1 d . .
H27A H -0.0837 0.2699 0.9228 0.045 Uiso 1 calc . .
H27B H -0.15 0.1736 0.8996 0.045 Uiso 1 calc . .
H27C H -0.1544 0.3501 0.8983 0.045 Uiso 1 calc . .
C28 C -0.1231(3) 0.2573(5) 0.82829(12) 0.0303(10) Uani 1 d . .
H28A H -0.1569 0.3451 0.8263 0.046 Uiso 1 calc . .
H28B H -0.1562 0.1687 0.8288 0.046 Uiso 1 calc . .
H28C H -0.0909 0.2528 0.8063 0.046 Uiso 1 calc . .
N1 N 0.0457(2) 0.6319(3) 0.87155(10) 0.0136(7) Uani 1 d . .
N2 N -0.02563(17) 0.4083(3) 0.86352(8) 0.0157(7) Uani 1 d . .
P1 P 0.06449(5) 0.45658(10) 0.87493(3) 0.0129(2) Uani 1 d . .
Cl1 Cl -0.11730(6) 0.66687(13) 0.91349(3) 0.0284(2) Uani 1 d . .
Ge1 Ge -0.067890(18) 0.61174(4) 0.854913(10) 0.01816(10) Uani 1 d . .
C29 C -0.0945(2) 0.5103(4) 1.12911(11) 0.0160(8) Uani 1 d . .
C30 C -0.1228(2) 0.5849(4) 1.09574(11) 0.0186(9) Uani 1 d . .
C31 C -0.1725(2) 0.7046(4) 1.09923(11) 0.0212(9) Uani 1 d . .
H31 H -0.1928 0.7547 1.0769 0.025 Uiso 1 calc . .
C32 C -0.1934(2) 0.7531(4) 1.13430(11) 0.0207(9) Uani 1 d . .
H32 H -0.2279 0.8352 1.136 0.025 Uiso 1 calc . .
C33 C -0.1643(2) 0.6821(5) 1.16662(12) 0.0206(9) Uani 1 d . .
H33 H -0.1783 0.7171 1.1906 0.025 Uiso 1 calc . .
C34 C -0.1148(2) 0.5603(4) 1.16521(11) 0.0161(8) Uani 1 d . .
C35 C -0.0997(2) 0.5411(4) 1.05633(11) 0.0225(9) Uani 1 d . .
H35 H -0.0613 0.4574 1.0596 0.027 Uiso 1 calc . .
C36 C -0.1710(3) 0.4860(6) 1.03148(14) 0.0353(12) Uani 1 d . .
H36A H -0.1901 0.3934 1.0419 0.053 Uiso 1 calc . .
H36B H -0.1557 0.469 1.0056 0.053 Uiso 1 calc . .
H36C H -0.2132 0.5601 1.031 0.053 Uiso 1 calc . .
C37 C -0.0583(3) 0.6664(6) 1.03668(14) 0.0339(13) Uani 1 d . .
H37A H -0.0931 0.7528 1.0346 0.051 Uiso 1 calc . .
H37B H -0.046 0.6347 1.0112 0.051 Uiso 1 calc . .
H37C H -0.0092 0.6921 1.0516 0.051 Uiso 1 calc . .
C38 C -0.0816(2) 0.4933(4) 1.20222(11) 0.0193(8) Uani 1 d . .
H38 H -0.054 0.3998 1.1959 0.023 Uiso 1 calc . .
C39 C -0.1450(3) 0.4540(5) 1.22890(11) 0.0275(10) Uani 1 d . .
H39A H -0.1744 0.5431 1.2349 0.041 Uiso 1 calc . .
H39B H -0.12 0.412 1.2524 0.041 Uiso 1 calc . .
H39C H -0.1813 0.3815 1.2166 0.041 Uiso 1 calc . .
C40 C -0.0193(3) 0.5967(5) 1.22251(12) 0.0287(10) Uani 1 d . .
H40A H 0.0234 0.6151 1.2058 0.043 Uiso 1 calc . .
H40B H 0.0026 0.55 1.2461 0.043 Uiso 1 calc . .
H40C H -0.0443 0.6905 1.2285 0.043 Uiso 1 calc . .
C41 C -0.0931(2) 0.1502(4) 1.07537(10) 0.0168(8) Uani 1 d . .
C42 C -0.1642(2) 0.0744(4) 1.06617(11) 0.0193(8) Uani 1 d . .
H42 H -0.1986 0.0519 1.0855 0.023 Uiso 1 calc . .
C43 C -0.1840(3) 0.0326(5) 1.02891(13) 0.0246(10) Uani 1 d . .
H43 H -0.2331 -0.0152 1.0225 0.029 Uiso 1 calc . .
C44 C -0.1330(2) 0.0598(4) 1.00106(11) 0.0246(9) Uani 1 d . .
H44 H -0.1466 0.0288 0.9757 0.03 Uiso 1 calc . .
C45 C -0.0621(2) 0.1317(5) 1.00975(11) 0.0238(9) Uani 1 d . .
H45 H -0.0274 0.1502 0.9903 0.029 Uiso 1 calc . .
C46 C -0.0418(3) 0.1766(5) 1.04648(12) 0.0196(10) Uani 1 d . .
H46 H 0.0071 0.2256 1.0523 0.024 Uiso 1 calc . .
C47 C -0.1340(2) 0.1566(4) 1.15380(11) 0.0182(8) Uani 1 d . .
C48 C -0.1117(2) 0.0798(4) 1.18714(11) 0.0206(9) Uani 1 d . .
H48 H -0.0575 0.0578 1.1933 0.025 Uiso 1 calc . .
C49 C -0.1682(3) 0.0352(4) 1.21139(11) 0.0251(9) Uani 1 d . .
H49 H -0.1525 -0.0159 1.2342 0.03 Uiso 1 calc . .
C50 C -0.2476(3) 0.0654(5) 1.20226(12) 0.0276(10) Uani 1 d . .
H50 H -0.2863 0.0321 1.2184 0.033 Uiso 1 calc . .
C51 C -0.2702(2) 0.1439(5) 1.16971(11) 0.0244(9) Uani 1 d . .
H51 H -0.3246 0.1645 1.1634 0.029 Uiso 1 calc . .
C52 C -0.2128(2) 0.1931(5) 1.14593(12) 0.0197(9) Uani 1 d . .
H52 H -0.228 0.2518 1.1243 0.024 Uiso 1 calc . .
C53 C 0.0745(2) 0.0230(4) 1.13448(11) 0.0219(9) Uani 1 d . .
C54 C 0.0186(3) -0.1084(4) 1.13126(14) 0.0255(11) Uani 1 d . .
H54A H -0.0143 -0.1092 1.153 0.038 Uiso 1 calc . .
H54B H 0.0494 -0.1999 1.1311 0.038 Uiso 1 calc . .
H54C H -0.0154 -0.1009 1.1076 0.038 Uiso 1 calc . .
C55 C 0.1274(2) 0.0217(5) 1.10122(13) 0.0306(10) Uani 1 d . .
H55A H 0.0945 0.0225 1.0772 0.046 Uiso 1 calc . .
H55B H 0.1603 -0.0675 1.1025 0.046 Uiso 1 calc . .
H55C H 0.1615 0.1092 1.1026 0.046 Uiso 1 calc . .
C56 C 0.1256(3) 0.0156(5) 1.17204(13) 0.0326(11) Uani 1 d . .
H56A H 0.162 0.0998 1.1737 0.049 Uiso 1 calc . .
H56B H 0.1561 -0.0765 1.1731 0.049 Uiso 1 calc . .
H56C H 0.0916 0.0187 1.1933 0.049 Uiso 1 calc . .
N3 N -0.0416(2) 0.3890(3) 1.12645(10) 0.0170(8) Uani 1 d . .
N4 N 0.03012(18) 0.1649(3) 1.13516(9) 0.0171(7) Uani 1 d . .
P2 P -0.05961(5) 0.21228(11) 1.12243(3) 0.0144(2) Uani 1 d . .
Cl2 Cl 0.12497(6) 0.43111(12) 1.08899(3) 0.0245(2) Uani 1 d . .
Ge2 Ge 0.071070(17) 0.36791(4) 1.145878(10) 0.01671(10) Uani 1 d . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.411(5) . ?
C1 C6 1.418(5) . ?
C1 N1 1.436(5) . ?
C2 C3 1.390(6) . ?
C2 C7 1.520(5) . ?
C3 H3 0.95 . ?
C3 C4 1.374(6) . ?
C4 H4 0.95 . ?
C4 C5 1.387(6) . ?
C5 H5 0.95 . ?
C5 C6 1.400(5) . ?
C6 C10 1.508(5) . ?
C7 H7 1 . ?
C7 C8 1.538(5) . ?
C7 C9 1.544(6) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 H10 1 . ?
C10 C11 1.545(6) . ?
C10 C12 1.535(6) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 C14 1.400(5) . ?
C13 C18 1.397(6) . ?
C13 P1 1.807(4) . ?
C14 H14 0.95 . ?
C14 C15 1.394(6) . ?
C15 H15 0.95 . ?
C15 C16 1.393(6) . ?
C16 H16 0.95 . ?
C16 C17 1.385(6) . ?
C17 H17 0.95 . ?
C17 C18 1.394(5) . ?
C18 H18 0.95 . ?
C19 C20 1.391(6) . ?
C19 C24 1.395(6) . ?
C19 P1 1.811(4) . ?
C20 H20 0.95 . ?
C20 C21 1.390(6) . ?
C21 H21 0.95 . ?
C21 C22 1.382(6) . ?
C22 H22 0.95 . ?
C22 C23 1.381(6) . ?
C23 H23 0.95 . ?
C23 C24 1.383(6) . ?
C24 H24 0.95 . ?
C25 C26 1.526(6) . ?
C25 C27 1.537(6) . ?
C25 C28 1.524(5) . ?
C25 N2 1.491(5) . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
C27 H27A 0.98 . ?
C27 H27B 0.98 . ?
C27 H27C 0.98 . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 0.98 . ?
N1 P1 1.622(3) . ?
N1 Ge1 1.981(4) . ?
N2 P1 1.612(3) . ?
N2 Ge1 1.992(3) . ?
P1 Ge1 2.6981(15) . ?
Cl1 Ge1 2.3381(15) . ?
C29 C30 1.410(5) . ?
C29 C34 1.417(6) . ?
C29 N3 1.426(5) . ?
C30 C31 1.384(5) . ?
C30 C35 1.523(5) . ?
C31 H31 0.95 . ?
C31 C32 1.382(6) . ?
C32 H32 0.95 . ?
C32 C33 1.369(6) . ?
C33 H33 0.95 . ?
C33 C34 1.389(6) . ?
C34 C38 1.510(5) . ?
C35 H35 1 . ?
C35 C36 1.525(6) . ?
C35 C37 1.526(6) . ?
C36 H36A 0.98 . ?
C36 H36B 0.98 . ?
C36 H36C 0.98 . ?
C37 H37A 0.98 . ?
C37 H37B 0.98 . ?
C37 H37C 0.98 . ?
C38 H38 1 . ?
C38 C39 1.521(6) . ?
C38 C40 1.547(5) . ?
C39 H39A 0.98 . ?
C39 H39B 0.98 . ?
C39 H39C 0.98 . ?
C40 H40A 0.98 . ?
C40 H40B 0.98 . ?
C40 H40C 0.98 . ?
C41 C42 1.405(5) . ?
C41 C46 1.407(6) . ?
C41 P2 1.804(4) . ?
C42 H42 0.95 . ?
C42 C43 1.385(6) . ?
C43 H43 0.95 . ?
C43 C44 1.378(6) . ?
C44 H44 0.95 . ?
C44 C45 1.381(6) . ?
C45 H45 0.95 . ?
C45 C46 1.377(6) . ?
C46 H46 0.95 . ?
C47 C48 1.394(6) . ?
C47 C52 1.384(6) . ?
C47 P2 1.809(4) . ?
C48 H48 0.95 . ?
C48 C49 1.389(6) . ?
C49 H49 0.95 . ?
C49 C50 1.388(6) . ?
C50 H50 0.95 . ?
C50 C51 1.380(6) . ?
C51 H51 0.95 . ?
C51 C52 1.403(5) . ?
C52 H52 0.95 . ?
C53 C54 1.521(6) . ?
C53 C55 1.528(6) . ?
C53 C56 1.531(6) . ?
C53 N4 1.490(5) . ?
C54 H54A 0.98 . ?
C54 H54B 0.98 . ?
C54 H54C 0.98 . ?
C55 H55A 0.98 . ?
C55 H55B 0.98 . ?
C55 H55C 0.98 . ?
C56 H56A 0.98 . ?
C56 H56B 0.98 . ?
C56 H56C 0.98 . ?
N3 P2 1.634(3) . ?
N3 Ge2 1.991(4) . ?
N4 P2 1.613(3) . ?
N4 Ge2 1.992(3) . ?
P2 Ge2 2.7042(15) . ?
Cl2 Ge2 2.3347(15) . ?

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 C1 C6 120.6(4) . . ?
C2 C1 N1 120.7(3) . . ?
C6 C1 N1 118.6(3) . . ?
C1 C2 C7 123.2(4) . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 C7 118.4(4) . . ?
C2 C3 H3 119 . . ?
C4 C3 C2 122.1(4) . . ?
C4 C3 H3 119 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.5(4) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.5(4) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C10 122.4(3) . . ?
C5 C6 C1 117.9(3) . . ?
C5 C6 C10 119.6(3) . . ?
C2 C7 H7 107.7 . . ?
C2 C7 C8 110.3(3) . . ?
C2 C7 C9 112.2(3) . . ?
C8 C7 H7 107.7 . . ?
C8 C7 C9 111.0(3) . . ?
C9 C7 H7 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10 107.4 . . ?
C6 C10 C11 111.1(4) . . ?
C6 C10 C12 112.1(3) . . ?
C11 C10 H10 107.4 . . ?
C12 C10 H10 107.4 . . ?
C12 C10 C11 111.1(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 P1 123.8(3) . . ?
C18 C13 C14 119.5(4) . . ?
C18 C13 P1 116.6(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(4) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.8(4) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C24 119.0(4) . . ?
C20 C19 P1 120.1(3) . . ?
C24 C19 P1 120.8(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(4) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.8(4) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.6(4) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.7(4) . . ?
C24 C23 H23 120.2 . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.6(4) . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C27 109.1(3) . . ?
C28 C25 C26 110.8(4) . . ?
C28 C25 C27 110.0(3) . . ?
N2 C25 C26 111.1(3) . . ?
N2 C25 C27 109.2(3) . . ?
N2 C25 C28 106.6(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C1 N1 P1 129.1(3) . . ?
C1 N1 Ge1 130.4(2) . . ?
P1 N1 Ge1 96.49(16) . . ?
C25 N2 P1 133.6(2) . . ?
C25 N2 Ge1 129.3(2) . . ?
P1 N2 Ge1 96.37(15) . . ?
C13 P1 C19 106.43(18) . . ?
C13 P1 Ge1 128.82(14) . . ?
C19 P1 Ge1 124.71(13) . . ?
N1 P1 C13 115.13(19) . . ?
N1 P1 C19 111.52(19) . . ?
N1 P1 Ge1 46.83(12) . . ?
N2 P1 C13 113.73(17) . . ?
N2 P1 C19 116.04(18) . . ?
N2 P1 N1 94.00(16) . . ?
N2 P1 Ge1 47.21(11) . . ?
N1 Ge1 N2 73.08(12) . . ?
N1 Ge1 P1 36.68(9) . . ?
N1 Ge1 Cl1 97.01(11) . . ?
N2 Ge1 P1 36.42(9) . . ?
N2 Ge1 Cl1 102.19(9) . . ?
Cl1 Ge1 P1 103.00(4) . . ?
C30 C29 C34 120.4(3) . . ?
C30 C29 N3 119.5(3) . . ?
C34 C29 N3 120.0(3) . . ?
C29 C30 C35 122.8(3) . . ?
C31 C30 C29 118.3(4) . . ?
C31 C30 C35 118.9(4) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 C30 121.7(4) . . ?
C32 C31 H31 119.1 . . ?
C31 C32 H32 120.2 . . ?
C33 C32 C31 119.7(4) . . ?
C33 C32 H32 120.2 . . ?
C32 C33 H33 119.1 . . ?
C32 C33 C34 121.7(4) . . ?
C34 C33 H33 119.1 . . ?
C29 C34 C38 123.2(3) . . ?
C33 C34 C29 118.2(4) . . ?
C33 C34 C38 118.5(4) . . ?
C30 C35 H35 107.5 . . ?
C30 C35 C36 111.3(4) . . ?
C30 C35 C37 112.2(3) . . ?
C36 C35 H35 107.5 . . ?
C36 C35 C37 110.7(4) . . ?
C37 C35 H35 107.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C34 C38 H38 107.5 . . ?
C34 C38 C39 113.1(3) . . ?
C34 C38 C40 110.8(3) . . ?
C39 C38 H38 107.5 . . ?
C39 C38 C40 110.2(3) . . ?
C40 C38 H38 107.5 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 C46 118.8(4) . . ?
C42 C41 P2 124.9(3) . . ?
C46 C41 P2 116.3(3) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 C41 119.9(4) . . ?
C43 C42 H42 120.1 . . ?
C42 C43 H43 119.8 . . ?
C44 C43 C42 120.3(4) . . ?
C44 C43 H43 119.8 . . ?
C43 C44 H44 119.7 . . ?
C43 C44 C45 120.5(4) . . ?
C45 C44 H44 119.7 . . ?
C44 C45 H45 119.9 . . ?
C46 C45 C44 120.2(4) . . ?
C46 C45 H45 119.9 . . ?
C41 C46 H46 119.8 . . ?
C45 C46 C41 120.3(4) . . ?
C45 C46 H46 119.8 . . ?
C48 C47 P2 119.7(3) . . ?
C52 C47 C48 119.1(4) . . ?
C52 C47 P2 121.1(3) . . ?
C47 C48 H48 119.8 . . ?
C49 C48 C47 120.5(4) . . ?
C49 C48 H48 119.8 . . ?
C48 C49 H49 120 . . ?
C50 C49 C48 120.0(4) . . ?
C50 C49 H49 120 . . ?
C49 C50 H50 120 . . ?
C51 C50 C49 120.0(4) . . ?
C51 C50 H50 120 . . ?
C50 C51 H51 120.1 . . ?
C50 C51 C52 119.8(4) . . ?
C52 C51 H51 120.1 . . ?
C47 C52 C51 120.4(4) . . ?
C47 C52 H52 119.8 . . ?
C51 C52 H52 119.8 . . ?
C54 C53 C55 109.5(4) . . ?
C54 C53 C56 109.9(4) . . ?
C55 C53 C56 109.6(4) . . ?
N4 C53 C54 111.4(3) . . ?
N4 C53 C55 110.2(3) . . ?
N4 C53 C56 106.2(3) . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C53 C55 H55A 109.5 . . ?
C53 C55 H55B 109.5 . . ?
C53 C55 H55C 109.5 . . ?
H55A C55 H55B 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C53 C56 H56A 109.5 . . ?
C53 C56 H56B 109.5 . . ?
C53 C56 H56C 109.5 . . ?
H56A C56 H56B 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C29 N3 P2 130.3(3) . . ?
C29 N3 Ge2 130.0(3) . . ?
P2 N3 Ge2 95.99(16) . . ?
C53 N4 P2 133.8(3) . . ?
C53 N4 Ge2 129.0(2) . . ?
P2 N4 Ge2 96.64(15) . . ?
C41 P2 C47 106.78(19) . . ?
C41 P2 Ge2 129.76(13) . . ?
C47 P2 Ge2 123.43(14) . . ?
N3 P2 C41 115.43(19) . . ?
N3 P2 C47 110.75(19) . . ?
N3 P2 Ge2 47.08(13) . . ?
N4 P2 C41 113.60(17) . . ?
N4 P2 C47 116.20(18) . . ?
N4 P2 N3 94.03(17) . . ?
N4 P2 Ge2 47.03(12) . . ?
N3 Ge2 N4 73.19(13) . . ?
N3 Ge2 P2 36.93(9) . . ?
N3 Ge2 Cl2 96.13(11) . . ?
N4 Ge2 P2 36.32(9) . . ?
N4 Ge2 Cl2 102.48(10) . . ?
Cl2 Ge2 P2 103.20(5) . . ?

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

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_Compound_2
_database_code_depnum_ccdc_archive 'CCDC 1402722'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-09-30 downloaded from the CCDC.
;

_audit_creation_date             2015-05-24T22:05:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H36 Cl Fe Ge N2 O4 P'
_chemical_formula_sum            'C32 H36 Cl Fe Ge N2 O4 P'
_chemical_formula_weight         707.49

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6544(15)
_cell_length_b                   12.518(2)
_cell_length_c                   16.755(3)
_cell_angle_alpha                68.117(10)
_cell_angle_beta                 83.597(14)
_cell_angle_gamma                71.997(10)
_cell_volume                     1786.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3442
_cell_measurement_theta_min      2.571
_cell_measurement_theta_max      20.817

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.1145 before and 0.0812 after correction.
        The Ratio of minimum to maximum transmission is 0.8491.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_T_max  0.7467

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_reflns_av_R_equivalents  0.089
_diffrn_reflns_number            18364
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             6463
_reflns_number_gt                3712
_reflns_threshold_expression     >2sigma(I)

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

_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          SQUEEZE
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 225 48 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
;

_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)+(0.0537P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6463
_refine_ls_number_parameters     386
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   0.93
_refine_ls_restrained_S_all      0.93
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.832
_refine_diff_density_min         -0.891
_refine_diff_density_rms         0.098

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8927(6) 0.5804(5) 0.8377(3) 0.0403(14) Uani 1 d . .
C2 C 0.7875(7) 0.6347(5) 0.8966(3) 0.0529(16) Uani 1 d . .
H2A H 0.827 0.689 0.9106 0.079 Uiso 1 calc . .
H2B H 0.7745 0.5703 0.9497 0.079 Uiso 1 calc . .
H2C H 0.6933 0.6799 0.8675 0.079 Uiso 1 calc . .
C3 C 0.9139(7) 0.6823(5) 0.7556(3) 0.0533(16) Uani 1 d . .
H3A H 0.8193 0.7305 0.7277 0.08 Uiso 1 calc . .
H3B H 0.9784 0.648 0.7163 0.08 Uiso 1 calc . .
H3C H 0.9576 0.7336 0.7704 0.08 Uiso 1 calc . .
C4 C 1.0397(6) 0.5076(5) 0.8824(4) 0.0498(15) Uani 1 d . .
H4A H 1.0801 0.56 0.8981 0.075 Uiso 1 calc . .
H4B H 1.1068 0.4746 0.8433 0.075 Uiso 1 calc . .
H4C H 1.0266 0.4417 0.9344 0.075 Uiso 1 calc . .
C5 C 0.9068(5) 0.2709(4) 0.9478(3) 0.0268(12) Uani 1 d . .
C6 C 1.0337(5) 0.1779(4) 0.9822(3) 0.0354(13) Uani 1 d . .
H6 H 1.1096 0.1572 0.9446 0.042 Uiso 1 calc . .
C7 C 1.0503(6) 0.1157(5) 1.0699(3) 0.0407(14) Uani 1 d . .
H7 H 1.136 0.0516 1.0921 0.049 Uiso 1 calc . .
C8 C 0.9425(6) 0.1471(4) 1.1249(3) 0.0387(14) Uani 1 d . .
H8 H 0.9532 0.1042 1.1851 0.046 Uiso 1 calc . .
C9 C 0.8197(6) 0.2401(4) 1.0928(3) 0.0357(13) Uani 1 d . .
H9 H 0.7463 0.262 1.1313 0.043 Uiso 1 calc . .
C10 C 0.8007(5) 0.3024(4) 1.0059(3) 0.0330(13) Uani 1 d . .
H10 H 0.7151 0.3673 0.985 0.04 Uiso 1 calc . .
C11 C 1.0343(5) 0.2968(5) 0.7798(3) 0.0311(12) Uani 1 d . .
C12 C 1.0802(5) 0.1748(5) 0.7943(3) 0.0374(13) Uani 1 d . .
H12 H 1.0271 0.1238 0.8323 0.045 Uiso 1 calc . .
C13 C 1.2027(6) 0.1269(5) 0.7538(4) 0.0492(16) Uani 1 d . .
H13 H 1.235 0.0429 0.7647 0.059 Uiso 1 calc . .
C14 C 1.2771(6) 0.2006(7) 0.6981(4) 0.0568(18) Uani 1 d . .
H14 H 1.362 0.1671 0.6709 0.068 Uiso 1 calc . .
C15 C 1.2319(6) 0.3217(6) 0.6805(3) 0.0538(17) Uani 1 d . .
H15 H 1.2838 0.3718 0.6403 0.065 Uiso 1 calc . .
C16 C 1.1098(5) 0.3720(5) 0.7215(3) 0.0415(14) Uani 1 d . .
H16 H 1.0783 0.4561 0.7099 0.05 Uiso 1 calc . .
C17 C 0.6974(5) 0.2692(4) 0.7782(3) 0.0278(12) Uani 1 d . .
C18 C 0.7382(5) 0.2529(5) 0.6984(3) 0.0350(13) Uani 1 d . .
C19 C 0.7222(6) 0.1531(5) 0.6880(4) 0.0446(15) Uani 1 d . .
H19 H 0.7527 0.1404 0.6355 0.054 Uiso 1 calc . .
C20 C 0.6641(6) 0.0718(5) 0.7502(4) 0.0498(16) Uani 1 d . .
H20 H 0.6584 0.002 0.7422 0.06 Uiso 1 calc . .
C21 C 0.6139(6) 0.0931(5) 0.8247(4) 0.0433(14) Uani 1 d . .
H21 H 0.5664 0.0404 0.8662 0.052 Uiso 1 calc . .
C22 C 0.6309(5) 0.1899(4) 0.8407(3) 0.0299(12) Uani 1 d . .
C23 C 0.7845(5) 0.3473(5) 0.6224(3) 0.0423(14) Uani 1 d . .
H23 H 0.8058 0.4053 0.6437 0.051 Uiso 1 calc . .
C24 C 0.9179(6) 0.2987(6) 0.5751(4) 0.074(2) Uani 1 d . .
H24A H 0.9967 0.2461 0.6165 0.111 Uiso 1 calc . .
H24B H 0.9493 0.3658 0.5332 0.111 Uiso 1 calc . .
H24C H 0.8939 0.2527 0.5451 0.111 Uiso 1 calc . .
C25 C 0.6564(6) 0.4156(5) 0.5598(3) 0.0522(16) Uani 1 d . .
H25A H 0.6412 0.3628 0.5328 0.078 Uiso 1 calc . .
H25B H 0.6773 0.4861 0.5154 0.078 Uiso 1 calc . .
H25C H 0.5684 0.4418 0.5911 0.078 Uiso 1 calc . .
C26 C 0.5675(5) 0.2115(5) 0.9227(3) 0.0399(14) Uani 1 d . .
H26 H 0.5932 0.2822 0.9242 0.048 Uiso 1 calc . .
C27 C 0.6314(7) 0.1033(5) 1.0037(4) 0.0601(18) Uani 1 d . .
H27A H 0.603 0.0338 1.0053 0.09 Uiso 1 calc . .
H27B H 0.594 0.1231 1.0549 0.09 Uiso 1 calc . .
H27C H 0.7378 0.084 1.0026 0.09 Uiso 1 calc . .
C28 C 0.4034(6) 0.2427(6) 0.9208(4) 0.0658(19) Uani 1 d . .
H28A H 0.3652 0.3148 0.8704 0.099 Uiso 1 calc . .
H28B H 0.3632 0.258 0.9732 0.099 Uiso 1 calc . .
H28C H 0.3753 0.1755 0.9177 0.099 Uiso 1 calc . .
C29 C 0.7204(7) 0.6512(5) 0.6009(3) 0.0474(16) Uani 1 d . .
C30 C 0.4849(7) 0.7991(6) 0.5421(4) 0.0574(17) Uani 1 d . .
C31 C 0.5045(6) 0.7936(5) 0.6994(3) 0.0500(16) Uani 1 d . .
C32 C 0.3971(7) 0.6247(5) 0.6552(4) 0.0474(15) Uani 1 d . .
N1 N 0.8287(4) 0.5017(3) 0.8137(2) 0.0304(10) Uani 1 d . .
N2 N 0.7247(4) 0.3648(3) 0.7953(2) 0.0236(9) Uani 1 d . .
O1 O 0.8322(5) 0.6268(4) 0.5734(3) 0.0780(15) Uani 1 d . .
O2 O 0.4526(6) 0.8695(5) 0.4745(3) 0.0929(17) Uani 1 d . .
O3 O 0.4768(5) 0.8622(4) 0.7333(3) 0.0734(14) Uani 1 d . .
O4 O 0.3007(5) 0.5876(4) 0.6620(3) 0.0741(14) Uani 1 d . .
P1 P 0.87686(13) 0.35795(11) 0.83454(8) 0.0267(3) Uani 1 d . .
Cl1 Cl 0.48753(14) 0.53224(12) 0.88000(8) 0.0492(4) Uani 1 d . .
Fe1 Fe 0.54248(8) 0.68918(7) 0.64494(5) 0.0384(2) Uani 1 d . .
Ge1 Ge 0.63830(6) 0.53480(5) 0.76900(3) 0.03014(18) Uani 1 d . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.523(7) . ?
C1 C3 1.533(7) . ?
C1 C4 1.528(7) . ?
C1 N1 1.496(6) . ?
C2 H2A 0.98 . ?
C2 H2B 0.98 . ?
C2 H2C 0.98 . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 C6 1.401(6) . ?
C5 C10 1.402(6) . ?
C5 P1 1.806(5) . ?
C6 H6 0.95 . ?
C6 C7 1.383(6) . ?
C7 H7 0.95 . ?
C7 C8 1.374(6) . ?
C8 H8 0.95 . ?
C8 C9 1.369(7) . ?
C9 H9 0.95 . ?
C9 C10 1.373(6) . ?
C10 H10 0.95 . ?
C11 C12 1.384(6) . ?
C11 C16 1.398(7) . ?
C11 P1 1.797(5) . ?
C12 H12 0.95 . ?
C12 C13 1.381(7) . ?
C13 H13 0.95 . ?
C13 C14 1.362(8) . ?
C14 H14 0.95 . ?
C14 C15 1.365(8) . ?
C15 H15 0.95 . ?
C15 C16 1.392(7) . ?
C16 H16 0.95 . ?
C17 C18 1.420(6) . ?
C17 C22 1.401(7) . ?
C17 N2 1.432(6) . ?
C18 C19 1.380(7) . ?
C18 C23 1.516(7) . ?
C19 H19 0.95 . ?
C19 C20 1.367(8) . ?
C20 H20 0.95 . ?
C20 C21 1.377(7) . ?
C21 H21 0.95 . ?
C21 C22 1.394(7) . ?
C22 C26 1.525(7) . ?
C23 H23 1 . ?
C23 C24 1.517(7) . ?
C23 C25 1.525(7) . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
C26 H26 1 . ?
C26 C27 1.535(7) . ?
C26 C28 1.511(7) . ?
C27 H27A 0.98 . ?
C27 H27B 0.98 . ?
C27 H27C 0.98 . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 0.98 . ?
C29 O1 1.123(6) . ?
C29 Fe1 1.787(7) . ?
C30 O2 1.149(6) . ?
C30 Fe1 1.773(6) . ?
C31 O3 1.149(6) . ?
C31 Fe1 1.786(7) . ?
C32 O4 1.140(6) . ?
C32 Fe1 1.787(7) . ?
N1 P1 1.621(4) . ?
N1 Ge1 1.928(4) . ?
N2 P1 1.641(4) . ?
N2 Ge1 1.925(4) . ?
P1 Ge1 2.6479(14) . ?
Cl1 Ge1 2.2270(14) . ?
Fe1 Ge1 2.2891(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
C2 C1 C3 108.9(4) . . ?
C2 C1 C4 110.4(4) . . ?
C4 C1 C3 109.4(5) . . ?
N1 C1 C2 109.1(4) . . ?
N1 C1 C3 108.7(4) . . ?
N1 C1 C4 110.3(4) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 117.5(4) . . ?
C6 C5 P1 124.2(3) . . ?
C10 C5 P1 118.3(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.2(4) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(5) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 120 . . ?
C9 C8 C7 120.0(5) . . ?
C9 C8 H8 120 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.1(4) . . ?
C10 C9 H9 119.4 . . ?
C5 C10 H10 119.8 . . ?
C9 C10 C5 120.4(4) . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C16 119.5(4) . . ?
C12 C11 P1 120.1(4) . . ?
C16 C11 P1 120.4(4) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(5) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.7(6) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.3(5) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.1(6) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 120.5 . . ?
C15 C16 C11 119.0(5) . . ?
C15 C16 H16 120.5 . . ?
C18 C17 N2 120.7(4) . . ?
C22 C17 C18 119.3(5) . . ?
C22 C17 N2 120.0(4) . . ?
C17 C18 C23 122.0(5) . . ?
C19 C18 C17 118.5(5) . . ?
C19 C18 C23 119.2(5) . . ?
C18 C19 H19 118.7 . . ?
C20 C19 C18 122.6(5) . . ?
C20 C19 H19 118.7 . . ?
C19 C20 H20 120.7 . . ?
C19 C20 C21 118.7(5) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 H21 119.1 . . ?
C20 C21 C22 121.7(5) . . ?
C22 C21 H21 119.1 . . ?
C17 C22 C26 121.8(5) . . ?
C21 C22 C17 118.9(5) . . ?
C21 C22 C26 119.1(5) . . ?
C18 C23 H23 108.1 . . ?
C18 C23 C24 115.0(5) . . ?
C18 C23 C25 108.0(5) . . ?
C24 C23 H23 108.1 . . ?
C24 C23 C25 109.4(4) . . ?
C25 C23 H23 108.1 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 H26 107.9 . . ?
C22 C26 C27 111.9(4) . . ?
C27 C26 H26 107.9 . . ?
C28 C26 C22 109.9(5) . . ?
C28 C26 H26 107.9 . . ?
C28 C26 C27 111.2(4) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O1 C29 Fe1 179.7(7) . . ?
O2 C30 Fe1 177.6(6) . . ?
O3 C31 Fe1 178.3(5) . . ?
O4 C32 Fe1 177.3(5) . . ?
C1 N1 P1 132.7(3) . . ?
C1 N1 Ge1 130.0(3) . . ?
P1 N1 Ge1 96.1(2) . . ?
C17 N2 P1 125.3(3) . . ?
C17 N2 Ge1 138.2(3) . . ?
P1 N2 Ge1 95.58(19) . . ?
C5 P1 Ge1 124.39(15) . . ?
C11 P1 C5 106.5(2) . . ?
C11 P1 Ge1 129.04(17) . . ?
N1 P1 C5 112.8(2) . . ?
N1 P1 C11 117.3(2) . . ?
N1 P1 N2 92.67(19) . . ?
N1 P1 Ge1 46.39(14) . . ?
N2 P1 C5 115.3(2) . . ?
N2 P1 C11 112.1(2) . . ?
N2 P1 Ge1 46.34(13) . . ?
C29 Fe1 Ge1 85.83(17) . . ?
C30 Fe1 C29 87.9(3) . . ?
C30 Fe1 C31 95.6(3) . . ?
C30 Fe1 C32 94.0(3) . . ?
C30 Fe1 Ge1 173.0(2) . . ?
C31 Fe1 C29 117.9(3) . . ?
C31 Fe1 C32 112.1(3) . . ?
C31 Fe1 Ge1 90.16(17) . . ?
C32 Fe1 C29 129.6(3) . . ?
C32 Fe1 Ge1 87.60(18) . . ?
N1 Ge1 P1 37.50(11) . . ?
N1 Ge1 Cl1 105.37(12) . . ?
N1 Ge1 Fe1 124.26(12) . . ?
N2 Ge1 N1 75.54(16) . . ?
N2 Ge1 P1 38.08(11) . . ?
N2 Ge1 Cl1 100.14(11) . . ?
N2 Ge1 Fe1 132.33(11) . . ?
Cl1 Ge1 P1 104.88(5) . . ?
Cl1 Ge1 Fe1 112.26(4) . . ?
Fe1 Ge1 P1 142.74(4) . . ?

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

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_Compound_3
_database_code_depnum_ccdc_archive 'CCDC 1402723'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-09-30 downloaded from the CCDC.
;

_audit_creation_date             2015-05-25T10:52:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H45 Ge N2 O P'
_chemical_formula_sum            'C32 H45 Ge N2 O P'
_chemical_formula_weight         577.26

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   9.112(3)
_cell_length_b                   21.799(5)
_cell_length_c                   15.386(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.351(19)
_cell_angle_gamma                90
_cell_volume                     3042.8(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    7554
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.26
_exptl_crystal_density_method    "'not measured"
_exptl_crystal_F_000             1224
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        Pflugrath, JW (1999) Acta Cryst. D55, 1718-1725.
       Although that is the official publication, Thad Niemeyer
       of Rigaku/MSC has re-written the bulk of the crystal-
       lographic code in d*TREK.  Robert Bolotovsky of Rigaku
       has made numerous contributions as well.  The reqab
       absorption correction algorithm is written by Robert
       Jacobson of Iowa State University.  The habscor absorption
       correction algorithm is written by Tsuneyuki Higashi
       of Rigaku.  We also want to acknowledge the works of many
       others.
;
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'Sealed Tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_ub_11      -0.10811
_diffrn_orient_matrix_ub_12      0.005302
_diffrn_orient_matrix_ub_13      0.020835
_diffrn_orient_matrix_ub_21      -0.009493
_diffrn_orient_matrix_ub_22      -0.064581
_diffrn_orient_matrix_ub_23      -0.000608
_diffrn_orient_matrix_ub_31      0.008805
_diffrn_orient_matrix_ub_32      -0.001548
_diffrn_orient_matrix_ub_33      0.044996
_diffrn_measurement_device       
;
        XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.2054
_diffrn_reflns_number            17781
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.1
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_full        25.41
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             5570
_reflns_number_gt                3821
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement       
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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)+(0.1138P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5570
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0844
_refine_ls_wR_factor_ref         0.2302
_refine_ls_wR_factor_gt          0.2048
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.849
_refine_diff_density_min         -1.47
_refine_diff_density_rms         0.163

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2551(6) 0.7357(2) 0.2194(4) 0.0251(12) Uani 1 d . .
C2 C 0.2616(6) 0.7688(2) 0.1310(3) 0.0275(12) Uani 1 d . .
H2A H 0.2677 0.7384 0.0846 0.041 Uiso 1 calc . .
H2B H 0.3486 0.7954 0.1339 0.041 Uiso 1 calc . .
H2C H 0.1726 0.7937 0.1184 0.041 Uiso 1 calc . .
C3 C 0.2566(6) 0.7843(2) 0.2902(3) 0.0296(12) Uani 1 d . .
H3A H 0.1702 0.8109 0.2789 0.044 Uiso 1 calc . .
H3B H 0.3465 0.809 0.2902 0.044 Uiso 1 calc . .
H3C H 0.2539 0.7644 0.3471 0.044 Uiso 1 calc . .
C4 C 0.3889(6) 0.6940(2) 0.2353(4) 0.0317(12) Uani 1 d . .
H4A H 0.3953 0.6785 0.2953 0.048 Uiso 1 calc . .
H4B H 0.4784 0.7172 0.2263 0.048 Uiso 1 calc . .
H4C H 0.3792 0.6594 0.1945 0.048 Uiso 1 calc . .
C5 C 0.1130(6) 0.5686(2) 0.2374(3) 0.0200(10) Uani 1 d . .
C6 C 0.2044(6) 0.5707(2) 0.3151(3) 0.0242(11) Uani 1 d . .
H6 H 0.2391 0.6092 0.3376 0.029 Uiso 1 calc . .
C7 C 0.2452(6) 0.5173(2) 0.3600(3) 0.0299(12) Uani 1 d . .
H7 H 0.3085 0.5193 0.4126 0.036 Uiso 1 calc . .
C8 C 0.1932(6) 0.4606(2) 0.3279(3) 0.0307(12) Uani 1 d . .
H8 H 0.2224 0.4239 0.3579 0.037 Uiso 1 calc . .
C9 C 0.0988(6) 0.4583(2) 0.2520(3) 0.0291(12) Uani 1 d . .
H9 H 0.0619 0.4198 0.2306 0.035 Uiso 1 calc . .
C10 C 0.0578(6) 0.5115(2) 0.2070(3) 0.0232(11) Uani 1 d . .
H10 H -0.008 0.5095 0.1554 0.028 Uiso 1 calc . .
C11 C 0.0990(5) 0.6277(2) 0.0684(3) 0.0209(10) Uani 1 d . .
C12 C 0.1757(6) 0.5769(2) 0.0401(3) 0.0235(11) Uani 1 d . .
H12 H 0.2049 0.5451 0.0802 0.028 Uiso 1 calc . .
C13 C 0.2093(6) 0.5726(2) -0.0451(3) 0.0264(11) Uani 1 d . .
H13 H 0.2581 0.5372 -0.0641 0.032 Uiso 1 calc . .
C14 C 0.1718(6) 0.6201(2) -0.1034(3) 0.0283(12) Uani 1 d . .
H14 H 0.1978 0.6179 -0.1617 0.034 Uiso 1 calc . .
C15 C 0.0958(6) 0.6710(2) -0.0756(3) 0.0269(12) Uani 1 d . .
H15 H 0.0693 0.7033 -0.1154 0.032 Uiso 1 calc . .
C16 C 0.0585(6) 0.6748(2) 0.0093(3) 0.0250(11) Uani 1 d . .
H16 H 0.0056 0.7093 0.0275 0.03 Uiso 1 calc . .
C17 C -0.2364(6) 0.6119(2) 0.1931(3) 0.0228(11) Uani 1 d . .
C18 C -0.3269(6) 0.6006(2) 0.1155(3) 0.0229(11) Uani 1 d . .
C19 C -0.4438(6) 0.5587(2) 0.1194(3) 0.0242(11) Uani 1 d . .
H19 H -0.5032 0.5485 0.0673 0.029 Uiso 1 calc . .
C20 C -0.4741(6) 0.5322(2) 0.1974(3) 0.0260(11) Uani 1 d . .
H20 H -0.553 0.5038 0.1985 0.031 Uiso 1 calc . .
C21 C -0.3897(6) 0.5469(2) 0.2732(3) 0.0275(12) Uani 1 d . .
H21 H -0.4145 0.5299 0.3267 0.033 Uiso 1 calc . .
C22 C -0.2684(6) 0.5863(2) 0.2738(3) 0.0218(11) Uani 1 d . .
C23 C -0.3058(6) 0.6324(2) 0.0304(3) 0.0230(11) Uani 1 d . .
H23 H -0.2235 0.6625 0.0416 0.028 Uiso 1 calc . .
C24 C -0.4441(6) 0.6680(2) -0.0024(4) 0.0311(12) Uani 1 d . .
H24A H -0.4263 0.6904 -0.0556 0.047 Uiso 1 calc . .
H24B H -0.4688 0.6971 0.0425 0.047 Uiso 1 calc . .
H24C H -0.5262 0.6393 -0.0152 0.047 Uiso 1 calc . .
C25 C -0.2643(7) 0.5880(2) -0.0402(3) 0.0301(12) Uani 1 d . .
H25A H -0.3404 0.5563 -0.0497 0.045 Uiso 1 calc . .
H25B H -0.1695 0.5687 -0.0216 0.045 Uiso 1 calc . .
H25C H -0.2565 0.6105 -0.0947 0.045 Uiso 1 calc . .
C26 C -0.1830(6) 0.6018(2) 0.3591(3) 0.0252(11) Uani 1 d . .
H26 H -0.0913 0.6237 0.3459 0.03 Uiso 1 calc . .
C27 C -0.2705(7) 0.6452(3) 0.4135(4) 0.0364(14) Uani 1 d . .
H27A H -0.2891 0.6838 0.3819 0.055 Uiso 1 calc . .
H27B H -0.2136 0.6534 0.4696 0.055 Uiso 1 calc . .
H27C H -0.3646 0.626 0.4239 0.055 Uiso 1 calc . .
C28 C -0.1366(7) 0.5453(3) 0.4142(3) 0.0337(13) Uani 1 d . .
H28A H -0.2245 0.5245 0.4316 0.051 Uiso 1 calc . .
H28B H -0.0743 0.5581 0.4664 0.051 Uiso 1 calc . .
H28C H -0.0812 0.5172 0.3797 0.051 Uiso 1 calc . .
C29 C -0.1836(6) 0.8324(2) 0.1181(3) 0.0259(11) Uani 1 d . .
C30 C -0.1057(7) 0.8836(3) 0.1713(5) 0.0499(18) Uani 1 d . .
H30A H -0.1102 0.8754 0.2336 0.075 Uiso 1 calc . .
H30B H -0.1542 0.9227 0.1561 0.075 Uiso 1 calc . .
H30C H -0.0024 0.8856 0.1585 0.075 Uiso 1 calc . .
C31 C -0.1906(8) 0.8443(3) 0.0204(4) 0.0546(19) Uani 1 d . .
H31A H -0.0905 0.8451 0.002 0.082 Uiso 1 calc . .
H31B H -0.2384 0.884 0.0071 0.082 Uiso 1 calc . .
H31C H -0.2474 0.8117 -0.011 0.082 Uiso 1 calc . .
C32 C -0.3375(6) 0.8260(3) 0.1440(4) 0.0365(13) Uani 1 d . .
H32A H -0.3853 0.7906 0.1142 0.055 Uiso 1 calc . .
H32B H -0.3936 0.8633 0.1276 0.055 Uiso 1 calc . .
H32C H -0.3341 0.8201 0.2073 0.055 Uiso 1 calc . .
N1 N 0.1165(5) 0.70135(17) 0.2232(3) 0.0216(9) Uani 1 d . .
N2 N -0.1147(5) 0.65275(17) 0.1901(3) 0.0214(9) Uani 1 d . .
O1 O -0.1048(4) 0.77588(15) 0.1324(2) 0.0285(8) Uani 1 d . .
P1 P 0.05532(14) 0.63799(5) 0.18017(8) 0.0191(3) Uani 1 d . .
Ge1 Ge -0.08291(6) 0.73767(2) 0.23999(3) 0.0230(2) Uani 1 d . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.545(7) . ?
C1 C3 1.519(7) . ?
C1 C4 1.522(7) . ?
C1 N1 1.475(6) . ?
C5 C6 1.392(7) . ?
C5 C10 1.405(7) . ?
C5 P1 1.804(5) . ?
C6 C7 1.387(7) . ?
C7 C8 1.398(7) . ?
C8 C9 1.385(7) . ?
C9 C10 1.385(7) . ?
C11 C12 1.399(7) . ?
C11 C16 1.398(7) . ?
C11 P1 1.816(5) . ?
C12 C13 1.378(8) . ?
C13 C14 1.390(7) . ?
C14 C15 1.397(7) . ?
C15 C16 1.383(7) . ?
C17 C18 1.409(7) . ?
C17 C22 1.415(7) . ?
C17 N2 1.427(6) . ?
C18 C19 1.408(7) . ?
C18 C23 1.510(7) . ?
C19 C20 1.383(7) . ?
C20 C21 1.374(7) . ?
C21 C22 1.399(7) . ?
C22 C26 1.501(7) . ?
C23 C24 1.525(7) . ?
C23 C25 1.529(7) . ?
C26 C27 1.535(7) . ?
C26 C28 1.531(7) . ?
C29 C30 1.520(8) . ?
C29 C31 1.521(8) . ?
C29 C32 1.500(8) . ?
C29 O1 1.432(6) . ?
N1 P1 1.609(4) . ?
N1 Ge1 2.020(4) . ?
N2 P1 1.604(4) . ?
N2 Ge1 2.015(4) . ?
O1 Ge1 1.848(3) . ?
P1 Ge1 2.7151(14) . ?

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
C3 C1 C2 107.9(4) . . ?
C3 C1 C4 110.4(4) . . ?
C4 C1 C2 108.9(5) . . ?
N1 C1 C2 112.1(4) . . ?
N1 C1 C3 106.0(4) . . ?
N1 C1 C4 111.5(4) . . ?
C6 C5 C10 118.8(4) . . ?
C6 C5 P1 121.0(3) . . ?
C10 C5 P1 120.1(4) . . ?
C7 C6 C5 120.7(5) . . ?
C6 C7 C8 120.0(5) . . ?
C9 C8 C7 119.6(5) . . ?
C10 C9 C8 120.5(5) . . ?
C9 C10 C5 120.3(5) . . ?
C12 C11 P1 123.5(4) . . ?
C16 C11 C12 119.2(5) . . ?
C16 C11 P1 117.2(4) . . ?
C13 C12 C11 120.7(5) . . ?
C12 C13 C14 120.0(5) . . ?
C13 C14 C15 119.6(5) . . ?
C16 C15 C14 120.6(5) . . ?
C15 C16 C11 119.8(5) . . ?
C18 C17 C22 121.5(5) . . ?
C18 C17 N2 118.5(4) . . ?
C22 C17 N2 119.9(4) . . ?
C17 C18 C23 122.9(4) . . ?
C19 C18 C17 117.5(5) . . ?
C19 C18 C23 119.5(4) . . ?
C20 C19 C18 121.4(5) . . ?
C21 C20 C19 119.9(5) . . ?
C20 C21 C22 121.9(5) . . ?
C17 C22 C26 123.1(5) . . ?
C21 C22 C17 117.6(5) . . ?
C21 C22 C26 119.3(5) . . ?
C18 C23 C24 110.7(4) . . ?
C18 C23 C25 112.7(4) . . ?
C24 C23 C25 109.8(4) . . ?
C22 C26 C27 111.2(4) . . ?
C22 C26 C28 113.4(4) . . ?
C28 C26 C27 109.0(4) . . ?
C30 C29 C31 112.4(5) . . ?
C32 C29 C30 109.0(5) . . ?
C32 C29 C31 108.9(5) . . ?
O1 C29 C30 110.3(4) . . ?
O1 C29 C31 105.9(4) . . ?
O1 C29 C32 110.3(4) . . ?
C1 N1 P1 133.2(3) . . ?
C1 N1 Ge1 126.2(3) . . ?
P1 N1 Ge1 96.2(2) . . ?
C17 N2 P1 129.7(3) . . ?
C17 N2 Ge1 130.3(3) . . ?
P1 N2 Ge1 96.58(19) . . ?
C29 O1 Ge1 122.4(3) . . ?
C5 P1 C11 106.2(2) . . ?
C5 P1 Ge1 128.99(17) . . ?
C11 P1 Ge1 124.73(16) . . ?
N1 P1 C5 116.4(2) . . ?
N1 P1 C11 113.5(2) . . ?
N1 P1 Ge1 47.71(15) . . ?
N2 P1 C5 111.2(2) . . ?
N2 P1 C11 114.5(2) . . ?
N2 P1 N1 95.1(2) . . ?
N2 P1 Ge1 47.49(14) . . ?
N1 Ge1 P1 36.08(11) . . ?
N2 Ge1 N1 71.96(16) . . ?
N2 Ge1 P1 35.93(12) . . ?
O1 Ge1 N1 94.90(16) . . ?
O1 Ge1 N2 94.20(16) . . ?
O1 Ge1 P1 94.11(11) . . ?

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

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_Compound_5
_database_code_depnum_ccdc_archive 'CCDC 1402724'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-09-30 downloaded from the CCDC.
;

_audit_creation_date             2015-05-25T10:57:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C28 H36 Cl Ge N2 P S'
_chemical_formula_sum            'C28 H36 Cl Ge N2 P S'
_chemical_formula_weight         571.66

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.161(6)
_cell_length_b                   10.434(6)
_cell_length_c                   14.996(8)
_cell_angle_alpha                103.237(9)
_cell_angle_beta                 95.103(12)
_cell_angle_gamma                113.16(2)
_cell_volume                     1394.1(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3147
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    "'not measured"
_exptl_crystal_F_000             596
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        Pflugrath, JW (1999) Acta Cryst. D55, 1718-1725.
       Although that is the official publication, Thad Niemeyer
       of Rigaku/MSC has re-written the bulk of the crystal-
       lographic code in d*TREK.  Robert Bolotovsky of Rigaku
       has made numerous contributions as well.  The reqab
       absorption correction algorithm is written by Robert
       Jacobson of Iowa State University.  The habscor absorption
       correction algorithm is written by Tsuneyuki Higashi
       of Rigaku.  We also want to acknowledge the works of many
       others.
;
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'Sealed Tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_ub_11      -0.021985
_diffrn_orient_matrix_ub_12      -0.102136
_diffrn_orient_matrix_ub_13      0.03196
_diffrn_orient_matrix_ub_21      0.079624
_diffrn_orient_matrix_ub_22      -0.049522
_diffrn_orient_matrix_ub_23      0.05531
_diffrn_orient_matrix_ub_31      -0.013848
_diffrn_orient_matrix_ub_32      0.009269
_diffrn_orient_matrix_ub_33      0.067904
_diffrn_measurement_device       
;
        XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.1226
_diffrn_reflns_number            12709
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             5104
_reflns_number_gt                3068
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement       
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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)+(0.0660P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5104
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.1924
_refine_ls_wR_factor_gt          0.1569
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.529
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.133

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2604(8) 0.2138(7) 0.3635(5) 0.0268(16) Uani 1 d . .
C2 C 0.1202(8) 0.1933(8) 0.3984(6) 0.043(2) Uani 1 d . .
H2A H 0.1311 0.2863 0.4393 0.065 Uiso 1 calc . .
H2B H 0.0991 0.1214 0.4335 0.065 Uiso 1 calc . .
H2C H 0.0397 0.159 0.345 0.065 Uiso 1 calc . .
C3 C 0.3855(8) 0.2645(8) 0.4460(5) 0.041(2) Uani 1 d . .
H3A H 0.4781 0.2911 0.4241 0.061 Uiso 1 calc . .
H3B H 0.3707 0.1857 0.4748 0.061 Uiso 1 calc . .
H3C H 0.3883 0.3494 0.4922 0.061 Uiso 1 calc . .
C4 C 0.2423(9) 0.0684(7) 0.2973(5) 0.044(2) Uani 1 d . .
H4A H 0.1526 0.0281 0.2499 0.067 Uiso 1 calc . .
H4B H 0.2364 -0.0004 0.3334 0.067 Uiso 1 calc . .
H4C H 0.3263 0.0852 0.2667 0.067 Uiso 1 calc . .
C5 C 0.0328(7) 0.2766(6) 0.2012(5) 0.0211(14) Uani 1 d . .
C6 C 0.0257(7) 0.1533(7) 0.1364(5) 0.0236(15) Uani 1 d . .
H6 H 0.1134 0.1446 0.1268 0.028 Uiso 1 calc . .
C7 C -0.1064(7) 0.0443(7) 0.0863(5) 0.0262(15) Uani 1 d . .
H7 H -0.1097 -0.0379 0.0412 0.031 Uiso 1 calc . .
C8 C -0.2353(7) 0.0546(7) 0.1019(5) 0.0269(16) Uani 1 d . .
H8 H -0.3271 -0.0206 0.0679 0.032 Uiso 1 calc . .
C9 C -0.2283(7) 0.1762(7) 0.1677(5) 0.0292(17) Uani 1 d . .
H9 H -0.3162 0.1838 0.1779 0.035 Uiso 1 calc . .
C10 C -0.0955(7) 0.2865(7) 0.2189(4) 0.0229(14) Uani 1 d . .
H10 H -0.0922 0.3675 0.2653 0.027 Uiso 1 calc . .
C11 C 0.1846(7) 0.5448(7) 0.3509(5) 0.0245(15) Uani 1 d . .
C12 C 0.1123(7) 0.6195(7) 0.3186(5) 0.0314(12) Uani 1 d . .
H12 H 0.0803 0.5988 0.2533 0.038 Uiso 1 calc . .
C13 C 0.0863(8) 0.7239(7) 0.3807(6) 0.039(2) Uani 1 d . .
H13 H 0.0318 0.7701 0.3584 0.047 Uiso 1 calc . .
C14 C 0.1402(7) 0.7599(7) 0.4751(5) 0.0314(12) Uani 1 d . .
H14 H 0.1273 0.8347 0.5178 0.038 Uiso 1 calc . .
C15 C 0.2119(8) 0.6880(7) 0.5071(5) 0.0385(19) Uani 1 d . .
H15 H 0.246 0.7115 0.5725 0.046 Uiso 1 calc . .
C16 C 0.2360(8) 0.5817(7) 0.4466(5) 0.0324(17) Uani 1 d . .
H16 H 0.2876 0.5339 0.4702 0.039 Uiso 1 calc . .
C17 C 0.3532(7) 0.5856(6) 0.1635(4) 0.0194(14) Uani 1 d . .
C18 C 0.2881(7) 0.5427(7) 0.0684(4) 0.0205(14) Uani 1 d . .
C19 C 0.3001(7) 0.6534(7) 0.0270(5) 0.0257(15) Uani 1 d . .
H19 H 0.2583 0.6271 -0.0374 0.031 Uiso 1 calc . .
C20 C 0.3706(8) 0.7989(7) 0.0763(5) 0.0288(16) Uani 1 d . .
H20 H 0.3719 0.8715 0.0475 0.035 Uiso 1 calc . .
C21 C 0.4386(7) 0.8369(7) 0.1676(5) 0.0265(15) Uani 1 d . .
H21 H 0.4913 0.9372 0.2007 0.032 Uiso 1 calc . .
C22 C 0.4333(6) 0.7340(6) 0.2135(4) 0.0162(13) Uani 1 d . .
C23 C 0.2127(7) 0.3847(7) 0.0081(4) 0.0237(15) Uani 1 d . .
H23 H 0.2147 0.322 0.0492 0.028 Uiso 1 calc . .
C24 C 0.0534(8) 0.3390(8) -0.0343(5) 0.0373(18) Uani 1 d . .
H24A H 0.0016 0.3581 0.0155 0.056 Uiso 1 calc . .
H24B H 0.0078 0.2349 -0.0679 0.056 Uiso 1 calc . .
H24C H 0.0484 0.3948 -0.078 0.056 Uiso 1 calc . .
C25 C 0.2973(8) 0.3572(7) -0.0699(5) 0.0365(19) Uani 1 d . .
H25A H 0.298 0.4181 -0.111 0.055 Uiso 1 calc . .
H25B H 0.2493 0.2544 -0.1065 0.055 Uiso 1 calc . .
H25C H 0.398 0.3816 -0.0415 0.055 Uiso 1 calc . .
C26 C 0.5231(7) 0.7859(7) 0.3118(5) 0.0245(15) Uani 1 d . .
H26 H 0.4962 0.7003 0.3372 0.029 Uiso 1 calc . .
C27 C 0.6869(7) 0.8448(7) 0.3108(5) 0.0308(16) Uani 1 d . .
H27A H 0.7083 0.7663 0.2755 0.046 Uiso 1 calc . .
H27B H 0.7427 0.882 0.3751 0.046 Uiso 1 calc . .
H27C H 0.7143 0.9236 0.2812 0.046 Uiso 1 calc . .
C28 C 0.4913(8) 0.9019(7) 0.3773(5) 0.0303(16) Uani 1 d . .
H28A H 0.5148 0.9863 0.353 0.046 Uiso 1 calc . .
H28B H 0.5511 0.9323 0.4398 0.046 Uiso 1 calc . .
H28C H 0.3877 0.8613 0.3808 0.046 Uiso 1 calc . .
N1 N 0.3011(6) 0.3261(5) 0.3116(4) 0.0206(12) Uani 1 d . .
N2 N 0.3367(5) 0.4730(5) 0.2095(3) 0.0179(11) Uani 1 d . .
P1 P 0.21128(18) 0.40523(17) 0.26910(11) 0.0183(4) Uani 1 d . .
S1 S 0.6735(2) 0.4897(2) 0.31486(14) 0.0396(5) Uani 1 d . .
Cl1 Cl 0.41375(19) 0.20445(18) 0.12311(12) 0.0299(4) Uani 1 d . .
Ge1 Ge 0.45898(8) 0.38795(8) 0.24760(5) 0.0250(2) Uani 1 d . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.514(9) . ?
C1 C3 1.522(9) . ?
C1 C4 1.542(9) . ?
C1 N1 1.498(7) . ?
C2 H2A 0.98 . ?
C2 H2B 0.98 . ?
C2 H2C 0.98 . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 C6 1.395(8) . ?
C5 C10 1.391(8) . ?
C5 P1 1.805(7) . ?
C6 H6 0.95 . ?
C6 C7 1.374(9) . ?
C7 H7 0.95 . ?
C7 C8 1.391(9) . ?
C8 H8 0.95 . ?
C8 C9 1.390(9) . ?
C9 H9 0.95 . ?
C9 C10 1.388(9) . ?
C10 H10 0.95 . ?
C11 C12 1.394(9) . ?
C11 C16 1.391(9) . ?
C11 P1 1.803(6) . ?
C12 H12 0.95 . ?
C12 C13 1.389(9) . ?
C13 H13 0.95 . ?
C13 C14 1.379(10) . ?
C14 H14 0.95 . ?
C14 C15 1.362(10) . ?
C15 H15 0.95 . ?
C15 C16 1.381(9) . ?
C16 H16 0.95 . ?
C17 C18 1.406(8) . ?
C17 C22 1.411(8) . ?
C17 N2 1.457(7) . ?
C18 C19 1.402(8) . ?
C18 C23 1.524(9) . ?
C19 H19 0.95 . ?
C19 C20 1.379(9) . ?
C20 H20 0.95 . ?
C20 C21 1.370(9) . ?
C21 H21 0.95 . ?
C21 C22 1.389(8) . ?
C22 C26 1.518(9) . ?
C23 H23 1 . ?
C23 C24 1.525(9) . ?
C23 C25 1.552(8) . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
C26 H26 1 . ?
C26 C27 1.533(9) . ?
C26 C28 1.534(8) . ?
C27 H27A 0.98 . ?
C27 H27B 0.98 . ?
C27 H27C 0.98 . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 0.98 . ?
N1 P1 1.629(5) . ?
N1 Ge1 1.912(5) . ?
N2 P1 1.645(5) . ?
N2 Ge1 1.905(5) . ?
P1 Ge1 2.635(2) . ?
S1 Ge1 2.048(2) . ?
Cl1 Ge1 2.209(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
C2 C1 C3 109.8(6) . . ?
C2 C1 C4 109.6(6) . . ?
C3 C1 C4 109.6(6) . . ?
N1 C1 C2 112.1(5) . . ?
N1 C1 C3 107.4(5) . . ?
N1 C1 C4 108.4(5) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 P1 116.6(5) . . ?
C10 C5 C6 119.8(6) . . ?
C10 C5 P1 123.1(5) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.8(6) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.8(6) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.3(6) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(6) . . ?
C10 C9 H9 119.4 . . ?
C5 C10 H10 120.6 . . ?
C9 C10 C5 118.9(6) . . ?
C9 C10 H10 120.6 . . ?
C12 C11 P1 119.9(5) . . ?
C16 C11 C12 118.5(6) . . ?
C16 C11 P1 121.5(5) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(7) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.5(7) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 120 . . ?
C15 C14 C13 119.9(6) . . ?
C15 C14 H14 120 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.4(7) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 H16 120.1 . . ?
C15 C16 C11 119.8(6) . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C22 121.1(5) . . ?
C18 C17 N2 118.5(5) . . ?
C22 C17 N2 120.4(5) . . ?
C17 C18 C23 123.7(5) . . ?
C19 C18 C17 117.3(6) . . ?
C19 C18 C23 119.0(6) . . ?
C18 C19 H19 118.8 . . ?
C20 C19 C18 122.4(6) . . ?
C20 C19 H19 118.8 . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.8(6) . . ?
C21 C20 H20 120.6 . . ?
C20 C21 H21 118.8 . . ?
C20 C21 C22 122.4(6) . . ?
C22 C21 H21 118.8 . . ?
C17 C22 C26 123.3(5) . . ?
C21 C22 C17 118.0(6) . . ?
C21 C22 C26 118.6(5) . . ?
C18 C23 H23 107.7 . . ?
C18 C23 C24 112.7(5) . . ?
C18 C23 C25 110.6(5) . . ?
C24 C23 H23 107.7 . . ?
C24 C23 C25 110.3(6) . . ?
C25 C23 H23 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 H26 107.9 . . ?
C22 C26 C27 110.9(5) . . ?
C22 C26 C28 112.1(5) . . ?
C27 C26 H26 107.9 . . ?
C27 C26 C28 110.0(6) . . ?
C28 C26 H26 107.9 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C1 N1 P1 132.6(4) . . ?
C1 N1 Ge1 130.1(4) . . ?
P1 N1 Ge1 95.9(2) . . ?
C17 N2 P1 127.8(4) . . ?
C17 N2 Ge1 135.2(4) . . ?
P1 N2 Ge1 95.6(2) . . ?
C5 P1 Ge1 125.5(2) . . ?
C11 P1 C5 106.5(3) . . ?
C11 P1 Ge1 128.0(2) . . ?
N1 P1 C5 112.3(3) . . ?
N1 P1 C11 117.2(3) . . ?
N1 P1 N2 92.2(3) . . ?
N1 P1 Ge1 46.19(18) . . ?
N2 P1 C5 116.2(3) . . ?
N2 P1 C11 112.3(3) . . ?
N2 P1 Ge1 46.01(16) . . ?
N1 Ge1 P1 37.95(14) . . ?
N1 Ge1 S1 122.71(18) . . ?
N1 Ge1 Cl1 106.88(17) . . ?
N2 Ge1 N1 76.3(2) . . ?
N2 Ge1 P1 38.39(14) . . ?
N2 Ge1 S1 128.48(16) . . ?
N2 Ge1 Cl1 102.88(16) . . ?
S1 Ge1 P1 138.30(8) . . ?
S1 Ge1 Cl1 113.23(8) . . ?
Cl1 Ge1 P1 108.42(7) . . ?

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

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
####################################################################### 
# 
# 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_Compound_8
_database_code_depnum_ccdc_archive 'CCDC 1402725'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-09-30 downloaded from the CCDC.
;

_audit_creation_date             2015-05-25T11:36:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C32 H45 Ge N2 O P Se, C7 H8'
_chemical_formula_sum            'C39 H53 Ge N2 O P Se'
_chemical_formula_weight         748.35

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   23.504(4)
_cell_length_b                   8.9246(13)
_cell_length_c                   20.470(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.724(8)
_cell_angle_gamma                90
_cell_volume                     4042.0(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    10719
_cell_measurement_theta_min      3
_cell_measurement_theta_max      27.5

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.23
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1560
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        Pflugrath, JW (1999) Acta Cryst. D55, 1718-1725.
       Although that is the official publication, Thad Niemeyer
       of Rigaku/MSC has re-written the bulk of the crystal-
       lographic code in d*TREK.  Robert Bolotovsky of Rigaku
       has made numerous contributions as well.  The reqab
       absorption correction algorithm is written by Robert
       Jacobson of Iowa State University.  The habscor absorption
       correction algorithm is written by Tsuneyuki Higashi
       of Rigaku.  We also want to acknowledge the works of many
       others.
;
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'Sealed Tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_ub_11      -0.047126
_diffrn_orient_matrix_ub_12      0.091258
_diffrn_orient_matrix_ub_13      0.044792
_diffrn_orient_matrix_ub_21      -0.039331
_diffrn_orient_matrix_ub_22      -0.028897
_diffrn_orient_matrix_ub_23      0.017643
_diffrn_orient_matrix_ub_31      0.009671
_diffrn_orient_matrix_ub_32      -0.015264
_diffrn_orient_matrix_ub_33      0.041428
_diffrn_measurement_device       
;
        XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
        Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_number            34873
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             7388
_reflns_number_gt                6446
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement       
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          SQUEEZE
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.026 0.000 242 48 ' '
2 1.000 -0.020 0.500 242 48 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
;

_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)+(0.0702P)²+13.8235P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7388
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1507
_refine_ls_wR_factor_gt          0.1468
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.357
_refine_diff_density_min         -0.66
_refine_diff_density_rms         0.104

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C20 C 0.7470(2) 0.1896(5) 0.8041(2) 0.0258(9) Uani 1 d . .
H20 H 0.7052 0.1662 0.7849 0.031 Uiso 1 calc . .
C1 C 0.71405(18) 0.6401(4) 0.6892(2) 0.0204(8) Uani 1 d . .
C6 C 0.73660(18) 0.7009(5) 0.7574(2) 0.0237(8) Uani 1 d . .
C5 C 0.7033(2) 0.8131(5) 0.7755(2) 0.0280(9) Uani 1 d . .
H5 H 0.717 0.8528 0.8213 0.034 Uiso 1 calc . .
C4 C 0.6505(2) 0.8672(5) 0.7271(2) 0.0318(10) Uani 1 d . .
H4 H 0.6282 0.9436 0.74 0.038 Uiso 1 calc . .
C3 C 0.63025(18) 0.8113(4) 0.6609(2) 0.0258(9) Uani 1 d . .
H3 H 0.5942 0.8505 0.6284 0.031 Uiso 1 calc . .
C2 C 0.66119(17) 0.6986(4) 0.6401(2) 0.0221(8) Uani 1 d . .
C10 C 0.7961(2) 0.6527(5) 0.8105(2) 0.0281(9) Uani 1 d . .
H10 H 0.8151 0.5769 0.7883 0.034 Uiso 1 calc . .
C12 C 0.8394(2) 0.7853(6) 0.8336(3) 0.0486(14) Uani 1 d . .
H12A H 0.8384 0.8447 0.7929 0.073 Uiso 1 calc . .
H12B H 0.8806 0.7482 0.8569 0.073 Uiso 1 calc . .
H12C H 0.8271 0.8481 0.8658 0.073 Uiso 1 calc . .
C11 C 0.7869(3) 0.5797(6) 0.8740(2) 0.0445(13) Uani 1 d . .
H11A H 0.768 0.6519 0.8964 0.067 Uiso 1 calc . .
H11B H 0.8261 0.5487 0.9069 0.067 Uiso 1 calc . .
H11C H 0.7607 0.4918 0.8593 0.067 Uiso 1 calc . .
C7 C 0.63565(18) 0.6443(5) 0.5652(2) 0.0231(8) Uani 1 d . .
H7 H 0.6615 0.5598 0.5592 0.028 Uiso 1 calc . .
C9 C 0.57090(19) 0.5866(5) 0.5471(2) 0.0280(9) Uani 1 d . .
H9A H 0.5694 0.5107 0.5811 0.042 Uiso 1 calc . .
H9B H 0.5577 0.5421 0.5006 0.042 Uiso 1 calc . .
H9C H 0.5441 0.6701 0.5481 0.042 Uiso 1 calc . .
C8 C 0.6376(2) 0.7693(5) 0.5150(2) 0.0303(9) Uani 1 d . .
H8A H 0.6132 0.8542 0.5207 0.046 Uiso 1 calc . .
H8B H 0.6213 0.7322 0.4672 0.046 Uiso 1 calc . .
H8C H 0.6795 0.8019 0.5249 0.046 Uiso 1 calc . .
C13 C 0.66013(17) 0.2842(4) 0.6491(2) 0.0200(8) Uani 1 d . .
C14 C 0.62355(19) 0.3025(5) 0.6902(2) 0.0263(9) Uani 1 d . .
H14 H 0.6398 0.3459 0.735 0.032 Uiso 1 calc . .
C15 C 0.5639(2) 0.2576(5) 0.6654(2) 0.0326(10) Uani 1 d . .
H15 H 0.5393 0.2694 0.6936 0.039 Uiso 1 calc . .
C16 C 0.53943(19) 0.1953(5) 0.5996(3) 0.0347(10) Uani 1 d . .
H16 H 0.4987 0.1619 0.5834 0.042 Uiso 1 calc . .
C17 C 0.57462(19) 0.1822(5) 0.5579(2) 0.0288(9) Uani 1 d . .
H17 H 0.5576 0.1434 0.5122 0.035 Uiso 1 calc . .
C18 C 0.63467(18) 0.2253(4) 0.5824(2) 0.0232(8) Uani 1 d . .
H18 H 0.6587 0.2148 0.5536 0.028 Uiso 1 calc . .
C19 C 0.77509(18) 0.2691(4) 0.76544(19) 0.0218(8) Uani 1 d . .
C24 C 0.83732(19) 0.2990(5) 0.7938(2) 0.0247(8) Uani 1 d . .
H24 H 0.857 0.352 0.7673 0.03 Uiso 1 calc . .
C23 C 0.8701(2) 0.2509(5) 0.8607(2) 0.0311(10) Uani 1 d . .
H23 H 0.9122 0.2705 0.8797 0.037 Uiso 1 calc . .
C22 C 0.8409(2) 0.1739(5) 0.8997(2) 0.0331(10) Uani 1 d . .
H22 H 0.8629 0.1425 0.9456 0.04 Uiso 1 calc . .
C21 C 0.7803(2) 0.1438(5) 0.8714(2) 0.0300(9) Uani 1 d . .
H21 H 0.7606 0.091 0.898 0.036 Uiso 1 calc . .
C25 C 0.79853(18) 0.1509(4) 0.6125(2) 0.0212(8) Uani 1 d . .
C26 C 0.7727(2) 0.0206(5) 0.6414(3) 0.0283(9) Uani 1 d . .
H26A H 0.7285 0.0253 0.6234 0.043 Uiso 1 calc . .
H26B H 0.7869 0.0265 0.6921 0.043 Uiso 1 calc . .
H26C H 0.7861 -0.0741 0.6272 0.043 Uiso 1 calc . .
C27 C 0.7801(3) 0.1348(6) 0.5334(2) 0.0431(13) Uani 1 d . .
H27A H 0.7977 0.0429 0.5222 0.065 Uiso 1 calc . .
H27B H 0.7948 0.2214 0.5144 0.065 Uiso 1 calc . .
H27C H 0.7359 0.1297 0.5131 0.065 Uiso 1 calc . .
C28 C 0.8671(2) 0.1486(5) 0.6448(3) 0.0361(11) Uani 1 d . .
H28A H 0.8787 0.1547 0.6954 0.054 Uiso 1 calc . .
H28B H 0.8841 0.2343 0.6277 0.054 Uiso 1 calc . .
H28C H 0.8828 0.0554 0.6321 0.054 Uiso 1 calc . .
C29 C 0.9248(2) 0.5896(6) 0.6915(4) 0.0521(16) Uani 1 d . .
C30 C 0.9559(3) 0.5249(8) 0.6443(6) 0.086(3) Uani 1 d . .
H30A H 0.9295 0.535 0.5959 0.129 Uiso 1 calc . .
H30B H 0.9647 0.4187 0.6552 0.129 Uiso 1 calc . .
H30C H 0.9937 0.5791 0.651 0.129 Uiso 1 calc . .
C31 C 0.9096(3) 0.7543(6) 0.6747(4) 0.065(2) Uani 1 d . .
H31A H 0.9469 0.8107 0.6813 0.097 Uiso 1 calc . .
H31B H 0.8892 0.7942 0.7056 0.097 Uiso 1 calc . .
H31C H 0.8828 0.7638 0.6264 0.097 Uiso 1 calc . .
C32 C 0.9634(3) 0.5717(7) 0.7686(4) 0.074(2) Uani 1 d . .
H32A H 0.9719 0.4653 0.7793 0.111 Uiso 1 calc . .
H32B H 0.9413 0.6122 0.7976 0.111 Uiso 1 calc . .
H32C H 1.0015 0.6263 0.7781 0.111 Uiso 1 calc . .
N1 N 0.74629(14) 0.5190(3) 0.67053(17) 0.0186(7) Uani 1 d . .
N2 N 0.77463(14) 0.2969(4) 0.62630(16) 0.0195(7) Uani 1 d . .
O1 O 0.87139(13) 0.5049(3) 0.68397(18) 0.0339(8) Uani 1 d . .
P1 P 0.73821(4) 0.33959(11) 0.67869(5) 0.0176(2) Uani 1 d . .
Ge1 Ge 0.799423(18) 0.49900(4) 0.61707(2) 0.02091(14) Uani 1 d . .
Se1 Se 0.78452(2) 0.60889(5) 0.51647(2) 0.03289(15) Uani 1 d . .
C33 C 0.3983(4) 1.0517(9) 0.6619(4) 0.073(2) Uani 1 d . .
H33A H 0.3892 1.0604 0.7051 0.11 Uiso 1 calc . .
H33B H 0.3633 1.0849 0.6229 0.11 Uiso 1 calc . .
H33C H 0.4333 1.1144 0.6648 0.11 Uiso 1 calc . .
C34 C 0.4121(3) 0.8930(8) 0.6512(3) 0.0563(16) Uani 1 d . .
C35 C 0.4717(3) 0.8410(9) 0.6732(3) 0.0587(18) Uani 1 d . .
H35 H 0.5041 0.9084 0.6938 0.07 Uiso 1 calc . .
C36 C 0.4835(3) 0.6927(9) 0.6652(3) 0.0621(18) Uani 1 d . .
H36 H 0.5241 0.6583 0.6808 0.075 Uiso 1 calc . .
C37 C 0.4373(3) 0.5930(9) 0.6347(3) 0.0660(19) Uani 1 d . .
H37 H 0.4463 0.4912 0.6287 0.079 Uiso 1 calc . .
C38 C 0.3788(3) 0.6411(10) 0.6132(3) 0.066(2) Uani 1 d . .
H38 H 0.3467 0.5721 0.5935 0.079 Uiso 1 calc . .
C39 C 0.3664(2) 0.7887(8) 0.6200(3) 0.0492(14) Uani 1 d . .
H39 H 0.3256 0.8217 0.603 0.059 Uiso 1 calc . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C20 C19 1.385(6) . ?
C20 C21 1.397(6) . ?
C1 C6 1.423(6) . ?
C1 C2 1.408(6) . ?
C1 N1 1.444(5) . ?
C6 C5 1.396(6) . ?
C6 C10 1.516(6) . ?
C5 C4 1.388(7) . ?
C4 C3 1.370(6) . ?
C3 C2 1.389(6) . ?
C2 C7 1.526(6) . ?
C10 C12 1.528(6) . ?
C10 C11 1.533(7) . ?
C7 C9 1.529(6) . ?
C7 C8 1.528(6) . ?
C13 C14 1.400(6) . ?
C13 C18 1.396(6) . ?
C13 P1 1.797(4) . ?
C14 C15 1.381(6) . ?
C15 C16 1.390(7) . ?
C16 C17 1.379(7) . ?
C17 C18 1.383(6) . ?
C19 C24 1.405(6) . ?
C19 P1 1.806(4) . ?
C24 C23 1.393(6) . ?
C23 C22 1.397(7) . ?
C22 C21 1.372(7) . ?
C25 C26 1.522(6) . ?
C25 C27 1.534(6) . ?
C25 C28 1.523(6) . ?
C25 N2 1.483(5) . ?
C29 C30 1.510(10) . ?
C29 C31 1.524(7) . ?
C29 C32 1.541(10) . ?
C29 O1 1.429(5) . ?
N1 P1 1.628(3) . ?
N1 Ge1 1.927(3) . ?
N2 P1 1.627(3) . ?
N2 Ge1 1.925(3) . ?
O1 Ge1 1.782(3) . ?
P1 Ge1 2.6287(11) . ?
Ge1 Se1 2.1996(7) . ?
C33 C34 1.485(11) . ?
C34 C35 1.399(9) . ?
C34 C39 1.401(9) . ?
C35 C36 1.374(11) . ?
C36 C37 1.379(10) . ?
C37 C38 1.365(10) . ?
C38 C39 1.367(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
C19 C20 C21 119.8(4) . . ?
C6 C1 N1 119.3(3) . . ?
C2 C1 C6 120.4(4) . . ?
C2 C1 N1 120.3(3) . . ?
C1 C6 C10 122.9(4) . . ?
C5 C6 C1 118.5(4) . . ?
C5 C6 C10 118.5(4) . . ?
C4 C5 C6 120.5(4) . . ?
C3 C4 C5 120.5(4) . . ?
C4 C3 C2 121.6(4) . . ?
C1 C2 C7 123.6(4) . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 C7 118.0(4) . . ?
C6 C10 C12 111.0(4) . . ?
C6 C10 C11 111.6(4) . . ?
C12 C10 C11 109.7(4) . . ?
C2 C7 C9 111.8(3) . . ?
C2 C7 C8 110.7(3) . . ?
C8 C7 C9 109.7(3) . . ?
C14 C13 P1 122.0(3) . . ?
C18 C13 C14 119.0(4) . . ?
C18 C13 P1 119.0(3) . . ?
C15 C14 C13 120.0(4) . . ?
C14 C15 C16 120.5(4) . . ?
C17 C16 C15 119.7(4) . . ?
C16 C17 C18 120.3(4) . . ?
C17 C18 C13 120.5(4) . . ?
C20 C19 C24 119.5(4) . . ?
C20 C19 P1 125.2(3) . . ?
C24 C19 P1 115.3(3) . . ?
C23 C24 C19 120.1(4) . . ?
C24 C23 C22 119.8(4) . . ?
C21 C22 C23 119.8(4) . . ?
C22 C21 C20 121.0(4) . . ?
C26 C25 C27 109.3(4) . . ?
C26 C25 C28 108.9(3) . . ?
C28 C25 C27 109.7(4) . . ?
N2 C25 C26 111.8(3) . . ?
N2 C25 C27 107.1(3) . . ?
N2 C25 C28 110.0(3) . . ?
C30 C29 C31 110.6(6) . . ?
C30 C29 C32 111.8(6) . . ?
C31 C29 C32 110.1(5) . . ?
O1 C29 C30 109.0(5) . . ?
O1 C29 C31 110.8(4) . . ?
O1 C29 C32 104.3(5) . . ?
C1 N1 P1 128.3(3) . . ?
C1 N1 Ge1 135.9(3) . . ?
P1 N1 Ge1 95.02(15) . . ?
C25 N2 P1 130.5(3) . . ?
C25 N2 Ge1 131.1(2) . . ?
P1 N2 Ge1 95.11(16) . . ?
C29 O1 Ge1 132.1(3) . . ?
C13 P1 C19 109.38(19) . . ?
C13 P1 Ge1 130.50(13) . . ?
C19 P1 Ge1 120.11(14) . . ?
N1 P1 C13 112.17(17) . . ?
N1 P1 C19 114.20(18) . . ?
N1 P1 Ge1 46.89(12) . . ?
N2 P1 C13 114.72(18) . . ?
N2 P1 C19 112.44(18) . . ?
N2 P1 N1 93.29(17) . . ?
N2 P1 Ge1 46.82(12) . . ?
N1 Ge1 P1 38.09(10) . . ?
N1 Ge1 Se1 124.16(10) . . ?
N2 Ge1 N1 75.84(13) . . ?
N2 Ge1 P1 38.07(10) . . ?
N2 Ge1 Se1 123.50(10) . . ?
O1 Ge1 N1 100.94(15) . . ?
O1 Ge1 N2 101.10(14) . . ?
O1 Ge1 P1 100.28(11) . . ?
O1 Ge1 Se1 121.08(11) . . ?
Se1 Ge1 P1 138.64(3) . . ?
C35 C34 C33 120.9(7) . . ?
C35 C34 C39 117.2(7) . . ?
C39 C34 C33 121.9(6) . . ?
C36 C35 C34 120.1(6) . . ?
C35 C36 C37 121.1(6) . . ?
C38 C37 C36 119.8(8) . . ?
C37 C38 C39 119.7(7) . . ?
C38 C39 C34 122.0(6) . . ?

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

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
