# Electronic Supplementary Material (ESI) for ChemComm.
# 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_ch1ppx203_0m
_database_code_depnum_ccdc_archive 'CCDC 1030031'
_audit_update_record             
;
2015-01-26 deposited with the CCDC.
2015-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        'Tetraphenylphosphonium triazidostannate(II)'
_chemical_name_common            (PPh4)[Sn(N3)3]
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 P, N9 Sn'
_chemical_formula_sum            'C24 H20 N9 P Sn'
_chemical_formula_weight         584.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7560(6)
_cell_length_b                   11.0605(6)
_cell_length_c                   12.3540(7)
_cell_angle_alpha                91.668(4)
_cell_angle_beta                 108.414(4)
_cell_angle_gamma                116.545(3)
_cell_volume                     1222.11(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6545
_cell_measurement_theta_min      2.2761
_cell_measurement_theta_max      26.9402

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.143
_shelx_estimated_absorpt_T_min   0.748
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22380
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.101
_diffrn_reflns_theta_max         27.202
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5407
_reflns_number_gt                4484
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS-2014
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  'ORTEP-3 for Windows'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+1.3033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5407
_refine_ls_number_parameters     334
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.21121(3) 0.03245(2) 0.03802(2) 0.02621(10) Uani 1 1 d . . . . .
N1 N 0.3698(4) 0.0473(3) 0.2157(3) 0.0308(7) Uani 1 1 d . . . . .
N2 N 0.3733(4) 0.0964(3) 0.3055(3) 0.0298(7) Uani 1 1 d . . . . .
N3 N 0.3818(5) 0.1440(4) 0.3931(3) 0.0435(9) Uani 1 1 d . . . . .
N4 N 0.2722(4) 0.2483(3) 0.0923(3) 0.0351(8) Uani 1 1 d . . . . .
N5 N 0.1770(4) 0.2765(3) 0.0935(3) 0.0272(7) Uani 1 1 d . . . . .
N6 N 0.0894(4) 0.3080(4) 0.0938(3) 0.0395(8) Uani 1 1 d . . . . .
N7 N 0.0324(4) -0.0317(3) 0.1096(3) 0.0317(7) Uani 1 1 d D . . . .
N8A N 0.0122(16) -0.1023(12) 0.1793(8) 0.0293(18) Uani 0.5 1 d D U P A -1
N9A N -0.0055(11) -0.1674(9) 0.2500(7) 0.0467(19) Uani 0.5 1 d D U P A -1
N8B N 0.0431(15) -0.0791(12) 0.1955(8) 0.0273(18) Uani 0.5 1 d D U P A 1
N9B N 0.0480(10) -0.1214(9) 0.2814(6) 0.0403(18) Uani 0.5 1 d D U P A 1
P1 P 0.18907(9) 0.60134(8) 0.76326(7) 0.01634(18) Uani 1 1 d . . . . .
C1 C 0.2484(4) 0.5099(3) 0.6861(3) 0.0170(6) Uani 1 1 d . . . . .
C2 C 0.3996(4) 0.5720(3) 0.7014(3) 0.0205(7) Uani 1 1 d . . . . .
H2 H 0.4678 0.6597 0.7514 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4500(4) 0.5049(4) 0.6433(3) 0.0235(7) Uani 1 1 d . . . . .
H3 H 0.5528 0.5465 0.6536 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3500(4) 0.3773(4) 0.5705(3) 0.0258(8) Uani 1 1 d . . . . .
H4 H 0.3843 0.3321 0.5300 0.031 Uiso 1 1 calc R U . . .
C5 C 0.2003(4) 0.3148(4) 0.5563(3) 0.0253(8) Uani 1 1 d . . . . .
H5 H 0.1331 0.2266 0.5070 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1477(4) 0.3808(3) 0.6137(3) 0.0207(7) Uani 1 1 d . . . . .
H6 H 0.0450 0.3383 0.6037 0.025 Uiso 1 1 calc R U . . .
C7 C 0.0020(4) 0.4895(3) 0.7529(3) 0.0194(7) Uani 1 1 d . . . . .
C8 C -0.1155(4) 0.4635(4) 0.6497(3) 0.0261(8) Uani 1 1 d . . . . .
H8 H -0.0965 0.5124 0.5898 0.031 Uiso 1 1 calc R U . . .
C9 C -0.2603(4) 0.3660(4) 0.6346(3) 0.0299(8) Uani 1 1 d . . . . .
H9 H -0.3406 0.3481 0.5643 0.036 Uiso 1 1 calc R U . . .
C10 C -0.2878(4) 0.2948(4) 0.7218(4) 0.0318(9) Uani 1 1 d . . . . .
H10 H -0.3865 0.2257 0.7101 0.038 Uiso 1 1 calc R U . . .
C11 C -0.1725(4) 0.3237(4) 0.8258(4) 0.0297(8) Uani 1 1 d . . . . .
H11 H -0.1929 0.2766 0.8864 0.036 Uiso 1 1 calc R U . . .
C12 C -0.0273(4) 0.4208(3) 0.8427(3) 0.0213(7) Uani 1 1 d . . . . .
H12 H 0.0517 0.4406 0.9144 0.026 Uiso 1 1 calc R U . . .
C13 C 0.3169(4) 0.6563(3) 0.9115(3) 0.0181(7) Uani 1 1 d . . . . .
C14 C 0.3868(4) 0.7918(3) 0.9714(3) 0.0199(7) Uani 1 1 d . . . . .
H14 H 0.3657 0.8582 0.9345 0.024 Uiso 1 1 calc R U . . .
C15 C 0.4879(4) 0.8297(3) 1.0859(3) 0.0237(7) Uani 1 1 d . . . . .
H15 H 0.5346 0.9218 1.1275 0.028 Uiso 1 1 calc R U . . .
C16 C 0.5200(4) 0.7332(3) 1.1388(3) 0.0226(7) Uani 1 1 d . . . . .
H16 H 0.5913 0.7599 1.2159 0.027 Uiso 1 1 calc R U . . .
C17 C 0.4489(4) 0.5978(4) 1.0798(3) 0.0230(7) Uani 1 1 d . . . . .
H17 H 0.4693 0.5315 1.1175 0.028 Uiso 1 1 calc R U . . .
C18 C 0.3486(4) 0.5587(3) 0.9667(3) 0.0212(7) Uani 1 1 d . . . . .
H18 H 0.3011 0.4660 0.9262 0.025 Uiso 1 1 calc R U . . .
C19 C 0.1950(4) 0.7475(3) 0.7000(3) 0.0184(7) Uani 1 1 d . . . . .
C20 C 0.1236(4) 0.8150(4) 0.7300(3) 0.0244(7) Uani 1 1 d . . . . .
H20 H 0.0716 0.7834 0.7814 0.029 Uiso 1 1 calc R U . . .
C21 C 0.1308(5) 0.9291(4) 0.6828(3) 0.0311(9) Uani 1 1 d . . . . .
H21 H 0.0854 0.9778 0.7038 0.037 Uiso 1 1 calc R U . . .
C22 C 0.2038(5) 0.9730(4) 0.6051(3) 0.0330(9) Uani 1 1 d . . . . .
H22 H 0.2061 1.0501 0.5721 0.040 Uiso 1 1 calc R U . . .
C23 C 0.2723(4) 0.9056(4) 0.5758(3) 0.0302(8) Uani 1 1 d . . . . .
H23 H 0.3220 0.9360 0.5227 0.036 Uiso 1 1 calc R U . . .
C24 C 0.2692(4) 0.7927(3) 0.6237(3) 0.0232(7) Uani 1 1 d . . . . .
H24 H 0.3179 0.7466 0.6043 0.028 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sn1 N4 2.193(3) . ?
Sn1 N7 2.207(3) . ?
Sn1 N1 2.262(3) . ?
N1 N2 1.203(4) . ?
N2 N3 1.148(5) . ?
N4 N5 1.200(5) . ?
N5 N6 1.143(5) . ?
N7 N8A 1.185(5) . ?
N7 N8B 1.193(5) . ?
N8A N9A 1.157(6) . ?
N8B N9B 1.168(6) . ?
P1 C7 1.788(3) . ?
P1 C13 1.792(3) . ?
P1 C1 1.800(3) . ?
P1 C19 1.800(3) . ?
C1 C6 1.394(5) . ?
C1 C2 1.398(5) . ?
C2 C3 1.391(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.393(5) . ?
C7 C12 1.400(4) . ?
C8 C9 1.389(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.391(5) . ?
C13 C18 1.404(4) . ?
C14 C15 1.395(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.387(5) . ?
C19 C20 1.400(5) . ?
C20 C21 1.386(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.369(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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
N4 Sn1 N7 89.14(13) . . ?
N4 Sn1 N1 88.35(12) . . ?
N7 Sn1 N1 88.59(12) . . ?
N2 N1 Sn1 123.6(3) . . ?
N3 N2 N1 177.5(4) . . ?
N5 N4 Sn1 119.4(2) . . ?
N6 N5 N4 177.5(4) . . ?
N8A N7 Sn1 128.2(9) . . ?
N8B N7 Sn1 120.2(8) . . ?
N9A N8A N7 177.8(15) . . ?
N9B N8B N7 175.3(18) . . ?
C7 P1 C13 111.20(15) . . ?
C7 P1 C1 109.68(15) . . ?
C13 P1 C1 106.55(15) . . ?
C7 P1 C19 109.14(15) . . ?
C13 P1 C19 110.73(15) . . ?
C1 P1 C19 109.50(15) . . ?
C6 C1 C2 120.5(3) . . ?
C6 C1 P1 121.5(3) . . ?
C2 C1 P1 117.9(2) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C12 119.8(3) . . ?
C8 C7 P1 118.7(3) . . ?
C12 C7 P1 121.4(3) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
C14 C13 C18 119.8(3) . . ?
C14 C13 P1 122.1(2) . . ?
C18 C13 P1 118.1(2) . . ?
C13 C14 C15 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.3(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C24 C19 C20 120.7(3) . . ?
C24 C19 P1 120.8(3) . . ?
C20 C19 P1 118.6(2) . . ?
C21 C20 C19 118.4(3) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C20 C21 C22 120.7(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.0(3) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 119.8(3) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?

_refine_diff_density_max         2.295
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.109

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_ch1ppx202_0m
_database_code_depnum_ccdc_archive 'CCDC 1030032'
_audit_update_record             
;
2014-10-18 deposited with the CCDC.
2015-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        (PPh4)[Ge(N3)3]
_chemical_name_common            (PPh4)[Ge(N3)3]
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 P, Ge N9'
_chemical_formula_sum            'C24 H20 Ge N9 P'
_chemical_formula_weight         538.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7712(2)
_cell_length_b                   11.4711(4)
_cell_length_c                   14.2003(4)
_cell_angle_alpha                93.278(2)
_cell_angle_beta                 99.357(2)
_cell_angle_gamma                100.865(2)
_cell_volume                     1221.59(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4545
_cell_measurement_theta_min      2.4303
_cell_measurement_theta_max      24.4081

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.351
_shelx_estimated_absorpt_T_min   0.712
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7117
_exptl_absorpt_correction_T_max  0.9233
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24413
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.815
_diffrn_reflns_theta_max         27.571
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5613
_reflns_number_gt                4124
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  'ORTEP-3 for Windows'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0319P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5613
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0807
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge1 Ge 0.47171(3) 0.29007(2) 0.68416(2) 0.02765(9) Uani 1 1 d . . . . .
N1 N 0.5845(3) 0.37359(19) 0.58397(15) 0.0365(5) Uani 1 1 d . . . . .
N2 N 0.6861(3) 0.3245(2) 0.54775(14) 0.0337(5) Uani 1 1 d . . . . .
N3 N 0.7808(3) 0.2800(2) 0.51064(16) 0.0489(7) Uani 1 1 d . . . . .
N4 N 0.6713(3) 0.3758(2) 0.78702(16) 0.0387(6) Uani 1 1 d . . . . .
N5 N 0.6515(3) 0.37344(18) 0.86967(16) 0.0299(5) Uani 1 1 d . . . . .
N6 N 0.6393(3) 0.3735(2) 0.94887(16) 0.0455(6) Uani 1 1 d . . . . .
N7 N 0.5808(3) 0.14890(18) 0.66729(14) 0.0302(5) Uani 1 1 d . . . . .
N8 N 0.7244(3) 0.14444(18) 0.71238(15) 0.0326(5) Uani 1 1 d . . . . .
N9 N 0.8565(3) 0.1319(2) 0.75448(19) 0.0589(8) Uani 1 1 d . . . . .
P1 P 0.54012(8) 0.77428(5) 0.76571(4) 0.02009(14) Uani 1 1 d . . . . .
C1 C 0.6533(3) 0.7889(2) 0.66530(15) 0.0208(5) Uani 1 1 d . . . . .
C2 C 0.7692(3) 0.7114(2) 0.65349(16) 0.0252(5) Uani 1 1 d . . . . .
H2 H 0.7782 0.6493 0.6944 0.030 Uiso 1 1 calc R U . . .
C3 C 0.8704(3) 0.7260(2) 0.58192(16) 0.0280(6) Uani 1 1 d . . . . .
H3 H 0.9486 0.6734 0.5731 0.034 Uiso 1 1 calc R U . . .
C4 C 0.8581(3) 0.8171(2) 0.52305(16) 0.0297(6) Uani 1 1 d . . . . .
H4 H 0.9304 0.8281 0.4751 0.036 Uiso 1 1 calc R U . . .
C5 C 0.7419(3) 0.8923(2) 0.53330(16) 0.0297(6) Uani 1 1 d . . . . .
H5 H 0.7324 0.9534 0.4914 0.036 Uiso 1 1 calc R U . . .
C6 C 0.6387(3) 0.8789(2) 0.60476(16) 0.0249(5) Uani 1 1 d . . . . .
H6 H 0.5590 0.9308 0.6121 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4397(3) 0.8996(2) 0.78618(16) 0.0206(5) Uani 1 1 d . . . . .
C8 C 0.2832(3) 0.9071(2) 0.72465(16) 0.0245(5) Uani 1 1 d . . . . .
H8 H 0.2372 0.8495 0.6714 0.029 Uiso 1 1 calc R U . . .
C9 C 0.1956(3) 0.9979(2) 0.74118(17) 0.0282(6) Uani 1 1 d . . . . .
H9 H 0.0894 1.0029 0.6991 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2617(3) 1.0819(2) 0.81890(17) 0.0301(6) Uani 1 1 d . . . . .
H10 H 0.2002 1.1439 0.8303 0.036 Uiso 1 1 calc R U . . .
C11 C 0.4173(3) 1.0758(2) 0.87998(17) 0.0285(6) Uani 1 1 d . . . . .
H11 H 0.4630 1.1342 0.9327 0.034 Uiso 1 1 calc R U . . .
C12 C 0.5064(3) 0.9845(2) 0.86427(16) 0.0250(5) Uani 1 1 d . . . . .
H12 H 0.6124 0.9798 0.9066 0.030 Uiso 1 1 calc R U . . .
C13 C 0.7064(3) 0.7630(2) 0.86687(16) 0.0235(5) Uani 1 1 d . . . . .
C14 C 0.8666(3) 0.8460(2) 0.88210(17) 0.0311(6) Uani 1 1 d . . . . .
H14 H 0.8851 0.9075 0.8406 0.037 Uiso 1 1 calc R U . . .
C15 C 0.9981(3) 0.8377(3) 0.95825(19) 0.0389(7) Uani 1 1 d . . . . .
H15 H 1.1077 0.8937 0.9691 0.047 Uiso 1 1 calc R U . . .
C16 C 0.9710(4) 0.7485(3) 1.01846(18) 0.0394(7) Uani 1 1 d . . . . .
H16 H 1.0617 0.7437 1.0708 0.047 Uiso 1 1 calc R U . . .
C17 C 0.8130(4) 0.6663(3) 1.00308(18) 0.0377(7) Uani 1 1 d . . . . .
H17 H 0.7955 0.6048 1.0446 0.045 Uiso 1 1 calc R U . . .
C18 C 0.6795(3) 0.6732(2) 0.92706(16) 0.0294(6) Uani 1 1 d . . . . .
H18 H 0.5703 0.6167 0.9164 0.035 Uiso 1 1 calc R U . . .
C19 C 0.3607(3) 0.6476(2) 0.74614(15) 0.0211(5) Uani 1 1 d . . . . .
C20 C 0.3290(3) 0.5673(2) 0.66522(16) 0.0248(5) Uani 1 1 d . . . . .
H20 H 0.4094 0.5744 0.6211 0.030 Uiso 1 1 calc R U . . .
C21 C 0.1796(3) 0.4771(2) 0.64957(18) 0.0310(6) Uani 1 1 d . . . . .
H21 H 0.1571 0.4224 0.5941 0.037 Uiso 1 1 calc R U . . .
C22 C 0.0627(3) 0.4652(2) 0.71323(18) 0.0327(6) Uani 1 1 d . . . . .
H22 H -0.0400 0.4030 0.7013 0.039 Uiso 1 1 calc R U . . .
C23 C 0.0950(3) 0.5439(2) 0.79452(18) 0.0304(6) Uani 1 1 d . . . . .
H23 H 0.0155 0.5345 0.8391 0.036 Uiso 1 1 calc R U . . .
C24 C 0.2412(3) 0.6354(2) 0.81121(16) 0.0257(5) Uani 1 1 d . . . . .
H24 H 0.2616 0.6903 0.8664 0.031 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ge1 N7 1.984(2) . ?
Ge1 N1 1.989(2) . ?
Ge1 N4 2.007(2) . ?
N1 N2 1.213(3) . ?
N2 N3 1.148(3) . ?
N4 N5 1.209(3) . ?
N5 N6 1.144(3) . ?
N7 N8 1.204(3) . ?
N8 N9 1.139(3) . ?
P1 C19 1.788(2) . ?
P1 C1 1.793(2) . ?
P1 C7 1.791(2) . ?
P1 C13 1.797(2) . ?
C1 C6 1.390(3) . ?
C1 C2 1.402(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.395(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.376(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.383(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.390(3) . ?
C19 C24 1.407(3) . ?
C20 C21 1.380(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.373(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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
N7 Ge1 N1 93.50(9) . . ?
N7 Ge1 N4 94.37(9) . . ?
N1 Ge1 N4 90.98(9) . . ?
N2 N1 Ge1 116.40(17) . . ?
N3 N2 N1 177.6(3) . . ?
N5 N4 Ge1 118.61(17) . . ?
N6 N5 N4 177.4(3) . . ?
N8 N7 Ge1 121.20(17) . . ?
N9 N8 N7 175.3(3) . . ?
C19 P1 C1 111.75(10) . . ?
C19 P1 C7 105.22(10) . . ?
C1 P1 C7 111.57(11) . . ?
C19 P1 C13 111.77(11) . . ?
C1 P1 C13 105.91(10) . . ?
C7 P1 C13 110.74(10) . . ?
C6 C1 C2 120.2(2) . . ?
C6 C1 P1 122.02(17) . . ?
C2 C1 P1 117.57(17) . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.4(2) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C12 C7 C8 119.6(2) . . ?
C12 C7 P1 122.16(18) . . ?
C8 C7 P1 118.08(17) . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.2(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
C18 C13 C14 120.4(2) . . ?
C18 C13 P1 121.45(18) . . ?
C14 C13 P1 118.13(19) . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.3(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 119.5(2) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C24 119.7(2) . . ?
C20 C19 P1 121.83(18) . . ?
C24 C19 P1 118.27(17) . . ?
C21 C20 C19 119.3(2) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C22 C21 C20 120.9(2) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 119.9(2) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C19 119.7(2) . . ?
C23 C24 H24 120.1 . . ?
C19 C24 H24 120.1 . . ?

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-3

