# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ld181112Ge1
_database_code_depnum_ccdc_archive 'CCDC 2032972'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2020-09-21 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Ge N6'
_chemical_formula_weight         412.98

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   7.7879(4)
_cell_length_b                   18.4219(11)
_cell_length_c                   24.4619(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3509.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    31981
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             1680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.764
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5370
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.720
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            31981
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.1190
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.363
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4018
_reflns_number_gt                2848
_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 Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0235P)²+4.0132P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4018
_refine_ls_number_parameters     244
_refine_ls_number_restraints     222
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.0821
_refine_ls_wR_factor_gt          0.0740
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.86515(4) 0.53320(2) 0.37083(2) 0.01812(9) Uani 1 1 d . . . . .
N1 N 0.7942(3) 0.50871(13) 0.44793(10) 0.0189(5) Uani 1 1 d . . . . .
C1 C 0.8007(4) 0.55324(17) 0.49266(12) 0.0239(7) Uani 1 1 d . . . . .
C2 C 0.7400(4) 0.5246(2) 0.54310(13) 0.0356(9) Uani 1 1 d . . . . .
H2 H 0.743458 0.554154 0.574897 0.043 Uiso 1 1 calc R U . . .
N2 N 0.8656(4) 0.62089(14) 0.49335(10) 0.0291(6) Uani 1 1 d . . . . .
N3 N 0.9666(3) 0.62597(13) 0.40054(10) 0.0184(5) Uani 1 1 d . . . . .
C3 C 0.6775(4) 0.4563(2) 0.54687(15) 0.0389(9) Uani 1 1 d . . . . .
H3 H 0.635546 0.438791 0.580866 0.047 Uiso 1 1 calc R U . . .
N4 N 0.6508(3) 0.58387(13) 0.34983(9) 0.0187(5) Uani 1 1 d . . . . .
C4 C 0.6746(4) 0.4118(2) 0.50103(14) 0.0336(8) Uani 1 1 d . . . . .
H4 H 0.632956 0.363366 0.502935 0.040 Uiso 1 1 calc R U . . .
C5 C 0.7335(4) 0.44022(18) 0.45348(13) 0.0262(7) Uani 1 1 d . . . . .
H5 H 0.732149 0.410096 0.421958 0.031 Uiso 1 1 calc R U . . .
N5 N 0.5822(3) 0.46549(14) 0.33925(9) 0.0201(5) Uani 1 1 d . . . . .
C6 C 0.9499(4) 0.65304(17) 0.45221(13) 0.0251(7) Uani 1 1 d . . . . .
N6 N 0.6210(4) 0.68289(15) 0.28962(11) 0.0344(7) Uani 1 1 d . . . . .
C7 C 1.0298(5) 0.72040(19) 0.46368(15) 0.0385(9) Uani 1 1 d . . . . .
H7 H 1.015133 0.741536 0.498794 0.046 Uiso 1 1 calc R U . . .
C8 C 1.1263(5) 0.75549(19) 0.42615(16) 0.0439(10) Uani 1 1 d . . . . .
H8 H 1.181580 0.799839 0.435226 0.053 Uiso 1 1 calc R U . . .
C9 C 1.1439(4) 0.72586(18) 0.37374(16) 0.0368(8) Uani 1 1 d . . . . .
H9 H 1.211571 0.749318 0.346675 0.044 Uiso 1 1 calc R U . . .
C10 C 1.0620(4) 0.66304(17) 0.36285(14) 0.0259(7) Uani 1 1 d . . . . .
H10 H 1.071005 0.643473 0.327031 0.031 Uiso 1 1 calc R U . . .
C11 C 0.5370(4) 0.53462(17) 0.32817(10) 0.0174(6) Uani 1 1 d . . . . .
C12 C 0.4784(4) 0.41192(18) 0.32330(13) 0.0258(7) Uani 1 1 d . . . . .
H12 H 0.512817 0.363328 0.330303 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3252(4) 0.42322(19) 0.29743(13) 0.0303(8) Uani 1 1 d . . . . .
H13 H 0.253232 0.383647 0.287672 0.036 Uiso 1 1 calc R U . . .
C14 C 0.2778(4) 0.49425(19) 0.28582(12) 0.0290(8) Uani 1 1 d . . . . .
H14 H 0.171332 0.503835 0.268276 0.035 Uiso 1 1 calc R U . . .
C15 C 0.3853(4) 0.55097(17) 0.29976(11) 0.0224(7) Uani 1 1 d . . . . .
H15 H 0.357308 0.599599 0.290397 0.027 Uiso 1 1 calc R U . . .
C16 C 0.6273(4) 0.65872(15) 0.34124(12) 0.0198(6) Uani 1 1 d . . . . .
C17 C 0.6011(5) 0.75456(19) 0.28286(14) 0.0433(10) Uani 1 1 d . . . . .
H17 H 0.594328 0.772331 0.246470 0.052 Uiso 1 1 calc R U . . .
C18 C 0.5896(4) 0.80460(19) 0.32477(15) 0.0353(9) Uani 1 1 d . . . . .
H18 H 0.579516 0.855084 0.317528 0.042 Uiso 1 1 calc R U . . .
C19 C 0.5933(4) 0.77837(17) 0.37746(14) 0.0299(8) Uani 1 1 d . . . . .
H19 H 0.582913 0.810467 0.407672 0.036 Uiso 1 1 calc R U . . .
C20 C 0.6124(4) 0.70464(16) 0.38568(12) 0.0212(7) Uani 1 1 d . . . . .
H20 H 0.615291 0.685554 0.421751 0.025 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 N4 1.980(2) . ?
Ge1 N1 2.016(2) . ?
Ge1 N3 2.018(2) . ?
N1 C5 1.354(4) . ?
N1 C1 1.368(4) . ?
C1 N2 1.345(4) . ?
C1 C2 1.423(4) . ?
C2 C3 1.352(5) . ?
C2 H2 0.9500 . ?
N2 C6 1.340(4) . ?
N3 C6 1.365(4) . ?
N3 C10 1.367(4) . ?
C3 C4 1.390(5) . ?
C3 H3 0.9500 . ?
N4 C11 1.375(4) . ?
N4 C16 1.407(4) . ?
C4 C5 1.356(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
N5 C12 1.334(4) . ?
N5 C11 1.349(4) . ?
C6 C7 1.416(5) . ?
N6 C17 1.340(4) . ?
N6 C16 1.340(4) . ?
C7 C8 1.351(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.400(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.348(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C15 1.404(4) . ?
C12 C13 1.366(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C20 1.382(4) . ?
C17 C18 1.382(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(4) . ?
C19 H19 0.9500 . ?
C20 H20 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 Ge1 N1 96.72(10) . . ?
N4 Ge1 N3 91.40(9) . . ?
N1 Ge1 N3 87.71(10) . . ?
C5 N1 C1 119.4(3) . . ?
C5 N1 Ge1 113.4(2) . . ?
C1 N1 Ge1 127.1(2) . . ?
N2 C1 N1 125.4(3) . . ?
N2 C1 C2 117.2(3) . . ?
N1 C1 C2 117.3(3) . . ?
C3 C2 C1 121.6(3) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C6 N2 C1 125.8(3) . . ?
C6 N3 C10 119.6(3) . . ?
C6 N3 Ge1 127.3(2) . . ?
C10 N3 Ge1 113.1(2) . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C11 N4 C16 120.4(2) . . ?
C11 N4 Ge1 109.41(19) . . ?
C16 N4 Ge1 127.6(2) . . ?
C5 C4 C3 117.3(3) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
N1 C5 C4 124.3(3) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C12 N5 C11 118.8(3) . . ?
N2 C6 N3 125.5(3) . . ?
N2 C6 C7 117.0(3) . . ?
N3 C6 C7 117.5(3) . . ?
C17 N6 C16 116.6(3) . . ?
C8 C7 C6 121.9(3) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C9 119.4(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 118.0(3) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 N3 123.6(3) . . ?
C9 C10 H10 118.2 . . ?
N3 C10 H10 118.2 . . ?
N5 C11 N4 112.2(2) . . ?
N5 C11 C15 121.4(3) . . ?
N4 C11 C15 126.3(3) . . ?
N5 C12 C13 123.5(3) . . ?
N5 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C12 C13 C14 118.1(3) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C11 118.0(3) . . ?
C14 C15 H15 121.0 . . ?
C11 C15 H15 121.0 . . ?
N6 C16 C20 122.3(3) . . ?
N6 C16 N4 118.1(3) . . ?
C20 C16 N4 119.6(3) . . ?
N6 C17 C18 125.0(3) . . ?
N6 C17 H17 117.5 . . ?
C18 C17 H17 117.5 . . ?
C19 C18 C17 117.3(3) . . ?
C19 C18 H18 121.3 . . ?
C17 C18 H18 121.3 . . ?
C18 C19 C20 118.9(3) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C19 C20 C16 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C16 C20 H20 120.1 . . ?

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.081

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

data_ld190513Ge1
_database_code_depnum_ccdc_archive 'CCDC 2032978'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2020-09-21 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Cl Ge N3'
_chemical_formula_weight         306.29

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'
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'

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

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

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

_cell_length_a                   7.9626(5)
_cell_length_b                   9.3447(5)
_cell_length_c                   17.4878(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.358(2)
_cell_angle_gamma                90
_cell_volume                     1295.55(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    33637
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.592
_exptl_crystal_size_mid          0.392
_exptl_crystal_size_min          0.382
_exptl_absorpt_coefficient_mu    2.551
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3951
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.530
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            33637
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.474
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2972
_reflns_number_gt                2561
_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 Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0136P)²+1.4804P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2972
_refine_ls_number_parameters     156
_refine_ls_number_restraints     135
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0633
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.067
_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 0.82089(3) 0.63505(3) 0.50200(2) 0.02309(8) Uani 1 1 d . U . . .
Cl1 Cl 0.91415(7) 0.79695(7) 0.41797(4) 0.03085(14) Uani 1 1 d . U . . .
N1 N 0.6368(2) 0.76927(19) 0.53517(10) 0.0197(4) Uani 1 1 d . U . . .
C1 C 0.5153(3) 0.7122(2) 0.48440(12) 0.0183(4) Uani 1 1 d . U . . .
N2 N 0.5963(2) 0.61217(19) 0.44393(11) 0.0214(4) Uani 1 1 d . U . . .
C2 C 0.6062(3) 0.8716(2) 0.58573(12) 0.0213(4) Uani 1 1 d . U . . .
C3 C 0.4433(3) 0.9229(2) 0.58584(13) 0.0238(5) Uani 1 1 d . U . . .
H3 H 0.4179 0.9962 0.6207 0.029 Uiso 1 1 calc R U . . .
N3 N 0.3671(2) 0.5435(2) 0.35836(11) 0.0275(4) Uani 1 1 d . U . . .
C4 C 0.3170(3) 0.8661(2) 0.53441(13) 0.0240(5) Uani 1 1 d . U . . .
H4 H 0.2053 0.9016 0.5347 0.029 Uiso 1 1 calc R U . . .
C5 C 0.3487(3) 0.7593(2) 0.48278(13) 0.0211(4) Uani 1 1 d . U . . .
H5 H 0.2617 0.7203 0.4481 0.025 Uiso 1 1 calc R U . . .
C7 C 0.5309(3) 0.5313(2) 0.38222(12) 0.0206(4) Uani 1 1 d . U . . .
C6 C 0.7526(3) 0.9245(3) 0.63747(14) 0.0305(5) Uani 1 1 d . U . . .
H6A H 0.8361 0.9674 0.6066 0.046 Uiso 1 1 calc R U . . .
H6B H 0.8040 0.8444 0.6673 0.046 Uiso 1 1 calc R U . . .
H6C H 0.7138 0.9966 0.6725 0.046 Uiso 1 1 calc R U . . .
C8 C 0.3048(3) 0.4626(3) 0.29827(14) 0.0317(5) Uani 1 1 d . U . . .
C9 C 0.4022(3) 0.3674(3) 0.26176(13) 0.0325(5) Uani 1 1 d . U . . .
H9 H 0.3541 0.3110 0.2201 0.039 Uiso 1 1 calc R U . . .
C10 C 0.5717(4) 0.3555(3) 0.28695(14) 0.0336(6) Uani 1 1 d . U . . .
H10 H 0.6413 0.2902 0.2628 0.040 Uiso 1 1 calc R U . . .
C11 C 0.6389(3) 0.4388(3) 0.34736(14) 0.0269(5) Uani 1 1 d . U . . .
H11 H 0.7554 0.4335 0.3648 0.032 Uiso 1 1 calc R U . . .
C12 C 0.1204(4) 0.4841(4) 0.27447(19) 0.0579(9) Uani 1 1 d . U . . .
H12A H 0.0928 0.4446 0.2229 0.087 Uiso 1 1 calc R U . . .
H12B H 0.0943 0.5866 0.2741 0.087 Uiso 1 1 calc R U . . .
H12C H 0.0536 0.4351 0.3109 0.087 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ge1 N2 1.9843(18) . ?
Ge1 N1 2.0536(18) . ?
Ge1 Cl1 2.2812(6) . ?
N1 C2 1.340(3) . ?
N1 C1 1.359(3) . ?
C1 N2 1.370(3) . ?
C1 C5 1.396(3) . ?
N2 C7 1.379(3) . ?
C2 C3 1.384(3) . ?
C2 C6 1.492(3) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
N3 C7 1.337(3) . ?
N3 C8 1.351(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C11 1.398(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 C9 1.376(4) . ?
C8 C12 1.502(4) . ?
C9 C10 1.385(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ge1 N1 64.99(7) . . ?
N2 Ge1 Cl1 94.24(6) . . ?
N1 Ge1 Cl1 93.48(5) . . ?
C2 N1 C1 123.29(19) . . ?
C2 N1 Ge1 143.19(15) . . ?
C1 N1 Ge1 93.39(13) . . ?
N1 C1 N2 105.34(18) . . ?
N1 C1 C5 120.4(2) . . ?
N2 C1 C5 134.2(2) . . ?
C1 N2 C7 128.10(19) . . ?
C1 N2 Ge1 96.16(13) . . ?
C7 N2 Ge1 135.71(15) . . ?
N1 C2 C3 118.4(2) . . ?
N1 C2 C6 117.2(2) . . ?
C3 C2 C6 124.3(2) . . ?
C2 C3 C4 119.2(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C7 N3 C8 118.2(2) . . ?
C5 C4 C3 122.2(2) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C1 116.4(2) . . ?
C4 C5 H5 121.8 . . ?
C1 C5 H5 121.8 . . ?
N3 C7 N2 118.9(2) . . ?
N3 C7 C11 122.6(2) . . ?
N2 C7 C11 118.5(2) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C8 C9 122.7(2) . . ?
N3 C8 C12 114.8(2) . . ?
C9 C8 C12 122.5(2) . . ?
C8 C9 C10 118.6(2) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C7 118.2(2) . . ?
C10 C11 H11 120.9 . . ?
C7 C11 H11 120.9 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.068

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

data_ld200204Bi1
_database_code_depnum_ccdc_archive 'CCDC 2032981'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2020-09-21 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 N6 Sn'
_chemical_formula_weight         515.18

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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.4993(5)
_cell_length_b                   21.1590(8)
_cell_length_c                   9.1723(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.591(2)
_cell_angle_gamma                90
_cell_volume                     2229.46(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    51074
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.594
_exptl_crystal_size_mid          0.339
_exptl_crystal_size_min          0.278
_exptl_absorpt_coefficient_mu    1.170
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5601
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.751
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            51074
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.617
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5118
_reflns_number_gt                4672
_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 Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0219P)²+1.4615P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5118
_refine_ls_number_parameters     284
_refine_ls_number_restraints     264
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0541
_refine_ls_wR_factor_gt          0.0519
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.82738(2) 0.40295(2) 0.58664(2) 0.02154(5) Uani 1 1 d . U . . .
N1 N 0.84643(13) 0.47862(7) 0.41989(16) 0.0202(3) Uani 1 1 d . U . . .
C1 C 0.87226(15) 0.44199(8) 0.3034(2) 0.0205(3) Uani 1 1 d . U . . .
C2 C 0.89380(16) 0.33394(8) 0.2487(2) 0.0251(4) Uani 1 1 d . U . . .
N2 N 0.86190(13) 0.37982(7) 0.33975(17) 0.0213(3) Uani 1 1 d . U . . .
N3 N 0.83260(13) 0.57594(7) 0.29415(17) 0.0206(3) Uani 1 1 d . U . . .
C3 C 0.93699(19) 0.34849(9) 0.1146(2) 0.0320(4) Uani 1 1 d . U . . .
H3 H 0.9617 0.3160 0.0516 0.038 Uiso 1 1 calc R U . . .
N4 N 0.64528(13) 0.38622(7) 0.52966(18) 0.0240(3) Uani 1 1 d . U . . .
C4 C 0.9435(2) 0.41154(10) 0.0735(2) 0.0335(5) Uani 1 1 d . U . . .
H4 H 0.9708 0.4221 -0.0196 0.040 Uiso 1 1 calc R U . . .
N5 N 0.66951(13) 0.46534(7) 0.68895(16) 0.0208(3) Uani 1 1 d . U . . .
C5 C 0.91108(18) 0.45894(9) 0.1659(2) 0.0275(4) Uani 1 1 d . U . . .
H5 H 0.9149 0.5020 0.1374 0.033 Uiso 1 1 calc R U . . .
C6 C 0.8786(2) 0.26707(9) 0.2963(3) 0.0399(5) Uani 1 1 d . U . . .
H6A H 0.8099 0.2489 0.2450 0.060 Uiso 1 1 calc R U . . .
H6B H 0.8683 0.2659 0.4018 0.060 Uiso 1 1 calc R U . . .
H6C H 0.9477 0.2425 0.2735 0.060 Uiso 1 1 calc R U . . .
N6 N 0.63894(14) 0.27861(7) 0.48596(18) 0.0262(3) Uani 1 1 d . U . . .
C7 C 0.84480(14) 0.54398(8) 0.4204(2) 0.0200(3) Uani 1 1 d . U . . .
C9 C 0.83042(19) 0.67306(9) 0.4289(2) 0.0318(4) Uani 1 1 d . U . . .
H9 H 0.8239 0.7178 0.4287 0.038 Uiso 1 1 calc R U . . .
C8 C 0.82599(16) 0.63945(8) 0.2997(2) 0.0246(4) Uani 1 1 d . U . . .
C10 C 0.84469(19) 0.63983(10) 0.5592(2) 0.0324(4) Uani 1 1 d . U . . .
H10 H 0.8490 0.6617 0.6497 0.039 Uiso 1 1 calc R U . . .
C11 C 0.85255(17) 0.57497(9) 0.5560(2) 0.0260(4) Uani 1 1 d . U . . .
H11 H 0.8630 0.5515 0.6439 0.031 Uiso 1 1 calc R U . . .
C12 C 0.8110(2) 0.67209(9) 0.1546(2) 0.0354(5) Uani 1 1 d . U . . .
H12A H 0.8728 0.6587 0.0914 0.053 Uiso 1 1 calc R U . . .
H12B H 0.8152 0.7179 0.1690 0.053 Uiso 1 1 calc R U . . .
H12C H 0.7351 0.6609 0.1089 0.053 Uiso 1 1 calc R U . . .
C13 C 0.59002(16) 0.42840(8) 0.61444(19) 0.0210(3) Uani 1 1 d . U . . .
C14 C 0.63492(17) 0.50564(8) 0.79184(19) 0.0232(4) Uani 1 1 d . U . . .
C15 C 0.51853(17) 0.51337(9) 0.8182(2) 0.0276(4) Uani 1 1 d . U . . .
H15 H 0.4950 0.5425 0.8900 0.033 Uiso 1 1 calc R U . . .
C16 C 0.43630(17) 0.47794(9) 0.7382(2) 0.0282(4) Uani 1 1 d . U . . .
H16 H 0.3559 0.4837 0.7537 0.034 Uiso 1 1 calc R U . . .
C17 C 0.47036(16) 0.43452(9) 0.6367(2) 0.0258(4) Uani 1 1 d . U . . .
H17 H 0.4147 0.4095 0.5833 0.031 Uiso 1 1 calc R U . . .
C18 C 0.7273(2) 0.54145(10) 0.8785(2) 0.0346(5) Uani 1 1 d . U . . .
H18A H 0.8016 0.5190 0.8747 0.052 Uiso 1 1 calc R U . . .
H18B H 0.7052 0.5449 0.9801 0.052 Uiso 1 1 calc R U . . .
H18C H 0.7353 0.5839 0.8371 0.052 Uiso 1 1 calc R U . . .
C19 C 0.59007(16) 0.33516(8) 0.4586(2) 0.0235(4) Uani 1 1 d . U . . .
C20 C 0.59088(18) 0.22739(9) 0.4199(2) 0.0299(4) Uani 1 1 d . U . . .
C21 C 0.4941(2) 0.23157(11) 0.3240(3) 0.0382(5) Uani 1 1 d . U . . .
H21 H 0.4619 0.1947 0.2789 0.046 Uiso 1 1 calc R U . . .
C22 C 0.4461(2) 0.28980(12) 0.2958(3) 0.0416(5) Uani 1 1 d . U . . .
H22 H 0.3806 0.2936 0.2294 0.050 Uiso 1 1 calc R U . . .
C23 C 0.49255(19) 0.34301(10) 0.3637(2) 0.0338(4) Uani 1 1 d . U . . .
H23 H 0.4593 0.3836 0.3464 0.041 Uiso 1 1 calc R U . . .
C24 C 0.6462(2) 0.16486(10) 0.4576(3) 0.0450(6) Uani 1 1 d . U . . .
H24A H 0.5976 0.1306 0.4165 0.068 Uiso 1 1 calc R U . . .
H24B H 0.6538 0.1603 0.5639 0.068 Uiso 1 1 calc R U . . .
H24C H 0.7235 0.1628 0.4170 0.068 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 2.1643(16) . ?
Sn1 N1 2.2319(14) . ?
Sn1 N2 2.3678(15) . ?
Sn1 N5 2.4643(15) . ?
N1 C1 1.364(2) . ?
N1 C7 1.383(2) . ?
C1 N2 1.364(2) . ?
C1 C5 1.403(3) . ?
C2 N2 1.342(2) . ?
C2 C3 1.382(3) . ?
C2 C6 1.493(3) . ?
N3 C7 1.343(2) . ?
N3 C8 1.347(2) . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
N4 C13 1.360(2) . ?
N4 C19 1.399(2) . ?
C4 C5 1.376(3) . ?
C4 H4 0.9500 . ?
N5 C14 1.345(2) . ?
N5 C13 1.363(2) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
N6 C19 1.341(2) . ?
N6 C20 1.348(2) . ?
C7 C11 1.405(3) . ?
C9 C8 1.381(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C8 C12 1.502(3) . ?
C10 C11 1.376(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C17 1.406(3) . ?
C14 C15 1.381(3) . ?
C14 C18 1.502(3) . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C23 1.398(3) . ?
C20 C21 1.390(3) . ?
C20 C24 1.502(3) . ?
C21 C22 1.370(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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 N1 94.34(6) . . ?
N4 Sn1 N2 86.41(6) . . ?
N1 Sn1 N2 57.79(5) . . ?
N4 Sn1 N5 57.20(5) . . ?
N1 Sn1 N5 88.48(5) . . ?
N2 Sn1 N5 129.28(5) . . ?
C1 N1 C7 125.08(15) . . ?
C1 N1 Sn1 99.26(10) . . ?
C7 N1 Sn1 135.48(12) . . ?
N1 C1 N2 109.40(15) . . ?
N1 C1 C5 130.42(16) . . ?
N2 C1 C5 120.08(16) . . ?
N2 C2 C3 120.79(17) . . ?
N2 C2 C6 117.67(17) . . ?
C3 C2 C6 121.53(18) . . ?
C2 N2 C1 121.07(15) . . ?
C2 N2 Sn1 143.78(12) . . ?
C1 N2 Sn1 93.14(11) . . ?
C7 N3 C8 118.24(16) . . ?
C2 C3 C4 118.76(18) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C13 N4 C19 123.99(16) . . ?
C13 N4 Sn1 103.10(11) . . ?
C19 N4 Sn1 130.73(12) . . ?
C5 C4 C3 120.92(19) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C14 N5 C13 120.17(16) . . ?
C14 N5 Sn1 148.53(13) . . ?
C13 N5 Sn1 89.47(10) . . ?
C4 C5 C1 118.26(17) . . ?
C4 C5 H5 120.9 . . ?
C1 C5 H5 120.9 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C19 N6 C20 118.28(17) . . ?
N3 C7 N1 120.07(16) . . ?
N3 C7 C11 121.88(16) . . ?
N1 C7 C11 118.01(16) . . ?
C8 C9 C10 118.39(18) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
N3 C8 C9 123.13(18) . . ?
N3 C8 C12 115.42(17) . . ?
C9 C8 C12 121.44(17) . . ?
C11 C10 C9 119.45(18) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C7 118.88(18) . . ?
C10 C11 H11 120.6 . . ?
C7 C11 H11 120.6 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 N5 110.06(16) . . ?
N4 C13 C17 128.98(17) . . ?
N5 C13 C17 120.86(16) . . ?
N5 C14 C15 121.17(17) . . ?
N5 C14 C18 117.81(17) . . ?
C15 C14 C18 121.02(17) . . ?
C14 C15 C16 119.05(17) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 120.61(18) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C13 118.01(18) . . ?
C16 C17 H17 121.0 . . ?
C13 C17 H17 121.0 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N6 C19 C23 122.68(17) . . ?
N6 C19 N4 115.12(17) . . ?
C23 C19 N4 122.19(17) . . ?
N6 C20 C21 122.25(19) . . ?
N6 C20 C24 116.36(19) . . ?
C21 C20 C24 121.38(19) . . ?
C22 C21 C20 118.77(19) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C19 117.8(2) . . ?
C22 C23 H23 121.1 . . ?
C19 C23 H23 121.1 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_ld191121Pb1
_database_code_depnum_ccdc_archive 'CCDC 2032980'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2020-09-21 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H36 Li N9 Pb'
_chemical_formula_weight         808.87

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'
Li Li -0.0003 0.0001 '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'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   19.4667(12)
_cell_length_b                   19.4667(12)
_cell_length_c                   15.6860(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5147.9(7)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    20507
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             2400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.184
_exptl_absorpt_coefficient_mu    4.955
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3371
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.452
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            20507
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_av_R_equivalents  0.0968
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.743
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2619
_reflns_number_gt                2295
_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 Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2619
_refine_ls_number_parameters     144
_refine_ls_number_restraints     153
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.6667 0.3333 0.71537(2) 0.01876(10) Uani 1 3 d S TU P . .
N1 N 0.7276(2) 0.44427(19) 0.6185(2) 0.0190(7) Uani 1 1 d . U . . .
C1 C 0.6899(2) 0.4748(2) 0.5700(3) 0.0199(8) Uani 1 1 d . U . . .
Li1 Li 0.6667 0.3333 0.5212(8) 0.021(2) Uani 1 3 d S TU P . .
C2 C 0.5955(3) 0.4441(3) 0.4632(3) 0.0257(9) Uani 1 1 d . U . . .
N2 N 0.6441(2) 0.4257(2) 0.5073(2) 0.0204(7) Uani 1 1 d . U . . .
N3 N 0.8249(2) 0.4517(2) 0.7051(2) 0.0225(7) Uani 1 1 d . U . . .
C3 C 0.5949(3) 0.5135(3) 0.4771(3) 0.0345(11) Uani 1 1 d . U . . .
H3 H 0.5606 0.5252 0.4452 0.041 Uiso 1 1 calc R U . . .
C4 C 0.6451(3) 0.5662(3) 0.5382(3) 0.0367(11) Uani 1 1 d . U . . .
H4 H 0.6466 0.6152 0.5474 0.044 Uiso 1 1 calc R U . . .
C5 C 0.6927(3) 0.5470(3) 0.5855(3) 0.0297(10) Uani 1 1 d . U . . .
H5 H 0.7269 0.5822 0.6281 0.036 Uiso 1 1 calc R U . . .
C7 C 0.8040(2) 0.4887(2) 0.6462(3) 0.0193(8) Uani 1 1 d . U . . .
C6 C 0.5414(3) 0.3831(3) 0.3996(3) 0.0369(12) Uani 1 1 d . U . . .
H6A H 0.5102 0.4027 0.3699 0.055 Uiso 1 1 calc R U . . .
H6B H 0.5055 0.3336 0.4293 0.055 Uiso 1 1 calc R U . . .
H6C H 0.5731 0.3733 0.3581 0.055 Uiso 1 1 calc R U . . .
C8 C 0.8983(3) 0.4852(3) 0.7349(3) 0.0267(9) Uani 1 1 d . U . . .
C9 C 0.9566(3) 0.5595(3) 0.7087(3) 0.0322(10) Uani 1 1 d . U . . .
H9 H 1.0087 0.5833 0.7315 0.039 Uiso 1 1 calc R U . . .
C10 C 0.9364(3) 0.5985(3) 0.6480(3) 0.0308(10) Uani 1 1 d . U . . .
H10 H 0.9756 0.6495 0.6287 0.037 Uiso 1 1 calc R U . . .
C11 C 0.8610(3) 0.5646(3) 0.6154(3) 0.0266(9) Uani 1 1 d . U . . .
H11 H 0.8475 0.5911 0.5735 0.032 Uiso 1 1 calc R U . . .
C12 C 0.9148(3) 0.4382(3) 0.7990(4) 0.0444(14) Uani 1 1 d . U . . .
H12A H 0.8966 0.3848 0.7767 0.067 Uiso 1 1 calc R U . . .
H12B H 0.8868 0.4345 0.8522 0.067 Uiso 1 1 calc R U . . .
H12C H 0.9720 0.4646 0.8101 0.067 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
Pb1 N1 2.412(3) . ?
Pb1 N1 2.412(3) 3_665 ?
Pb1 N1 2.412(3) 2_655 ?
Pb1 N3 2.779(4) . ?
Pb1 N3 2.779(3) 3_665 ?
Pb1 N3 2.779(3) 2_655 ?
Pb1 Li1 3.045(13) . ?
N1 C7 1.365(5) . ?
N1 C1 1.381(5) . ?
N1 Li1 2.416(9) . ?
C1 N2 1.350(5) . ?
C1 C5 1.401(6) . ?
C1 Li1 2.670(5) . ?
Li1 N2 2.065(4) 3_665 ?
Li1 N2 2.065(4) 2_655 ?
Li1 N2 2.065(4) . ?
Li1 N1 2.416(9) 3_665 ?
Li1 N1 2.416(9) 2_655 ?
Li1 C1 2.670(5) 3_665 ?
Li1 C1 2.670(5) 2_655 ?
C2 N2 1.356(5) . ?
C2 C3 1.374(7) . ?
C2 C6 1.506(7) . ?
N3 C8 1.325(5) . ?
N3 C7 1.352(5) . ?
C3 C4 1.387(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(7) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C11 1.417(6) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 C9 1.382(7) . ?
C8 C12 1.499(7) . ?
C9 C10 1.390(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.372(7) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Pb1 N1 84.55(12) . 3_665 ?
N1 Pb1 N1 84.55(12) . 2_655 ?
N1 Pb1 N1 84.55(12) 3_665 2_655 ?
N1 Pb1 N3 51.38(11) . . ?
N1 Pb1 N3 79.57(11) 3_665 . ?
N1 Pb1 N3 134.06(11) 2_655 . ?
N1 Pb1 N3 134.06(11) . 3_665 ?
N1 Pb1 N3 51.38(11) 3_665 3_665 ?
N1 Pb1 N3 79.57(11) 2_655 3_665 ?
N3 Pb1 N3 119.665(16) . 3_665 ?
N1 Pb1 N3 79.56(11) . 2_655 ?
N1 Pb1 N3 134.06(11) 3_665 2_655 ?
N1 Pb1 N3 51.38(11) 2_655 2_655 ?
N3 Pb1 N3 119.664(16) . 2_655 ?
N3 Pb1 N3 119.665(16) 3_665 2_655 ?
N1 Pb1 Li1 50.96(8) . . ?
N1 Pb1 Li1 50.96(8) 3_665 . ?
N1 Pb1 Li1 50.96(8) 2_655 . ?
N3 Pb1 Li1 86.66(8) . . ?
N3 Pb1 Li1 86.67(8) 3_665 . ?
N3 Pb1 Li1 86.67(8) 2_655 . ?
C7 N1 C1 123.2(3) . . ?
C7 N1 Pb1 105.0(2) . . ?
C1 N1 Pb1 127.2(3) . . ?
C7 N1 Li1 131.3(3) . . ?
C1 N1 Li1 84.7(3) . . ?
Pb1 N1 Li1 78.2(3) . . ?
N2 C1 N1 113.7(4) . . ?
N2 C1 C5 121.2(4) . . ?
N1 C1 C5 125.0(4) . . ?
N2 C1 Li1 49.4(3) . . ?
N1 C1 Li1 64.3(3) . . ?
C5 C1 Li1 170.6(4) . . ?
N2 Li1 N2 118.90(13) 3_665 2_655 ?
N2 Li1 N2 118.90(13) 3_665 . ?
N2 Li1 N2 118.90(13) 2_655 . ?
N2 Li1 N1 60.76(18) 3_665 3_665 ?
N2 Li1 N1 83.2(2) 2_655 3_665 ?
N2 Li1 N1 143.8(5) . 3_665 ?
N2 Li1 N1 143.8(5) 3_665 2_655 ?
N2 Li1 N1 60.76(18) 2_655 2_655 ?
N2 Li1 N1 83.2(2) . 2_655 ?
N1 Li1 N1 84.3(4) 3_665 2_655 ?
N2 Li1 N1 83.2(2) 3_665 . ?
N2 Li1 N1 143.8(5) 2_655 . ?
N2 Li1 N1 60.76(18) . . ?
N1 Li1 N1 84.3(4) 3_665 . ?
N1 Li1 N1 84.3(4) 2_655 . ?
N2 Li1 C1 29.79(15) 3_665 3_665 ?
N2 Li1 C1 101.75(15) 2_655 3_665 ?
N2 Li1 C1 139.0(2) . 3_665 ?
N1 Li1 C1 31.00(13) 3_665 3_665 ?
N1 Li1 C1 115.0(4) 2_655 3_665 ?
N1 Li1 C1 83.8(3) . 3_665 ?
N2 Li1 C1 139.0(2) 3_665 2_655 ?
N2 Li1 C1 29.79(15) 2_655 2_655 ?
N2 Li1 C1 101.75(15) . 2_655 ?
N1 Li1 C1 83.8(3) 3_665 2_655 ?
N1 Li1 C1 31.00(13) 2_655 2_655 ?
N1 Li1 C1 115.0(4) . 2_655 ?
C1 Li1 C1 112.1(2) 3_665 2_655 ?
N2 Li1 C1 101.75(15) 3_665 . ?
N2 Li1 C1 139.0(2) 2_655 . ?
N2 Li1 C1 29.79(15) . . ?
N1 Li1 C1 115.0(4) 3_665 . ?
N1 Li1 C1 83.8(3) 2_655 . ?
N1 Li1 C1 31.00(13) . . ?
C1 Li1 C1 112.1(2) 3_665 . ?
C1 Li1 C1 112.1(2) 2_655 . ?
N2 Li1 Pb1 96.1(4) 3_665 . ?
N2 Li1 Pb1 96.1(4) 2_655 . ?
N2 Li1 Pb1 96.1(4) . . ?
N1 Li1 Pb1 50.8(2) 3_665 . ?
N1 Li1 Pb1 50.8(2) 2_655 . ?
N1 Li1 Pb1 50.8(2) . . ?
C1 Li1 Pb1 73.4(3) 3_665 . ?
C1 Li1 Pb1 73.4(3) 2_655 . ?
C1 Li1 Pb1 73.4(3) . . ?
N2 C2 C3 121.9(4) . . ?
N2 C2 C6 115.8(4) . . ?
C3 C2 C6 122.2(4) . . ?
C1 N2 C2 119.0(4) . . ?
C1 N2 Li1 100.8(4) . . ?
C2 N2 Li1 139.8(4) . . ?
C8 N3 C7 121.2(4) . . ?
C8 N3 Pb1 149.6(3) . . ?
C7 N3 Pb1 88.7(2) . . ?
C2 C3 C4 119.2(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.5(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C1 119.0(5) . . ?
C4 C5 H5 120.5 . . ?
C1 C5 H5 120.5 . . ?
N3 C7 N1 113.7(4) . . ?
N3 C7 C11 120.0(4) . . ?
N1 C7 C11 126.1(4) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C8 C9 121.9(4) . . ?
N3 C8 C12 116.5(4) . . ?
C9 C8 C12 121.6(4) . . ?
C8 C9 C10 117.8(4) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
C11 C10 C9 121.2(4) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C7 117.8(4) . . ?
C10 C11 H11 121.1 . . ?
C7 C11 H11 121.1 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         1.899
_refine_diff_density_min         -1.527
_refine_diff_density_rms         0.148

####################################################################### 
# 
# 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_ld191111Ge1
_database_code_depnum_ccdc_archive 'CCDC 2032979'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2020-09-21 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H36 Ge Li N9'
_chemical_formula_weight         674.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li -0.0003 0.0001 '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'

_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c :H'
_space_group_name_Hall           'R 3 -2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   12.0113(9)
_cell_length_b                   12.0113(9)
_cell_length_c                   41.778(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5219.9(9)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    16052
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             2100
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.593
_exptl_crystal_size_mid          0.588
_exptl_crystal_size_min          0.478
_exptl_absorpt_coefficient_mu    0.919
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6142
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.824
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            16052
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         2.764
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2666
_reflns_number_gt                2430
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.997

_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 Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.033(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2666
_refine_ls_number_parameters     145
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0681
_refine_ls_wR_factor_gt          0.0659
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.001

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 0.666667 0.333333 0.54009(2) 0.01893(13) Uani 1 3 d S T P . .
C1 C 0.6459(2) 0.5243(2) 0.49385(6) 0.0225(5) Uani 1 1 d . . . . .
N1 N 0.7252(2) 0.4938(2) 0.51195(5) 0.0212(5) Uani 1 1 d . . . . .
Li1 Li 0.666667 0.333333 0.4683(2) 0.0283(17) Uani 1 3 d S T P . .
N2 N 0.5956(2) 0.4546(2) 0.46723(5) 0.0245(5) Uani 1 1 d . . . . .
C2 C 0.5104(3) 0.4714(3) 0.45006(8) 0.0296(7) Uani 1 1 d . . . . .
C3 C 0.4772(3) 0.5622(4) 0.45808(10) 0.0372(8) Uani 1 1 d . . . . .
H3 H 0.418214 0.573639 0.445311 0.045 Uiso 1 1 calc R U . . .
N3 N 0.9025(2) 0.5545(2) 0.54312(5) 0.0264(5) Uani 1 1 d . . . . .
C4 C 0.5317(3) 0.6368(3) 0.48521(7) 0.0380(7) Uani 1 1 d . . . . .
H4 H 0.510751 0.700435 0.491220 0.046 Uiso 1 1 calc R U . . .
C5 C 0.6159(3) 0.6175(3) 0.50320(7) 0.0320(6) Uani 1 1 d . . . . .
H5 H 0.653627 0.667346 0.521897 0.038 Uiso 1 1 calc R U . . .
C7 C 0.8464(2) 0.5898(2) 0.52034(6) 0.0236(5) Uani 1 1 d . . . . .
C8 C 1.0213(3) 0.6385(3) 0.55303(7) 0.0341(7) Uani 1 1 d . . . . .
C9 C 1.0897(3) 0.7614(3) 0.54042(9) 0.0446(7) Uani 1 1 d . . . . .
H9 H 1.173604 0.820068 0.547996 0.054 Uiso 1 1 calc R U . . .
C10 C 1.0343(3) 0.7972(3) 0.51680(8) 0.0463(8) Uani 1 1 d . . . . .
H10 H 1.080413 0.880754 0.507682 0.056 Uiso 1 1 calc R U . . .
C11 C 0.9120(3) 0.7122(3) 0.50636(7) 0.0345(7) Uani 1 1 d . . . . .
H11 H 0.872811 0.735822 0.490024 0.041 Uiso 1 1 calc R U . . .
C12 C 1.0780(3) 0.5915(4) 0.57820(9) 0.0493(9) Uani 1 1 d . . . . .
H12A H 1.008543 0.522117 0.590535 0.074 Uiso 1 1 calc R U . . .
H12B H 1.132736 0.662528 0.592581 0.074 Uiso 1 1 calc R U . . .
H12C H 1.129528 0.559221 0.567849 0.074 Uiso 1 1 calc R U . . .
C6 C 0.4562(4) 0.3866(3) 0.42135(8) 0.0456(8) Uani 1 1 d . . . . .
H6A H 0.392646 0.403233 0.411016 0.068 Uiso 1 1 calc R U . . .
H6B H 0.414682 0.296346 0.427990 0.068 Uiso 1 1 calc R U . . .
H6C H 0.525552 0.404683 0.406220 0.068 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 N1 2.058(2) 3_665 ?
Ge1 N1 2.058(2) 2_655 ?
Ge1 N1 2.058(2) . ?
Ge1 Li1 2.999(9) . ?
C1 N2 1.341(3) . ?
C1 C5 1.392(4) . ?
C1 N1 1.401(3) . ?
C1 Li1 2.652(4) . ?
N1 C7 1.376(3) . ?
N1 Li1 2.485(7) . ?
Li1 N2 2.024(2) . ?
Li1 N2 2.024(2) 3_665 ?
Li1 N2 2.024(3) 2_655 ?
N2 C2 1.344(4) . ?
C2 C3 1.378(6) . ?
C2 C6 1.496(5) . ?
C3 C4 1.389(5) . ?
C3 H3 0.9500 . ?
N3 C8 1.336(4) . ?
N3 C7 1.351(4) . ?
C4 C5 1.370(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C11 1.402(4) . ?
C8 C9 1.385(5) . ?
C8 C12 1.508(5) . ?
C9 C10 1.374(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ge1 N1 90.59(9) 3_665 2_655 ?
N1 Ge1 N1 90.59(9) 3_665 . ?
N1 Ge1 N1 90.59(9) 2_655 . ?
N1 Ge1 Li1 55.16(6) 3_665 . ?
N1 Ge1 Li1 55.16(6) 2_655 . ?
N1 Ge1 Li1 55.15(6) . . ?
N2 C1 C5 121.2(2) . . ?
N2 C1 N1 115.9(2) . . ?
C5 C1 N1 122.8(2) . . ?
N2 C1 Li1 48.2(2) . . ?
C5 C1 Li1 169.2(2) . . ?
N1 C1 Li1 67.7(2) . . ?
C7 N1 C1 119.4(2) . . ?
C7 N1 Ge1 111.22(17) . . ?
C1 N1 Ge1 126.50(17) . . ?
C7 N1 Li1 127.39(17) . . ?
C1 N1 Li1 80.87(17) . . ?
Ge1 N1 Li1 82.02(16) . . ?
N2 Li1 N2 119.95(2) . 3_665 ?
N2 Li1 N2 119.95(2) . 2_655 ?
N2 Li1 N2 119.95(2) 3_665 2_655 ?
N2 Li1 N1 61.06(15) . . ?
N2 Li1 N1 82.45(19) 3_665 . ?
N2 Li1 N1 131.7(4) 2_655 . ?
N2 Li1 N1 131.7(4) . 3_665 ?
N2 Li1 N1 61.06(15) 3_665 3_665 ?
N2 Li1 N1 82.45(19) 2_655 3_665 ?
N1 Li1 N1 72.1(2) . 3_665 ?
N2 Li1 N1 82.45(19) . 2_655 ?
N2 Li1 N1 131.7(4) 3_665 2_655 ?
N2 Li1 N1 61.06(15) 2_655 2_655 ?
N1 Li1 N1 72.1(2) . 2_655 ?
N1 Li1 N1 72.1(2) 3_665 2_655 ?
N2 Li1 C1 132.2(2) . 3_665 ?
N2 Li1 C1 29.62(11) 3_665 3_665 ?
N2 Li1 C1 103.02(15) 2_655 3_665 ?
N1 Li1 C1 75.28(19) . 3_665 ?
N1 Li1 C1 31.44(10) 3_665 3_665 ?
N1 Li1 C1 102.8(3) 2_655 3_665 ?
N2 Li1 C1 29.62(11) . . ?
N2 Li1 C1 103.02(15) 3_665 . ?
N2 Li1 C1 132.2(2) 2_655 . ?
N1 Li1 C1 31.44(9) . . ?
N1 Li1 C1 102.8(3) 3_665 . ?
N1 Li1 C1 75.28(19) 2_655 . ?
C1 Li1 C1 104.9(2) 3_665 . ?
N2 Li1 C1 103.02(15) . 2_655 ?
N2 Li1 C1 132.2(2) 3_665 2_655 ?
N2 Li1 C1 29.62(11) 2_655 2_655 ?
N1 Li1 C1 102.8(3) . 2_655 ?
N1 Li1 C1 75.28(19) 3_665 2_655 ?
N1 Li1 C1 31.44(9) 2_655 2_655 ?
C1 Li1 C1 104.9(2) 3_665 2_655 ?
C1 Li1 C1 104.9(2) . 2_655 ?
N2 Li1 Ge1 91.3(3) . . ?
N2 Li1 Ge1 91.3(3) 3_665 . ?
N2 Li1 Ge1 91.3(3) 2_655 . ?
N1 Li1 Ge1 42.82(15) . . ?
N1 Li1 Ge1 42.82(15) 3_665 . ?
N1 Li1 Ge1 42.82(15) 2_655 . ?
C1 Li1 Ge1 66.28(19) 3_665 . ?
C1 Li1 Ge1 66.29(19) . . ?
C1 Li1 Ge1 66.28(19) 2_655 . ?
C1 N2 C2 119.2(3) . . ?
C1 N2 Li1 102.1(3) . . ?
C2 N2 Li1 138.3(3) . . ?
N2 C2 C3 122.2(3) . . ?
N2 C2 C6 115.5(3) . . ?
C3 C2 C6 122.3(3) . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C8 N3 C7 119.5(2) . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C1 119.5(3) . . ?
C4 C5 H5 120.3 . . ?
C1 C5 H5 120.3 . . ?
N3 C7 N1 113.7(2) . . ?
N3 C7 C11 121.0(2) . . ?
N1 C7 C11 125.3(3) . . ?
N3 C8 C9 121.8(3) . . ?
N3 C8 C12 116.4(3) . . ?
C9 C8 C12 121.8(3) . . ?
C10 C9 C8 119.0(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C7 118.6(3) . . ?
C10 C11 H11 120.7 . . ?
C7 C11 H11 120.7 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_ld190415Sn1
_database_code_depnum_ccdc_archive 'CCDC 2032976'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2020-09-21 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H36 Li N9 Sn'
_chemical_formula_weight         720.37

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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c :H'
_space_group_name_Hall           'R 3 -2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   12.1232(12)
_cell_length_b                   12.1232(12)
_cell_length_c                   41.793(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5319.4(12)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12733
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             2208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.598
_exptl_crystal_size_mid          0.514
_exptl_crystal_size_min          0.420
_exptl_absorpt_coefficient_mu    0.759
_shelx_estimated_absorpt_T_min   0.660
_shelx_estimated_absorpt_T_max   0.741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5631
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.755
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            12733
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_theta_min         2.171
_diffrn_reflns_theta_max         31.572
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3500
_reflns_number_gt                2737
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_max     0.928
_reflns_Friedel_fraction_full    0.999

_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 Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+1.3198P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.10(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3500
_refine_ls_number_parameters     145
_refine_ls_number_restraints     127
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.003
_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 0.666667 0.333333 0.45393(4) 0.01880(14) Uani 1 3 d S T P . .
N1 N 0.6105(4) 0.4430(4) 0.48753(10) 0.0221(9) Uani 1 1 d . . . . .
C1 C 0.6881(4) 0.5488(4) 0.50594(11) 0.0227(9) Uani 1 1 d . . . . .
Li1 Li 0.666667 0.333333 0.3790(5) 0.034(4) Uani 1 3 d S T P . .
N2 N 0.7387(5) 0.5259(5) 0.53191(10) 0.0246(9) Uani 1 1 d . . . . .
C2 C 0.8255(5) 0.6246(7) 0.54949(16) 0.0331(12) Uani 1 1 d . . . . .
C3 C 0.8588(7) 0.7488(8) 0.5418(2) 0.0429(16) Uani 1 1 d . . . . .
H3 H 0.918324 0.817564 0.554638 0.051 Uiso 1 1 calc R U . . .
N3 N 0.4329(4) 0.3232(5) 0.45705(10) 0.0265(9) Uani 1 1 d . . . . .
C4 C 0.8047(6) 0.7720(5) 0.51529(14) 0.0436(15) Uani 1 1 d . . . . .
H4 H 0.826909 0.856691 0.509770 0.052 Uiso 1 1 calc R U . . .
C5 C 0.7194(6) 0.6721(5) 0.49729(13) 0.0337(12) Uani 1 1 d . . . . .
H5 H 0.681590 0.686180 0.479002 0.040 Uiso 1 1 calc R U . . .
C6 C 0.8780(7) 0.5931(7) 0.57760(14) 0.0502(16) Uani 1 1 d . . . . .
H6A H 0.913294 0.539514 0.570944 0.075 Uiso 1 1 calc R U . . .
H6B H 0.810190 0.547127 0.593324 0.075 Uiso 1 1 calc R U . . .
H6C H 0.945504 0.671801 0.587223 0.075 Uiso 1 1 calc R U . . .
C7 C 0.4880(5) 0.4153(5) 0.47967(12) 0.0242(9) Uani 1 1 d . . . . .
C9 C 0.2450(6) 0.3384(8) 0.45985(16) 0.0494(16) Uani 1 1 d . . . . .
H9 H 0.160891 0.310723 0.452583 0.059 Uiso 1 1 calc R U . . .
C8 C 0.3151(5) 0.2869(6) 0.44719(12) 0.0358(13) Uani 1 1 d . . . . .
C10 C 0.2996(6) 0.4300(7) 0.48307(17) 0.0514(16) Uani 1 1 d . . . . .
H10 H 0.253055 0.466780 0.491830 0.062 Uiso 1 1 calc R U . . .
C11 C 0.4229(6) 0.4701(6) 0.49400(13) 0.0339(13) Uani 1 1 d . . . . .
H11 H 0.460711 0.531875 0.510479 0.041 Uiso 1 1 calc R U . . .
C12 C 0.2592(6) 0.1835(8) 0.42241(18) 0.0514(18) Uani 1 1 d . . . . .
H12A H 0.318351 0.206353 0.404376 0.077 Uiso 1 1 calc R U . . .
H12B H 0.178107 0.173274 0.414843 0.077 Uiso 1 1 calc R U . . .
H12C H 0.244674 0.103275 0.431845 0.077 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 N1 2.260(4) 3_665 ?
Sn1 N1 2.260(4) 2_655 ?
Sn1 N1 2.260(4) . ?
Sn1 Li1 3.130(19) . ?
N1 C1 1.384(6) . ?
N1 C7 1.389(7) . ?
C1 N2 1.342(6) . ?
C1 C5 1.394(7) . ?
Li1 C3 2.649(8) 11_544 ?
Li1 C3 2.649(8) 10_664 ?
Li1 C3 2.649(8) 12_454 ?
N2 C2 1.349(8) . ?
C2 C3 1.388(11) . ?
C2 C6 1.475(9) . ?
C3 C4 1.386(10) . ?
C3 H3 0.9500 . ?
N3 C8 1.332(7) . ?
N3 C7 1.356(7) . ?
C4 C5 1.361(8) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C11 1.395(7) . ?
C9 C10 1.371(10) . ?
C9 C8 1.386(8) . ?
C9 H9 0.9500 . ?
C8 C12 1.501(9) . ?
C10 C11 1.397(9) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Sn1 N1 85.47(17) 3_665 2_655 ?
N1 Sn1 N1 85.47(16) 3_665 . ?
N1 Sn1 N1 85.47(16) 2_655 . ?
N1 Sn1 Li1 128.41(11) 3_665 . ?
N1 Sn1 Li1 128.41(11) 2_655 . ?
N1 Sn1 Li1 128.41(11) . . ?
C1 N1 C7 120.3(4) . . ?
C1 N1 Sn1 128.7(3) . . ?
C7 N1 Sn1 108.1(3) . . ?
N2 C1 N1 115.3(4) . . ?
N2 C1 C5 121.6(5) . . ?
N1 C1 C5 123.0(4) . . ?
C3 Li1 C3 119.63(10) 11_544 10_664 ?
C3 Li1 C3 119.62(10) 11_544 12_454 ?
C3 Li1 C3 119.62(10) 10_664 12_454 ?
C3 Li1 Sn1 93.5(5) 11_544 . ?
C3 Li1 Sn1 93.5(5) 10_664 . ?
C3 Li1 Sn1 93.5(5) 12_454 . ?
C1 N2 C2 119.5(5) . . ?
N2 C2 C3 120.7(6) . . ?
N2 C2 C6 116.8(6) . . ?
C3 C2 C6 122.5(7) . . ?
C4 C3 C2 119.7(7) . . ?
C4 C3 Li1 85.1(6) . 16_664 ?
C2 C3 Li1 154.6(6) . 16_664 ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
Li1 C3 H3 35.5 16_664 . ?
C8 N3 C7 119.6(5) . . ?
C5 C4 C3 119.1(6) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C1 119.4(5) . . ?
C4 C5 H5 120.3 . . ?
C1 C5 H5 120.3 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 N1 113.0(4) . . ?
N3 C7 C11 121.9(5) . . ?
N1 C7 C11 125.1(5) . . ?
C10 C9 C8 118.6(5) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
N3 C8 C9 122.0(5) . . ?
N3 C8 C12 116.8(5) . . ?
C9 C8 C12 121.1(5) . . ?
C9 C10 C11 120.8(6) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C7 C11 C10 117.1(6) . . ?
C7 C11 H11 121.5 . . ?
C10 C11 H11 121.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.755
_refine_diff_density_min         -1.001
_refine_diff_density_rms         0.198

####################################################################### 
# 
# 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_ld190219Ge1
_database_code_depnum_ccdc_archive 'CCDC 2032974'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2020-09-21 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Cl Ge N3'
_chemical_formula_weight         278.23

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'
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'

_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                   8.2653(5)
_cell_length_b                   9.9478(6)
_cell_length_c                   12.6110(7)
_cell_angle_alpha                91.910(3)
_cell_angle_beta                 92.733(3)
_cell_angle_gamma                91.899(3)
_cell_volume                     1034.51(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    30605
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.592
_exptl_crystal_size_mid          0.383
_exptl_crystal_size_min          0.202
_exptl_absorpt_coefficient_mu    3.185
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2472
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.332
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            30605
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.468
_diffrn_reflns_theta_max         27.609
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4750
_reflns_number_gt                3956
_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 Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0351P)²+0.5482P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4750
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0726
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Ge1 Ge 0.08767(3) 0.74150(3) 1.08079(2) 0.02023(8) Uani 1 1 d . . . . .
Cl1 Cl 0.32609(8) 0.86615(7) 1.06879(5) 0.03071(15) Uani 1 1 d . . . . .
N1 N 0.0333(2) 0.74442(19) 0.92687(14) 0.0167(4) Uani 1 1 d . . . . .
C1 C 0.0947(3) 0.6633(2) 0.84977(18) 0.0189(5) Uani 1 1 d . . . . .
Ge2 Ge 0.28824(3) 0.87680(3) 0.41554(2) 0.02065(8) Uani 1 1 d . . . . .
Cl2 Cl 0.09443(7) 0.70988(7) 0.43581(5) 0.02967(15) Uani 1 1 d . . . . .
N2 N 0.1895(3) 0.5589(2) 0.86738(15) 0.0222(4) Uani 1 1 d . . . . .
C2 C 0.0534(3) 0.6915(3) 0.74211(18) 0.0243(5) Uani 1 1 d . . . . .
H2 H 0.0957 0.6377 0.6870 0.029 Uiso 1 1 calc R U . . .
N3 N 0.1948(2) 0.5684(2) 1.05856(15) 0.0191(4) Uani 1 1 d . . . . .
C3 C -0.0446(3) 0.7931(3) 0.7162(2) 0.0255(5) Uani 1 1 d . . . . .
H3 H -0.0698 0.8102 0.6437 0.031 Uiso 1 1 calc R U . . .
N4 N 0.3099(2) 0.9316(2) 0.56782(15) 0.0194(4) Uani 1 1 d . . . . .
C4 C -0.1089(3) 0.8734(2) 0.79694(19) 0.0238(5) Uani 1 1 d . . . . .
H4 H -0.1794 0.9441 0.7806 0.029 Uiso 1 1 calc R U . . .
N5 N 0.5071(3) 0.7741(2) 0.62775(15) 0.0227(4) Uani 1 1 d . . . . .
C5 C -0.0667(3) 0.8459(2) 0.89857(19) 0.0212(5) Uani 1 1 d . . . . .
H5 H -0.1086 0.9000 0.9536 0.025 Uiso 1 1 calc R U . . .
C6 C 0.2334(3) 0.5130(2) 0.96281(18) 0.0187(5) Uani 1 1 d . . . . .
N6 N 0.4699(2) 0.7539(2) 0.43694(15) 0.0185(4) Uani 1 1 d . . . . .
C7 C 0.3287(3) 0.3967(3) 0.96433(19) 0.0234(5) Uani 1 1 d . . . . .
H7 H 0.3543 0.3539 0.8991 0.028 Uiso 1 1 calc R U . . .
C8 C 0.3840(3) 0.3452(3) 1.0575(2) 0.0249(5) Uani 1 1 d . . . . .
H8 H 0.4506 0.2692 1.0567 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3429(3) 0.4041(2) 1.15427(19) 0.0241(5) Uani 1 1 d . . . . .
H9 H 0.3803 0.3693 1.2199 0.029 Uiso 1 1 calc R U . . .
C10 C 0.2481(3) 0.5125(2) 1.15143(18) 0.0223(5) Uani 1 1 d . . . . .
H10 H 0.2171 0.5518 1.2168 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4034(3) 0.8723(2) 0.64490(18) 0.0200(5) Uani 1 1 d . . . . .
C12 C 0.3921(3) 0.9213(3) 0.7515(2) 0.0286(6) Uani 1 1 d . . . . .
H12 H 0.4561 0.8825 0.8063 0.034 Uiso 1 1 calc R U . . .
C13 C 0.2928(3) 1.0215(3) 0.7771(2) 0.0291(6) Uani 1 1 d . . . . .
H13 H 0.2872 1.0521 0.8490 0.035 Uiso 1 1 calc R U . . .
C14 C 0.1976(3) 1.0805(3) 0.6966(2) 0.0267(5) Uani 1 1 d . . . . .
H14 H 0.1268 1.1509 0.7128 0.032 Uiso 1 1 calc R U . . .
C15 C 0.2104(3) 1.0334(2) 0.5956(2) 0.0229(5) Uani 1 1 d . . . . .
H15 H 0.1471 1.0729 0.5409 0.027 Uiso 1 1 calc R U . . .
C16 C 0.5402(3) 0.7211(2) 0.53246(18) 0.0177(4) Uani 1 1 d . . . . .
C17 C 0.6605(3) 0.6230(2) 0.53121(19) 0.0217(5) Uani 1 1 d . . . . .
H17 H 0.7132 0.5995 0.5962 0.026 Uiso 1 1 calc R U . . .
C18 C 0.7021(3) 0.5618(2) 0.4387(2) 0.0239(5) Uani 1 1 d . . . . .
H18 H 0.7819 0.4952 0.4395 0.029 Uiso 1 1 calc R U . . .
C19 C 0.6264(3) 0.5975(3) 0.3421(2) 0.0258(5) Uani 1 1 d . . . . .
H19 H 0.6535 0.5558 0.2768 0.031 Uiso 1 1 calc R U . . .
C20 C 0.5144(3) 0.6927(3) 0.34489(19) 0.0230(5) Uani 1 1 d . . . . .
H20 H 0.4640 0.7183 0.2797 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
Ge1 N1 1.9728(18) . ?
Ge1 N3 1.980(2) . ?
Ge1 Cl1 2.3071(7) . ?
N1 C1 1.370(3) . ?
N1 C5 1.371(3) . ?
C1 N2 1.340(3) . ?
C1 C2 1.423(3) . ?
Ge2 N4 1.977(2) . ?
Ge2 N6 1.982(2) . ?
Ge2 Cl2 2.2978(7) . ?
N2 C6 1.339(3) . ?
C2 C3 1.355(4) . ?
C2 H2 0.9500 . ?
N3 C6 1.367(3) . ?
N3 C10 1.373(3) . ?
C3 C4 1.408(4) . ?
C3 H3 0.9500 . ?
N4 C15 1.372(3) . ?
N4 C11 1.374(3) . ?
C4 C5 1.351(3) . ?
C4 H4 0.9500 . ?
N5 C11 1.339(3) . ?
N5 C16 1.340(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.421(3) . ?
N6 C20 1.365(3) . ?
N6 C16 1.366(3) . ?
C7 C8 1.363(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.354(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.423(3) . ?
C12 C13 1.353(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.410(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.353(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.416(3) . ?
C17 C18 1.362(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.404(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.347(4) . ?
C19 H19 0.9500 . ?
C20 H20 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
N1 Ge1 N3 89.50(8) . . ?
N1 Ge1 Cl1 93.53(6) . . ?
N3 Ge1 Cl1 92.96(6) . . ?
C1 N1 C5 119.77(19) . . ?
C1 N1 Ge1 126.26(15) . . ?
C5 N1 Ge1 113.78(15) . . ?
N2 C1 N1 125.4(2) . . ?
N2 C1 C2 117.3(2) . . ?
N1 C1 C2 117.4(2) . . ?
N4 Ge2 N6 89.50(8) . . ?
N4 Ge2 Cl2 95.26(6) . . ?
N6 Ge2 Cl2 93.29(6) . . ?
C6 N2 C1 125.6(2) . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C6 N3 C10 120.3(2) . . ?
C6 N3 Ge1 125.85(15) . . ?
C10 N3 Ge1 113.39(16) . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C15 N4 C11 119.7(2) . . ?
C15 N4 Ge2 113.63(16) . . ?
C11 N4 Ge2 126.46(16) . . ?
C5 C4 C3 117.5(2) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C11 N5 C16 125.5(2) . . ?
C4 C5 N1 123.8(2) . . ?
C4 C5 H5 118.1 . . ?
N1 C5 H5 118.1 . . ?
N2 C6 N3 125.7(2) . . ?
N2 C6 C7 117.0(2) . . ?
N3 C6 C7 117.3(2) . . ?
C20 N6 C16 120.6(2) . . ?
C20 N6 Ge2 113.20(15) . . ?
C16 N6 Ge2 126.06(16) . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 117.8(2) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C9 C10 N3 123.1(2) . . ?
C9 C10 H10 118.5 . . ?
N3 C10 H10 118.5 . . ?
N5 C11 N4 125.4(2) . . ?
N5 C11 C12 117.3(2) . . ?
N4 C11 C12 117.3(2) . . ?
C13 C12 C11 121.9(2) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 117.7(2) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C14 C15 N4 123.6(2) . . ?
C14 C15 H15 118.2 . . ?
N4 C15 H15 118.2 . . ?
N5 C16 N6 126.1(2) . . ?
N5 C16 C17 116.6(2) . . ?
N6 C16 C17 117.3(2) . . ?
C18 C17 C16 121.3(2) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 119.7(2) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 118.0(2) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C19 C20 N6 123.0(2) . . ?
C19 C20 H20 118.5 . . ?
N6 C20 H20 118.5 . . ?

_refine_diff_density_max         0.693
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_ld200205Li1
_database_code_depnum_ccdc_archive 'CCDC 2032982'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2020-09-21 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_ld200205Li1         
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: poorly diffracting material
;
_vrf_PLAT020_ld200205Li1         
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.287 Report
RESPONSE: poorly diffracting material
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H48 Li4 N12'
_chemical_formula_weight         820.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.1572(4)
_cell_length_b                   11.5648(4)
_cell_length_c                   19.6657(7)
_cell_angle_alpha                79.294(2)
_cell_angle_beta                 76.670(2)
_cell_angle_gamma                62.192(2)
_cell_volume                     2174.94(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    52110
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.126
_exptl_absorpt_coefficient_mu    0.593
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5079
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.673
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            52110
_diffrn_reflns_av_unetI/netI     0.1578
_diffrn_reflns_av_R_equivalents  0.2871
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.318
_diffrn_reflns_theta_max         79.532
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             9155
_reflns_number_gt                4900
_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 Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1140P)²+0.1250P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0111(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9155
_refine_ls_number_parameters     586
_refine_ls_number_restraints     987
_refine_ls_R_factor_all          0.2008
_refine_ls_R_factor_gt           0.1095
_refine_ls_wR_factor_ref         0.2939
_refine_ls_wR_factor_gt          0.2443
_refine_ls_goodness_of_fit_ref   1.297
_refine_ls_restrained_S_all      1.232
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3673(4) 0.8045(3) 0.58820(18) 0.0288(8) Uani 1 1 d . . . . .
C1 C 0.5020(5) 0.7625(3) 0.5573(2) 0.0262(9) Uani 1 1 d . . . . .
Li1 Li 0.4326(8) 0.6358(6) 0.6644(4) 0.0312(15) Uani 1 1 d . . . . .
N2 N 0.5852(4) 0.6441(3) 0.58809(18) 0.0278(8) Uani 1 1 d . . . . .
C2 C 0.7229(5) 0.5947(4) 0.5699(2) 0.0312(10) Uani 1 1 d . . . . .
Li2 Li 0.2355(8) 0.8695(6) 0.6920(4) 0.0313(15) Uani 1 1 d . . . . .
N3 N 0.1491(4) 0.9647(3) 0.60785(19) 0.0304(8) Uani 1 1 d . . . . .
C3 C 0.7842(5) 0.6601(4) 0.5197(2) 0.0339(10) Uani 1 1 d . . . . .
H3 H 0.881346 0.624716 0.507869 0.041 Uiso 1 1 calc R U . . .
Li3 Li 0.2618(8) 0.8534(7) 0.8234(4) 0.0308(14) Uani 1 1 d . . . . .
C4 C 0.7004(5) 0.7787(4) 0.4869(2) 0.0362(11) Uani 1 1 d . . . . .
H4 H 0.740600 0.825089 0.452190 0.043 Uiso 1 1 calc R U . . .
N4 N 0.1331(4) 0.7753(3) 0.76184(17) 0.0270(8) Uani 1 1 d . . . . .
Li4 Li 0.3129(8) 0.6206(6) 0.7965(4) 0.0281(14) Uani 1 1 d . . . . .
N5 N 0.2425(4) 0.6197(3) 0.68513(18) 0.0297(8) Uani 1 1 d . . . . .
C5 C 0.5611(5) 0.8294(4) 0.5039(2) 0.0324(10) Uani 1 1 d . . . . .
H5 H 0.504286 0.909060 0.480092 0.039 Uiso 1 1 calc R U . . .
N6 N 0.0531(4) 0.9342(3) 0.83674(18) 0.0290(8) Uani 1 1 d . . . . .
C6 C 0.8046(5) 0.4647(4) 0.6060(3) 0.0449(13) Uani 1 1 d . . . . .
H6A H 0.779273 0.399543 0.596321 0.067 Uiso 1 1 calc R U . . .
H6B H 0.785493 0.471358 0.656670 0.067 Uiso 1 1 calc R U . . .
H6C H 0.902680 0.437745 0.588682 0.067 Uiso 1 1 calc R U . . .
N7 N 0.4516(4) 0.7344(3) 0.74379(18) 0.0270(8) Uani 1 1 d . . . . .
C7 C 0.2618(5) 0.9070(4) 0.5590(2) 0.0288(10) Uani 1 1 d . . . . .
C8 C 0.0341(5) 1.0669(4) 0.5891(2) 0.0330(10) Uani 1 1 d . . . . .
N8 N 0.3371(4) 0.9543(3) 0.72636(17) 0.0265(8) Uani 1 1 d . . . . .
N9 N 0.5337(4) 0.5135(3) 0.76018(18) 0.0291(8) Uani 1 1 d . . . . .
C9 C 0.0293(5) 1.1190(4) 0.5190(2) 0.0362(11) Uani 1 1 d . . . . .
H9 H -0.048899 1.195173 0.506194 0.043 Uiso 1 1 calc R U . . .
C11 C 0.2564(5) 0.9503(4) 0.4876(2) 0.0337(11) Uani 1 1 d . . . . .
H11 H 0.331568 0.906593 0.452512 0.040 Uiso 1 1 calc R U . . .
N11 N 0.3597(4) 0.8374(3) 0.90053(17) 0.0253(8) Uani 1 1 d . . . . .
C10 C 0.1402(5) 1.0574(4) 0.4696(2) 0.0365(11) Uani 1 1 d . . . . .
H10 H 0.136939 1.089218 0.421557 0.044 Uiso 1 1 calc R U . . .
N10 N 0.2977(4) 0.6775(3) 0.89972(17) 0.0255(8) Uani 1 1 d . . . . .
C13 C 0.1203(5) 0.7050(4) 0.7184(2) 0.0276(9) Uani 1 1 d . . . . .
C12 C -0.0852(5) 1.1146(4) 0.6467(3) 0.0430(12) Uani 1 1 d . . . . .
H12A H -0.170145 1.163332 0.626772 0.064 Uiso 1 1 calc R U . . .
H12B H -0.074956 1.172332 0.673267 0.064 Uiso 1 1 calc R U . . .
H12C H -0.089154 1.039478 0.678052 0.064 Uiso 1 1 calc R U . . .
N12 N 0.2433(4) 0.5240(3) 0.87861(18) 0.0277(8) Uani 1 1 d . . . . .
C14 C 0.2460(5) 0.5462(4) 0.6375(2) 0.0337(10) Uani 1 1 d . . . . .
C15 C 0.1271(6) 0.5548(5) 0.6222(3) 0.0430(12) Uani 1 1 d . . . . .
H15 H 0.131710 0.501074 0.589643 0.052 Uiso 1 1 calc R U . . .
C16 C 0.0017(6) 0.6425(5) 0.6549(3) 0.0454(13) Uani 1 1 d . . . . .
H16 H -0.080985 0.650312 0.644576 0.055 Uiso 1 1 calc R U . . .
C17 C -0.0031(5) 0.7179(4) 0.7020(3) 0.0364(11) Uani 1 1 d . . . . .
H17 H -0.089396 0.779428 0.723907 0.044 Uiso 1 1 calc R U . . .
C18 C 0.3858(6) 0.4610(4) 0.6000(3) 0.0428(12) Uani 1 1 d . . . . .
H18A H 0.378435 0.401571 0.573275 0.064 Uiso 1 1 calc R U . . .
H18B H 0.446972 0.409491 0.634270 0.064 Uiso 1 1 calc R U . . .
H18C H 0.423103 0.516349 0.567779 0.064 Uiso 1 1 calc R U . . .
C19 C 0.0295(5) 0.8439(4) 0.8132(2) 0.0281(9) Uani 1 1 d . . . . .
C20 C -0.0355(5) 1.0065(4) 0.8887(2) 0.0343(10) Uani 1 1 d . . . . .
C21 C -0.1546(5) 0.9949(5) 0.9200(3) 0.0446(12) Uani 1 1 d . . . . .
H21 H -0.219065 1.050351 0.954760 0.054 Uiso 1 1 calc R U . . .
C22 C -0.1762(6) 0.8985(5) 0.8983(3) 0.0499(13) Uani 1 1 d . . . . .
H22 H -0.255079 0.885817 0.920135 0.060 Uiso 1 1 calc R U . . .
C23 C -0.0867(5) 0.8228(5) 0.8467(3) 0.0394(11) Uani 1 1 d . . . . .
H23 H -0.101654 0.756546 0.833144 0.047 Uiso 1 1 calc R U . . .
C24 C 0.0016(5) 1.0994(4) 0.9121(3) 0.0429(13) Uani 1 1 d . . . . .
H24A H 0.095430 1.052309 0.922538 0.064 Uiso 1 1 calc R U . . .
H24B H -0.062340 1.136959 0.954402 0.064 Uiso 1 1 calc R U . . .
H24C H -0.003961 1.170015 0.874795 0.064 Uiso 1 1 calc R U . . .
C25 C 0.4626(5) 0.8491(4) 0.7254(2) 0.0288(9) Uani 1 1 d . . . . .
C26 C 0.3261(5) 1.0772(4) 0.7073(2) 0.0313(10) Uani 1 1 d . . . . .
C27 C 0.4422(6) 1.0986(5) 0.6874(2) 0.0404(11) Uani 1 1 d . . . . .
H27 H 0.434102 1.185107 0.675380 0.049 Uiso 1 1 calc R U . . .
C28 C 0.5706(6) 0.9913(5) 0.6855(3) 0.0455(12) Uani 1 1 d . . . . .
H28 H 0.650934 1.004771 0.671800 0.055 Uiso 1 1 calc R U . . .
C29 C 0.5832(5) 0.8669(5) 0.7030(2) 0.0376(11) Uani 1 1 d . . . . .
H29 H 0.671241 0.793638 0.700129 0.045 Uiso 1 1 calc R U . . .
C30 C 0.1836(6) 1.1860(4) 0.7084(3) 0.0428(13) Uani 1 1 d . . . . .
H30A H 0.187645 1.270270 0.695829 0.064 Uiso 1 1 calc R U . . .
H30B H 0.130282 1.185511 0.755558 0.064 Uiso 1 1 calc R U . . .
H30C H 0.139504 1.173276 0.674582 0.064 Uiso 1 1 calc R U . . .
C31 C 0.5546(5) 0.6183(4) 0.7656(2) 0.0300(9) Uani 1 1 d . . . . .
C32 C 0.6208(5) 0.3914(4) 0.7813(2) 0.0335(10) Uani 1 1 d . . . . .
C33 C 0.7365(5) 0.3679(4) 0.8067(3) 0.0418(12) Uani 1 1 d . . . . .
H33 H 0.800300 0.280785 0.819397 0.050 Uiso 1 1 calc R U . . .
C34 C 0.7573(5) 0.4737(5) 0.8134(3) 0.0428(12) Uani 1 1 d . . . . .
H34 H 0.835471 0.458890 0.831653 0.051 Uiso 1 1 calc R U . . .
C35 C 0.6684(5) 0.5982(5) 0.7943(2) 0.0363(11) Uani 1 1 d . . . . .
H35 H 0.682442 0.670438 0.800191 0.044 Uiso 1 1 calc R U . . .
C36 C 0.5874(6) 0.2821(4) 0.7754(3) 0.0439(13) Uani 1 1 d . . . . .
H36A H 0.491575 0.304743 0.796802 0.066 Uiso 1 1 calc R U . . .
H36B H 0.648114 0.200859 0.799845 0.066 Uiso 1 1 calc R U . . .
H36C H 0.600722 0.269432 0.725846 0.066 Uiso 1 1 calc R U . . .
C37 C 0.3533(5) 0.7261(3) 0.9350(2) 0.0261(9) Uani 1 1 d . . . . .
C38 C 0.4264(5) 0.8911(3) 0.9236(2) 0.0264(9) Uani 1 1 d . . . . .
C39 C 0.4892(5) 0.8364(4) 0.9821(2) 0.0293(10) Uani 1 1 d . . . . .
H39 H 0.537903 0.873908 0.996725 0.035 Uiso 1 1 calc R U . . .
C40 C 0.4800(5) 0.7256(4) 1.0193(2) 0.0308(10) Uani 1 1 d . . . . .
H40 H 0.521190 0.687654 1.060236 0.037 Uiso 1 1 calc R U . . .
C41 C 0.4114(5) 0.6705(4) 0.9971(2) 0.0303(10) Uani 1 1 d . . . . .
H41 H 0.402996 0.596022 1.023180 0.036 Uiso 1 1 calc R U . . .
C42 C 0.4263(6) 1.0142(4) 0.8828(3) 0.0392(12) Uani 1 1 d . . . . .
H42A H 0.437644 1.007297 0.832585 0.059 Uiso 1 1 calc R U . . .
H42B H 0.502286 1.026458 0.891864 0.059 Uiso 1 1 calc R U . . .
H42C H 0.339029 1.089456 0.897296 0.059 Uiso 1 1 calc R U . . .
C43 C 0.2529(4) 0.5849(3) 0.9286(2) 0.0255(9) Uani 1 1 d . . . . .
C44 C 0.1983(5) 0.4307(4) 0.8971(2) 0.0322(10) Uani 1 1 d . . . . .
C45 C 0.1644(5) 0.3906(4) 0.9668(3) 0.0373(11) Uani 1 1 d . . . . .
H45 H 0.137672 0.321554 0.978963 0.045 Uiso 1 1 calc R U . . .
C46 C 0.1705(5) 0.4541(4) 1.0182(3) 0.0393(11) Uani 1 1 d . . . . .
H46 H 0.145976 0.429388 1.066200 0.047 Uiso 1 1 calc R U . . .
C47 C 0.2118(5) 0.5526(4) 1.0005(2) 0.0343(11) Uani 1 1 d . . . . .
H47 H 0.212674 0.598121 1.035769 0.041 Uiso 1 1 calc R U . . .
C48 C 0.1812(5) 0.3764(4) 0.8386(3) 0.0397(12) Uani 1 1 d . . . . .
H48A H 0.122349 0.448543 0.808588 0.060 Uiso 1 1 calc R U . . .
H48B H 0.138659 0.317277 0.858120 0.060 Uiso 1 1 calc R U . . .
H48C H 0.271316 0.327683 0.810778 0.060 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
N1 C1 1.367(6) . ?
N1 C7 1.371(5) . ?
N1 Li1 2.162(7) . ?
N1 Li2 2.246(8) . ?
C1 N2 1.367(5) . ?
C1 C5 1.411(6) . ?
C1 Li1 2.519(8) . ?
Li1 N2 2.021(9) . ?
Li1 N5 2.154(10) . ?
Li1 N7 2.196(8) . ?
Li1 N9 2.307(8) . ?
Li1 C31 2.587(9) . ?
Li1 Li2 2.623(10) . ?
Li1 Li4 2.647(10) . ?
N2 C2 1.348(6) . ?
C2 C3 1.382(6) . ?
C2 C6 1.488(6) . ?
Li2 N3 1.987(8) . ?
Li2 N4 2.064(8) . ?
Li2 N8 2.084(9) . ?
Li2 N7 2.514(8) . ?
Li2 C7 2.541(8) . ?
Li2 Li3 2.631(10) . ?
Li2 C25 2.657(10) . ?
Li2 C13 2.673(9) . ?
Li2 Li4 3.091(9) . ?
N3 C8 1.349(5) . ?
N3 C7 1.360(6) . ?
C3 C4 1.387(6) . ?
C3 H3 0.9500 . ?
Li3 N11 2.000(9) . ?
Li3 N6 2.035(9) . ?
Li3 N10 2.221(7) . ?
Li3 N8 2.249(8) . ?
Li3 N7 2.320(8) . ?
Li3 C37 2.542(8) . ?
Li3 C25 2.584(9) . ?
Li3 N4 2.600(9) . ?
Li3 Li4 2.610(10) . ?
Li3 C19 2.699(10) . ?
C4 C5 1.361(7) . ?
C4 H4 0.9500 . ?
N4 C13 1.354(5) . ?
N4 C19 1.374(5) . ?
N4 Li4 2.126(7) . ?
Li4 N12 2.006(8) . ?
Li4 N9 2.187(8) . ?
Li4 N10 2.195(8) . ?
Li4 N7 2.419(8) . ?
Li4 N5 2.494(8) . ?
Li4 C43 2.536(8) . ?
Li4 C31 2.612(9) . ?
Li4 C13 2.633(8) . ?
N5 C13 1.355(6) . ?
N5 C14 1.360(5) . ?
C5 H5 0.9500 . ?
N6 C20 1.343(5) . ?
N6 C19 1.366(6) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
N7 C25 1.363(5) . ?
N7 C31 1.371(5) . ?
C7 C11 1.405(6) . ?
C8 C9 1.401(6) . ?
C8 C12 1.487(7) . ?
N8 C26 1.356(5) . ?
N8 C25 1.359(5) . ?
N9 C32 1.341(5) . ?
N9 C31 1.362(6) . ?
C9 C10 1.365(7) . ?
C9 H9 0.9500 . ?
C11 C10 1.375(6) . ?
C11 H11 0.9500 . ?
N11 C38 1.355(6) . ?
N11 C37 1.364(5) . ?
C10 H10 0.9500 . ?
N10 C37 1.361(6) . ?
N10 C43 1.365(5) . ?
C13 C17 1.421(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N12 C44 1.350(6) . ?
N12 C43 1.361(5) . ?
C14 C15 1.382(7) . ?
C14 C18 1.501(7) . ?
C15 C16 1.380(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.361(7) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C23 1.420(7) . ?
C20 C21 1.385(7) . ?
C20 C24 1.491(7) . ?
C21 C22 1.400(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.356(7) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C29 1.414(7) . ?
C26 C27 1.386(7) . ?
C26 C30 1.496(7) . ?
C27 C28 1.388(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.363(7) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C35 1.412(7) . ?
C32 C33 1.382(7) . ?
C32 C36 1.504(7) . ?
C33 C34 1.381(8) . ?
C33 H33 0.9500 . ?
C34 C35 1.354(6) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C41 1.417(6) . ?
C38 C39 1.380(6) . ?
C38 C42 1.499(6) . ?
C39 C40 1.389(6) . ?
C39 H39 0.9500 . ?
C40 C41 1.376(7) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C47 1.418(6) . ?
C44 C45 1.387(7) . ?
C44 C48 1.496(7) . ?
C45 C46 1.385(7) . ?
C45 H45 0.9500 . ?
C46 C47 1.379(7) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C7 122.7(4) . . ?
C1 N1 Li1 88.1(3) . . ?
C7 N1 Li1 148.3(4) . . ?
C1 N1 Li2 138.8(4) . . ?
C7 N1 Li2 85.7(3) . . ?
Li1 N1 Li2 73.0(3) . . ?
N2 C1 N1 112.1(4) . . ?
N2 C1 C5 119.4(4) . . ?
N1 C1 C5 128.4(4) . . ?
N2 C1 Li1 53.2(3) . . ?
N1 C1 Li1 59.1(3) . . ?
C5 C1 Li1 169.1(4) . . ?
N2 Li1 N5 144.2(4) . . ?
N2 Li1 N1 65.6(3) . . ?
N5 Li1 N1 95.3(3) . . ?
N2 Li1 N7 99.2(4) . . ?
N5 Li1 N7 113.5(4) . . ?
N1 Li1 N7 96.7(3) . . ?
N2 Li1 N9 106.7(4) . . ?
N5 Li1 N9 102.2(3) . . ?
N1 Li1 N9 155.2(4) . . ?
N7 Li1 N9 60.2(2) . . ?
N2 Li1 C1 32.77(17) . . ?
N5 Li1 C1 123.6(3) . . ?
N1 Li1 C1 32.86(17) . . ?
N7 Li1 C1 97.7(3) . . ?
N9 Li1 C1 134.2(4) . . ?
N2 Li1 C31 94.2(3) . . ?
N5 Li1 C31 121.2(3) . . ?
N1 Li1 C31 123.5(4) . . ?
N7 Li1 C31 32.01(16) . . ?
N9 Li1 C31 31.66(17) . . ?
C1 Li1 C31 110.3(3) . . ?
N2 Li1 Li2 112.4(3) . . ?
N5 Li1 Li2 73.4(3) . . ?
N1 Li1 Li2 55.0(2) . . ?
N7 Li1 Li2 62.1(3) . . ?
N9 Li1 Li2 113.6(3) . . ?
C1 Li1 Li2 82.7(3) . . ?
C31 Li1 Li2 93.4(3) . . ?
N2 Li1 Li4 154.1(4) . . ?
N5 Li1 Li4 61.6(3) . . ?
N1 Li1 Li4 126.5(3) . . ?
N7 Li1 Li4 59.1(3) . . ?
N9 Li1 Li4 51.8(2) . . ?
C1 Li1 Li4 151.3(3) . . ?
C31 Li1 Li4 59.9(3) . . ?
Li2 Li1 Li4 71.8(3) . . ?
C2 N2 C1 120.3(4) . . ?
C2 N2 Li1 143.6(3) . . ?
C1 N2 Li1 94.1(3) . . ?
N2 C2 C3 121.7(4) . . ?
N2 C2 C6 116.2(4) . . ?
C3 C2 C6 122.1(5) . . ?
N3 Li2 N4 114.8(4) . . ?
N3 Li2 N8 114.8(4) . . ?
N4 Li2 N8 121.4(4) . . ?
N3 Li2 N1 64.4(2) . . ?
N4 Li2 N1 127.0(4) . . ?
N8 Li2 N1 101.6(4) . . ?
N3 Li2 N7 148.3(4) . . ?
N4 Li2 N7 91.7(3) . . ?
N8 Li2 N7 57.7(2) . . ?
N1 Li2 N7 86.1(3) . . ?
N3 Li2 C7 32.08(18) . . ?
N4 Li2 C7 129.8(4) . . ?
N8 Li2 C7 108.8(3) . . ?
N1 Li2 C7 32.54(16) . . ?
N7 Li2 C7 117.0(3) . . ?
N3 Li2 Li1 110.8(4) . . ?
N4 Li2 Li1 87.2(3) . . ?
N8 Li2 Li1 102.5(4) . . ?
N1 Li2 Li1 52.0(2) . . ?
N7 Li2 Li1 50.5(2) . . ?
C7 Li2 Li1 82.5(3) . . ?
N3 Li2 Li3 152.3(4) . . ?
N4 Li2 Li3 66.0(3) . . ?
N8 Li2 Li3 55.5(3) . . ?
N1 Li2 Li3 139.4(4) . . ?
N7 Li2 Li3 53.6(2) . . ?
C7 Li2 Li3 163.9(4) . . ?
Li1 Li2 Li3 96.8(3) . . ?
N3 Li2 C25 128.5(4) . . ?
N4 Li2 C25 116.6(3) . . ?
N8 Li2 C25 30.36(17) . . ?
N1 Li2 C25 84.8(3) . . ?
N7 Li2 C25 30.41(15) . . ?
C7 Li2 C25 106.5(3) . . ?
Li1 Li2 C25 72.2(3) . . ?
Li3 Li2 C25 58.5(3) . . ?
N3 Li2 C13 94.9(3) . . ?
N4 Li2 C13 29.83(17) . . ?
N8 Li2 C13 149.0(3) . . ?
N1 Li2 C13 99.1(3) . . ?
N7 Li2 C13 101.4(2) . . ?
C7 Li2 C13 101.1(3) . . ?
Li1 Li2 C13 73.0(3) . . ?
Li3 Li2 C13 94.0(3) . . ?
C25 Li2 C13 131.6(3) . . ?
N3 Li2 Li4 146.9(4) . . ?
N4 Li2 Li4 43.2(2) . . ?
N8 Li2 Li4 98.0(3) . . ?
N1 Li2 Li4 106.2(3) . . ?
N7 Li2 Li4 49.8(2) . . ?
C7 Li2 Li4 133.5(3) . . ?
Li1 Li2 Li4 54.4(2) . . ?
Li3 Li2 Li4 53.5(2) . . ?
C25 Li2 Li4 78.7(2) . . ?
C13 Li2 Li4 53.8(2) . . ?
C8 N3 C7 120.9(4) . . ?
C8 N3 Li2 141.3(4) . . ?
C7 N3 Li2 97.0(3) . . ?
C2 C3 C4 118.4(5) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
N11 Li3 N6 121.6(4) . . ?
N11 Li3 N10 64.5(2) . . ?
N6 Li3 N10 98.6(3) . . ?
N11 Li3 N8 109.0(4) . . ?
N6 Li3 N8 108.7(3) . . ?
N10 Li3 N8 149.8(4) . . ?
N11 Li3 N7 98.4(3) . . ?
N6 Li3 N7 139.3(4) . . ?
N10 Li3 N7 91.9(3) . . ?
N8 Li3 N7 59.0(2) . . ?
N11 Li3 C37 32.24(17) . . ?
N6 Li3 C37 112.0(3) . . ?
N10 Li3 C37 32.33(16) . . ?
N8 Li3 C37 135.8(4) . . ?
N7 Li3 C37 97.7(3) . . ?
N11 Li3 C25 93.7(3) . . ?
N6 Li3 C25 138.0(4) . . ?
N10 Li3 C25 118.3(3) . . ?
N8 Li3 C25 31.71(16) . . ?
N7 Li3 C25 31.71(16) . . ?
C37 Li3 C25 110.0(3) . . ?
N11 Li3 N4 152.1(4) . . ?
N6 Li3 N4 57.5(2) . . ?
N10 Li3 N4 87.7(3) . . ?
N8 Li3 N4 96.2(3) . . ?
N7 Li3 N4 84.0(3) . . ?
C37 Li3 N4 119.8(3) . . ?
C25 Li3 N4 102.1(3) . . ?
N11 Li3 Li4 109.9(3) . . ?
N6 Li3 Li4 97.7(4) . . ?
N10 Li3 Li4 53.3(2) . . ?
N8 Li3 Li4 109.0(3) . . ?
N7 Li3 Li4 58.4(2) . . ?
C37 Li3 Li4 82.0(3) . . ?
C25 Li3 Li4 89.6(3) . . ?
N4 Li3 Li4 48.2(2) . . ?
N11 Li3 Li2 155.0(5) . . ?
N6 Li3 Li2 81.6(3) . . ?
N10 Li3 Li2 125.3(4) . . ?
N8 Li3 Li2 49.8(2) . . ?
N7 Li3 Li2 60.6(3) . . ?
C37 Li3 Li2 152.5(3) . . ?
C25 Li3 Li2 61.3(3) . . ?
N4 Li3 Li2 46.5(2) . . ?
Li4 Li3 Li2 72.3(3) . . ?
N11 Li3 C19 136.7(4) . . ?
N6 Li3 C19 29.52(17) . . ?
N10 Li3 C19 85.6(3) . . ?
N8 Li3 C19 112.1(3) . . ?
N7 Li3 C19 114.0(3) . . ?
C37 Li3 C19 111.8(3) . . ?
C25 Li3 C19 128.9(3) . . ?
N4 Li3 C19 29.99(15) . . ?
Li4 Li3 C19 68.8(3) . . ?
Li2 Li3 C19 68.1(3) . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C13 N4 C19 124.0(4) . . ?
C13 N4 Li2 100.9(3) . . ?
C19 N4 Li2 119.0(3) . . ?
C13 N4 Li4 95.8(3) . . ?
C19 N4 Li4 116.2(3) . . ?
Li2 N4 Li4 95.1(3) . . ?
C13 N4 Li3 156.4(3) . . ?
C19 N4 Li3 79.0(3) . . ?
Li2 N4 Li3 67.5(3) . . ?
Li4 N4 Li3 66.2(3) . . ?
N12 Li4 N4 104.8(4) . . ?
N12 Li4 N9 112.7(3) . . ?
N4 Li4 N9 140.6(4) . . ?
N12 Li4 N10 64.8(3) . . ?
N4 Li4 N10 101.7(3) . . ?
N9 Li4 N10 104.5(3) . . ?
N12 Li4 N7 151.3(4) . . ?
N4 Li4 N7 92.9(3) . . ?
N9 Li4 N7 58.5(2) . . ?
N10 Li4 N7 89.9(3) . . ?
N12 Li4 N5 113.0(4) . . ?
N4 Li4 N5 58.0(2) . . ?
N9 Li4 N5 95.5(3) . . ?
N10 Li4 N5 159.1(4) . . ?
N7 Li4 N5 95.5(3) . . ?
N12 Li4 C43 32.27(18) . . ?
N4 Li4 C43 106.4(3) . . ?
N9 Li4 C43 111.5(3) . . ?
N10 Li4 C43 32.53(16) . . ?
N7 Li4 C43 121.2(3) . . ?
N5 Li4 C43 141.9(4) . . ?
N12 Li4 Li3 112.4(4) . . ?
N4 Li4 Li3 65.7(3) . . ?
N9 Li4 Li3 108.1(4) . . ?
N10 Li4 Li3 54.2(2) . . ?
N7 Li4 Li3 54.8(2) . . ?
N5 Li4 Li3 113.8(3) . . ?
C43 Li4 Li3 83.5(3) . . ?
N12 Li4 C31 127.8(3) . . ?
N4 Li4 C31 124.1(3) . . ?
N9 Li4 C31 31.41(17) . . ?
N10 Li4 C31 86.8(3) . . ?
N7 Li4 C31 31.33(15) . . ?
N5 Li4 C31 108.1(3) . . ?
C43 Li4 C31 108.9(3) . . ?
Li3 Li4 C31 76.7(3) . . ?
N12 Li4 C13 101.4(3) . . ?
N4 Li4 C13 30.77(16) . . ?
N9 Li4 C13 125.4(3) . . ?
N10 Li4 C13 128.7(3) . . ?
N7 Li4 C13 105.1(3) . . ?
N5 Li4 C13 30.49(15) . . ?
C43 Li4 C13 119.7(3) . . ?
Li3 Li4 C13 95.4(3) . . ?
C31 Li4 C13 129.7(3) . . ?
N12 Li4 Li1 150.8(4) . . ?
N4 Li4 Li1 85.3(3) . . ?
N9 Li4 Li1 56.0(3) . . ?
N10 Li4 Li1 140.9(4) . . ?
N7 Li4 Li1 51.1(2) . . ?
N5 Li4 Li1 49.4(2) . . ?
C43 Li4 Li1 167.1(4) . . ?
Li3 Li4 Li1 96.7(3) . . ?
C31 Li4 Li1 58.9(3) . . ?
C13 Li4 Li1 73.2(3) . . ?
N12 Li4 Li2 145.7(4) . . ?
N4 Li4 Li2 41.7(2) . . ?
N9 Li4 Li2 101.5(3) . . ?
N10 Li4 Li2 108.2(3) . . ?
N7 Li4 Li2 52.6(2) . . ?
N5 Li4 Li2 61.0(2) . . ?
C43 Li4 Li2 132.9(3) . . ?
Li3 Li4 Li2 54.2(2) . . ?
C31 Li4 Li2 82.9(3) . . ?
C13 Li4 Li2 55.0(2) . . ?
Li1 Li4 Li2 53.7(2) . . ?
C13 N5 C14 120.0(4) . . ?
C13 N5 Li1 126.2(3) . . ?
C14 N5 Li1 109.2(4) . . ?
C13 N5 Li4 80.5(3) . . ?
C14 N5 Li4 146.8(3) . . ?
Li1 N5 Li4 69.0(3) . . ?
C4 C5 C1 119.4(4) . . ?
C4 C5 H5 120.3 . . ?
C1 C5 H5 120.3 . . ?
C20 N6 C19 120.6(4) . . ?
C20 N6 Li3 126.4(4) . . ?
C19 N6 Li3 103.3(3) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C25 N7 C31 124.2(4) . . ?
C25 N7 Li1 120.2(3) . . ?
C31 N7 Li1 89.9(3) . . ?
C25 N7 Li3 84.9(3) . . ?
C31 N7 Li3 120.7(3) . . ?
Li1 N7 Li3 120.9(3) . . ?
C25 N7 Li4 149.4(3) . . ?
C31 N7 Li4 82.1(3) . . ?
Li1 N7 Li4 69.8(3) . . ?
Li3 N7 Li4 66.8(3) . . ?
C25 N7 Li2 80.6(3) . . ?
C31 N7 Li2 153.5(3) . . ?
Li1 N7 Li2 67.3(3) . . ?
Li3 N7 Li2 65.8(3) . . ?
Li4 N7 Li2 77.6(3) . . ?
N3 C7 N1 112.2(4) . . ?
N3 C7 C11 119.6(4) . . ?
N1 C7 C11 128.2(4) . . ?
N3 C7 Li2 50.9(3) . . ?
N1 C7 Li2 61.8(3) . . ?
C11 C7 Li2 169.6(4) . . ?
N3 C8 C9 120.8(4) . . ?
N3 C8 C12 115.6(4) . . ?
C9 C8 C12 123.6(4) . . ?
C26 N8 C25 120.6(4) . . ?
C26 N8 Li2 126.8(3) . . ?
C25 N8 Li2 98.8(3) . . ?
C26 N8 Li3 135.1(3) . . ?
C25 N8 Li3 87.9(3) . . ?
Li2 N8 Li3 74.7(3) . . ?
C32 N9 C31 120.8(4) . . ?
C32 N9 Li4 128.6(4) . . ?
C31 N9 Li4 91.8(3) . . ?
C32 N9 Li1 141.4(3) . . ?
C31 N9 Li1 85.6(3) . . ?
Li4 N9 Li1 72.1(3) . . ?
C10 C9 C8 118.2(4) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C10 C11 C7 118.7(4) . . ?
C10 C11 H11 120.7 . . ?
C7 C11 H11 120.7 . . ?
C38 N11 C37 120.3(3) . . ?
C38 N11 Li3 143.3(3) . . ?
C37 N11 Li3 96.3(3) . . ?
C9 C10 C11 121.6(4) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C37 N10 C43 123.9(3) . . ?
C37 N10 Li4 142.8(4) . . ?
C43 N10 Li4 87.6(3) . . ?
C37 N10 Li3 86.9(3) . . ?
C43 N10 Li3 144.6(4) . . ?
Li4 N10 Li3 72.5(3) . . ?
N4 C13 N5 113.2(4) . . ?
N4 C13 C17 127.5(4) . . ?
N5 C13 C17 119.1(4) . . ?
N4 C13 Li4 53.4(2) . . ?
N5 C13 Li4 69.1(3) . . ?
C17 C13 Li4 154.3(3) . . ?
N4 C13 Li2 49.3(3) . . ?
N5 C13 Li2 84.6(3) . . ?
C17 C13 Li2 131.4(3) . . ?
Li4 C13 Li2 71.3(2) . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C44 N12 C43 120.4(4) . . ?
C44 N12 Li4 143.8(4) . . ?
C43 N12 Li4 95.8(3) . . ?
N5 C14 C15 121.7(4) . . ?
N5 C14 C18 116.1(4) . . ?
C15 C14 C18 122.1(4) . . ?
C16 C15 C14 119.1(5) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C15 119.7(5) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C13 120.3(5) . . ?
C16 C17 H17 119.8 . . ?
C13 C17 H17 119.8 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N6 C19 N4 112.8(4) . . ?
N6 C19 C23 119.1(4) . . ?
N4 C19 C23 127.8(4) . . ?
N6 C19 Li3 47.2(3) . . ?
N4 C19 Li3 71.0(3) . . ?
C23 C19 Li3 148.8(3) . . ?
N6 C20 C21 122.1(5) . . ?
N6 C20 C24 116.5(5) . . ?
C21 C20 C24 121.3(4) . . ?
C20 C21 C22 117.5(4) . . ?
C20 C21 H21 121.3 . . ?
C22 C21 H21 121.3 . . ?
C23 C22 C21 121.2(5) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C19 119.2(5) . . ?
C22 C23 H23 120.4 . . ?
C19 C23 H23 120.4 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N8 C25 N7 111.5(4) . . ?
N8 C25 C29 120.1(4) . . ?
N7 C25 C29 128.3(4) . . ?
N8 C25 Li3 60.4(3) . . ?
N7 C25 Li3 63.4(3) . . ?
C29 C25 Li3 149.4(4) . . ?
N8 C25 Li2 50.8(3) . . ?
N7 C25 Li2 69.0(3) . . ?
C29 C25 Li2 147.2(4) . . ?
Li3 C25 Li2 60.2(3) . . ?
N8 C26 C27 120.8(4) . . ?
N8 C26 C30 116.4(4) . . ?
C27 C26 C30 122.8(4) . . ?
C26 C27 C28 118.8(4) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
C29 C28 C27 120.9(5) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C28 C29 C25 118.7(5) . . ?
C28 C29 H29 120.6 . . ?
C25 C29 H29 120.6 . . ?
C26 C30 H30A 109.5 . . ?
C26 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C26 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N9 C31 N7 111.7(4) . . ?
N9 C31 C35 119.6(4) . . ?
N7 C31 C35 128.6(4) . . ?
N9 C31 Li1 62.8(3) . . ?
N7 C31 Li1 58.1(3) . . ?
C35 C31 Li1 154.1(4) . . ?
N9 C31 Li4 56.8(3) . . ?
N7 C31 Li4 66.6(3) . . ?
C35 C31 Li4 143.8(4) . . ?
Li1 C31 Li4 61.2(3) . . ?
N9 C32 C33 121.0(4) . . ?
N9 C32 C36 117.1(4) . . ?
C33 C32 C36 121.9(4) . . ?
C34 C33 C32 118.5(4) . . ?
C34 C33 H33 120.7 . . ?
C32 C33 H33 120.7 . . ?
C35 C34 C33 121.3(5) . . ?
C35 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C34 C35 C31 118.6(5) . . ?
C34 C35 H35 120.7 . . ?
C31 C35 H35 120.7 . . ?
C32 C36 H36A 109.5 . . ?
C32 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C32 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N10 C37 N11 112.1(3) . . ?
N10 C37 C41 128.3(4) . . ?
N11 C37 C41 119.4(4) . . ?
N10 C37 Li3 60.8(3) . . ?
N11 C37 Li3 51.5(3) . . ?
C41 C37 Li3 170.9(4) . . ?
N11 C38 C39 121.8(4) . . ?
N11 C38 C42 116.4(4) . . ?
C39 C38 C42 121.8(4) . . ?
C38 C39 C40 118.7(4) . . ?
C38 C39 H39 120.6 . . ?
C40 C39 H39 120.6 . . ?
C41 C40 C39 120.3(4) . . ?
C41 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?
C40 C41 C37 119.3(4) . . ?
C40 C41 H41 120.3 . . ?
C37 C41 H41 120.3 . . ?
C38 C42 H42A 109.5 . . ?
C38 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C38 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
N12 C43 N10 111.7(4) . . ?
N12 C43 C47 119.7(4) . . ?
N10 C43 C47 128.5(4) . . ?
N12 C43 Li4 51.9(3) . . ?
N10 C43 Li4 59.8(3) . . ?
C47 C43 Li4 171.5(4) . . ?
N12 C44 C45 121.9(4) . . ?
N12 C44 C48 116.6(4) . . ?
C45 C44 C48 121.4(4) . . ?
C46 C45 C44 118.2(4) . . ?
C46 C45 H45 120.9 . . ?
C44 C45 H45 120.9 . . ?
C47 C46 C45 120.8(4) . . ?
C47 C46 H46 119.6 . . ?
C45 C46 H46 119.6 . . ?
C46 C47 C43 118.8(4) . . ?
C46 C47 H47 120.6 . . ?
C43 C47 H47 120.6 . . ?
C44 C48 H48A 109.5 . . ?
C44 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C44 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?

_refine_diff_density_max         0.648
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.168

####################################################################### 
# 
# 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_ld190306sn1
_database_code_depnum_ccdc_archive 'CCDC 2032975'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2020-09-21 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N6 Sn'
_chemical_formula_weight         459.08

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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.8487(6)
_cell_length_b                   9.2747(4)
_cell_length_c                   16.9821(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.129(2)
_cell_angle_gamma                90
_cell_volume                     1809.76(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    38955
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.587
_exptl_crystal_size_mid          0.567
_exptl_crystal_size_min          0.158
_exptl_absorpt_coefficient_mu    1.429
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6017
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.802
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            38955
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.473
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4154
_reflns_number_gt                3733
_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 Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0249P)²+1.2224P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4154
_refine_ls_number_parameters     244
_refine_ls_number_restraints     228
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_ref         0.0564
_refine_ls_wR_factor_gt          0.0530
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.116
_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
Sn1 Sn 0.24428(2) 0.38494(2) 0.60324(2) 0.02420(5) Uani 1 1 d . . . . .
N1 N 0.23619(14) 0.63538(19) 0.61054(10) 0.0227(3) Uani 1 1 d . . . . .
C1 C 0.17501(16) 0.6517(2) 0.53220(12) 0.0207(4) Uani 1 1 d . . . . .
C2 C 0.25580(17) 0.7473(2) 0.66156(12) 0.0275(4) Uani 1 1 d . . . . .
H2 H 0.297611 0.731829 0.716188 0.033 Uiso 1 1 calc R U . . .
N2 N 0.16158(14) 0.51973(18) 0.49575(10) 0.0220(3) Uani 1 1 d . . . . .
N3 N 0.07281(15) 0.59579(18) 0.36195(10) 0.0238(3) Uani 1 1 d . . . . .
C3 C 0.21761(18) 0.8842(2) 0.63779(14) 0.0290(4) Uani 1 1 d . . . . .
H3 H 0.231932 0.962544 0.674906 0.035 Uiso 1 1 calc R U . . .
C4 C 0.15690(19) 0.9035(2) 0.55692(14) 0.0291(4) Uani 1 1 d . . . . .
H4 H 0.130339 0.997197 0.538598 0.035 Uiso 1 1 calc R U . . .
N4 N 0.32386(14) 0.24663(18) 0.49681(10) 0.0235(3) Uani 1 1 d . . . . .
N5 N 0.41984(14) 0.40024(18) 0.58996(10) 0.0223(3) Uani 1 1 d . . . . .
C5 C 0.13473(17) 0.7895(2) 0.50313(12) 0.0252(4) Uani 1 1 d . . . . .
H5 H 0.093582 0.803398 0.448196 0.030 Uiso 1 1 calc R U . . .
C6 C 0.09923(15) 0.4900(2) 0.41731(11) 0.0197(4) Uani 1 1 d . . . . .
N6 N 0.46274(14) 0.50537(18) 0.71346(10) 0.0234(3) Uani 1 1 d . . . . .
C7 C 0.01552(18) 0.5588(2) 0.28627(13) 0.0272(4) Uani 1 1 d . . . . .
H7 H -0.003830 0.633550 0.247021 0.033 Uiso 1 1 calc R U . . .
C9 C 0.00993(17) 0.3118(2) 0.31969(13) 0.0273(4) Uani 1 1 d . . . . .
H9 H -0.011277 0.214713 0.305492 0.033 Uiso 1 1 calc R U . . .
C8 C -0.01723(18) 0.4201(2) 0.26147(13) 0.0282(4) Uani 1 1 d . . . . .
H8 H -0.056682 0.399389 0.206903 0.034 Uiso 1 1 calc R U . . .
C10 C 0.06739(17) 0.3459(2) 0.39757(13) 0.0248(4) Uani 1 1 d . . . . .
H10 H 0.085607 0.272967 0.437939 0.030 Uiso 1 1 calc R U . . .
C11 C 0.43003(17) 0.3031(2) 0.53135(12) 0.0214(4) Uani 1 1 d . . . . .
C12 C 0.31295(19) 0.1502(2) 0.43684(13) 0.0279(4) Uani 1 1 d . . . . .
H12 H 0.237917 0.112231 0.412985 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4062(2) 0.1034(2) 0.40813(14) 0.0328(5) Uani 1 1 d . . . . .
H13 H 0.395974 0.035755 0.364957 0.039 Uiso 1 1 calc R U . . .
C14 C 0.5146(2) 0.1584(3) 0.44439(15) 0.0347(5) Uani 1 1 d . . . . .
H14 H 0.580535 0.126959 0.426512 0.042 Uiso 1 1 calc R U . . .
C15 C 0.52884(18) 0.2582(2) 0.50606(14) 0.0298(5) Uani 1 1 d . . . . .
H15 H 0.603648 0.295717 0.530921 0.036 Uiso 1 1 calc R U . . .
C16 C 0.50435(16) 0.4656(2) 0.64933(11) 0.0204(4) Uani 1 1 d . . . . .
C17 C 0.53433(19) 0.5747(2) 0.77476(13) 0.0275(4) Uani 1 1 d . . . . .
H17 H 0.504382 0.603670 0.819337 0.033 Uiso 1 1 calc R U . . .
C18 C 0.64900(19) 0.6069(2) 0.77754(14) 0.0305(5) Uani 1 1 d . . . . .
H18 H 0.697303 0.654220 0.823074 0.037 Uiso 1 1 calc R U . . .
C19 C 0.69079(19) 0.5673(3) 0.71124(15) 0.0329(5) Uani 1 1 d . . . . .
H19 H 0.768885 0.588886 0.710462 0.039 Uiso 1 1 calc R U . . .
C20 C 0.61935(18) 0.4967(2) 0.64630(13) 0.0284(4) Uani 1 1 d . . . . .
H20 H 0.647322 0.469595 0.600535 0.034 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 N5 2.1512(16) . ?
Sn1 N2 2.2321(16) . ?
Sn1 N1 2.3293(17) . ?
Sn1 N4 2.5756(16) . ?
N1 C2 1.336(3) . ?
N1 C1 1.359(2) . ?
C1 N2 1.364(3) . ?
C1 C5 1.410(3) . ?
C2 C3 1.374(3) . ?
C2 H2 0.9500 . ?
N2 C6 1.384(2) . ?
N3 C6 1.342(2) . ?
N3 C7 1.343(3) . ?
C3 C4 1.398(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
N4 C12 1.338(3) . ?
N4 C11 1.357(3) . ?
N5 C11 1.370(3) . ?
N5 C16 1.376(3) . ?
C5 H5 0.9500 . ?
C6 C10 1.407(3) . ?
N6 C17 1.336(3) . ?
N6 C16 1.352(3) . ?
C7 C8 1.380(3) . ?
C7 H7 0.9500 . ?
C9 C10 1.369(3) . ?
C9 C8 1.391(3) . ?
C9 H9 0.9500 . ?
C8 H8 0.9500 . ?
C10 H10 0.9500 . ?
C11 C15 1.405(3) . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C20 1.406(3) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9500 . ?
C20 H20 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
N5 Sn1 N2 96.89(6) . . ?
N5 Sn1 N1 89.61(6) . . ?
N2 Sn1 N1 57.96(6) . . ?
N5 Sn1 N4 55.26(6) . . ?
N2 Sn1 N4 82.40(6) . . ?
N1 Sn1 N4 124.12(5) . . ?
C2 N1 C1 120.98(18) . . ?
C2 N1 Sn1 143.78(14) . . ?
C1 N1 Sn1 94.49(12) . . ?
N1 C1 N2 108.63(17) . . ?
N1 C1 C5 119.86(18) . . ?
N2 C1 C5 131.49(18) . . ?
N1 C2 C3 122.32(19) . . ?
N1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C1 N2 C6 126.26(16) . . ?
C1 N2 Sn1 98.76(12) . . ?
C6 N2 Sn1 134.45(13) . . ?
C6 N3 C7 117.44(17) . . ?
C2 C3 C4 117.45(19) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C12 N4 C11 119.62(17) . . ?
C12 N4 Sn1 152.04(14) . . ?
C11 N4 Sn1 87.95(11) . . ?
C11 N5 C16 130.15(16) . . ?
C11 N5 Sn1 106.97(12) . . ?
C16 N5 Sn1 120.10(13) . . ?
C4 C5 C1 117.97(19) . . ?
C4 C5 H5 121.0 . . ?
C1 C5 H5 121.0 . . ?
N3 C6 N2 120.47(17) . . ?
N3 C6 C10 121.63(18) . . ?
N2 C6 C10 117.88(17) . . ?
C17 N6 C16 118.16(18) . . ?
N3 C7 C8 124.7(2) . . ?
N3 C7 H7 117.7 . . ?
C8 C7 H7 117.7 . . ?
C10 C9 C8 119.61(19) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C7 C8 C9 117.21(19) . . ?
C7 C8 H8 121.4 . . ?
C9 C8 H8 121.4 . . ?
C9 C10 C6 119.43(19) . . ?
C9 C10 H10 120.3 . . ?
C6 C10 H10 120.3 . . ?
N4 C11 N5 109.34(16) . . ?
N4 C11 C15 120.49(19) . . ?
N5 C11 C15 130.17(19) . . ?
N4 C12 C13 122.8(2) . . ?
N4 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C14 C13 C12 117.7(2) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C11 118.4(2) . . ?
C14 C15 H15 120.8 . . ?
C11 C15 H15 120.8 . . ?
N6 C16 N5 111.55(16) . . ?
N6 C16 C20 121.40(18) . . ?
N5 C16 C20 126.99(18) . . ?
N6 C17 C18 124.3(2) . . ?
N6 C17 H17 117.9 . . ?
C18 C17 H17 117.9 . . ?
C17 C18 C19 117.3(2) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 H18 121.3 . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C16 118.6(2) . . ?
C19 C20 H20 120.7 . . ?
C16 C20 H20 120.7 . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_ld190507Ge1
_database_code_depnum_ccdc_archive 'CCDC 2032977'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2020-09-21 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 Ge N6'
_chemical_formula_weight         469.08

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

_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                   8.8339(5)
_cell_length_b                   12.1659(6)
_cell_length_c                   12.3964(6)
_cell_angle_alpha                111.554(2)
_cell_angle_beta                 96.379(2)
_cell_angle_gamma                110.358(2)
_cell_volume                     1117.25(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    36087
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.591
_exptl_crystal_size_mid          0.575
_exptl_crystal_size_min          0.228
_exptl_absorpt_coefficient_mu    1.394
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4381
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.588
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            36087
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.492
_diffrn_reflns_theta_max         27.574
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5147
_reflns_number_gt                4703
_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 Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0298P)²+0.6353P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5147
_refine_ls_number_parameters     284
_refine_ls_number_restraints     252
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0644
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.015
_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 0.24340(2) 0.12874(2) 0.44229(2) 0.02156(6) Uani 1 1 d . U . . .
N1 N 0.40872(16) 0.15847(13) 0.58784(12) 0.0214(3) Uani 1 1 d . U . . .
C1 C 0.53978(18) 0.17003(14) 0.53784(14) 0.0198(3) Uani 1 1 d . U . . .
N2 N 0.48881(16) 0.17404(12) 0.43222(12) 0.0207(3) Uani 1 1 d . U . . .
C2 C 0.5872(2) 0.18437(16) 0.35810(14) 0.0244(3) Uani 1 1 d . U . . .
C3 C 0.7464(2) 0.19106(16) 0.38936(16) 0.0277(3) Uani 1 1 d . U . . .
H3 H 0.8186 0.2002 0.3388 0.033 Uiso 1 1 calc R U . . .
N3 N 0.53567(17) 0.16254(14) 0.76648(12) 0.0254(3) Uani 1 1 d . U . . .
C4 C 0.7996(2) 0.18426(16) 0.49563(16) 0.0277(3) Uani 1 1 d . U . . .
H4 H 0.9079 0.1866 0.5160 0.033 Uiso 1 1 calc R U . . .
N4 N 0.26806(17) 0.30709(13) 0.51507(12) 0.0224(3) Uani 1 1 d . U . . .
C5 C 0.69895(19) 0.17417(15) 0.57220(15) 0.0242(3) Uani 1 1 d . U . . .
H5 H 0.7360 0.1702 0.6451 0.029 Uiso 1 1 calc R U . . .
N5 N 0.18786(17) 0.36242(14) 0.69434(12) 0.0268(3) Uani 1 1 d . U . . .
C6 C 0.5179(3) 0.1905(2) 0.24594(17) 0.0370(4) Uani 1 1 d . U . . .
H6A H 0.6057 0.2086 0.2049 0.055 Uiso 1 1 calc R U . . .
H6B H 0.4791 0.2601 0.2670 0.055 Uiso 1 1 calc R U . . .
H6C H 0.4235 0.1070 0.1924 0.055 Uiso 1 1 calc R U . . .
N6 N 0.17125(16) 0.25485(12) 0.31841(11) 0.0203(3) Uani 1 1 d . U . . .
C7 C 0.39799(19) 0.14579(14) 0.69271(14) 0.0213(3) Uani 1 1 d . U . . .
C8 C 0.5206(2) 0.14875(18) 0.86829(16) 0.0310(4) Uani 1 1 d . U . . .
C9 C 0.3715(2) 0.1179(2) 0.89878(16) 0.0356(4) Uani 1 1 d . U . . .
H9 H 0.3654 0.1081 0.9710 0.043 Uiso 1 1 calc R U . . .
C10 C 0.2293(2) 0.10127(19) 0.82189(17) 0.0328(4) Uani 1 1 d . U . . .
H10 H 0.1248 0.0802 0.8411 0.039 Uiso 1 1 calc R U . . .
C11 C 0.2420(2) 0.11566(16) 0.71837(15) 0.0259(3) Uani 1 1 d . U . . .
H11 H 0.1470 0.1054 0.6649 0.031 Uiso 1 1 calc R U . . .
C12 C 0.6807(3) 0.1717(2) 0.94760(19) 0.0463(5) Uani 1 1 d . U . . .
H12A H 0.7420 0.1309 0.8976 0.069 Uiso 1 1 calc R U . . .
H12B H 0.6542 0.1336 1.0041 0.069 Uiso 1 1 calc R U . . .
H12C H 0.7501 0.2656 0.9928 0.069 Uiso 1 1 calc R U . . .
C13 C 0.31051(19) 0.38427(15) 0.64113(14) 0.0209(3) Uani 1 1 d . U . . .
C14 C 0.2257(2) 0.42872(18) 0.81468(16) 0.0305(4) Uani 1 1 d . U . . .
C15 C 0.3859(3) 0.51920(18) 0.88379(16) 0.0351(4) Uani 1 1 d . U . . .
H15 H 0.4089 0.5659 0.9686 0.042 Uiso 1 1 calc R U . . .
C16 C 0.5121(3) 0.5406(2) 0.82754(18) 0.0432(5) Uani 1 1 d . U . . .
H16 H 0.6237 0.6017 0.8734 0.052 Uiso 1 1 calc R U . . .
C17 C 0.4750(2) 0.47217(19) 0.70352(17) 0.0348(4) Uani 1 1 d . U . . .
H17 H 0.5598 0.4852 0.6627 0.042 Uiso 1 1 calc R U . . .
C18 C 0.0834(3) 0.3954(3) 0.8701(2) 0.0552(6) Uani 1 1 d . U . . .
H18A H -0.0105 0.4054 0.8311 0.083 Uiso 1 1 calc R U . . .
H18B H 0.1211 0.4540 0.9565 0.083 Uiso 1 1 calc R U . . .
H18C H 0.0469 0.3051 0.8589 0.083 Uiso 1 1 calc R U . . .
C19 C 0.20413(18) 0.34136(15) 0.43371(13) 0.0193(3) Uani 1 1 d . U . . .
C20 C 0.10107(19) 0.27340(15) 0.22887(14) 0.0221(3) Uani 1 1 d . U . . .
C21 C 0.0653(2) 0.38052(16) 0.25026(15) 0.0266(3) Uani 1 1 d . U . . .
H21 H 0.0154 0.3916 0.1853 0.032 Uiso 1 1 calc R U . . .
C22 C 0.1039(2) 0.47144(16) 0.36892(16) 0.0268(3) Uani 1 1 d . U . . .
H22 H 0.0824 0.5465 0.3855 0.032 Uiso 1 1 calc R U . . .
C23 C 0.1729(2) 0.45317(15) 0.46220(14) 0.0236(3) Uani 1 1 d . U . . .
H23 H 0.1989 0.5142 0.5436 0.028 Uiso 1 1 calc R U . . .
C24 C 0.0634(2) 0.17066(18) 0.10331(15) 0.0315(4) Uani 1 1 d . U . . .
H24A H 0.0566 0.2074 0.0456 0.047 Uiso 1 1 calc R U . . .
H24B H -0.0440 0.0971 0.0844 0.047 Uiso 1 1 calc R U . . .
H24C H 0.1529 0.1405 0.0982 0.047 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 N4 1.9387(13) . ?
Ge1 N1 2.0215(13) . ?
Ge1 N2 2.0733(13) . ?
N1 C1 1.3619(19) . ?
N1 C7 1.374(2) . ?
C1 N2 1.360(2) . ?
C1 C5 1.401(2) . ?
N2 C2 1.342(2) . ?
C2 C3 1.383(2) . ?
C2 C6 1.494(2) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
N3 C7 1.342(2) . ?
N3 C8 1.348(2) . ?
C4 C5 1.380(2) . ?
C4 H4 0.9500 . ?
N4 C19 1.3624(19) . ?
N4 C13 1.418(2) . ?
C5 H5 0.9500 . ?
N5 C13 1.329(2) . ?
N5 C14 1.344(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
N6 C20 1.340(2) . ?
N6 C19 1.3508(19) . ?
C7 C11 1.402(2) . ?
C8 C9 1.375(3) . ?
C8 C12 1.503(3) . ?
C9 C10 1.394(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.369(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C17 1.384(2) . ?
C14 C15 1.380(3) . ?
C14 C18 1.503(3) . ?
C15 C16 1.379(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C23 1.407(2) . ?
C20 C21 1.386(2) . ?
C20 C24 1.504(2) . ?
C21 C22 1.391(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.373(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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 Ge1 N1 92.15(5) . . ?
N4 Ge1 N2 96.00(5) . . ?
N1 Ge1 N2 64.20(5) . . ?
C1 N1 C7 127.79(13) . . ?
C1 N1 Ge1 95.50(9) . . ?
C7 N1 Ge1 135.46(10) . . ?
N2 C1 N1 106.16(13) . . ?
N2 C1 C5 120.31(14) . . ?
N1 C1 C5 133.50(15) . . ?
C2 N2 C1 122.46(13) . . ?
C2 N2 Ge1 143.32(11) . . ?
C1 N2 Ge1 93.25(9) . . ?
N2 C2 C3 119.24(15) . . ?
N2 C2 C6 117.32(15) . . ?
C3 C2 C6 123.43(15) . . ?
C2 C3 C4 119.20(15) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C7 N3 C8 117.80(14) . . ?
C5 C4 C3 121.65(15) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C19 N4 C13 121.78(13) . . ?
C19 N4 Ge1 112.56(10) . . ?
C13 N4 Ge1 124.12(10) . . ?
C4 C5 C1 117.11(15) . . ?
C4 C5 H5 121.4 . . ?
C1 C5 H5 121.4 . . ?
C13 N5 C14 118.35(15) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C20 N6 C19 119.09(13) . . ?
N3 C7 N1 119.32(14) . . ?
N3 C7 C11 122.49(14) . . ?
N1 C7 C11 118.20(14) . . ?
N3 C8 C9 122.98(16) . . ?
N3 C8 C12 114.77(16) . . ?
C9 C8 C12 122.24(17) . . ?
C8 C9 C10 118.83(16) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 119.15(16) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C7 118.75(15) . . ?
C10 C11 H11 120.6 . . ?
C7 C11 H11 120.6 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C13 C17 123.23(15) . . ?
N5 C13 N4 116.78(14) . . ?
C17 C13 N4 119.91(15) . . ?
N5 C14 C15 122.28(16) . . ?
N5 C14 C18 115.83(17) . . ?
C15 C14 C18 121.87(18) . . ?
C16 C15 C14 118.79(17) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 119.50(17) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.3 . . ?
C13 C17 C16 117.85(17) . . ?
C13 C17 H17 121.1 . . ?
C16 C17 H17 121.1 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N6 C19 N4 112.65(13) . . ?
N6 C19 C23 121.79(14) . . ?
N4 C19 C23 125.56(14) . . ?
N6 C20 C21 122.23(14) . . ?
N6 C20 C24 115.89(14) . . ?
C21 C20 C24 121.88(15) . . ?
C20 C21 C22 118.53(15) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C23 C22 C21 120.23(15) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C19 118.08(15) . . ?
C22 C23 H23 121.0 . . ?
C19 C23 H23 121.0 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_ld181112Sn1
_database_code_depnum_ccdc_archive 'CCDC 2032973'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2020-09-21 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Cl2 N6 Sn2'
_chemical_formula_weight         648.67

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'
Cl Cl 0.1484 0.1585 '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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   17.1415(8)
_cell_length_b                   8.3019(4)
_cell_length_c                   14.9727(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2130.72(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    19086
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.022
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.158
_exptl_absorpt_coefficient_mu    2.616
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.815
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            19086
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.376
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4850
_reflns_number_gt                3907
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.12(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4850
_refine_ls_number_parameters     272
_refine_ls_number_restraints     247
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.004
_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 0.31563(4) 0.97018(9) 0.60078(4) 0.01424(18) Uani 1 1 d . . . . .
Cl1 Cl 0.2466(2) 0.9995(3) 0.7506(5) 0.0211(12) Uani 1 1 d . . . . .
N1 N 0.2036(4) 0.8511(9) 0.5545(5) 0.0155(16) Uani 1 1 d . . . . .
C1 C 0.2178(5) 0.7776(12) 0.4754(7) 0.0136(19) Uani 1 1 d . . . . .
Sn2 Sn 0.43161(4) 0.97362(8) 0.39920(4) 0.01451(19) Uani 1 1 d . . . . .
Cl2 Cl 0.5011(2) 1.0061(3) 0.2509(4) 0.0204(11) Uani 1 1 d . . . . .
N2 N 0.2942(4) 0.7862(10) 0.4505(5) 0.0135(16) Uani 1 1 d . . . . .
C2 C 0.1553(5) 0.7111(12) 0.4263(7) 0.018(2) Uani 1 1 d . . . . .
H2 H 0.164139 0.660658 0.370305 0.021 Uiso 1 1 calc R U . . .
N3 N 0.3976(4) 0.7237(9) 0.3617(5) 0.0145(16) Uani 1 1 d . . . . .
C3 C 0.0820(6) 0.7210(12) 0.4613(7) 0.020(2) Uani 1 1 d . . . . .
H3 H 0.039473 0.675118 0.429445 0.024 Uiso 1 1 calc R U . . .
N4 N 0.3502(4) 0.7202(9) 0.6385(5) 0.0128(15) Uani 1 1 d . . . . .
C4 C 0.0680(6) 0.7976(12) 0.5431(8) 0.020(2) Uani 1 1 d . . . . .
H4 H 0.016862 0.804774 0.567067 0.024 Uiso 1 1 calc R U . . .
C5 C 0.1310(5) 0.8620(11) 0.5875(6) 0.0166(19) Uani 1 1 d . . . . .
H5 H 0.122882 0.915532 0.642824 0.020 Uiso 1 1 calc R U . . .
N5 N 0.4537(4) 0.7870(9) 0.5494(5) 0.0147(15) Uani 1 1 d . . . . .
C6 C 0.3291(5) 0.6759(11) 0.3992(7) 0.0138(17) Uani 1 1 d . . . . .
N6 N 0.5441(4) 0.8531(10) 0.4452(5) 0.0133(16) Uani 1 1 d . . . . .
C7 C 0.3060(7) 0.5123(11) 0.3850(17) 0.015(3) Uani 1 1 d . . . . .
H7 H 0.257644 0.475191 0.408100 0.018 Uiso 1 1 calc R U . . .
C8 C 0.3524(5) 0.4101(13) 0.3390(7) 0.020(2) Uani 1 1 d . . . . .
H8 H 0.336371 0.301489 0.330998 0.024 Uiso 1 1 calc R U . . .
C9 C 0.4235(7) 0.4608(17) 0.3030(10) 0.022(3) Uani 1 1 d . . . . .
H9 H 0.456420 0.389153 0.271005 0.027 Uiso 1 1 calc R U . . .
C10 C 0.4432(5) 0.6173(14) 0.3159(7) 0.017(2) Uani 1 1 d . . . . .
H10 H 0.491156 0.654766 0.291914 0.020 Uiso 1 1 calc R U . . .
C11 C 0.4190(5) 0.6730(11) 0.6006(7) 0.0142(17) Uani 1 1 d . . . . .
C12 C 0.4431(8) 0.5092(11) 0.612(2) 0.019(4) Uani 1 1 d . . . . .
H12 H 0.490528 0.472141 0.585876 0.022 Uiso 1 1 calc R U . . .
C13 C 0.3970(5) 0.4068(13) 0.6597(7) 0.020(2) Uani 1 1 d . . . . .
H13 H 0.412815 0.297939 0.667040 0.024 Uiso 1 1 calc R U . . .
C14 C 0.3274(6) 0.4585(17) 0.6982(9) 0.019(2) Uani 1 1 d . . . . .
H14 H 0.295408 0.386818 0.731460 0.023 Uiso 1 1 calc R U . . .
C15 C 0.3068(6) 0.6154(14) 0.6864(7) 0.020(2) Uani 1 1 d . . . . .
H15 H 0.259811 0.652807 0.712959 0.024 Uiso 1 1 calc R U . . .
C16 C 0.5299(5) 0.7763(11) 0.5240(6) 0.0125(18) Uani 1 1 d . . . . .
C17 C 0.5930(5) 0.7074(12) 0.5705(6) 0.018(2) Uani 1 1 d . . . . .
H17 H 0.584476 0.652332 0.625240 0.021 Uiso 1 1 calc R U . . .
C18 C 0.6674(5) 0.7204(12) 0.5358(7) 0.022(2) Uani 1 1 d . . . . .
H18 H 0.710244 0.675539 0.567410 0.026 Uiso 1 1 calc R U . . .
C19 C 0.6802(6) 0.7986(13) 0.4549(7) 0.019(2) Uani 1 1 d . . . . .
H19 H 0.731040 0.805576 0.429930 0.023 Uiso 1 1 calc R U . . .
C20 C 0.6175(5) 0.8650(11) 0.4127(6) 0.0176(19) Uani 1 1 d . . . . .
H20 H 0.625607 0.921656 0.358367 0.021 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 2.231(8) . ?
Sn1 N1 2.269(8) . ?
Sn1 Cl1 2.547(7) . ?
N1 C5 1.342(10) . ?
N1 C1 1.353(11) . ?
C1 N2 1.364(11) . ?
C1 C2 1.411(13) . ?
Sn2 N3 2.228(8) . ?
Sn2 N6 2.280(7) . ?
Sn2 Cl2 2.535(6) . ?
N2 C6 1.337(12) . ?
C2 C3 1.364(13) . ?
C2 H2 0.9500 . ?
N3 C6 1.360(11) . ?
N3 C10 1.364(12) . ?
C3 C4 1.400(13) . ?
C3 H3 0.9500 . ?
N4 C15 1.351(12) . ?
N4 C11 1.367(11) . ?
C4 C5 1.376(13) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
N5 C11 1.355(12) . ?
N5 C16 1.362(11) . ?
C6 C7 1.430(14) . ?
N6 C20 1.351(10) . ?
N6 C16 1.364(11) . ?
C7 C8 1.35(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.356(16) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.431(13) . ?
C12 C13 1.37(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.361(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.407(12) . ?
C17 C18 1.382(13) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(13) . ?
C18 H18 0.9500 . ?
C19 C20 1.364(13) . ?
C19 H19 0.9500 . ?
C20 H20 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 N1 84.1(3) . . ?
N4 Sn1 Cl1 89.4(2) . . ?
N1 Sn1 Cl1 85.3(2) . . ?
C5 N1 C1 121.3(8) . . ?
C5 N1 Sn1 130.0(6) . . ?
C1 N1 Sn1 108.1(6) . . ?
N1 C1 N2 112.9(8) . . ?
N1 C1 C2 119.6(8) . . ?
N2 C1 C2 127.3(9) . . ?
N3 Sn2 N6 83.6(3) . . ?
N3 Sn2 Cl2 90.1(2) . . ?
N6 Sn2 Cl2 85.0(2) . . ?
C6 N2 C1 123.5(8) . . ?
C3 C2 C1 118.4(9) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C6 N3 C10 120.9(8) . . ?
C6 N3 Sn2 113.2(6) . . ?
C10 N3 Sn2 125.4(6) . . ?
C2 C3 C4 121.3(9) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C15 N4 C11 120.7(8) . . ?
C15 N4 Sn1 126.0(7) . . ?
C11 N4 Sn1 113.0(6) . . ?
C5 C4 C3 117.8(9) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
N1 C5 C4 121.5(9) . . ?
N1 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C11 N5 C16 122.1(8) . . ?
N2 C6 N3 115.1(8) . . ?
N2 C6 C7 127.8(11) . . ?
N3 C6 C7 117.0(10) . . ?
C20 N6 C16 120.8(8) . . ?
C20 N6 Sn2 130.3(6) . . ?
C16 N6 Sn2 108.4(6) . . ?
C8 C7 C6 120.6(12) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.3(10) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C10 C9 C8 116.8(11) . . ?
C10 C9 H9 121.6 . . ?
C8 C9 H9 121.6 . . ?
C9 C10 N3 123.3(10) . . ?
C9 C10 H10 118.3 . . ?
N3 C10 H10 118.3 . . ?
N5 C11 N4 114.4(8) . . ?
N5 C11 C12 127.0(11) . . ?
N4 C11 C12 118.3(11) . . ?
C13 C12 C11 119.0(12) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 121.5(11) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 117.6(11) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
N4 C15 C14 122.9(10) . . ?
N4 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
N5 C16 N6 112.5(8) . . ?
N5 C16 C17 128.7(8) . . ?
N6 C16 C17 118.7(8) . . ?
C18 C17 C16 119.5(9) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.6(9) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 117.9(9) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
N6 C20 C19 122.5(9) . . ?
N6 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?

_refine_diff_density_max         2.453
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.159

