# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_nb030
_database_code_depnum_ccdc_archive 'CCDC 1546731'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;
_audit_creation_date             2017-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Cl Ge N2, C F3 O3 S'
_chemical_formula_sum            'C11 H8 Cl F3 Ge N2 O3 S'
_chemical_formula_weight         413.29
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.5779(7)
_cell_length_b                   16.7991(14)
_cell_length_c                   11.0317(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.030(3)
_cell_angle_gamma                90
_cell_volume                     1402.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6406
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.21
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.571
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0812 before and 0.0545 after correction. The Ratio of minimum to maximum transmission is 0.8605. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.957
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14581
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.041
_diffrn_reflns_theta_min         2.211
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker-Nonius APEXII CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       
'Bruker-Nonius APEXII CCD area detector and D8 diffractometer'
_diffrn_measurement_device_type  'Bruker D8 diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3326
_reflns_number_total             4100
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0256P)²+0.4378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0759
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.88691(3) 0.42468(2) 0.13345(2) 0.01547(7) Uani 1 1 d . . . . .
N1 N 0.8926(2) 0.41723(10) 0.32022(16) 0.0141(3) Uani 1 1 d . . . . .
N2 N 0.7225(2) 0.51838(10) 0.18085(16) 0.0148(4) Uani 1 1 d . . . . .
C1 C 0.9818(3) 0.35932(12) 0.3807(2) 0.0171(4) Uani 1 1 d . . . . .
H1 H 1.0502 0.3241 0.3381 0.021 Uiso 1 1 calc R . . . .
C2 C 0.9745(3) 0.35081(13) 0.5047(2) 0.0191(4) Uani 1 1 d . . . . .
H2 H 1.0370 0.3105 0.5457 0.023 Uiso 1 1 calc R . . . .
C3 C 0.8721(3) 0.40363(13) 0.5667(2) 0.0182(4) Uani 1 1 d . . . . .
H3 H 0.8645 0.3987 0.6503 0.022 Uiso 1 1 calc R . . . .
C5 C 0.7920(3) 0.46935(11) 0.3804(2) 0.0140(4) Uani 1 1 d . . . . .
C6 C 0.7002(3) 0.52852(12) 0.3011(2) 0.0142(4) Uani 1 1 d . . . . .
C7 C 0.5973(3) 0.59019(12) 0.3422(2) 0.0176(4) Uani 1 1 d . . . . .
H7 H 0.5856 0.5978 0.4249 0.021 Uiso 1 1 calc R . . . .
C8 C 0.5121(3) 0.64028(13) 0.2581(2) 0.0211(5) Uani 1 1 d . . . . .
H8 H 0.4412 0.6815 0.2837 0.025 Uiso 1 1 calc R . . . .
C9 C 0.5334(3) 0.62841(13) 0.1353(2) 0.0211(5) Uani 1 1 d . . . . .
H9 H 0.4764 0.6612 0.0777 0.025 Uiso 1 1 calc R . . . .
C10 C 0.6408(3) 0.56702(12) 0.0997(2) 0.0181(4) Uani 1 1 d . . . . .
H10 H 0.6566 0.5593 0.0175 0.022 Uiso 1 1 calc R . . . .
Cl1 Cl 1.12614(7) 0.50909(3) 0.14435(5) 0.01823(11) Uani 1 1 d . . . . .
C4 C 0.7806(3) 0.46397(12) 0.5048(2) 0.0166(4) Uani 1 1 d . . . . .
H4 H 0.7129 0.5001 0.5462 0.020 Uiso 1 1 calc R . . . .
C11 C 0.4923(3) 0.25086(13) 0.3555(2) 0.0231(5) Uani 1 1 d . . . . .
F1 F 0.5410(2) 0.18670(8) 0.29479(17) 0.0429(4) Uani 1 1 d . . . . .
F2 F 0.6263(2) 0.27122(9) 0.43150(15) 0.0368(4) Uani 1 1 d . . . . .
F3 F 0.3582(2) 0.22993(10) 0.42242(16) 0.0459(4) Uani 1 1 d . . . . .
S1 S 0.42516(7) 0.33231(3) 0.25372(5) 0.01537(11) Uani 1 1 d . . . . .
O1 O 0.5726(2) 0.34129(10) 0.17678(15) 0.0270(4) Uani 1 1 d . . . . .
O2 O 0.2656(2) 0.30233(9) 0.19249(15) 0.0222(4) Uani 1 1 d . . . . .
O3 O 0.4025(2) 0.39648(9) 0.33771(15) 0.0247(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ge1 N1 2.0624(18) . ?
Ge1 N2 2.0912(17) . ?
Ge1 Cl1 2.2997(6) . ?
N1 C1 1.342(3) . ?
N1 C5 1.357(2) . ?
N2 C6 1.356(3) . ?
N2 C10 1.339(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C5 C6 1.475(3) . ?
C5 C4 1.383(3) . ?
C6 C7 1.388(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
C11 F1 1.332(3) . ?
C11 F2 1.327(3) . ?
C11 F3 1.334(3) . ?
C11 S1 1.825(2) . ?
S1 O1 1.4461(16) . ?
S1 O2 1.4442(16) . ?
S1 O3 1.4377(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ge1 N2 77.12(7) . . ?
N1 Ge1 Cl1 90.59(5) . . ?
N2 Ge1 Cl1 90.08(5) . . ?
C1 N1 Ge1 121.61(14) . . ?
C1 N1 C5 120.36(19) . . ?
C5 N1 Ge1 117.85(14) . . ?
C6 N2 Ge1 116.45(14) . . ?
C10 N2 Ge1 123.54(15) . . ?
C10 N2 C6 120.01(18) . . ?
N1 C1 H1 119.2 . . ?
N1 C1 C2 121.51(19) . . ?
C2 C1 H1 119.2 . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.5(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
N1 C5 C6 113.81(18) . . ?
N1 C5 C4 120.65(19) . . ?
C4 C5 C6 125.53(18) . . ?
N2 C6 C5 114.64(17) . . ?
N2 C6 C7 121.0(2) . . ?
C7 C6 C5 124.4(2) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 118.9(2) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.5(2) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.0(2) . . ?
C10 C9 H9 120.5 . . ?
N2 C10 C9 121.6(2) . . ?
N2 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.72(19) . . ?
C5 C4 H4 120.6 . . ?
F1 C11 F3 107.72(19) . . ?
F1 C11 S1 111.88(17) . . ?
F2 C11 F1 107.64(19) . . ?
F2 C11 F3 107.4(2) . . ?
F2 C11 S1 111.99(15) . . ?
F3 C11 S1 110.02(16) . . ?
O1 S1 C11 103.93(11) . . ?
O2 S1 C11 103.04(10) . . ?
O2 S1 O1 114.56(10) . . ?
O3 S1 C11 101.79(11) . . ?
O3 S1 O1 114.96(10) . . ?
O3 S1 O2 115.94(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ge1 N1 C1 C2 -174.97(15) . . . . ?
Ge1 N1 C5 C6 -3.9(2) . . . . ?
Ge1 N1 C5 C4 175.55(14) . . . . ?
Ge1 N2 C6 C5 -2.0(2) . . . . ?
Ge1 N2 C6 C7 178.37(15) . . . . ?
Ge1 N2 C10 C9 -179.83(16) . . . . ?
N1 C1 C2 C3 0.1(3) . . . . ?
N1 C5 C6 N2 3.8(2) . . . . ?
N1 C5 C6 C7 -176.59(19) . . . . ?
N1 C5 C4 C3 -0.8(3) . . . . ?
N2 C6 C7 C8 2.0(3) . . . . ?
C1 N1 C5 C6 -179.05(17) . . . . ?
C1 N1 C5 C4 0.4(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C5 N1 C1 C2 0.0(3) . . . . ?
C5 C6 C7 C8 -177.56(19) . . . . ?
C6 N2 C10 C9 0.3(3) . . . . ?
C6 C5 C4 C3 178.52(19) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 N2 0.8(3) . . . . ?
C10 N2 C6 C5 177.89(18) . . . . ?
C10 N2 C6 C7 -1.7(3) . . . . ?
C4 C5 C6 N2 -175.62(19) . . . . ?
C4 C5 C6 C7 4.0(3) . . . . ?
F1 C11 S1 O1 -52.86(18) . . . . ?
F1 C11 S1 O2 66.94(17) . . . . ?
F1 C11 S1 O3 -172.59(16) . . . . ?
F2 C11 S1 O1 68.10(19) . . . . ?
F2 C11 S1 O2 -172.10(16) . . . . ?
F2 C11 S1 O3 -51.63(19) . . . . ?
F3 C11 S1 O1 -172.57(16) . . . . ?
F3 C11 S1 O2 -52.77(18) . . . . ?
F3 C11 S1 O3 67.70(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_nb024_0m
_database_code_depnum_ccdc_archive 'CCDC 1546732'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_mo_nb024_0m         
;
PROBLEM: Short Inter D...A Contact  O1     ..  N2      ..       2.87 Ang.
RESPONSE: We rationalize this as a packing effect as the oxygen should actually be interacting with Ge1, based on cation-anion pairing. From a charge and electronegativity point-of-view, the interaction of O1 and N2 makes little sense.
;
# Added during the CSD deposition process: Thursday 27 April 2017 07:19 PM
# end Validation Reply Form

_audit_creation_date             2017-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Ge N4, 2(C F3 O3 S), C2 H3 N'
_chemical_formula_sum            'C24 H19 F6 Ge N5 O6 S2'
_chemical_formula_weight         724.15
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6827(5)
_cell_length_b                   12.2345(7)
_cell_length_c                   13.5264(8)
_cell_angle_alpha                105.9780(10)
_cell_angle_beta                 96.5280(10)
_cell_angle_gamma                109.6380(10)
_cell_volume                     1412.75(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9850
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      30.06
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   0.837
_shelx_estimated_absorpt_T_min   0.760
_exptl_absorpt_coefficient_mu    1.321
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0461 before and 0.0372 after correction. The Ratio of minimum to maximum transmission is 0.8761. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30486
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.078
_diffrn_reflns_theta_min         1.608
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker-Nonius APEXII CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       
'Bruker-Nonius APEXII CCD area detector and D8 diffractometer'
_diffrn_measurement_device_type  'Bruker D8 diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7542
_reflns_number_total             8260
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         8260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0244
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0294P)²+0.6741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0630
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C4(H4)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.89769(2) 0.60125(2) 0.44008(2) 0.00834(4) Uani 1 1 d . . . . .
N1 N 0.93921(12) 0.54271(10) 0.27886(8) 0.01086(19) Uani 1 1 d . . . . .
N2 N 0.71889(11) 0.60172(10) 0.33796(8) 0.00903(18) Uani 1 1 d . . . . .
N3 N 0.83678(12) 0.70852(10) 0.57874(8) 0.00985(19) Uani 1 1 d . . . . .
N4 N 1.01806(12) 0.78687(10) 0.46042(8) 0.00950(19) Uani 1 1 d . . . . .
C1 C 1.05482(14) 0.50873(12) 0.26045(10) 0.0136(2) Uani 1 1 d . . . . .
H1 H 1.1367 0.5329 0.3160 0.016 Uiso 1 1 calc R . . . .
C2 C 1.05505(15) 0.43862(13) 0.16078(10) 0.0150(2) Uani 1 1 d . . . . .
H2 H 1.1361 0.4161 0.1493 0.018 Uiso 1 1 calc R . . . .
C3 C 0.93244(16) 0.40262(13) 0.07836(10) 0.0166(3) Uani 1 1 d . . . . .
H3 H 0.9313 0.3570 0.0105 0.020 Uiso 1 1 calc R . . . .
C5 C 0.81839(14) 0.50555(11) 0.20004(9) 0.0102(2) Uani 1 1 d . . . . .
C6 C 0.69740(14) 0.54493(11) 0.23277(9) 0.0098(2) Uani 1 1 d . . . . .
C7 C 0.56999(14) 0.52726(12) 0.16190(10) 0.0124(2) Uani 1 1 d . . . . .
H7 H 0.5543 0.4844 0.0905 0.015 Uiso 1 1 calc R . . . .
C8 C 0.46623(14) 0.57408(12) 0.19837(10) 0.0129(2) Uani 1 1 d . . . . .
H8 H 0.3817 0.5649 0.1516 0.015 Uiso 1 1 calc R . . . .
C9 C 0.49035(14) 0.63487(12) 0.30576(10) 0.0127(2) Uani 1 1 d . . . . .
H9 H 0.4235 0.6686 0.3318 0.015 Uiso 1 1 calc R . . . .
C10 C 0.61579(14) 0.64436(12) 0.37333(10) 0.0110(2) Uani 1 1 d . . . . .
H10 H 0.6294 0.6814 0.4456 0.013 Uiso 1 1 calc R . . . .
C11 C 0.74417(14) 0.65667(12) 0.63437(10) 0.0124(2) Uani 1 1 d . . . . .
H11 H 0.6727 0.5769 0.6020 0.015 Uiso 1 1 calc R . . . .
C12 C 0.75235(15) 0.71919(13) 0.73904(10) 0.0145(2) Uani 1 1 d . . . . .
H12 H 0.6866 0.6822 0.7761 0.017 Uiso 1 1 calc R . . . .
C13 C 0.86024(16) 0.83772(13) 0.78725(10) 0.0161(2) Uani 1 1 d . . . . .
H13 H 0.8693 0.8804 0.8577 0.019 Uiso 1 1 calc R . . . .
C14 C 0.95465(15) 0.89212(13) 0.72935(10) 0.0148(2) Uani 1 1 d . . . . .
H14 H 1.0260 0.9722 0.7598 0.018 Uiso 1 1 calc R . . . .
C15 C 0.94016(13) 0.82425(11) 0.62484(9) 0.0098(2) Uani 1 1 d . . . . .
C16 C 1.03786(13) 0.87025(11) 0.55671(9) 0.0095(2) Uani 1 1 d . . . . .
C17 C 1.14447(15) 0.98978(12) 0.58772(10) 0.0133(2) Uani 1 1 d . . . . .
H17 H 1.1569 1.0458 0.6537 0.016 Uiso 1 1 calc R . . . .
C18 C 1.23208(15) 1.02440(12) 0.51886(11) 0.0152(2) Uani 1 1 d . . . . .
H18 H 1.3062 1.1032 0.5391 0.018 Uiso 1 1 calc R . . . .
C19 C 1.20826(15) 0.94044(12) 0.41940(10) 0.0147(2) Uani 1 1 d . . . . .
H19 H 1.2637 0.9631 0.3714 0.018 Uiso 1 1 calc R . . . .
C20 C 1.10092(14) 0.82262(12) 0.39280(10) 0.0125(2) Uani 1 1 d . . . . .
H20 H 1.0853 0.7662 0.3263 0.015 Uiso 1 1 calc R . . . .
C4 C 0.81138(15) 0.43527(13) 0.09779(10) 0.0152(2) Uani 1 1 d . . . . .
H4 H 0.7275 0.4108 0.0437 0.018 Uiso 1 1 calc R . . . .
C22 C 0.33157(15) 0.17575(13) -0.05098(10) 0.0157(2) Uani 1 1 d . . . . .
F4 F 0.36789(11) 0.18761(10) 0.05099(7) 0.0256(2) Uani 1 1 d . . . . .
F5 F 0.29377(12) 0.05735(9) -0.10687(8) 0.0302(2) Uani 1 1 d . . . . .
F6 F 0.45634(10) 0.24086(10) -0.07477(8) 0.0271(2) Uani 1 1 d . . . . .
S2 S 0.17932(3) 0.22844(3) -0.07674(2) 0.01143(6) Uani 1 1 d . . . . .
O4 O 0.24402(11) 0.35632(9) -0.01016(8) 0.01782(19) Uani 1 1 d . . . . .
O5 O 0.05798(11) 0.14973(10) -0.04458(8) 0.0208(2) Uani 1 1 d . . . . .
O6 O 0.15603(11) 0.20707(9) -0.18917(7) 0.01709(19) Uani 1 1 d . . . . .
C21 C 0.66826(15) 0.22251(13) 0.30739(10) 0.0150(2) Uani 1 1 d . . . . .
F1 F 0.81285(10) 0.28781(9) 0.31243(7) 0.02438(19) Uani 1 1 d . . . . .
F2 F 0.65310(11) 0.10649(8) 0.29261(7) 0.02348(19) Uani 1 1 d . . . . .
F3 F 0.58595(11) 0.22389(9) 0.22149(7) 0.0262(2) Uani 1 1 d . . . . .
S1 S 0.61032(3) 0.28680(3) 0.42703(2) 0.01090(6) Uani 1 1 d . . . . .
O1 O 0.61158(11) 0.40341(9) 0.42020(8) 0.01667(19) Uani 1 1 d . . . . .
O2 O 0.72616(12) 0.29812(10) 0.51107(8) 0.0202(2) Uani 1 1 d . . . . .
O3 O 0.46291(11) 0.19610(10) 0.41480(9) 0.0194(2) Uani 1 1 d . . . . .
C23 C 0.71332(17) 0.16660(15) -0.15828(13) 0.0236(3) Uani 1 1 d . . . . .
N5 N 0.73364(16) 0.24450(14) -0.19184(11) 0.0271(3) Uani 1 1 d . . . . .
C24 C 0.6903(2) 0.0680(2) -0.1142(2) 0.0530(7) Uani 1 1 d . . . . .
H24A H 0.6641 -0.0086 -0.1702 0.079 Uiso 1 1 calc GR . . . .
H24B H 0.6103 0.0629 -0.0776 0.079 Uiso 1 1 calc GR . . . .
H24C H 0.7812 0.0844 -0.0658 0.079 Uiso 1 1 calc GR . . . .


_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 2.2278(10) . ?
Ge1 N2 2.0911(10) . ?
Ge1 N3 2.2372(10) . ?
Ge1 N4 2.0965(11) . ?
N1 C1 1.3443(16) . ?
N1 C5 1.3431(15) . ?
N2 C6 1.3571(15) . ?
N2 C10 1.3486(15) . ?
N3 C11 1.3441(16) . ?
N3 C15 1.3472(16) . ?
N4 C16 1.3616(15) . ?
N4 C20 1.3500(16) . ?
C1 H1 0.9300 . ?
C1 C2 1.3852(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.3870(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.3890(18) . ?
C5 C6 1.4767(16) . ?
C5 C4 1.3935(17) . ?
C6 C7 1.3875(17) . ?
C7 H7 0.9300 . ?
C7 C8 1.3874(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.3889(17) . ?
C9 H9 0.9300 . ?
C9 C10 1.3851(17) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.3904(17) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.3903(18) . ?
C14 H14 0.9300 . ?
C14 C15 1.3921(17) . ?
C15 C16 1.4787(17) . ?
C16 C17 1.3890(18) . ?
C17 H17 0.9300 . ?
C17 C18 1.3863(18) . ?
C18 H18 0.9300 . ?
C18 C19 1.3885(18) . ?
C19 H19 0.9300 . ?
C19 C20 1.3820(19) . ?
C20 H20 0.9300 . ?
C4 H4 0.9300 . ?
C22 F4 1.3389(15) . ?
C22 F5 1.3348(16) . ?
C22 F6 1.3342(16) . ?
C22 S2 1.8319(14) . ?
S2 O4 1.4451(10) . ?
S2 O5 1.4433(10) . ?
S2 O6 1.4476(9) . ?
C21 F1 1.3415(16) . ?
C21 F2 1.3316(16) . ?
C21 F3 1.3397(15) . ?
C21 S1 1.8315(13) . ?
S1 O1 1.4509(10) . ?
S1 O2 1.4452(10) . ?
S1 O3 1.4410(10) . ?
C23 N5 1.134(2) . ?
C23 C24 1.451(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ge1 N3 159.26(4) . . ?
N2 Ge1 N1 74.31(4) . . ?
N2 Ge1 N3 90.30(4) . . ?
N2 Ge1 N4 89.55(4) . . ?
N4 Ge1 N1 91.11(4) . . ?
N4 Ge1 N3 74.63(4) . . ?
C1 N1 Ge1 122.44(8) . . ?
C5 N1 Ge1 114.39(8) . . ?
C5 N1 C1 119.83(11) . . ?
C6 N2 Ge1 118.25(8) . . ?
C10 N2 Ge1 122.39(8) . . ?
C10 N2 C6 118.97(10) . . ?
C11 N3 Ge1 123.85(9) . . ?
C11 N3 C15 119.55(11) . . ?
C15 N3 Ge1 112.40(8) . . ?
C16 N4 Ge1 116.69(8) . . ?
C20 N4 Ge1 122.66(8) . . ?
C20 N4 C16 119.08(11) . . ?
N1 C1 H1 119.2 . . ?
N1 C1 C2 121.62(12) . . ?
C2 C1 H1 119.2 . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.88(12) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.54(12) . . ?
C4 C3 H3 120.2 . . ?
N1 C5 C6 113.91(10) . . ?
N1 C5 C4 121.53(11) . . ?
C4 C5 C6 124.56(11) . . ?
N2 C6 C5 115.61(10) . . ?
N2 C6 C7 121.27(11) . . ?
C7 C6 C5 123.12(11) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.48(11) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.09(11) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.79(11) . . ?
C10 C9 H9 120.6 . . ?
N2 C10 C9 122.28(11) . . ?
N2 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
N3 C11 H11 119.1 . . ?
N3 C11 C12 121.73(12) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.87(12) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.45(12) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.62(12) . . ?
C15 C14 H14 120.7 . . ?
N3 C15 C14 121.76(11) . . ?
N3 C15 C16 114.63(10) . . ?
C14 C15 C16 123.59(12) . . ?
N4 C16 C15 115.55(11) . . ?
N4 C16 C17 121.34(11) . . ?
C17 C16 C15 123.11(11) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 119.07(12) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.47(12) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 118.98(12) . . ?
C20 C19 H19 120.5 . . ?
N4 C20 C19 122.00(12) . . ?
N4 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
C3 C4 C5 118.55(12) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
F4 C22 S2 111.41(9) . . ?
F5 C22 F4 107.07(11) . . ?
F5 C22 S2 111.98(9) . . ?
F6 C22 F4 107.01(11) . . ?
F6 C22 F5 107.61(11) . . ?
F6 C22 S2 111.48(10) . . ?
O4 S2 C22 102.58(6) . . ?
O4 S2 O6 115.33(6) . . ?
O5 S2 C22 102.98(6) . . ?
O5 S2 O4 115.25(6) . . ?
O5 S2 O6 115.05(6) . . ?
O6 S2 C22 102.94(6) . . ?
F1 C21 S1 111.24(9) . . ?
F2 C21 F1 107.67(11) . . ?
F2 C21 F3 107.77(11) . . ?
F2 C21 S1 111.57(9) . . ?
F3 C21 F1 107.12(11) . . ?
F3 C21 S1 111.25(9) . . ?
O1 S1 C21 103.23(6) . . ?
O2 S1 C21 103.26(6) . . ?
O2 S1 O1 114.36(6) . . ?
O3 S1 C21 103.37(6) . . ?
O3 S1 O1 114.72(6) . . ?
O3 S1 O2 115.57(7) . . ?
N5 C23 C24 178.91(18) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ge1 N1 C1 C2 160.10(10) . . . . ?
Ge1 N1 C5 C6 17.45(13) . . . . ?
Ge1 N1 C5 C4 -162.00(10) . . . . ?
Ge1 N2 C6 C5 -9.42(14) . . . . ?
Ge1 N2 C6 C7 171.27(9) . . . . ?
Ge1 N2 C10 C9 -174.29(10) . . . . ?
Ge1 N3 C11 C12 154.89(10) . . . . ?
Ge1 N3 C15 C14 -157.51(10) . . . . ?
Ge1 N3 C15 C16 20.75(12) . . . . ?
Ge1 N4 C16 C15 -15.24(13) . . . . ?
Ge1 N4 C16 C17 164.16(9) . . . . ?
Ge1 N4 C20 C19 -163.47(10) . . . . ?
N1 C1 C2 C3 -0.2(2) . . . . ?
N1 C5 C6 N2 -6.10(16) . . . . ?
N1 C5 C6 C7 173.19(12) . . . . ?
N1 C5 C4 C3 0.6(2) . . . . ?
N2 C6 C7 C8 3.39(19) . . . . ?
N3 C11 C12 C13 -0.70(19) . . . . ?
N3 C15 C16 N4 -4.86(15) . . . . ?
N3 C15 C16 C17 175.75(11) . . . . ?
N4 C16 C17 C18 0.05(18) . . . . ?
C1 N1 C5 C6 177.33(11) . . . . ?
C1 N1 C5 C4 -2.11(19) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C5 N1 C1 C2 1.9(2) . . . . ?
C5 C6 C7 C8 -175.86(12) . . . . ?
C6 N2 C10 C9 -1.59(18) . . . . ?
C6 C5 C4 C3 -178.76(13) . . . . ?
C6 C7 C8 C9 -1.74(19) . . . . ?
C7 C8 C9 C10 -1.42(19) . . . . ?
C8 C9 C10 N2 3.2(2) . . . . ?
C10 N2 C6 C5 177.57(11) . . . . ?
C10 N2 C6 C7 -1.74(18) . . . . ?
C11 N3 C15 C14 0.34(18) . . . . ?
C11 N3 C15 C16 178.60(10) . . . . ?
C11 C12 C13 C14 1.6(2) . . . . ?
C12 C13 C14 C15 -1.6(2) . . . . ?
C13 C14 C15 N3 0.59(19) . . . . ?
C13 C14 C15 C16 -177.51(12) . . . . ?
C14 C15 C16 N4 173.36(11) . . . . ?
C14 C15 C16 C17 -6.03(19) . . . . ?
C15 N3 C11 C12 -0.28(18) . . . . ?
C15 C16 C17 C18 179.40(12) . . . . ?
C16 N4 C20 C19 1.79(18) . . . . ?
C16 C17 C18 C19 2.06(19) . . . . ?
C17 C18 C19 C20 -2.2(2) . . . . ?
C18 C19 C20 N4 0.3(2) . . . . ?
C20 N4 C16 C15 178.63(11) . . . . ?
C20 N4 C16 C17 -1.96(17) . . . . ?
C4 C5 C6 N2 173.32(12) . . . . ?
C4 C5 C6 C7 -7.4(2) . . . . ?
F4 C22 S2 O4 60.58(11) . . . . ?
F4 C22 S2 O5 -59.42(11) . . . . ?
F4 C22 S2 O6 -179.35(10) . . . . ?
F5 C22 S2 O4 -179.53(10) . . . . ?
F5 C22 S2 O5 60.47(11) . . . . ?
F5 C22 S2 O6 -59.46(11) . . . . ?
F6 C22 S2 O4 -58.90(11) . . . . ?
F6 C22 S2 O5 -178.90(9) . . . . ?
F6 C22 S2 O6 61.17(11) . . . . ?
F1 C21 S1 O1 68.56(10) . . . . ?
F1 C21 S1 O2 -50.82(11) . . . . ?
F1 C21 S1 O3 -171.61(9) . . . . ?
F2 C21 S1 O1 -171.18(9) . . . . ?
F2 C21 S1 O2 69.44(11) . . . . ?
F2 C21 S1 O3 -51.35(11) . . . . ?
F3 C21 S1 O1 -50.79(11) . . . . ?
F3 C21 S1 O2 -170.17(10) . . . . ?
F3 C21 S1 O3 69.04(11) . . . . ?
# end Validation Reply Form

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nb015
_database_code_depnum_ccdc_archive 'CCDC 1546733'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT214_nb015               
;
PROBLEM: Atom F4C     (Anion/Solvent) ADP max/min Ratio          5.8 prolat
RESPONSE: The anions are severely disordered. Full resolution of this disorder was not possible.
;
# Added during the CSD deposition process: Thursday 27 April 2017 07:19 PM
# end Validation Reply Form

_audit_creation_date             2017-04-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C20 H16 N4 Sn, 2(C F3 O3 S), C1 H2 Cl2, 1.16(C2 H3 N)'
_chemical_formula_sum            'C25.32 H21.48 Cl2 F6.01 N5.16 O6.01 S2 Sn'
_chemical_formula_weight         862.12
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.3539(4)
_cell_length_b                   19.7280(9)
_cell_length_c                   17.8782(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.627(2)
_cell_angle_gamma                90
_cell_volume                     3206.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9691
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.040
_cell_measurement_theta_min      2.374
_shelx_estimated_absorpt_T_max   0.852
_shelx_estimated_absorpt_T_min   0.644
_exptl_absorpt_coefficient_mu    1.178
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0660 before and 0.0441 after correction. The Ratio of minimum to maximum transmission is 0.7272. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1711
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36861
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.103
_diffrn_reflns_theta_min         1.562
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker-Nonius APEXII CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       
'Bruker-Nonius APEXII CCD area detector and D8 diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7820
_reflns_number_total             9384
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.317
_refine_diff_density_min         -2.032
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         9384
_refine_ls_number_restraints     1332
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0099P)²+17.5371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1179
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C25A-C24A \\sim C25B-C24B
 with sigma of 0.02
 N5A-C24A \\sim N5B-C24B
 with sigma of 0.02
 Cl1B-C23B \\sim Cl1A-C23A \\sim Cl2B-C23B \\sim Cl2A-C23A
 with sigma of 0.02
 S2C-O6C \\sim S2C-O4C
 with sigma of 0.01
 S2C-O6C \\sim S2C-O4C \\sim S2C-O5A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C24A) = Uanis(C24B)
Uanis(S2A) = Uanis(S2B) = Uanis(S2C)
Uanis(O6A) = Uanis(O6B)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 1*[Sof(S2B)+Sof(C22B)+Sof(F4B)+Sof(F5B)+Sof(F6B)+Sof(O4B)+Sof(O5B)+Sof(O6B)]+
 1*[Sof(S2C)+Sof(C22C)+Sof(F4C)+Sof(F5C)+Sof(F6C)+Sof(O4C)+Sof(O5A)+Sof(O6C)]+1*
 [Sof(S2A)+Sof(C22A)+Sof(F4A)+Sof(F5A)+Sof(F6A)+Sof(O4A)+Sof(O5C)+Sof(O6A)]=1
 with esd of 0.01
 Sof(N5A)=Sof(C24A)=Sof(C25A)=Sof(H25A)=Sof(H25B)=Sof(H25C)=1-FVAR(1)
 Sof(C23B)=Sof(H23C)=Sof(H23D)=Sof(Cl1B)=Sof(Cl2B)=1-FVAR(2)
 Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(Cl1A)=Sof(Cl2A)=FVAR(2)
 Sof(S2B)=Sof(C22B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=Sof(O4B)=Sof(O5B)=Sof(O6B)=
 FVAR(3)
 Sof(S2C)=Sof(C22C)=Sof(F4C)=Sof(F5C)=Sof(F6C)=Sof(O4C)=Sof(O5A)=Sof(O6C)=
 FVAR(4)
 Sof(S2A)=Sof(C22A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(O4A)=Sof(O5C)=Sof(O6A)=
 FVAR(5)
 Fixed Sof: N5B(0.5) C24B(0.5) C25B(0.5) H25D(0.5) H25E(0.5) H25F(0.5)
6.a Free rotating group:
 S2A(C22A,F4A,F5A,F6A,O4A,O5C,O6A), S2B(C22B,F4B,F5B,F6B,O4B,O5B,O6B),
 S2C(C22C,F4C,F5C,F6C,O4C), N5B(C24B,C25B)
6.b Secondary CH2 refined with riding coordinates:
 C23A(H23A,H23B), C23B(H23C,H23D)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20)
6.d Idealised Me refined as rotating group:
 C25B(H25D,H25E,H25F), C25A(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.36082(3) 0.34207(2) 0.31201(2) 0.01692(7) Uani 1 1 d . U . . .
N1 N 0.1276(4) 0.29941(18) 0.24363(19) 0.0185(7) Uani 1 1 d . U . . .
N2 N 0.3869(4) 0.24963(17) 0.2313(2) 0.0189(7) Uani 1 1 d . U . . .
N3 N 0.6021(4) 0.30808(17) 0.37875(19) 0.0183(6) Uani 1 1 d . U . . .
N4 N 0.3544(4) 0.24728(17) 0.39139(19) 0.0183(6) Uani 1 1 d . U . . .
C1 C 0.0050(4) 0.3321(2) 0.2484(2) 0.0221(8) Uani 1 1 d . U . . .
H1 H 0.0107 0.3651 0.2862 0.027 Uiso 1 1 calc R . . . .
C2 C -0.1306(5) 0.3187(2) 0.1990(2) 0.0234(8) Uani 1 1 d . U . . .
H2 H -0.2148 0.3418 0.2036 0.028 Uiso 1 1 calc R . . . .
C3 C -0.1367(5) 0.2700(2) 0.1429(2) 0.0240(9) Uani 1 1 d . U . . .
H3 H -0.2262 0.2594 0.1094 0.029 Uiso 1 1 calc R . . . .
C4 C -0.0101(5) 0.2371(2) 0.1364(2) 0.0218(8) Uani 1 1 d . U . . .
H4 H -0.0127 0.2047 0.0983 0.026 Uiso 1 1 calc R . . . .
C5 C 0.1223(4) 0.2534(2) 0.1883(2) 0.0183(7) Uani 1 1 d . U . . .
C6 C 0.2654(4) 0.2226(2) 0.1847(2) 0.0182(7) Uani 1 1 d . U . . .
C7 C 0.2745(5) 0.1696(2) 0.1350(2) 0.0236(8) Uani 1 1 d . U . . .
H7 H 0.1896 0.1508 0.1042 0.028 Uiso 1 1 calc R . . . .
C8 C 0.4121(5) 0.1448(2) 0.1319(3) 0.0259(9) Uani 1 1 d . U . . .
H8 H 0.4206 0.1094 0.0988 0.031 Uiso 1 1 calc R . . . .
C9 C 0.5360(5) 0.1735(2) 0.1786(2) 0.0230(8) Uani 1 1 d . U . . .
H9 H 0.6292 0.1579 0.1774 0.028 Uiso 1 1 calc R . . . .
C10 C 0.5195(5) 0.2258(2) 0.2270(2) 0.0202(8) Uani 1 1 d . U . . .
H10 H 0.6033 0.2454 0.2579 0.024 Uiso 1 1 calc R . . . .
C11 C 0.7182(4) 0.3465(2) 0.3745(2) 0.0206(8) Uani 1 1 d . U . . .
H11 H 0.7041 0.3838 0.3417 0.025 Uiso 1 1 calc R . . . .
C12 C 0.8578(5) 0.3323(3) 0.4172(2) 0.0262(9) Uani 1 1 d . U . . .
H12 H 0.9369 0.3599 0.4143 0.031 Uiso 1 1 calc R . . . .
C13 C 0.8774(5) 0.2764(3) 0.4644(3) 0.0298(10) Uani 1 1 d . U . . .
H13 H 0.9710 0.2651 0.4928 0.036 Uiso 1 1 calc R . . . .
C14 C 0.7582(5) 0.2370(3) 0.4698(3) 0.0281(9) Uani 1 1 d . U . . .
H14 H 0.7705 0.1992 0.5017 0.034 Uiso 1 1 calc R . . . .
C15 C 0.6191(4) 0.2549(2) 0.4265(2) 0.0190(7) Uani 1 1 d . U . . .
C16 C 0.4818(4) 0.2191(2) 0.4312(2) 0.0189(7) Uani 1 1 d . U . . .
C17 C 0.4830(5) 0.1619(2) 0.4763(3) 0.0290(9) Uani 1 1 d . U . . .
H17 H 0.5718 0.1429 0.5023 0.035 Uiso 1 1 calc R . . . .
C18 C 0.3518(6) 0.1335(2) 0.4825(3) 0.0301(10) Uani 1 1 d . U . . .
H18 H 0.3509 0.0953 0.5128 0.036 Uiso 1 1 calc R . . . .
C19 C 0.2222(5) 0.1624(2) 0.4430(3) 0.0274(9) Uani 1 1 d . U . . .
H19 H 0.1322 0.1443 0.4465 0.033 Uiso 1 1 calc R . . . .
C20 C 0.2277(5) 0.2191(2) 0.3980(2) 0.0218(8) Uani 1 1 d . U . . .
H20 H 0.1398 0.2383 0.3712 0.026 Uiso 1 1 calc R . . . .
C21 C 0.2731(5) 0.4838(2) 0.4931(3) 0.0236(8) Uani 1 1 d . U . . .
F1 F 0.1366(3) 0.50572(14) 0.48900(19) 0.0370(7) Uani 1 1 d . U . . .
F2 F 0.3580(3) 0.50732(15) 0.55801(19) 0.0388(7) Uani 1 1 d . U . . .
F3 F 0.3187(3) 0.51193(14) 0.43514(18) 0.0349(7) Uani 1 1 d . U . . .
S1 S 0.27939(10) 0.39177(5) 0.48908(5) 0.01457(17) Uani 1 1 d . U . . .
O1 O 0.1878(3) 0.37700(16) 0.41335(17) 0.0230(6) Uani 1 1 d . U . . .
O2 O 0.2201(3) 0.37031(16) 0.55214(18) 0.0256(6) Uani 1 1 d . U . . .
O3 O 0.4328(3) 0.37666(14) 0.49611(17) 0.0193(6) Uani 1 1 d . U . . .
S2A S 0.0411(11) -0.1171(4) 0.3722(5) 0.0196(4) Uani 0.215(4) 1 d . U P A 3
C22A C 0.0596(8) -0.0473(3) 0.4430(4) 0.030(3) Uani 0.215(4) 1 d G U P A 3
F4A F -0.0701(10) -0.0302(5) 0.4569(6) 0.043(4) Uani 0.215(4) 1 d G U P A 3
F5A F 0.1487(11) -0.0640(6) 0.5107(5) 0.038(3) Uani 0.215(4) 1 d G U P A 3
F6A F 0.1151(14) 0.0088(4) 0.4185(7) 0.046(4) Uani 0.215(4) 1 d G U P A 3
O4A O -0.0575(15) -0.0885(6) 0.3051(4) 0.023(5) Uani 0.215(4) 1 d G U P A 3
O5C O -0.0194(15) -0.1711(4) 0.4098(7) 0.027(5) Uani 0.215(4) 1 d G U P A 3
O6A O 0.1911(13) -0.1269(6) 0.3661(8) 0.0213(11) Uani 0.215(4) 1 d G U P A 3
S2B S 0.0519(3) -0.10620(12) 0.37527(17) 0.0196(4) Uani 0.572(5) 1 d . U P B 1
C22B C 0.1132(3) -0.02126(11) 0.41391(14) 0.0234(15) Uani 0.572(5) 1 d G U P B
1
F4B F -0.0003(4) 0.01836(14) 0.4189(2) 0.0340(12) Uani 0.572(5) 1 d G U P B 1
F5B F 0.2018(4) -0.02481(18) 0.48449(17) 0.0363(13) Uani 0.572(5) 1 d G U P B 1
F6B F 0.1878(4) 0.01134(14) 0.3694(2) 0.0362(14) Uani 0.572(5) 1 d G U P B 1
O4B O -0.0402(5) -0.0904(2) 0.30039(16) 0.020(2) Uani 0.572(5) 1 d G U P B 1
O5B O -0.0242(4) -0.13145(16) 0.4311(2) 0.0304(14) Uani 0.572(5) 1 d G U P B 1
O6B O 0.1895(5) -0.13942(14) 0.3749(3) 0.0213(11) Uani 0.572(5) 1 d G U P B 1
S2C S -0.0281(5) -0.1047(2) 0.3776(2) 0.0196(4) Uani 0.217(3) 1 d D U P C 2
C22C C 0.1584(5) -0.0679(3) 0.4100(4) 0.024(3) Uani 0.217(3) 1 d G U P C 2
F4C F 0.2047(7) -0.0682(5) 0.4868(4) 0.024(3) Uani 0.217(3) 1 d G U P C 2
F5C F 0.2580(5) -0.1023(5) 0.3823(5) 0.031(3) Uani 0.217(3) 1 d G U P C 2
F6C F 0.1631(8) -0.0035(3) 0.3871(7) 0.037(4) Uani 0.217(3) 1 d G U P C 2
O4C O -0.1155(5) -0.0605(4) 0.4136(5) 0.029(3) Uani 0.217(3) 1 d DG U P C 2
O5A O -0.015(2) -0.1712(6) 0.4113(11) 0.028(5) Uani 0.217(3) 1 d D U P C 2
O6C O -0.043(2) -0.1072(11) 0.2951(5) 0.016(3) Uani 0.217(3) 1 d D U P C 2
C23A C 0.6580(8) 0.0140(4) 0.3046(4) 0.0455(17) Uani 0.838(10) 1 d D U P D 1
H23A H 0.7299 -0.0179 0.3327 0.055 Uiso 0.838(10) 1 calc R . P D 1
H23B H 0.6967 0.0594 0.3165 0.055 Uiso 0.838(10) 1 calc R . P D 1
Cl1A Cl 0.6323(4) -0.00072(11) 0.20503(14) 0.0394(6) Uani 0.838(10) 1 d D U P D
1
Cl2A Cl 0.4940(4) 0.00551(18) 0.33486(15) 0.0689(10) Uani 0.838(10) 1 d D U P D
1
C23B C 0.584(4) 0.020(2) 0.3138(15) 0.058(8) Uani 0.162(10) 1 d D U P D 2
H23C H 0.5792 0.0690 0.3189 0.070 Uiso 0.162(10) 1 calc R . P D 2
H23D H 0.6755 0.0043 0.3467 0.070 Uiso 0.162(10) 1 calc R . P D 2
Cl1B Cl 0.576(2) -0.0017(7) 0.2169(9) 0.051(3) Uani 0.162(10) 1 d D U P D 2
Cl2B Cl 0.4325(15) -0.0185(8) 0.3414(8) 0.065(4) Uani 0.162(10) 1 d D U P D 2
N5A N -0.1105(17) 0.1502(11) 0.3065(10) 0.044(3) Uani 0.657(9) 1 d D U P E 2
N5B N -0.1089(19) 0.1389(14) 0.2917(13) 0.045(4) Uani 0.5 1 d D U P F -1
C24B C -0.0213(14) 0.1107(8) 0.2668(8) 0.051(2) Uani 0.5 1 d DG U P F -1
C25B C 0.0882(14) 0.0754(6) 0.2356(8) 0.045(3) Uani 0.5 1 d DG U P F -1
H25D H 0.1199 0.1042 0.1994 0.068 Uiso 0.5 1 calc GR . P F -1
H25E H 0.0461 0.0347 0.2103 0.068 Uiso 0.5 1 calc GR . P F -1
H25F H 0.1710 0.0641 0.2767 0.068 Uiso 0.5 1 calc GR . P F -1
C24A C -0.0679(12) 0.1174(7) 0.2629(7) 0.051(2) Uani 0.657(9) 1 d D U P E 2
C25A C 0.0035(12) 0.0686(5) 0.2178(6) 0.049(2) Uani 0.657(9) 1 d D U P E 2
H25A H -0.0223 0.0808 0.1644 0.073 Uiso 0.657(9) 1 calc GR . P E 2
H25B H -0.0302 0.0234 0.2240 0.073 Uiso 0.657(9) 1 calc GR . P E 2
H25C H 0.1084 0.0706 0.2365 0.073 Uiso 0.657(9) 1 calc GR . P E 2


_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 2.389(3) . ?
Sn1 N2 2.373(3) . ?
Sn1 N3 2.387(3) . ?
Sn1 N4 2.357(3) . ?
N1 C1 1.335(5) . ?
N1 C5 1.336(5) . ?
N2 C6 1.351(5) . ?
N2 C10 1.345(5) . ?
N3 C11 1.341(5) . ?
N3 C15 1.338(5) . ?
N4 C16 1.355(5) . ?
N4 C20 1.339(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.390(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.399(5) . ?
C5 C6 1.484(6) . ?
C6 C7 1.389(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.390(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.377(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(6) . ?
C15 C16 1.486(6) . ?
C16 C17 1.385(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.377(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(6) . ?
C20 H20 0.9300 . ?
C21 F1 1.334(5) . ?
C21 F2 1.326(5) . ?
C21 F3 1.330(5) . ?
C21 S1 1.819(4) . ?
S1 O1 1.451(3) . ?
S1 O2 1.433(3) . ?
S1 O3 1.442(3) . ?
S2A C22A 1.8509 . ?
S2A O4A 1.4454 . ?
S2A O5C 1.4446 . ?
S2A O6A 1.4456 . ?
C22A F4A 1.3383 . ?
C22A F5A 1.3388 . ?
C22A F6A 1.3390 . ?
S2B C22B 1.8513 . ?
S2B O4B 1.4451 . ?
S2B O5B 1.4449 . ?
S2B O6B 1.4452 . ?
C22B F4B 1.3384 . ?
C22B F5B 1.3381 . ?
C22B F6B 1.3388 . ?
S2C C22C 1.8513 . ?
S2C O4C 1.4451 . ?
S2C O5A 1.438(9) . ?
S2C O6C 1.449(9) . ?
C22C F4C 1.3384 . ?
C22C F5C 1.3386 . ?
C22C F6C 1.3383 . ?
C23A H23A 0.9700 . ?
C23A H23B 0.9700 . ?
C23A Cl1A 1.763(7) . ?
C23A Cl2A 1.751(7) . ?
C23B H23C 0.9700 . ?
C23B H23D 0.9700 . ?
C23B Cl1B 1.769(17) . ?
C23B Cl2B 1.777(16) . ?
N5A C24A 1.153(12) . ?
N5B C24B 1.1626 . ?
C24B C25B 1.4534 . ?
C25B H25D 0.9600 . ?
C25B H25E 0.9600 . ?
C25B H25F 0.9600 . ?
C24A C25A 1.509(12) . ?
C25A H25A 0.9600 . ?
C25A H25B 0.9600 . ?
C25A H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Sn1 N1 68.32(12) . . ?
N2 Sn1 N3 82.38(12) . . ?
N3 Sn1 N1 143.02(12) . . ?
N4 Sn1 N1 83.04(12) . . ?
N4 Sn1 N2 77.13(11) . . ?
N4 Sn1 N3 68.38(12) . . ?
C1 N1 Sn1 119.4(3) . . ?
C1 N1 C5 119.6(4) . . ?
C5 N1 Sn1 119.2(3) . . ?
C6 N2 Sn1 119.1(3) . . ?
C10 N2 Sn1 122.1(3) . . ?
C10 N2 C6 118.7(4) . . ?
C11 N3 Sn1 119.7(3) . . ?
C15 N3 Sn1 119.7(3) . . ?
C15 N3 C11 120.2(4) . . ?
C16 N4 Sn1 119.9(3) . . ?
C20 N4 Sn1 122.1(3) . . ?
C20 N4 C16 118.0(4) . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.4(4) . . ?
C2 C1 H1 118.8 . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 118.0(4) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.7(4) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 121.3(4) . . ?
N1 C5 C6 115.7(3) . . ?
C4 C5 C6 123.0(4) . . ?
N2 C6 C5 116.7(3) . . ?
N2 C6 C7 121.5(4) . . ?
C7 C6 C5 121.8(4) . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.2(4) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.0(4) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.0(4) . . ?
C10 C9 H9 120.5 . . ?
N2 C10 C9 122.6(4) . . ?
N2 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
N3 C11 H11 119.1 . . ?
N3 C11 C12 121.9(4) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.4(4) . . ?
C13 C12 H12 120.8 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.1(4) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.9(4) . . ?
C15 C14 H14 120.6 . . ?
N3 C15 C14 120.5(4) . . ?
N3 C15 C16 115.8(4) . . ?
C14 C15 C16 123.7(4) . . ?
N4 C16 C15 116.1(4) . . ?
N4 C16 C17 121.7(4) . . ?
C17 C16 C15 122.1(4) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.5(4) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 119.0(4) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 120.5 . . ?
C18 C19 C20 118.9(4) . . ?
C20 C19 H19 120.5 . . ?
N4 C20 C19 122.8(4) . . ?
N4 C20 H20 118.6 . . ?
C19 C20 H20 118.6 . . ?
F1 C21 S1 111.1(3) . . ?
F2 C21 F1 107.6(4) . . ?
F2 C21 F3 107.5(4) . . ?
F2 C21 S1 111.4(3) . . ?
F3 C21 F1 107.5(4) . . ?
F3 C21 S1 111.5(3) . . ?
O1 S1 C21 102.7(2) . . ?
O2 S1 C21 104.0(2) . . ?
O2 S1 O1 114.96(19) . . ?
O2 S1 O3 115.62(18) . . ?
O3 S1 C21 104.10(18) . . ?
O3 S1 O1 113.35(18) . . ?
O4A S2A C22A 102.4 . . ?
O4A S2A O6A 115.5 . . ?
O5C S2A C22A 102.4 . . ?
O5C S2A O4A 115.5 . . ?
O5C S2A O6A 115.5 . . ?
O6A S2A C22A 102.4 . . ?
F4A C22A S2A 111.9 . . ?
F4A C22A F5A 107.0 . . ?
F4A C22A F6A 106.9 . . ?
F5A C22A S2A 111.9 . . ?
F5A C22A F6A 107.0 . . ?
F6A C22A S2A 111.9 . . ?
O4B S2B C22B 102.4 . . ?
O4B S2B O6B 115.5 . . ?
O5B S2B C22B 102.4 . . ?
O5B S2B O4B 115.5 . . ?
O5B S2B O6B 115.6 . . ?
O6B S2B C22B 102.4 . . ?
F4B C22B S2B 111.9 . . ?
F4B C22B F6B 106.9 . . ?
F5B C22B S2B 111.9 . . ?
F5B C22B F4B 107.0 . . ?
F5B C22B F6B 107.0 . . ?
F6B C22B S2B 111.8 . . ?
O4C S2C C22C 102.4 . . ?
O4C S2C O6C 123.1(9) . . ?
O5A S2C C22C 104.3(9) . . ?
O5A S2C O4C 111.3(9) . . ?
O5A S2C O6C 111.9(12) . . ?
O6C S2C C22C 100.9(9) . . ?
F4C C22C S2C 111.9 . . ?
F4C C22C F5C 107.0 . . ?
F5C C22C S2C 111.8 . . ?
F6C C22C S2C 111.9 . . ?
F6C C22C F4C 107.0 . . ?
F6C C22C F5C 107.0 . . ?
H23A C23A H23B 107.9 . . ?
Cl1A C23A H23A 109.2 . . ?
Cl1A C23A H23B 109.2 . . ?
Cl2A C23A H23A 109.2 . . ?
Cl2A C23A H23B 109.2 . . ?
Cl2A C23A Cl1A 112.0(4) . . ?
H23C C23B H23D 108.4 . . ?
Cl1B C23B H23C 110.0 . . ?
Cl1B C23B H23D 110.0 . . ?
Cl1B C23B Cl2B 108.4(15) . . ?
Cl2B C23B H23C 110.0 . . ?
Cl2B C23B H23D 110.0 . . ?
N5B C24B C25B 180.0 . . ?
C24B C25B H25D 109.5 . . ?
C24B C25B H25E 109.5 . . ?
C24B C25B H25F 109.5 . . ?
H25D C25B H25E 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 109.5 . . ?
N5A C24A C25A 170.2(13) . . ?
C24A C25A H25A 109.5 . . ?
C24A C25A H25B 109.5 . . ?
C24A C25A H25C 109.5 . . ?
H25A C25A H25B 109.5 . . ?
H25A C25A H25C 109.5 . . ?
H25B C25A H25C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
