# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_JF1_0m

# start Validation Reply Form
_vrf_PLAT412_JF1_0m              
;
PROBLEM: Short Intra XH3 .. XHn     H4A    ..  H8A     ..       1.78 Ang. 
RESPONSE: This short intramolecular contact is due to a disordered CH2Cl2
solvent molecule. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H26 N4 Si, 2(C F3 O3 S), 2(C H2 Cl2)'
_chemical_formula_sum            'C20 H30 Cl4 F6 N4 O6 S2 Si'
_chemical_formula_weight         770.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.1122(4)
_cell_length_b                   11.4867(6)
_cell_length_c                   18.7960(9)
_cell_angle_alpha                95.057(2)
_cell_angle_beta                 98.939(2)
_cell_angle_gamma                108.631(2)
_cell_volume                     1621.66(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6468
_cell_measurement_theta_min      4.11
_cell_measurement_theta_max      71.07

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.724
_exptl_crystal_size_mid          0.571
_exptl_crystal_size_min          0.312
_exptl_absorpt_coefficient_mu    5.574
_shelx_estimated_absorpt_T_min   0.107
_shelx_estimated_absorpt_T_max   0.275
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.1285
_exptl_absorpt_correction_T_max  0.4629
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
A crystal of suitable size was selected, mounted in Paratone oil 
on a MiTeGen loop, and placed in the cold stream of the diffractometer. 
Data were collected at -100C with CuK(alpha) radiation from a rotating 
anode, and fitted with a Bruker SMART 6K detector. 0.5degree omega 
scans were used; the data were integrated (SAINT) and corrected for 
absorption (SADABS) (both SHELXL2013.4), then solved in the triclinic
space group P-1. 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode'
_diffrn_measurement_device_type  'Bruker SMART6K CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17672
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.406
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             5782
_reflns_number_gt                4973
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 All non-hydrogen atoms were refined anisotropically. Hydrogen atoms
were placed in idealized positions and updated with each cycle of 
refinement. One molecule of CH2Cl2 solvent was disordered over two
positions (0.791(3)). 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)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         5782
_refine_ls_number_parameters     398
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1836
_refine_ls_wR_factor_gt          0.1757
_refine_ls_goodness_of_fit_ref   1.451
_refine_ls_restrained_S_all      1.454
_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
Si1 Si 0.74385(9) 1.01027(6) 0.63971(4) 0.0231(2) Uani 1 1 d . . . . .
N1 N 0.8154(3) 1.0981(2) 0.72941(12) 0.0253(5) Uani 1 1 d . . . . .
N2 N 0.9934(4) 1.3018(2) 0.93709(13) 0.0364(6) Uani 1 1 d . . . . .
N3 N 0.8450(3) 0.8912(2) 0.64224(12) 0.0251(5) Uani 1 1 d . . . . .
N4 N 1.0350(3) 0.5946(2) 0.63304(14) 0.0313(5) Uani 1 1 d . . . . .
C1 C 0.5039(4) 0.9295(3) 0.62186(16) 0.0310(6) Uani 1 1 d . . . . .
H1A H 0.4731 0.8782 0.6600 0.047 Uiso 1 1 calc R U . . .
H1B H 0.4674 0.8765 0.5744 0.047 Uiso 1 1 calc R U . . .
H1C H 0.4428 0.9906 0.6216 0.047 Uiso 1 1 calc R U . . .
C2 C 0.8266(4) 1.1115(3) 0.57350(15) 0.0291(6) Uani 1 1 d . . . . .
H2A H 0.9557 1.1501 0.5877 0.044 Uiso 1 1 calc R U . . .
H2B H 0.7720 1.1763 0.5724 0.044 Uiso 1 1 calc R U . . .
H2C H 0.7962 1.0622 0.5251 0.044 Uiso 1 1 calc R U . . .
C3 C 0.9624(4) 1.2041(3) 0.74494(15) 0.0272(6) Uani 1 1 d . . . . .
H3A H 1.0257 1.2291 0.7073 0.033 Uiso 1 1 calc R U . . .
C4 C 1.0212(4) 1.2745(3) 0.81145(15) 0.0302(6) Uani 1 1 d . . . . .
H4A H 1.1207 1.3488 0.8188 0.036 Uiso 1 1 calc R U . . .
C5 C 0.9358(4) 1.2384(3) 0.87013(15) 0.0307(6) Uani 1 1 d . . . . .
C6 C 0.7818(5) 1.1285(3) 0.85313(16) 0.0407(7) Uani 1 1 d . . . . .
H6A H 0.7168 1.1006 0.8899 0.049 Uiso 1 1 calc R U . . .
C7 C 0.7282(4) 1.0639(3) 0.78472(16) 0.0345(6) Uani 1 1 d . . . . .
H7A H 0.6253 0.9917 0.7750 0.041 Uiso 1 1 calc R U . . .
C8 C 1.1464(5) 1.4173(3) 0.95267(18) 0.0444(8) Uani 1 1 d . . . . .
H8A H 1.1875 1.4372 0.9074 0.067 Uiso 1 1 calc R U . . .
H8B H 1.2422 1.4067 0.9873 0.067 Uiso 1 1 calc R U . . .
H8C H 1.1117 1.4850 0.9737 0.067 Uiso 1 1 calc R U . . .
C9 C 0.9141(6) 1.2570(4) 0.99847(17) 0.0529(10) Uani 1 1 d . . . . .
H9A H 0.8136 1.1799 0.9811 0.079 Uiso 1 1 calc R U . . .
H9B H 0.8726 1.3198 1.0211 0.079 Uiso 1 1 calc R U . . .
H9C H 1.0028 1.2412 1.0344 0.079 Uiso 1 1 calc R U . . .
C10 C 0.7848(4) 0.7932(3) 0.67964(14) 0.0283(6) Uani 1 1 d . . . . .
H10A H 0.6948 0.7928 0.7066 0.034 Uiso 1 1 calc R U . . .
C11 C 0.8478(4) 0.6971(3) 0.67985(15) 0.0299(6) Uani 1 1 d . . . . .
H11A H 0.8040 0.6329 0.7077 0.036 Uiso 1 1 calc R U . . .
C12 C 0.9787(4) 0.6915(3) 0.63876(14) 0.0261(6) Uani 1 1 d . . . . .
C13 C 1.0426(4) 0.7955(3) 0.60190(15) 0.0285(6) Uani 1 1 d . . . . .
H13A H 1.1335 0.7990 0.5750 0.034 Uiso 1 1 calc R U . . .
C14 C 0.9754(4) 0.8890(3) 0.60483(14) 0.0272(6) Uani 1 1 d . . . . .
H14A H 1.0214 0.9566 0.5795 0.033 Uiso 1 1 calc R U . . .
C15 C 1.1733(5) 0.5923(3) 0.5927(2) 0.0438(8) Uani 1 1 d . . . . .
H15A H 1.2073 0.6673 0.5695 0.066 Uiso 1 1 calc R U . . .
H15B H 1.1290 0.5187 0.5553 0.066 Uiso 1 1 calc R U . . .
H15C H 1.2768 0.5892 0.6261 0.066 Uiso 1 1 calc R U . . .
C16 C 0.9674(5) 0.4863(3) 0.6696(2) 0.0437(8) Uani 1 1 d . . . . .
H16A H 0.8738 0.4962 0.6943 0.066 Uiso 1 1 calc R U . . .
H16B H 1.0642 0.4794 0.7053 0.066 Uiso 1 1 calc R U . . .
H16C H 0.9188 0.4110 0.6334 0.066 Uiso 1 1 calc R U . . .
S1 S 0.36792(11) 0.68641(7) 0.80897(4) 0.0388(2) Uani 1 1 d . . . . .
O3 O 0.3744(5) 0.5670(3) 0.7873(2) 0.0892(13) Uani 1 1 d . . . . .
O2 O 0.2120(4) 0.6836(3) 0.83600(19) 0.0723(9) Uani 1 1 d . . . . .
O1 O 0.4184(4) 0.7764(3) 0.76182(15) 0.0636(8) Uani 1 1 d . . . . .
C17 C 0.5443(6) 0.7493(4) 0.8894(2) 0.0573(10) Uani 1 1 d . . . . .
F3 F 0.7015(4) 0.7694(3) 0.8731(2) 0.0947(10) Uani 1 1 d . . . . .
F2 F 0.5409(5) 0.8563(3) 0.92015(18) 0.0945(10) Uani 1 1 d . . . . .
F1 F 0.5299(6) 0.6724(4) 0.93761(18) 0.1248(17) Uani 1 1 d . . . . .
S2 S 0.37896(9) 0.23541(6) 0.61005(4) 0.0315(2) Uani 1 1 d . . . . .
O6 O 0.5438(3) 0.2357(2) 0.65143(13) 0.0439(5) Uani 1 1 d . . . . .
O4 O 0.2855(4) 0.1272(2) 0.55630(14) 0.0507(6) Uani 1 1 d . . . . .
O5 O 0.2697(4) 0.2780(3) 0.65156(15) 0.0560(7) Uani 1 1 d . . . . .
C18 C 0.4473(4) 0.3580(3) 0.55504(18) 0.0374(7) Uani 1 1 d . . . . .
F6 F 0.3089(3) 0.3688(2) 0.51153(12) 0.0584(6) Uani 1 1 d . . . . .
F5 F 0.5304(3) 0.46762(18) 0.59551(14) 0.0597(6) Uani 1 1 d . . . . .
F4 F 0.5574(4) 0.3369(3) 0.51464(16) 0.0771(8) Uani 1 1 d . . . . .
C1S C 0.5816(5) 0.3793(3) 0.81654(17) 0.0458(8) Uani 1 1 d D . . . .
H1SA H 0.5817 0.3074 0.7834 0.055 Uiso 1 1 calc R U . . .
H1SB H 0.4910 0.4115 0.7926 0.055 Uiso 1 1 calc R U . . .
Cl1 Cl 0.79268(12) 0.49645(8) 0.83245(4) 0.0489(2) Uani 1 1 d D . . . .
Cl2 Cl 0.52698(14) 0.33083(10) 0.89826(5) 0.0592(3) Uani 1 1 d D . . . .
C2S C 0.1444(13) 0.9533(5) 0.8362(2) 0.108(3) Uani 0.791(3) 1 d D . P A 1
H2SA H 0.0142 0.9266 0.8197 0.130 Uiso 0.791(3) 1 calc R U P A 1
H2SB H 0.1776 0.8777 0.8384 0.130 Uiso 0.791(3) 1 calc R U P A 1
Cl3 Cl 0.2498(9) 1.0395(7) 0.7721(3) 0.0639(5) Uani 0.791(3) 1 d D . P A 1
Cl4 Cl 0.2021(3) 1.03868(15) 0.92299(9) 0.0989(7) Uani 0.791(3) 1 d D . P A 1
C2S' C 0.267(2) 0.986(2) 0.8496(10) 0.108(3) Uani 0.209(3) 1 d D . P A 2
H2SC H 0.3730 1.0409 0.8852 0.130 Uiso 0.209(3) 1 calc R U P A 2
H2SD H 0.2708 0.9008 0.8457 0.130 Uiso 0.209(3) 1 calc R U P A 2
Cl3' Cl 0.270(4) 1.038(3) 0.7633(11) 0.0639(5) Uani 0.209(3) 1 d D . P A 2
Cl4' Cl 0.0753(13) 0.9895(6) 0.8797(4) 0.0989(7) Uani 0.209(3) 1 d D . P A 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
Si1 N1 1.794(2) . ?
Si1 N3 1.806(2) . ?
Si1 C1 1.830(3) . ?
Si1 C2 1.835(3) . ?
N1 C7 1.363(4) . ?
N1 C3 1.375(4) . ?
N2 C5 1.331(4) . ?
N2 C9 1.461(4) . ?
N2 C8 1.467(4) . ?
N3 C14 1.364(4) . ?
N3 C10 1.377(3) . ?
N4 C12 1.333(4) . ?
N4 C15 1.454(4) . ?
N4 C16 1.467(4) . ?
C3 C4 1.355(4) . ?
C4 C5 1.415(4) . ?
C5 C6 1.433(5) . ?
C6 C7 1.358(4) . ?
C10 C11 1.357(4) . ?
C11 C12 1.421(4) . ?
C12 C13 1.427(4) . ?
C13 C14 1.352(4) . ?
S1 O3 1.416(3) . ?
S1 O1 1.423(3) . ?
S1 O2 1.426(3) . ?
S1 C17 1.825(4) . ?
C17 F3 1.312(6) . ?
C17 F1 1.312(5) . ?
C17 F2 1.322(6) . ?
S2 O5 1.435(3) . ?
S2 O6 1.438(2) . ?
S2 O4 1.442(2) . ?
S2 C18 1.815(3) . ?
C18 F5 1.322(4) . ?
C18 F4 1.323(4) . ?
C18 F6 1.329(4) . ?
C1S Cl1 1.769(4) . ?
C1S Cl2 1.752(3) . ?
C2S Cl4 1.740(4) . ?
C2S Cl3 1.776(5) . ?
C2S' Cl3' 1.777(6) . ?
C2S' Cl4' 1.746(5) . ?

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 Si1 N3 105.29(10) . . ?
N1 Si1 C1 110.01(13) . . ?
N3 Si1 C1 106.36(12) . . ?
N1 Si1 C2 109.39(12) . . ?
N3 Si1 C2 109.60(12) . . ?
C1 Si1 C2 115.66(13) . . ?
C7 N1 C3 117.2(2) . . ?
C7 N1 Si1 122.23(19) . . ?
C3 N1 Si1 120.62(18) . . ?
C5 N2 C9 121.9(3) . . ?
C5 N2 C8 120.7(3) . . ?
C9 N2 C8 117.3(3) . . ?
C14 N3 C10 116.7(2) . . ?
C14 N3 Si1 122.85(18) . . ?
C10 N3 Si1 120.39(18) . . ?
C12 N4 C15 121.9(3) . . ?
C12 N4 C16 122.2(3) . . ?
C15 N4 C16 115.8(2) . . ?
C4 C3 N1 123.1(3) . . ?
C3 C4 C5 120.6(3) . . ?
N2 C5 C4 122.6(3) . . ?
N2 C5 C6 121.6(3) . . ?
C4 C5 C6 115.8(3) . . ?
C7 C6 C5 120.4(3) . . ?
C6 C7 N1 123.0(3) . . ?
C11 C10 N3 123.1(2) . . ?
C10 C11 C12 120.6(2) . . ?
N4 C12 C11 122.7(3) . . ?
N4 C12 C13 121.9(3) . . ?
C11 C12 C13 115.4(2) . . ?
C14 C13 C12 120.9(3) . . ?
C13 C14 N3 123.3(2) . . ?
O3 S1 O1 116.9(3) . . ?
O3 S1 O2 113.5(2) . . ?
O1 S1 O2 114.3(2) . . ?
O3 S1 C17 104.1(2) . . ?
O1 S1 C17 102.34(19) . . ?
O2 S1 C17 103.4(2) . . ?
F3 C17 F1 106.5(4) . . ?
F3 C17 F2 107.5(4) . . ?
F1 C17 F2 108.9(4) . . ?
F3 C17 S1 111.7(3) . . ?
F1 C17 S1 111.6(3) . . ?
F2 C17 S1 110.5(3) . . ?
O5 S2 O6 115.06(16) . . ?
O5 S2 O4 115.07(17) . . ?
O6 S2 O4 115.27(15) . . ?
O5 S2 C18 102.38(16) . . ?
O6 S2 C18 103.49(15) . . ?
O4 S2 C18 102.96(15) . . ?
F5 C18 F4 107.1(3) . . ?
F5 C18 F6 106.4(3) . . ?
F4 C18 F6 108.6(3) . . ?
F5 C18 S2 112.0(2) . . ?
F4 C18 S2 111.0(2) . . ?
F6 C18 S2 111.5(2) . . ?
Cl1 C1S Cl2 110.95(18) . . ?
Cl4 C2S Cl3 112.4(3) . . ?
Cl3' C2S' Cl4' 109.9(6) . . ?

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
N3 Si1 N1 C7 -85.8(2) . . . . ?
C1 Si1 N1 C7 28.4(3) . . . . ?
C2 Si1 N1 C7 156.5(2) . . . . ?
N3 Si1 N1 C3 94.2(2) . . . . ?
C1 Si1 N1 C3 -151.6(2) . . . . ?
C2 Si1 N1 C3 -23.5(2) . . . . ?
N1 Si1 N3 C14 -111.6(2) . . . . ?
C1 Si1 N3 C14 131.6(2) . . . . ?
C2 Si1 N3 C14 5.9(3) . . . . ?
N1 Si1 N3 C10 72.1(2) . . . . ?
C1 Si1 N3 C10 -44.6(2) . . . . ?
C2 Si1 N3 C10 -170.3(2) . . . . ?
C7 N1 C3 C4 -0.6(4) . . . . ?
Si1 N1 C3 C4 179.3(2) . . . . ?
N1 C3 C4 C5 2.6(4) . . . . ?
C9 N2 C5 C4 -174.1(3) . . . . ?
C8 N2 C5 C4 2.7(5) . . . . ?
C9 N2 C5 C6 6.1(5) . . . . ?
C8 N2 C5 C6 -177.1(3) . . . . ?
C3 C4 C5 N2 177.2(3) . . . . ?
C3 C4 C5 C6 -3.0(4) . . . . ?
N2 C5 C6 C7 -178.6(3) . . . . ?
C4 C5 C6 C7 1.6(5) . . . . ?
C5 C6 C7 N1 0.3(5) . . . . ?
C3 N1 C7 C6 -0.9(5) . . . . ?
Si1 N1 C7 C6 179.2(3) . . . . ?
C14 N3 C10 C11 -0.6(4) . . . . ?
Si1 N3 C10 C11 175.8(2) . . . . ?
N3 C10 C11 C12 -1.8(4) . . . . ?
C15 N4 C12 C11 -178.0(3) . . . . ?
C16 N4 C12 C11 -0.7(4) . . . . ?
C15 N4 C12 C13 4.0(4) . . . . ?
C16 N4 C12 C13 -178.7(3) . . . . ?
C10 C11 C12 N4 -175.0(3) . . . . ?
C10 C11 C12 C13 3.2(4) . . . . ?
N4 C12 C13 C14 175.8(3) . . . . ?
C11 C12 C13 C14 -2.4(4) . . . . ?
C12 C13 C14 N3 0.0(4) . . . . ?
C10 N3 C14 C13 1.5(4) . . . . ?
Si1 N3 C14 C13 -174.8(2) . . . . ?
O3 S1 C17 F3 67.1(4) . . . . ?
O1 S1 C17 F3 -55.0(4) . . . . ?
O2 S1 C17 F3 -174.0(3) . . . . ?
O3 S1 C17 F1 -52.1(5) . . . . ?
O1 S1 C17 F1 -174.2(4) . . . . ?
O2 S1 C17 F1 66.8(4) . . . . ?
O3 S1 C17 F2 -173.3(4) . . . . ?
O1 S1 C17 F2 64.5(4) . . . . ?
O2 S1 C17 F2 -54.5(4) . . . . ?
O5 S2 C18 F5 57.7(3) . . . . ?
O6 S2 C18 F5 -62.3(3) . . . . ?
O4 S2 C18 F5 177.4(2) . . . . ?
O5 S2 C18 F4 177.2(3) . . . . ?
O6 S2 C18 F4 57.3(3) . . . . ?
O4 S2 C18 F4 -63.0(3) . . . . ?
O5 S2 C18 F6 -61.5(3) . . . . ?
O6 S2 C18 F6 178.6(2) . . . . ?
O4 S2 C18 F6 58.3(3) . . . . ?

_refine_diff_density_max         0.980
_refine_diff_density_min         -1.048
_refine_diff_density_rms         0.092

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 977497'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_JF0004_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H14 F3 N2 O3 S Si, C F3 O3 S'
_chemical_formula_sum            'C14 H14 F6 N2 O6 S2 Si'
_chemical_formula_weight         512.48

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'
O O 0.0106 0.0060 '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'
Si Si 0.0817 0.0704 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   14.1596(18)
_cell_length_b                   22.794(3)
_cell_length_c                   7.3679(9)
_cell_angle_alpha                90
_cell_angle_beta                 118.801(2)
_cell_angle_gamma                90
_cell_volume                     2083.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6972
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      29.40

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.155
_exptl_absorpt_coefficient_mu    0.401
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9087
_exptl_absorpt_correction_T_max  0.9716
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20167
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.787
_diffrn_reflns_theta_max         29.758
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5944
_reflns_number_gt                5301
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.992
_reflns_Friedel_fraction_max     0.997
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_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)+(0.0433P)²+0.1622P] 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 
; 
 Flack x determined using 2424 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.005(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5944
_refine_ls_number_parameters     280
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_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
S1 S 0.81290(6) 0.10536(3) -0.48159(9) 0.03085(16) Uani 1 1 d . . . . .
Si1 Si 0.89462(5) 0.16606(3) -0.05349(9) 0.02256(14) Uani 1 1 d . . . . .
F1 F 0.74875(18) -0.00273(9) -0.4973(4) 0.0564(6) Uani 1 1 d . . . . .
O1 O 0.86333(16) 0.10387(8) -0.2510(3) 0.0281(4) Uani 1 1 d . . . . .
N1 N 0.98440(17) 0.11288(9) 0.1505(3) 0.0215(4) Uani 1 1 d . . . . .
C1 C 0.7538(2) 0.16928(13) -0.1012(5) 0.0328(6) Uani 1 1 d . . . . .
H1A H 0.7088 0.1454 -0.2189 0.049 Uiso 1 1 calc R U . . .
H1B H 0.7288 0.2091 -0.1278 0.049 Uiso 1 1 calc R U . . .
H1C H 0.7507 0.1550 0.0184 0.049 Uiso 1 1 calc R U . . .
S2 S 0.74434(5) 0.35768(3) 0.59677(9) 0.02562(13) Uani 1 1 d . . . . .
F2 F 0.64657(16) 0.06099(10) -0.4651(3) 0.0528(5) Uani 1 1 d . . . . .
O2 O 0.7574(2) 0.15900(10) -0.5677(4) 0.0521(6) Uani 1 1 d . . . . .
N2 N 0.94773(18) 0.21890(10) 0.1863(3) 0.0248(4) Uani 1 1 d . . . . .
C2 C 0.9601(2) 0.21140(12) -0.1708(4) 0.0302(6) Uani 1 1 d . . . . .
H2B H 0.9464 0.1945 -0.3006 0.045 Uiso 1 1 calc R U . . .
H2C H 1.0364 0.2127 -0.0789 0.045 Uiso 1 1 calc R U . . .
H2D H 0.9314 0.2505 -0.1935 0.045 Uiso 1 1 calc R U . . .
F3 F 0.64424(19) 0.05119(11) -0.7578(3) 0.0636(6) Uani 1 1 d . . . . .
O3 O 0.88297(19) 0.08261(12) -0.5514(4) 0.0461(6) Uani 1 1 d . . . . .
C3 C 0.9882(2) 0.05437(11) 0.1247(4) 0.0264(5) Uani 1 1 d . . . . .
H3B H 0.9405 0.0377 -0.0020 0.032 Uiso 1 1 calc R U . . .
F4 F 0.8505(3) 0.43024(15) 0.9015(6) 0.1068(13) Uani 1 1 d . . . . .
O4 O 0.77444(19) 0.32885(11) 0.4591(3) 0.0437(5) Uani 1 1 d . . . . .
C4 C 1.0606(2) 0.01882(12) 0.2802(4) 0.0293(5) Uani 1 1 d . . . . .
H4B H 1.0596 -0.0215 0.2608 0.035 Uiso 1 1 calc R U . . .
F5 F 0.8849(2) 0.43921(13) 0.6537(6) 0.0953(11) Uani 1 1 d . . . . .
O5 O 0.66045(19) 0.40064(10) 0.5006(4) 0.0463(6) Uani 1 1 d . . . . .
C5 C 1.1350(2) 0.04373(12) 0.4657(4) 0.0299(6) Uani 1 1 d . . . . .
H5B H 1.1874 0.0205 0.5689 0.036 Uiso 1 1 calc R U . . .
F6 F 0.94989(17) 0.36722(11) 0.8609(4) 0.0685(7) Uani 1 1 d . . . . .
O6 O 0.73287(18) 0.31930(10) 0.7393(3) 0.0405(5) Uani 1 1 d . . . . .
C6 C 1.1310(2) 0.10326(12) 0.4972(4) 0.0278(5) Uani 1 1 d . . . . .
H6B H 1.1797 0.1206 0.6219 0.033 Uiso 1 1 calc R U . . .
C7 C 1.0531(2) 0.13639(11) 0.3387(4) 0.0226(5) Uani 1 1 d . . . . .
C8 C 1.0326(2) 0.19853(11) 0.3594(4) 0.0228(5) Uani 1 1 d . . . . .
C9 C 1.0866(2) 0.23325(13) 0.5335(4) 0.0272(6) Uani 1 1 d . . . . .
H9A H 1.1459 0.2188 0.6515 0.033 Uiso 1 1 calc R U . . .
C10 C 1.0504(2) 0.29000(13) 0.5280(4) 0.0312(6) Uani 1 1 d . . . . .
H10A H 1.0850 0.3142 0.6433 0.037 Uiso 1 1 calc R U . . .
C11 C 0.9624(2) 0.31053(13) 0.3499(5) 0.0330(6) Uani 1 1 d . . . . .
H11A H 0.9370 0.3484 0.3447 0.040 Uiso 1 1 calc R U . . .
C12 C 0.9130(2) 0.27397(12) 0.1802(4) 0.0312(6) Uani 1 1 d . . . . .
H12A H 0.8547 0.2878 0.0595 0.037 Uiso 1 1 calc R U . . .
C13 C 0.7066(2) 0.05031(15) -0.5524(5) 0.0384(7) Uani 1 1 d . . . . .
C14 C 0.8631(3) 0.40084(15) 0.7616(6) 0.0487(8) 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
S1 O3 1.418(2) . ?
S1 O2 1.426(2) . ?
S1 O1 1.4931(18) . ?
S1 C13 1.831(3) . ?
Si1 C1 1.852(3) . ?
Si1 C2 1.856(3) . ?
Si1 N1 1.872(2) . ?
Si1 O1 1.924(2) . ?
Si1 N2 1.964(2) . ?
F1 C13 1.322(4) . ?
N1 C3 1.352(3) . ?
N1 C7 1.363(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
S2 O5 1.436(2) . ?
S2 O6 1.435(2) . ?
S2 O4 1.435(2) . ?
S2 C14 1.818(4) . ?
F2 C13 1.313(4) . ?
N2 C8 1.346(3) . ?
N2 C12 1.341(3) . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 H2D 0.9600 . ?
F3 C13 1.335(4) . ?
C3 C4 1.374(4) . ?
C3 H3B 0.9300 . ?
F4 C14 1.313(5) . ?
C4 C5 1.383(4) . ?
C4 H4B 0.9300 . ?
F5 C14 1.314(5) . ?
C5 C6 1.382(4) . ?
C5 H5B 0.9300 . ?
F6 C14 1.329(5) . ?
C6 C7 1.382(3) . ?
C6 H6B 0.9300 . ?
C7 C8 1.468(4) . ?
C8 C9 1.382(4) . ?
C9 C10 1.385(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.385(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.380(4) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?

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
O3 S1 O2 118.94(17) . . ?
O3 S1 O1 111.73(13) . . ?
O2 S1 O1 112.62(14) . . ?
O3 S1 C13 105.58(15) . . ?
O2 S1 C13 105.04(16) . . ?
O1 S1 C13 100.69(13) . . ?
C1 Si1 C2 128.55(13) . . ?
C1 Si1 N1 115.51(12) . . ?
C2 Si1 N1 115.85(11) . . ?
C1 Si1 O1 92.93(12) . . ?
C2 Si1 O1 92.46(11) . . ?
N1 Si1 O1 87.13(9) . . ?
C1 Si1 N2 93.27(12) . . ?
C2 Si1 N2 90.95(11) . . ?
N1 Si1 N2 81.80(9) . . ?
O1 Si1 N2 168.81(9) . . ?
S1 O1 Si1 130.81(12) . . ?
C3 N1 C7 118.3(2) . . ?
C3 N1 Si1 125.72(18) . . ?
C7 N1 Si1 115.98(16) . . ?
Si1 C1 H1A 109.5 . . ?
Si1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Si1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O5 S2 O6 114.76(15) . . ?
O5 S2 O4 114.85(15) . . ?
O6 S2 O4 114.53(15) . . ?
O5 S2 C14 103.88(16) . . ?
O6 S2 C14 103.63(16) . . ?
O4 S2 C14 103.04(17) . . ?
C8 N2 C12 120.0(2) . . ?
C8 N2 Si1 114.91(17) . . ?
C12 N2 Si1 124.68(19) . . ?
Si1 C2 H2B 109.5 . . ?
Si1 C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
Si1 C2 H2D 109.5 . . ?
H2B C2 H2D 109.5 . . ?
H2C C2 H2D 109.5 . . ?
N1 C3 C4 121.9(2) . . ?
N1 C3 H3B 119.0 . . ?
C4 C3 H3B 119.0 . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 H4B 120.4 . . ?
C5 C4 H4B 120.4 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5B 120.1 . . ?
C6 C5 H5B 120.1 . . ?
C7 C6 C5 118.4(3) . . ?
C7 C6 H6B 120.8 . . ?
C5 C6 H6B 120.8 . . ?
N1 C7 C6 122.2(2) . . ?
N1 C7 C8 113.9(2) . . ?
C6 C7 C8 123.8(2) . . ?
N2 C8 C9 121.6(2) . . ?
N2 C8 C7 111.4(2) . . ?
C9 C8 C7 126.9(2) . . ?
C10 C9 C8 118.4(2) . . ?
C10 C9 H9A 120.8 . . ?
C8 C9 H9A 120.8 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10A 120.2 . . ?
C11 C10 H10A 120.2 . . ?
C12 C11 C10 119.1(3) . . ?
C12 C11 H11A 120.5 . . ?
C10 C11 H11A 120.5 . . ?
N2 C12 C11 121.2(3) . . ?
N2 C12 H12A 119.4 . . ?
C11 C12 H12A 119.4 . . ?
F1 C13 F2 108.8(3) . . ?
F1 C13 F3 108.4(3) . . ?
F2 C13 F3 108.7(3) . . ?
F1 C13 S1 110.6(2) . . ?
F2 C13 S1 111.8(2) . . ?
F3 C13 S1 108.5(2) . . ?
F4 C14 F5 107.2(3) . . ?
F4 C14 F6 107.6(4) . . ?
F5 C14 F6 107.0(3) . . ?
F4 C14 S2 111.6(3) . . ?
F5 C14 S2 111.6(3) . . ?
F6 C14 S2 111.6(2) . . ?

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
O3 S1 O1 Si1 120.37(18) . . . . ?
O2 S1 O1 Si1 -16.6(2) . . . . ?
C13 S1 O1 Si1 -127.95(18) . . . . ?
C1 Si1 N1 C3 80.1(2) . . . . ?
C2 Si1 N1 C3 -103.1(2) . . . . ?
O1 Si1 N1 C3 -11.8(2) . . . . ?
N2 Si1 N1 C3 169.8(2) . . . . ?
C1 Si1 N1 C7 -101.65(19) . . . . ?
C2 Si1 N1 C7 75.1(2) . . . . ?
O1 Si1 N1 C7 166.47(17) . . . . ?
N2 Si1 N1 C7 -11.93(17) . . . . ?
C7 N1 C3 C4 -1.6(4) . . . . ?
Si1 N1 C3 C4 176.6(2) . . . . ?
N1 C3 C4 C5 -2.9(4) . . . . ?
C3 C4 C5 C6 4.2(4) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C3 N1 C7 C6 4.9(3) . . . . ?
Si1 N1 C7 C6 -173.49(19) . . . . ?
C3 N1 C7 C8 -172.2(2) . . . . ?
Si1 N1 C7 C8 9.4(3) . . . . ?
C5 C6 C7 N1 -3.6(4) . . . . ?
C5 C6 C7 C8 173.2(2) . . . . ?
C12 N2 C8 C9 -0.5(4) . . . . ?
Si1 N2 C8 C9 172.51(18) . . . . ?
C12 N2 C8 C7 176.3(2) . . . . ?
Si1 N2 C8 C7 -10.7(3) . . . . ?
N1 C7 C8 N2 1.2(3) . . . . ?
C6 C7 C8 N2 -175.9(2) . . . . ?
N1 C7 C8 C9 177.8(2) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
N2 C8 C9 C10 1.0(4) . . . . ?
C7 C8 C9 C10 -175.3(2) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C8 N2 C12 C11 -0.5(4) . . . . ?
Si1 N2 C12 C11 -172.8(2) . . . . ?
C10 C11 C12 N2 1.0(4) . . . . ?
O3 S1 C13 F1 47.6(3) . . . . ?
O2 S1 C13 F1 174.1(2) . . . . ?
O1 S1 C13 F1 -68.8(2) . . . . ?
O3 S1 C13 F2 168.9(2) . . . . ?
O2 S1 C13 F2 -64.6(3) . . . . ?
O1 S1 C13 F2 52.6(3) . . . . ?
O3 S1 C13 F3 -71.2(3) . . . . ?
O2 S1 C13 F3 55.3(3) . . . . ?
O1 S1 C13 F3 172.4(2) . . . . ?
O5 S2 C14 F4 60.6(4) . . . . ?
O6 S2 C14 F4 -59.6(3) . . . . ?
O4 S2 C14 F4 -179.3(3) . . . . ?
O5 S2 C14 F5 -59.3(3) . . . . ?
O6 S2 C14 F5 -179.5(3) . . . . ?
O4 S2 C14 F5 60.8(3) . . . . ?
O5 S2 C14 F6 -179.0(3) . . . . ?
O6 S2 C14 F6 60.8(3) . . . . ?
O4 S2 C14 F6 -58.9(3) . . . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 977498'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_JF0003_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H26 Ge N4, 2(C F3 O3 S), C2 N'
_chemical_formula_sum            'C20 H26 F6 Ge N5 O6 S2'
_chemical_formula_weight         677.12

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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   10.6701(13)
_cell_length_b                   11.5348(14)
_cell_length_c                   23.336(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.922(2)
_cell_angle_gamma                90
_cell_volume                     2865.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7714
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.85

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_F_000             1364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.135
_exptl_absorpt_coefficient_mu    1.297
_shelx_estimated_absorpt_T_min   0.719
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8264
_exptl_absorpt_correction_T_max  0.9026
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45770
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.749
_diffrn_reflns_theta_max         29.673
_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             8101
_reflns_number_gt                6158
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_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)+(0.0595P)²+2.1710P] 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         8101
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.970
_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 0.42046(2) 0.53293(2) 0.36306(2) 0.01729(7) Uani 1 1 d . . . . .
C1 C 0.3452(2) 0.44913(18) 0.42234(9) 0.0211(4) Uani 1 1 d . . . . .
H1A H 0.4095 0.4033 0.4441 0.032 Uiso 1 1 calc R U . . .
H1B H 0.2802 0.3973 0.4052 0.032 Uiso 1 1 calc R U . . .
H1C H 0.3071 0.5038 0.4482 0.032 Uiso 1 1 calc R U . . .
C2 C 0.5162(2) 0.4677(2) 0.30487(10) 0.0260(5) Uani 1 1 d . . . . .
H2A H 0.5876 0.4245 0.3229 0.039 Uiso 1 1 calc R U . . .
H2B H 0.5472 0.5299 0.2810 0.039 Uiso 1 1 calc R U . . .
H2C H 0.4630 0.4151 0.2809 0.039 Uiso 1 1 calc R U . . .
N1 N 0.28070(17) 0.61713(16) 0.32509(7) 0.0201(4) Uani 1 1 d . . . . .
N3 N 0.50318(17) 0.67140(15) 0.39186(8) 0.0191(4) Uani 1 1 d . . . . .
N2 N 0.00052(19) 0.83846(18) 0.25712(8) 0.0260(4) Uani 1 1 d . . . . .
N4 N 0.6611(2) 0.98536(17) 0.44670(10) 0.0299(5) Uani 1 1 d . . . . .
C3 C 0.2766(2) 0.65157(19) 0.26921(9) 0.0211(4) Uani 1 1 d . . . . .
H3A H 0.3401 0.6245 0.2459 0.025 Uiso 1 1 calc R U . . .
C4 C 0.1863(2) 0.7226(2) 0.24496(9) 0.0223(4) Uani 1 1 d . . . . .
H4A H 0.1874 0.7432 0.2056 0.027 Uiso 1 1 calc R U . . .
C5 C 0.0900(2) 0.76625(19) 0.27846(9) 0.0211(4) Uani 1 1 d . . . . .
C6 C 0.0957(2) 0.7299(2) 0.33675(9) 0.0243(5) Uani 1 1 d . . . . .
H6A H 0.0335 0.7554 0.3611 0.029 Uiso 1 1 calc R U . . .
C7 C 0.1896(2) 0.6587(2) 0.35790(9) 0.0237(5) Uani 1 1 d . . . . .
H7A H 0.1919 0.6371 0.3972 0.028 Uiso 1 1 calc R U . . .
C8 C -0.0988(3) 0.8794(3) 0.29248(11) 0.0367(6) Uani 1 1 d . . . . .
H8A H -0.1402 0.8128 0.3092 0.055 Uiso 1 1 calc R U . . .
H8B H -0.1607 0.9240 0.2686 0.055 Uiso 1 1 calc R U . . .
H8C H -0.0621 0.9290 0.3233 0.055 Uiso 1 1 calc R U . . .
C9 C -0.0023(2) 0.8821(2) 0.19837(10) 0.0327(6) Uani 1 1 d . . . . .
H9A H 0.0681 0.8491 0.1790 0.049 Uiso 1 1 calc R U . . .
H9B H 0.0048 0.9668 0.1990 0.049 Uiso 1 1 calc R U . . .
H9C H -0.0816 0.8597 0.1777 0.049 Uiso 1 1 calc R U . . .
C10 C 0.5202(2) 0.69728(19) 0.44874(9) 0.0202(4) Uani 1 1 d . . . . .
H10A H 0.4936 0.6425 0.4758 0.024 Uiso 1 1 calc R U . . .
C11 C 0.5735(2) 0.79771(19) 0.46878(10) 0.0221(4) Uani 1 1 d . . . . .
H11A H 0.5846 0.8109 0.5090 0.027 Uiso 1 1 calc R U . . .
C12 C 0.6128(2) 0.88348(19) 0.42971(10) 0.0227(4) Uani 1 1 d . . . . .
C13 C 0.5955(2) 0.8535(2) 0.37037(11) 0.0290(5) Uani 1 1 d . . . . .
H13A H 0.6206 0.9064 0.3421 0.035 Uiso 1 1 calc R U . . .
C14 C 0.5436(2) 0.7506(2) 0.35373(10) 0.0265(5) Uani 1 1 d . . . . .
H14A H 0.5350 0.7328 0.3139 0.032 Uiso 1 1 calc R U . . .
C15 C 0.7019(3) 1.0695(2) 0.40462(14) 0.0431(7) Uani 1 1 d . . . . .
H15A H 0.6300 1.0916 0.3785 0.065 Uiso 1 1 calc R U . . .
H15B H 0.7670 1.0345 0.3825 0.065 Uiso 1 1 calc R U . . .
H15C H 0.7358 1.1384 0.4247 0.065 Uiso 1 1 calc R U . . .
C16 C 0.6852(3) 1.0154(2) 0.50701(13) 0.0369(6) Uani 1 1 d . . . . .
H16A H 0.6544 0.9532 0.5310 0.055 Uiso 1 1 calc R U . . .
H16B H 0.6416 1.0879 0.5150 0.055 Uiso 1 1 calc R U . . .
H16C H 0.7757 1.0255 0.5157 0.055 Uiso 1 1 calc R U . . .
S1 S 0.35481(6) 1.18403(6) 0.32774(3) 0.03044(14) Uani 1 1 d . . . . .
C17 C 0.2426(3) 1.0722(4) 0.30423(17) 0.0644(12) Uani 0.626(8) 1 d . . P A 1
F1 F 0.2741(7) 0.9742(7) 0.3074(4) 0.0689(16) Uani 0.626(8) 1 d . . P A 1
F2 F 0.1265(5) 1.0965(6) 0.3246(3) 0.0667(16) Uani 0.626(8) 1 d . . P A 1
F3 F 0.2052(7) 1.0960(6) 0.2435(3) 0.0603(16) Uani 0.626(8) 1 d . . P A 1
C17' C 0.2426(3) 1.0722(4) 0.30423(17) 0.0644(12) Uani 0.374(8) 1 d . . P A 2
F1' F 0.3180(11) 0.9564(13) 0.3205(8) 0.0689(16) Uani 0.374(8) 1 d . . P A 2
F2' F 0.1592(9) 1.0511(9) 0.3442(5) 0.0667(16) Uani 0.374(8) 1 d . . P A 2
F3' F 0.2170(14) 1.0554(11) 0.2577(5) 0.0603(16) Uani 0.374(8) 1 d . . P A 2
O1 O 0.3786(2) 1.1618(2) 0.38770(8) 0.0542(6) Uani 1 1 d . . . . .
O2 O 0.2885(2) 1.2905(2) 0.31450(10) 0.0520(6) Uani 1 1 d . . . . .
O3 O 0.45858(18) 1.16300(18) 0.29320(9) 0.0412(5) Uani 1 1 d . . . . .
S2 S 0.74709(5) 1.40284(5) 0.43652(2) 0.02029(12) Uani 1 1 d . . . . .
O4 O 0.77091(17) 1.33815(14) 0.38561(7) 0.0301(4) Uani 1 1 d . . . . .
O5 O 0.79172(17) 1.35012(15) 0.48990(7) 0.0325(4) Uani 1 1 d . . . . .
O6 O 0.62223(15) 1.45159(14) 0.43691(7) 0.0258(3) Uani 1 1 d . . . . .
C18 C 0.8464(2) 1.5305(2) 0.43093(11) 0.0288(5) Uani 1 1 d . . . . .
F4 F 0.81271(17) 1.59105(14) 0.38365(7) 0.0456(4) Uani 1 1 d . . . . .
F5 F 0.83763(17) 1.60108(14) 0.47591(7) 0.0476(4) Uani 1 1 d . . . . .
F6 F 0.96672(15) 1.50152(16) 0.42833(8) 0.0451(4) Uani 1 1 d . . . . .
N1S N 1.0429(3) 1.1182(3) 0.55607(12) 0.0533(7) Uani 1 1 d . . . . .
C2S C 1.0429(3) 1.1502(2) 0.50981(13) 0.0361(6) Uani 1 1 d . . . . .
C1S C 1.0433(3) 1.1882(3) 0.45002(12) 0.0420(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ge1 C2 1.909(2) . ?
Ge1 C1 1.909(2) . ?
Ge1 N3 1.9237(18) . ?
Ge1 N1 1.9420(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N1 C3 1.361(3) . ?
N1 C7 1.365(3) . ?
N3 C10 1.361(3) . ?
N3 C14 1.365(3) . ?
N2 C5 1.337(3) . ?
N2 C9 1.459(3) . ?
N2 C8 1.466(3) . ?
N4 C12 1.333(3) . ?
N4 C16 1.455(4) . ?
N4 C15 1.467(3) . ?
C3 C4 1.358(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.425(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.421(3) . ?
C6 C7 1.362(3) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.359(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.428(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.427(3) . ?
C13 C14 1.356(3) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
S1 O1 1.428(2) . ?
S1 O3 1.4341(19) . ?
S1 O2 1.440(2) . ?
S1 C17 1.819(3) . ?
C17 F1 1.181(9) . ?
C17 F2 1.385(6) . ?
C17 F3 1.472(8) . ?
S2 O5 1.4378(18) . ?
S2 O4 1.4401(17) . ?
S2 O6 1.4468(17) . ?
S2 C18 1.824(2) . ?
C18 F6 1.332(3) . ?
C18 F4 1.334(3) . ?
C18 F5 1.337(3) . ?
N1S C2S 1.141(4) . ?
C2S C1S 1.463(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Ge1 C1 126.01(10) . . ?
C2 Ge1 N3 108.71(9) . . ?
C1 Ge1 N3 111.90(8) . . ?
C2 Ge1 N1 107.71(9) . . ?
C1 Ge1 N1 103.63(9) . . ?
N3 Ge1 N1 93.66(8) . . ?
Ge1 C1 H1A 109.5 . . ?
Ge1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Ge1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Ge1 C2 H2A 109.5 . . ?
Ge1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Ge1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 N1 C7 117.20(19) . . ?
C3 N1 Ge1 123.83(15) . . ?
C7 N1 Ge1 118.29(15) . . ?
C10 N3 C14 117.51(19) . . ?
C10 N3 Ge1 123.40(14) . . ?
C14 N3 Ge1 119.05(15) . . ?
C5 N2 C9 122.2(2) . . ?
C5 N2 C8 121.1(2) . . ?
C9 N2 C8 116.7(2) . . ?
C12 N4 C16 122.5(2) . . ?
C12 N4 C15 120.7(2) . . ?
C16 N4 C15 116.7(2) . . ?
C4 C3 N1 123.4(2) . . ?
C4 C3 H3A 118.3 . . ?
N1 C3 H3A 118.3 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
N2 C5 C6 121.6(2) . . ?
N2 C5 C4 122.6(2) . . ?
C6 C5 C4 115.8(2) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
C6 C7 N1 122.9(2) . . ?
C6 C7 H7A 118.5 . . ?
N1 C7 H7A 118.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N3 123.2(2) . . ?
C11 C10 H10A 118.4 . . ?
N3 C10 H10A 118.4 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
N4 C12 C13 121.6(2) . . ?
N4 C12 C11 123.1(2) . . ?
C13 C12 C11 115.3(2) . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C13 C14 N3 122.7(2) . . ?
C13 C14 H14A 118.7 . . ?
N3 C14 H14A 118.7 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 S1 O3 115.35(14) . . ?
O1 S1 O2 114.50(14) . . ?
O3 S1 O2 114.23(14) . . ?
O1 S1 C17 103.75(17) . . ?
O3 S1 C17 103.20(13) . . ?
O2 S1 C17 103.67(18) . . ?
F1 C17 F2 115.4(5) . . ?
F1 C17 F3 107.3(5) . . ?
F2 C17 F3 95.9(5) . . ?
F1 C17 S1 118.8(4) . . ?
F2 C17 S1 109.8(3) . . ?
F3 C17 S1 106.7(4) . . ?
O5 S2 O4 115.40(11) . . ?
O5 S2 O6 114.17(10) . . ?
O4 S2 O6 114.91(11) . . ?
O5 S2 C18 104.11(12) . . ?
O4 S2 C18 102.89(11) . . ?
O6 S2 C18 103.09(11) . . ?
F6 C18 F4 107.4(2) . . ?
F6 C18 F5 107.9(2) . . ?
F4 C18 F5 107.5(2) . . ?
F6 C18 S2 111.55(18) . . ?
F4 C18 S2 110.89(17) . . ?
F5 C18 S2 111.30(17) . . ?
N1S C2S C1S 178.6(3) . . ?

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
C7 N1 C3 C4 -1.1(3) . . . . ?
Ge1 N1 C3 C4 -171.48(17) . . . . ?
N1 C3 C4 C5 0.7(3) . . . . ?
C9 N2 C5 C6 176.2(2) . . . . ?
C8 N2 C5 C6 -2.6(4) . . . . ?
C9 N2 C5 C4 -2.6(4) . . . . ?
C8 N2 C5 C4 178.5(2) . . . . ?
C3 C4 C5 N2 178.5(2) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
N2 C5 C6 C7 -178.2(2) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C5 C6 C7 N1 -1.2(4) . . . . ?
C3 N1 C7 C6 1.4(3) . . . . ?
Ge1 N1 C7 C6 172.29(19) . . . . ?
C14 N3 C10 C11 0.8(3) . . . . ?
Ge1 N3 C10 C11 -176.85(17) . . . . ?
N3 C10 C11 C12 1.2(3) . . . . ?
C16 N4 C12 C13 -177.0(2) . . . . ?
C15 N4 C12 C13 -1.8(4) . . . . ?
C16 N4 C12 C11 3.8(4) . . . . ?
C15 N4 C12 C11 179.0(2) . . . . ?
C10 C11 C12 N4 177.3(2) . . . . ?
C10 C11 C12 C13 -1.9(3) . . . . ?
N4 C12 C13 C14 -178.5(2) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 N3 1.3(4) . . . . ?
C10 N3 C14 C13 -2.0(3) . . . . ?
Ge1 N3 C14 C13 175.73(19) . . . . ?
O1 S1 C17 F1 -63.6(6) . . . . ?
O3 S1 C17 F1 57.1(6) . . . . ?
O2 S1 C17 F1 176.5(6) . . . . ?
O1 S1 C17 F2 72.3(5) . . . . ?
O3 S1 C17 F2 -167.0(4) . . . . ?
O2 S1 C17 F2 -47.6(5) . . . . ?
O1 S1 C17 F3 175.2(4) . . . . ?
O3 S1 C17 F3 -64.1(4) . . . . ?
O2 S1 C17 F3 55.3(4) . . . . ?
O5 S2 C18 F6 62.31(19) . . . . ?
O4 S2 C18 F6 -58.4(2) . . . . ?
O6 S2 C18 F6 -178.23(17) . . . . ?
O5 S2 C18 F4 -177.98(17) . . . . ?
O4 S2 C18 F4 61.3(2) . . . . ?
O6 S2 C18 F4 -58.5(2) . . . . ?
O5 S2 C18 F5 -58.3(2) . . . . ?
O4 S2 C18 F5 -179.07(18) . . . . ?
O6 S2 C18 F5 61.1(2) . . . . ?

_refine_diff_density_max         0.670
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.080

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 977499'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_JF0006_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 Ge N2, 2(C F3 O3 S)'
_chemical_formula_sum            'C14 H14 F6 Ge N2 O6 S2'
_chemical_formula_weight         556.98

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'
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'
F F 0.0171 0.0103 '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'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.7487(2)
_cell_length_b                   11.1678(3)
_cell_length_c                   12.4220(3)
_cell_angle_alpha                110.4190(10)
_cell_angle_beta                 95.6880(10)
_cell_angle_gamma                95.4360(10)
_cell_volume                     992.76(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      35.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.863
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.174
_exptl_absorpt_coefficient_mu    1.845
_shelx_estimated_absorpt_T_min   0.582
_shelx_estimated_absorpt_T_max   0.740
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6508
_exptl_absorpt_correction_T_max  0.7825
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25958
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.767
_diffrn_reflns_theta_max         32.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7179
_reflns_number_gt                6524
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_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)+(0.0418P)²+0.3562P] 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         7179
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.17392(2) 0.39136(2) 0.29010(2) 0.01898(4) Uani 1 1 d . . . . .
S1 S 0.89775(4) 0.28425(3) 0.91917(3) 0.02227(6) Uani 1 1 d . . . . .
F1 F 0.92777(19) 0.05125(11) 0.77953(11) 0.0550(3) Uani 1 1 d . . . . .
O1 O 1.07985(14) 0.32296(13) 0.91933(11) 0.0394(3) Uani 1 1 d . . . . .
N1 N 0.25034(13) 0.27185(10) 0.15330(9) 0.01870(17) Uani 1 1 d . . . . .
C1 C -0.01574(17) 0.47765(14) 0.25951(13) 0.0264(2) Uani 1 1 d . . . . .
H1E H -0.1264 0.4304 0.2639 0.040 Uiso 1 1 calc R U . . .
H1F H -0.0176 0.4814 0.1817 0.040 Uiso 1 1 calc R U . . .
H1G H -0.0006 0.5655 0.3172 0.040 Uiso 1 1 calc R U . . .
S2 S 0.78782(5) 0.23042(3) 0.33677(3) 0.02873(7) Uani 1 1 d . . . . .
F2 F 0.66714(16) 0.10134(12) 0.76688(11) 0.0542(3) Uani 1 1 d . . . . .
O2 O 0.78080(14) 0.37309(10) 0.90700(9) 0.0295(2) Uani 1 1 d . . . . .
N2 N 0.37102(13) 0.50937(10) 0.27462(9) 0.01922(18) Uani 1 1 d . . . . .
C2 C 0.27007(19) 0.36100(15) 0.42465(12) 0.0279(3) Uani 1 1 d . . . . .
H2B H 0.1846 0.3028 0.4427 0.042 Uiso 1 1 calc R U . . .
H2C H 0.2977 0.4431 0.4905 0.042 Uiso 1 1 calc R U . . .
H2D H 0.3772 0.3216 0.4096 0.042 Uiso 1 1 calc R U . . .
F3 F 0.86720(19) 0.18106(12) 0.69293(9) 0.0530(3) Uani 1 1 d . . . . .
O3 O 0.86194(14) 0.22873(12) 1.00504(9) 0.0323(2) Uani 1 1 d . . . . .
C3 C 0.18561(17) 0.14599(13) 0.10194(12) 0.0238(2) Uani 1 1 d . . . . .
H3B H 0.0905 0.1115 0.1299 0.029 Uiso 1 1 calc R U . . .
F4 F 0.65318(17) 0.10048(11) 0.45386(10) 0.0484(3) Uani 1 1 d . . . . .
O4 O 0.62220(18) 0.20865(19) 0.26641(16) 0.0610(4) Uani 1 1 d . . . . .
C4 C 0.25495(18) 0.06609(13) 0.00926(12) 0.0273(2) Uani 1 1 d . . . . .
H4C H 0.2099 -0.0230 -0.0252 0.033 Uiso 1 1 calc R U . . .
F5 F 0.93044(17) 0.09878(12) 0.45009(10) 0.0495(3) Uani 1 1 d . . . . .
O5 O 0.8179(2) 0.34131(11) 0.44314(13) 0.0502(4) Uani 1 1 d . . . . .
C5 C 0.39085(18) 0.11756(14) -0.03270(12) 0.0266(2) Uani 1 1 d . . . . .
H5C H 0.4394 0.0639 -0.0967 0.032 Uiso 1 1 calc R U . . .
F6 F 0.74784(17) -0.01716(10) 0.30024(10) 0.0492(3) Uani 1 1 d . . . . .
O6 O 0.93732(14) 0.21527(10) 0.27331(9) 0.0306(2) Uani 1 1 d . . . . .
C6 C 0.45611(16) 0.24759(13) 0.01884(11) 0.0234(2) Uani 1 1 d . . . . .
H6C H 0.5476 0.2844 -0.0103 0.028 Uiso 1 1 calc R U . . .
C7 C 0.38554(14) 0.32260(12) 0.11333(10) 0.01851(19) Uani 1 1 d . . . . .
C8 C 0.45213(14) 0.45887(12) 0.18102(10) 0.01847(19) Uani 1 1 d . . . . .
C9 C 0.58688(16) 0.53254(13) 0.15669(11) 0.0224(2) Uani 1 1 d . . . . .
H9B H 0.6441 0.4968 0.0908 0.027 Uiso 1 1 calc R U . . .
C10 C 0.63561(17) 0.65962(14) 0.23118(12) 0.0258(2) Uani 1 1 d . . . . .
H10B H 0.7277 0.7120 0.2168 0.031 Uiso 1 1 calc R U . . .
C11 C 0.55008(18) 0.71034(13) 0.32672(12) 0.0266(2) Uani 1 1 d . . . . .
H11B H 0.5828 0.7973 0.3779 0.032 Uiso 1 1 calc R U . . .
C12 C 0.41672(17) 0.63263(13) 0.34636(11) 0.0240(2) Uani 1 1 d . . . . .
H12D H 0.3568 0.6667 0.4112 0.029 Uiso 1 1 calc R U . . .
C13 C 0.8372(2) 0.14770(15) 0.78317(13) 0.0333(3) Uani 1 1 d . . . . .
C14 C 0.7804(2) 0.09592(14) 0.38789(12) 0.0306(3) 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 C1 1.9095(12) . ?
Ge1 C2 1.9131(13) . ?
Ge1 N1 1.9458(10) . ?
Ge1 N2 1.9901(10) . ?
S1 O1 1.4357(11) . ?
S1 O2 1.4410(10) . ?
S1 O3 1.4446(10) . ?
S1 C13 1.8192(16) . ?
F1 C13 1.3303(18) . ?
N1 C3 1.3460(16) . ?
N1 C7 1.3609(15) . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C1 H1G 0.9800 . ?
S2 O4 1.4284(15) . ?
S2 O5 1.4409(13) . ?
S2 O6 1.4550(11) . ?
S2 C14 1.8219(15) . ?
F2 C13 1.338(2) . ?
N2 C12 1.3430(16) . ?
N2 C8 1.3488(15) . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?
F3 C13 1.3326(18) . ?
C3 C4 1.3809(19) . ?
C3 H3B 0.9500 . ?
F4 C14 1.3366(18) . ?
C4 C5 1.384(2) . ?
C4 H4C 0.9500 . ?
F5 C14 1.322(2) . ?
C5 C6 1.3865(19) . ?
C5 H5C 0.9500 . ?
F6 C14 1.3303(17) . ?
C6 C7 1.3807(16) . ?
C6 H6C 0.9500 . ?
C7 C8 1.4702(17) . ?
C8 C9 1.3898(17) . ?
C9 C10 1.3878(19) . ?
C9 H9B 0.9500 . ?
C10 C11 1.3880(19) . ?
C10 H10B 0.9500 . ?
C11 C12 1.3814(19) . ?
C11 H11B 0.9500 . ?
C12 H12D 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
C1 Ge1 C2 133.34(6) . . ?
C1 Ge1 N1 115.19(5) . . ?
C2 Ge1 N1 109.28(5) . . ?
C1 Ge1 N2 98.91(5) . . ?
C2 Ge1 N2 100.66(5) . . ?
N1 Ge1 N2 81.81(4) . . ?
O1 S1 O2 115.85(7) . . ?
O1 S1 O3 114.89(7) . . ?
O2 S1 O3 114.47(6) . . ?
O1 S1 C13 103.49(8) . . ?
O2 S1 C13 102.65(7) . . ?
O3 S1 C13 102.95(7) . . ?
C3 N1 C7 119.95(11) . . ?
C3 N1 Ge1 124.97(9) . . ?
C7 N1 Ge1 114.99(8) . . ?
Ge1 C1 H1E 109.5 . . ?
Ge1 C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
Ge1 C1 H1G 109.5 . . ?
H1E C1 H1G 109.5 . . ?
H1F C1 H1G 109.5 . . ?
O4 S2 O5 116.58(11) . . ?
O4 S2 O6 114.71(9) . . ?
O5 S2 O6 113.27(8) . . ?
O4 S2 C14 103.97(9) . . ?
O5 S2 C14 102.85(8) . . ?
O6 S2 C14 103.13(7) . . ?
C12 N2 C8 121.04(11) . . ?
C12 N2 Ge1 124.00(8) . . ?
C8 N2 Ge1 114.85(8) . . ?
Ge1 C2 H2B 109.5 . . ?
Ge1 C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
Ge1 C2 H2D 109.5 . . ?
H2B C2 H2D 109.5 . . ?
H2C C2 H2D 109.5 . . ?
N1 C3 C4 121.17(12) . . ?
N1 C3 H3B 119.4 . . ?
C4 C3 H3B 119.4 . . ?
C3 C4 C5 119.10(13) . . ?
C3 C4 H4C 120.4 . . ?
C5 C4 H4C 120.4 . . ?
C4 C5 C6 119.89(12) . . ?
C4 C5 H5C 120.1 . . ?
C6 C5 H5C 120.1 . . ?
C7 C6 C5 118.74(12) . . ?
C7 C6 H6C 120.6 . . ?
C5 C6 H6C 120.6 . . ?
N1 C7 C6 121.09(11) . . ?
N1 C7 C8 114.90(10) . . ?
C6 C7 C8 123.96(11) . . ?
N2 C8 C9 120.93(11) . . ?
N2 C8 C7 113.31(10) . . ?
C9 C8 C7 125.74(11) . . ?
C10 C9 C8 118.22(11) . . ?
C10 C9 H9B 120.9 . . ?
C8 C9 H9B 120.9 . . ?
C9 C10 C11 120.11(12) . . ?
C9 C10 H10B 119.9 . . ?
C11 C10 H10B 119.9 . . ?
C12 C11 C10 119.10(13) . . ?
C12 C11 H11B 120.4 . . ?
C10 C11 H11B 120.4 . . ?
N2 C12 C11 120.58(12) . . ?
N2 C12 H12D 119.7 . . ?
C11 C12 H12D 119.7 . . ?
F1 C13 F3 107.23(13) . . ?
F1 C13 F2 107.45(14) . . ?
F3 C13 F2 107.36(14) . . ?
F1 C13 S1 111.83(12) . . ?
F3 C13 S1 111.20(11) . . ?
F2 C13 S1 111.52(11) . . ?
F5 C14 F6 107.81(14) . . ?
F5 C14 F4 108.33(13) . . ?
F6 C14 F4 107.34(13) . . ?
F5 C14 S2 111.19(11) . . ?
F6 C14 S2 111.70(10) . . ?
F4 C14 S2 110.31(11) . . ?

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
C7 N1 C3 C4 0.56(18) . . . . ?
Ge1 N1 C3 C4 -175.94(10) . . . . ?
N1 C3 C4 C5 -1.4(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C7 1.4(2) . . . . ?
C3 N1 C7 C6 1.32(17) . . . . ?
Ge1 N1 C7 C6 178.15(9) . . . . ?
C3 N1 C7 C8 -176.26(10) . . . . ?
Ge1 N1 C7 C8 0.57(12) . . . . ?
C5 C6 C7 N1 -2.28(18) . . . . ?
C5 C6 C7 C8 175.07(11) . . . . ?
C12 N2 C8 C9 0.72(17) . . . . ?
Ge1 N2 C8 C9 177.11(9) . . . . ?
C12 N2 C8 C7 179.57(11) . . . . ?
Ge1 N2 C8 C7 -4.04(12) . . . . ?
N1 C7 C8 N2 2.31(14) . . . . ?
C6 C7 C8 N2 -175.19(11) . . . . ?
N1 C7 C8 C9 -178.91(11) . . . . ?
C6 C7 C8 C9 3.59(19) . . . . ?
N2 C8 C9 C10 -0.13(18) . . . . ?
C7 C8 C9 C10 -178.82(11) . . . . ?
C8 C9 C10 C11 -0.27(19) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C8 N2 C12 C11 -0.90(19) . . . . ?
Ge1 N2 C12 C11 -176.95(10) . . . . ?
C10 C11 C12 N2 0.5(2) . . . . ?
O1 S1 C13 F1 61.65(13) . . . . ?
O2 S1 C13 F1 -177.46(11) . . . . ?
O3 S1 C13 F1 -58.30(13) . . . . ?
O1 S1 C13 F3 -58.20(13) . . . . ?
O2 S1 C13 F3 62.69(13) . . . . ?
O3 S1 C13 F3 -178.15(12) . . . . ?
O1 S1 C13 F2 -178.00(11) . . . . ?
O2 S1 C13 F2 -57.11(12) . . . . ?
O3 S1 C13 F2 62.05(12) . . . . ?
O4 S2 C14 F5 176.60(12) . . . . ?
O5 S2 C14 F5 -61.41(13) . . . . ?
O6 S2 C14 F5 56.58(12) . . . . ?
O4 S2 C14 F6 56.12(14) . . . . ?
O5 S2 C14 F6 178.10(12) . . . . ?
O6 S2 C14 F6 -63.91(13) . . . . ?
O4 S2 C14 F4 -63.18(14) . . . . ?
O5 S2 C14 F4 58.81(13) . . . . ?
O6 S2 C14 F4 176.80(11) . . . . ?

_refine_diff_density_max         0.789
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.065

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 977500'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cc

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H26 F6 N4 O6 S2 Sn'
_chemical_formula_sum            'C18 H26 F6 N4 O6 S2 Sn'
_chemical_formula_weight         691.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   9.4758(5)
_cell_length_b                   13.6913(6)
_cell_length_c                   21.1332(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.452(2)
_cell_angle_gamma                90
_cell_volume                     2696.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8995
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      26.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_F_000             1384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    1.184
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8654
_exptl_absorpt_correction_T_max  0.9525
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32769
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.960
_diffrn_reflns_theta_max         34.308
_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             5618
_reflns_number_gt                4648
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_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)+(0.0291P)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         5618
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0570
_refine_ls_wR_factor_gt          0.0553
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.0000 0.28717(2) 0.2500 0.01810(4) Uani 1 2 d S T P . .
S1 S 0.01949(4) 0.12162(2) 0.39064(2) 0.02401(7) Uani 1 1 d . . . . .
F1 F 0.11031(11) -0.03333(7) 0.33783(6) 0.0515(3) Uani 1 1 d . . . . .
F2 F -0.11474(11) -0.00324(8) 0.30743(5) 0.0528(3) Uani 1 1 d . . . . .
F3 F -0.03708(11) -0.06337(7) 0.40104(6) 0.0525(3) Uani 1 1 d . . . . .
O1 O 0.13042(13) 0.10956(9) 0.44579(5) 0.0423(3) Uani 1 1 d . . . . .
O2 O -0.11869(12) 0.15060(8) 0.40200(5) 0.0380(3) Uani 1 1 d . . . . .
O3 O 0.06781(11) 0.17409(8) 0.33832(5) 0.0337(2) Uani 1 1 d . . . . .
N1 N 0.02779(12) 0.40335(8) 0.32381(5) 0.0210(2) Uani 1 1 d . . . . .
N2 N 0.06649(12) 0.62247(8) 0.46284(5) 0.0251(2) Uani 1 1 d . . . . .
C1 C 0.21563(15) 0.25857(11) 0.24412(7) 0.0283(3) Uani 1 1 d . . . . .
H1B H 0.2367 0.2860 0.2051 0.042 Uiso 1 1 calc R U . . .
H1C H 0.2312 0.1893 0.2443 0.042 Uiso 1 1 calc R U . . .
H1D H 0.2773 0.2874 0.2804 0.042 Uiso 1 1 calc R U . . .
C3 C -0.06181(14) 0.48124(10) 0.31771(6) 0.0238(3) Uani 1 1 d . . . . .
H3A H -0.1331 0.4851 0.2812 0.029 Uiso 1 1 calc R U . . .
C4 C -0.05332(14) 0.55442(10) 0.36209(6) 0.0245(3) Uani 1 1 d . . . . .
H4B H -0.1178 0.6062 0.3552 0.029 Uiso 1 1 calc R U . . .
C5 C 0.05334(13) 0.55177(9) 0.41859(6) 0.0205(2) Uani 1 1 d . . . . .
C6 C 0.14431(14) 0.46832(9) 0.42534(6) 0.0222(2) Uani 1 1 d . . . . .
H6A H 0.2149 0.4610 0.4618 0.027 Uiso 1 1 calc R U . . .
C7 C 0.12797(13) 0.39907(9) 0.37825(6) 0.0218(2) Uani 1 1 d . . . . .
H7A H 0.1894 0.3456 0.3839 0.026 Uiso 1 1 calc R U . . .
C8 C 0.18154(15) 0.61983(11) 0.51890(6) 0.0296(3) Uani 1 1 d . . . . .
H8A H 0.1739 0.5611 0.5429 0.044 Uiso 1 1 calc R U . . .
H8B H 0.1739 0.6756 0.5456 0.044 Uiso 1 1 calc R U . . .
H8C H 0.2726 0.6211 0.5051 0.044 Uiso 1 1 calc R U . . .
C9 C -0.02448(19) 0.70880(10) 0.45249(8) 0.0365(3) Uani 1 1 d . . . . .
H9A H -0.1232 0.6898 0.4487 0.055 Uiso 1 1 calc R U . . .
H9B H -0.0109 0.7410 0.4137 0.055 Uiso 1 1 calc R U . . .
H9C H 0.0006 0.7526 0.4882 0.055 Uiso 1 1 calc R U . . .
C10 C -0.00719(16) -0.00107(10) 0.35708(8) 0.0322(3) 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
Sn1 C1 2.1062(13) . ?
Sn1 C1 2.1062(13) 2 ?
Sn1 N1 2.2097(10) 2 ?
Sn1 N1 2.2098(10) . ?
Sn1 O3 2.4204(10) 2 ?
Sn1 O3 2.4204(10) . ?
S1 O2 1.4296(11) . ?
S1 O1 1.4305(11) . ?
S1 O3 1.4601(10) . ?
S1 C10 1.8231(15) . ?
F1 C10 1.3284(17) . ?
F2 C10 1.3239(18) . ?
F3 C10 1.3290(18) . ?
N1 C3 1.3547(16) . ?
N1 C7 1.3535(16) . ?
N2 C5 1.3360(16) . ?
N2 C9 1.4559(18) . ?
N2 C8 1.4576(18) . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C3 C4 1.3647(18) . ?
C3 H3A 0.9300 . ?
C4 C5 1.4180(18) . ?
C4 H4B 0.9300 . ?
C5 C6 1.4227(17) . ?
C6 C7 1.3630(18) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
C1 Sn1 C1 158.57(8) . 2 ?
C1 Sn1 N1 94.87(5) . 2 ?
C1 Sn1 N1 100.53(5) 2 2 ?
C1 Sn1 N1 100.53(5) . . ?
C1 Sn1 N1 94.87(5) 2 . ?
N1 Sn1 N1 87.92(6) 2 . ?
C1 Sn1 O3 87.72(5) . 2 ?
C1 Sn1 O3 78.57(5) 2 2 ?
N1 Sn1 O3 86.28(4) 2 2 ?
N1 Sn1 O3 170.29(4) . 2 ?
C1 Sn1 O3 78.57(5) . . ?
C1 Sn1 O3 87.72(5) 2 . ?
N1 Sn1 O3 170.29(4) 2 . ?
N1 Sn1 O3 86.28(4) . . ?
O3 Sn1 O3 100.47(5) 2 . ?
O2 S1 O1 117.08(7) . . ?
O2 S1 O3 114.41(7) . . ?
O1 S1 O3 112.88(7) . . ?
O2 S1 C10 104.74(7) . . ?
O1 S1 C10 103.89(7) . . ?
O3 S1 C10 101.49(7) . . ?
S1 O3 Sn1 145.37(7) . . ?
C3 N1 C7 116.47(11) . . ?
C3 N1 Sn1 120.48(9) . . ?
C7 N1 Sn1 122.97(8) . . ?
C5 N2 C9 120.37(12) . . ?
C5 N2 C8 120.80(11) . . ?
C9 N2 C8 118.52(11) . . ?
Sn1 C1 H1B 109.5 . . ?
Sn1 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Sn1 C1 H1D 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
N1 C3 C4 123.70(12) . . ?
N1 C3 H3A 118.1 . . ?
C4 C3 H3A 118.1 . . ?
C3 C4 C5 120.26(12) . . ?
C3 C4 H4B 119.9 . . ?
C5 C4 H4B 119.9 . . ?
N2 C5 C4 122.18(12) . . ?
N2 C5 C6 122.26(12) . . ?
C4 C5 C6 115.55(11) . . ?
C7 C6 C5 119.93(12) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
N1 C7 C6 124.04(12) . . ?
N1 C7 H7A 118.0 . . ?
C6 C7 H7A 118.0 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F2 C10 F1 108.50(13) . . ?
F2 C10 F3 107.98(12) . . ?
F1 C10 F3 107.30(12) . . ?
F2 C10 S1 111.19(10) . . ?
F1 C10 S1 111.15(10) . . ?
F3 C10 S1 110.58(11) . . ?

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
O2 S1 O3 Sn1 -9.01(15) . . . . ?
O1 S1 O3 Sn1 -146.24(11) . . . . ?
C10 S1 O3 Sn1 103.16(12) . . . . ?
C7 N1 C3 C4 1.6(2) . . . . ?
Sn1 N1 C3 C4 178.33(10) . . . . ?
N1 C3 C4 C5 -0.2(2) . . . . ?
C9 N2 C5 C4 -3.7(2) . . . . ?
C8 N2 C5 C4 -177.08(12) . . . . ?
C9 N2 C5 C6 177.06(13) . . . . ?
C8 N2 C5 C6 3.64(19) . . . . ?
C3 C4 C5 N2 179.16(12) . . . . ?
C3 C4 C5 C6 -1.51(18) . . . . ?
N2 C5 C6 C7 -178.88(12) . . . . ?
C4 C5 C6 C7 1.79(18) . . . . ?
C3 N1 C7 C6 -1.25(19) . . . . ?
Sn1 N1 C7 C6 -177.93(10) . . . . ?
C5 C6 C7 N1 -0.4(2) . . . . ?
O2 S1 C10 F2 52.46(12) . . . . ?
O1 S1 C10 F2 175.82(11) . . . . ?
O3 S1 C10 F2 -66.86(11) . . . . ?
O2 S1 C10 F1 173.45(11) . . . . ?
O1 S1 C10 F1 -63.19(13) . . . . ?
O3 S1 C10 F1 54.13(13) . . . . ?
O2 S1 C10 F3 -67.49(12) . . . . ?
O1 S1 C10 F3 55.88(12) . . . . ?
O3 S1 C10 F3 173.20(10) . . . . ?

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.075

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 977501'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_JF0001_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 F6 N2 O6 S2 Sn'
_chemical_formula_sum            'C14 H14 F6 N2 O6 S2 Sn'
_chemical_formula_weight         603.08

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'
O O 0.0106 0.0060 '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'
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'

_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                   10.623(3)
_cell_length_b                   15.281(4)
_cell_length_c                   13.418(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.235(4)
_cell_angle_gamma                90
_cell_volume                     2001.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9941
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      32.47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.001
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.094
_exptl_absorpt_coefficient_mu    1.576
_shelx_estimated_absorpt_T_min   0.711
_shelx_estimated_absorpt_T_max   0.866
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7783
_exptl_absorpt_correction_T_max  0.9157
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 A crystal of suitable size was selected, mounted in Paratone oil 
on a MiTeGen loop, and placed in the cold stream of the diffractometer. 
Data were collected at -100C with MoK(alpha) radiation using a Bruker
Apex2 CCD diffractometer. 0.5degree phi and omega scans were used; the 
data were integrated (SAINT) and corrected for absorption (SADABS) 
(both SHELXL2013.4), then solved in the monoclinic space group P2(1)/c.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34376
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.122
_diffrn_reflns_theta_max         33.281
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7581
_reflns_number_gt                6304
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 All non-hydrogen atoms were refined anisotropically and hydrogen atoms
were place in idealized positions and updated with refinement. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0270P)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         7581
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0514
_refine_ls_wR_factor_gt          0.0503
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.49598(2) 0.68610(2) 0.10824(2) 0.00862(3) Uani 1 1 d . . . . .
S1 S 0.19543(3) 0.81761(2) 0.03250(3) 0.01316(6) Uani 1 1 d . . . . .
S2 S 0.37879(3) 0.50844(2) 0.23380(3) 0.01199(6) Uani 1 1 d . . . . .
F1 F 0.09684(10) 0.65947(6) -0.01533(9) 0.0312(2) Uani 1 1 d . . . . .
F2 F 0.10051(9) 0.73044(6) -0.15184(7) 0.02300(19) Uani 1 1 d . . . . .
F3 F -0.05148(8) 0.76172(7) -0.08910(8) 0.0260(2) Uani 1 1 d . . . . .
F4 F 0.28024(9) 0.38504(6) 0.08696(7) 0.02193(19) Uani 1 1 d . . . . .
F5 F 0.13640(8) 0.48714(6) 0.07705(8) 0.0274(2) Uani 1 1 d . . . . .
F6 F 0.18941(9) 0.39148(6) 0.20479(8) 0.0241(2) Uani 1 1 d . . . . .
O1 O 0.32699(9) 0.79192(6) 0.02940(8) 0.01442(19) Uani 1 1 d . . . . .
O2 O 0.14748(10) 0.90076(7) -0.01600(10) 0.0240(2) Uani 1 1 d . . . . .
O3 O 0.18501(11) 0.79987(8) 0.13390(9) 0.0233(2) Uani 1 1 d . . . . .
O4 O 0.41991(10) 0.55201(6) 0.15422(8) 0.0160(2) Uani 1 1 d . . . . .
O5 O 0.48052(10) 0.44800(7) 0.30101(9) 0.0199(2) Uani 1 1 d . . . . .
O6 O 0.31617(11) 0.56397(7) 0.28668(10) 0.0227(2) Uani 1 1 d . . . . .
N1 N 0.70759(10) 0.62452(7) 0.17202(9) 0.0109(2) Uani 1 1 d . . . . .
N2 N 0.63463(10) 0.78052(7) 0.07338(9) 0.0098(2) Uani 1 1 d . . . . .
C1 C 0.41502(13) 0.62667(9) -0.04552(11) 0.0153(3) Uani 1 1 d . . . . .
H1 H 0.3253 0.6013 -0.0581 0.023 Uiso 1 1 calc R U . . .
H2 H 0.4771 0.5804 -0.0487 0.023 Uiso 1 1 calc R U . . .
H3 H 0.4049 0.6706 -0.1014 0.023 Uiso 1 1 calc R U . . .
C2 C 0.50688(14) 0.73296(9) 0.25795(11) 0.0147(3) Uani 1 1 d . . . . .
H5 H 0.5097 0.7971 0.2580 0.022 Uiso 1 1 calc R U . . .
H4 H 0.5899 0.7104 0.3159 0.022 Uiso 1 1 calc R U . . .
H6 H 0.4262 0.7133 0.2700 0.022 Uiso 1 1 calc R U . . .
C3 C 0.07944(14) 0.73815(10) -0.06128(12) 0.0173(3) Uani 1 1 d . . . . .
C4 C 0.73681(13) 0.54630(9) 0.22155(11) 0.0146(3) Uani 1 1 d . . . . .
H14 H 0.6664 0.5151 0.2331 0.018 Uiso 1 1 calc R U . . .
C5 C 0.86617(13) 0.50964(9) 0.25623(12) 0.0169(3) Uani 1 1 d . . . . .
H13 H 0.8847 0.4546 0.2921 0.020 Uiso 1 1 calc R U . . .
C6 C 0.96839(13) 0.55458(9) 0.23771(12) 0.0163(3) Uani 1 1 d . . . . .
H12 H 1.0578 0.5305 0.2601 0.020 Uiso 1 1 calc R U . . .
C7 C 0.93838(13) 0.63489(9) 0.18617(11) 0.0145(3) Uani 1 1 d . . . . .
H11 H 1.0066 0.6661 0.1716 0.017 Uiso 1 1 calc R U . . .
C8 C 0.80723(13) 0.66976(9) 0.15574(11) 0.0111(2) Uani 1 1 d . . . . .
C9 C 0.76849(12) 0.75705(9) 0.10551(11) 0.0107(2) Uani 1 1 d . . . . .
C10 C 0.59240(13) 0.85861(8) 0.02609(11) 0.0114(2) Uani 1 1 d . . . . .
H10 H 0.4986 0.8741 0.0035 0.014 Uiso 1 1 calc R U . . .
C11 C 0.68149(13) 0.91723(9) 0.00924(11) 0.0137(2) Uani 1 1 d . . . . .
H9 H 0.6494 0.9720 -0.0249 0.016 Uiso 1 1 calc R U . . .
C12 C 0.81869(13) 0.89431(9) 0.04327(11) 0.0148(3) Uani 1 1 d . . . . .
H8 H 0.8819 0.9335 0.0330 0.018 Uiso 1 1 calc R U . . .
C13 C 0.86278(13) 0.81380(9) 0.09240(12) 0.0142(3) Uani 1 1 d . . . . .
H7 H 0.9565 0.7977 0.1168 0.017 Uiso 1 1 calc R U . . .
C14 C 0.23850(13) 0.43949(9) 0.14515(11) 0.0144(3) 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
Sn1 C2 2.0924(15) . ?
Sn1 C1 2.1027(14) . ?
Sn1 N2 2.2391(11) . ?
Sn1 N1 2.2701(11) . ?
Sn1 O1 2.3363(10) . ?
Sn1 O4 2.3718(10) . ?
S1 O2 1.4269(11) . ?
S1 O3 1.4339(12) . ?
S1 O1 1.4679(10) . ?
S1 C3 1.8311(15) . ?
S2 O6 1.4277(11) . ?
S2 O5 1.4370(11) . ?
S2 O4 1.4638(10) . ?
S2 C14 1.8295(14) . ?
F1 C3 1.3304(17) . ?
F2 C3 1.3248(18) . ?
F3 C3 1.3393(16) . ?
F4 C14 1.3311(16) . ?
F5 C14 1.3264(16) . ?
F6 C14 1.3341(16) . ?
N1 C4 1.3431(17) . ?
N1 C8 1.3522(17) . ?
N2 C10 1.3427(17) . ?
N2 C9 1.3613(15) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 H3 0.9800 . ?
C2 H5 0.9800 . ?
C2 H4 0.9800 . ?
C2 H6 0.9800 . ?
C4 C5 1.3836(18) . ?
C4 H14 0.9500 . ?
C5 C6 1.388(2) . ?
C5 H13 0.9500 . ?
C6 C7 1.383(2) . ?
C6 H12 0.9500 . ?
C7 C8 1.3938(18) . ?
C7 H11 0.9500 . ?
C8 C9 1.4779(19) . ?
C9 C13 1.3875(18) . ?
C10 C11 1.3849(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3893(19) . ?
C11 H9 0.9500 . ?
C12 C13 1.387(2) . ?
C12 H8 0.9500 . ?
C13 H7 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
C2 Sn1 C1 159.42(5) . . ?
C2 Sn1 N2 100.85(5) . . ?
C1 Sn1 N2 96.98(5) . . ?
C2 Sn1 N1 96.22(5) . . ?
C1 Sn1 N1 98.73(5) . . ?
N2 Sn1 N1 73.19(4) . . ?
C2 Sn1 O1 86.53(5) . . ?
C1 Sn1 O1 84.88(5) . . ?
N2 Sn1 O1 84.87(4) . . ?
N1 Sn1 O1 158.03(4) . . ?
C2 Sn1 O4 86.64(5) . . ?
C1 Sn1 O4 80.37(5) . . ?
N2 Sn1 O4 158.55(4) . . ?
N1 Sn1 O4 86.11(4) . . ?
O1 Sn1 O4 115.84(4) . . ?
O2 S1 O3 117.00(7) . . ?
O2 S1 O1 113.44(6) . . ?
O3 S1 O1 114.02(6) . . ?
O2 S1 C3 104.75(7) . . ?
O3 S1 C3 104.11(7) . . ?
O1 S1 C3 101.14(6) . . ?
O6 S2 O5 116.91(7) . . ?
O6 S2 O4 115.08(6) . . ?
O5 S2 O4 112.53(6) . . ?
O6 S2 C14 104.22(7) . . ?
O5 S2 C14 104.83(6) . . ?
O4 S2 C14 100.87(6) . . ?
S1 O1 Sn1 137.93(6) . . ?
S2 O4 Sn1 144.40(6) . . ?
C4 N1 C8 119.48(11) . . ?
C4 N1 Sn1 123.82(8) . . ?
C8 N1 Sn1 116.68(9) . . ?
C10 N2 C9 119.76(11) . . ?
C10 N2 Sn1 123.14(8) . . ?
C9 N2 Sn1 117.07(9) . . ?
Sn1 C1 H1 109.5 . . ?
Sn1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
Sn1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
Sn1 C2 H5 109.5 . . ?
Sn1 C2 H4 109.5 . . ?
H5 C2 H4 109.5 . . ?
Sn1 C2 H6 109.5 . . ?
H5 C2 H6 109.5 . . ?
H4 C2 H6 109.5 . . ?
F2 C3 F1 107.57(12) . . ?
F2 C3 F3 107.51(11) . . ?
F1 C3 F3 108.14(11) . . ?
F2 C3 S1 112.21(10) . . ?
F1 C3 S1 110.37(10) . . ?
F3 C3 S1 110.88(10) . . ?
N1 C4 C5 122.13(13) . . ?
N1 C4 H14 118.9 . . ?
C5 C4 H14 118.9 . . ?
C4 C5 C6 118.88(13) . . ?
C4 C5 H13 120.6 . . ?
C6 C5 H13 120.6 . . ?
C7 C6 C5 119.11(12) . . ?
C7 C6 H12 120.4 . . ?
C5 C6 H12 120.4 . . ?
C6 C7 C8 119.50(13) . . ?
C6 C7 H11 120.2 . . ?
C8 C7 H11 120.2 . . ?
N1 C8 C7 120.85(12) . . ?
N1 C8 C9 116.12(11) . . ?
C7 C8 C9 123.03(12) . . ?
N2 C9 C13 120.75(12) . . ?
N2 C9 C8 116.77(11) . . ?
C13 C9 C8 122.47(11) . . ?
N2 C10 C11 121.97(12) . . ?
N2 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C12 118.63(13) . . ?
C10 C11 H9 120.7 . . ?
C12 C11 H9 120.7 . . ?
C11 C12 C13 119.57(12) . . ?
C11 C12 H8 120.2 . . ?
C13 C12 H8 120.2 . . ?
C9 C13 C12 119.29(12) . . ?
C9 C13 H7 120.4 . . ?
C12 C13 H7 120.4 . . ?
F5 C14 F4 108.06(12) . . ?
F5 C14 F6 107.96(11) . . ?
F4 C14 F6 107.91(11) . . ?
F5 C14 S2 111.52(10) . . ?
F4 C14 S2 111.53(9) . . ?
F6 C14 S2 109.73(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
O2 S1 O1 Sn1 167.38(8) . . . . ?
O3 S1 O1 Sn1 30.07(11) . . . . ?
C3 S1 O1 Sn1 -81.02(10) . . . . ?
O6 S2 O4 Sn1 30.24(13) . . . . ?
O5 S2 O4 Sn1 -107.07(10) . . . . ?
C14 S2 O4 Sn1 141.71(10) . . . . ?
O2 S1 C3 F2 72.02(11) . . . . ?
O3 S1 C3 F2 -164.60(10) . . . . ?
O1 S1 C3 F2 -46.09(11) . . . . ?
O2 S1 C3 F1 -168.02(10) . . . . ?
O3 S1 C3 F1 -44.64(12) . . . . ?
O1 S1 C3 F1 73.87(11) . . . . ?
O2 S1 C3 F3 -48.22(12) . . . . ?
O3 S1 C3 F3 75.17(11) . . . . ?
O1 S1 C3 F3 -166.32(10) . . . . ?
C8 N1 C4 C5 -0.4(2) . . . . ?
Sn1 N1 C4 C5 177.87(10) . . . . ?
N1 C4 C5 C6 -1.0(2) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C5 C6 C7 C8 1.2(2) . . . . ?
C4 N1 C8 C7 2.30(19) . . . . ?
Sn1 N1 C8 C7 -176.13(10) . . . . ?
C4 N1 C8 C9 -177.16(12) . . . . ?
Sn1 N1 C8 C9 4.40(15) . . . . ?
C6 C7 C8 N1 -2.7(2) . . . . ?
C6 C7 C8 C9 176.75(13) . . . . ?
C10 N2 C9 C13 1.59(19) . . . . ?
Sn1 N2 C9 C13 -176.44(10) . . . . ?
C10 N2 C9 C8 -179.28(12) . . . . ?
Sn1 N2 C9 C8 2.68(15) . . . . ?
N1 C8 C9 N2 -4.72(18) . . . . ?
C7 C8 C9 N2 175.83(12) . . . . ?
N1 C8 C9 C13 174.39(13) . . . . ?
C7 C8 C9 C13 -5.1(2) . . . . ?
C9 N2 C10 C11 -0.5(2) . . . . ?
Sn1 N2 C10 C11 177.45(10) . . . . ?
N2 C10 C11 C12 -0.5(2) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
N2 C9 C13 C12 -1.7(2) . . . . ?
C8 C9 C13 C12 179.18(13) . . . . ?
C11 C12 C13 C9 0.8(2) . . . . ?
O6 S2 C14 F5 57.19(12) . . . . ?
O5 S2 C14 F5 -179.44(10) . . . . ?
O4 S2 C14 F5 -62.40(11) . . . . ?
O6 S2 C14 F4 178.11(10) . . . . ?
O5 S2 C14 F4 -58.52(11) . . . . ?
O4 S2 C14 F4 58.51(11) . . . . ?
O6 S2 C14 F6 -62.37(11) . . . . ?
O5 S2 C14 F6 60.99(11) . . . . ?
O4 S2 C14 F6 178.03(9) . . . . ?

_refine_diff_density_max         0.599
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.086

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 977502'
