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

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#                                CCDC 
# 
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# 
#  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.
#
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#  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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
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data_2013349_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 F3 N5 O2 S'
_chemical_formula_weight         537.56

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.765(2)
_cell_length_b                   11.596(3)
_cell_length_c                   12.705(3)
_cell_angle_alpha                77.594(11)
_cell_angle_beta                 65.275(11)
_cell_angle_gamma                65.336(11)
_cell_volume                     1307.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9156
_exptl_absorpt_correction_T_max  0.9650
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19388
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         28.00
_reflns_number_total             6123
_reflns_number_gt                4254
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0960P)²+0.5326P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6123
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1915
_refine_ls_wR_factor_gt          0.1720
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.27074(7) 0.13988(5) 0.39567(6) 0.0542(2) Uani 1 1 d . . .
F3 F 0.3196(5) 0.6028(3) 0.8465(3) 0.201(2) Uani 1 1 d . . .
C10' C 0.8052(3) 0.7082(3) 0.1590(3) 0.0627(7) Uani 1 1 d . . .
F2 F 0.3379(5) 0.7726(4) 0.7812(2) 0.1906(19) Uani 1 1 d . . .
C9' C 0.6895(3) 0.8237(3) 0.1855(3) 0.0698(8) Uani 1 1 d . . .
H6' H 0.6065 0.8369 0.1712 0.084 Uiso 1 1 calc R . .
N2' N 0.6902(3) 0.9167(2) 0.2300(2) 0.0716(7) Uani 1 1 d . . .
N2 N 0.2819(2) 0.58387(17) 0.55167(16) 0.0451(4) Uani 1 1 d . . .
C1 C 0.2680(3) 0.6838(2) 0.6795(2) 0.0526(6) Uani 1 1 d . . .
C6' C 0.9316(3) 0.6860(2) 0.1782(2) 0.0510(6) Uani 1 1 d . . .
C3' C 1.0599(3) 0.5638(2) 0.1528(2) 0.0524(6) Uani 1 1 d . . .
C4' C 1.0420(3) 0.4523(3) 0.1519(3) 0.0651(7) Uani 1 1 d . . .
H3' H 0.9500 0.4531 0.1648 0.078 Uiso 1 1 calc R . .
C5' C 1.1636(4) 0.3398(3) 0.1315(3) 0.0797(9) Uani 1 1 d . . .
H4' H 1.1493 0.2661 0.1314 0.096 Uiso 1 1 calc R . .
N1' N 1.2987(3) 0.3294(3) 0.1120(2) 0.0805(8) Uani 1 1 d . . .
C1' C 1.3153(3) 0.4368(4) 0.1112(3) 0.0798(9) Uani 1 1 d . . .
H1' H 1.4092 0.4330 0.0964 0.096 Uiso 1 1 calc R . .
C2' C 1.2010(3) 0.5543(3) 0.1312(3) 0.0652(7) Uani 1 1 d . . .
H2' H 1.2190 0.6265 0.1300 0.078 Uiso 1 1 calc R . .
C7' C 0.9316(3) 0.7824(3) 0.2265(3) 0.0687(7) Uani 1 1 d . . .
H7' H 1.0123 0.7718 0.2428 0.082 Uiso 1 1 calc R . .
C8' C 0.8103(4) 0.8942(3) 0.2501(3) 0.0775(9) Uani 1 1 d . . .
H8' H 0.8127 0.9580 0.2820 0.093 Uiso 1 1 calc R . .
C14 C 0.2789(3) 0.2720(2) 0.4388(2) 0.0450(5) Uani 1 1 d . . .
C15 C 0.3712(3) 0.2524(2) 0.4966(2) 0.0504(6) Uani 1 1 d . . .
H11 H 0.4311 0.1706 0.5112 0.060 Uiso 1 1 calc R . .
C16 C 0.3730(3) 0.3567(2) 0.5323(2) 0.0491(5) Uani 1 1 d . . .
H12 H 0.4339 0.3452 0.5714 0.059 Uiso 1 1 calc R . .
C11 C 0.2834(2) 0.47776(19) 0.50919(19) 0.0429(5) Uani 1 1 d . . .
C3 C 0.2577(3) 0.7063(2) 0.50676(19) 0.0448(5) Uani 1 1 d . . .
C4 C 0.2623(3) 0.7510(2) 0.38786(19) 0.0452(5) Uani 1 1 d . . .
C9 C 0.3738(3) 0.6858(2) 0.2913(2) 0.0537(6) Uani 1 1 d . . .
H8 H 0.4427 0.6067 0.3009 0.064 Uiso 1 1 calc R . .
C8 C 0.3828(3) 0.7379(3) 0.1810(2) 0.0651(7) Uani 1 1 d . . .
H7 H 0.4578 0.6927 0.1172 0.078 Uiso 1 1 calc R . .
C7 C 0.2829(4) 0.8558(3) 0.1628(2) 0.0682(8) Uani 1 1 d . . .
C10 C 0.2958(6) 0.9127(5) 0.0416(3) 0.1178(15) Uani 1 1 d . . .
H5 H 0.3172 0.9880 0.0299 0.177 Uiso 1 1 calc R . .
H4 H 0.2046 0.9341 0.0321 0.177 Uiso 1 1 calc R . .
H6 H 0.3735 0.8522 -0.0141 0.177 Uiso 1 1 calc R . .
N1 N 0.2889(2) 0.56850(18) 0.65873(17) 0.0522(5) Uani 1 1 d . . .
C2 C 0.2471(3) 0.7727(2) 0.5898(2) 0.0514(6) Uani 1 1 d . . .
H1 H 0.2296 0.8587 0.5865 0.062 Uiso 1 1 calc R . .
C5 C 0.1604(3) 0.8690(2) 0.3705(2) 0.0571(6) Uani 1 1 d . . .
H2 H 0.0841 0.9136 0.4340 0.068 Uiso 1 1 calc R . .
C6 C 0.1718(4) 0.9198(3) 0.2598(3) 0.0686(8) Uani 1 1 d . . .
H3 H 0.1033 0.9990 0.2500 0.082 Uiso 1 1 calc R . .
C17 C 0.2692(4) 0.7033(3) 0.7907(2) 0.0706(8) Uani 1 1 d . . .
F1 F 0.1417(4) 0.7583(5) 0.8642(3) 0.204(2) Uani 1 1 d . . .
C12 C 0.1920(3) 0.4972(2) 0.4509(2) 0.0478(5) Uani 1 1 d . . .
H9 H 0.1327 0.5791 0.4358 0.057 Uiso 1 1 calc R . .
C13 C 0.1897(3) 0.3931(2) 0.4152(2) 0.0474(5) Uani 1 1 d . . .
H10 H 0.1290 0.4047 0.3759 0.057 Uiso 1 1 calc R . .
O1 O 0.1290(2) 0.18331(19) 0.38687(19) 0.0728(6) Uani 1 1 d . . .
O2 O 0.3120(3) 0.03447(17) 0.47311(18) 0.0769(6) Uani 1 1 d . . .
N3 N 0.3931(3) 0.1049(2) 0.2698(2) 0.0602(6) Uani 1 1 d . . .
H13 H 0.377(3) 0.158(3) 0.218(3) 0.066(9) Uiso 1 1 d . . .
H5' H 0.798(3) 0.645(3) 0.130(3) 0.075(9) Uiso 1 1 d . . .
H14 H 0.483(4) 0.057(3) 0.270(3) 0.078(10) Uiso 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 O2 1.434(2) . ?
S1 O1 1.440(2) . ?
S1 N3 1.590(3) . ?
S1 C14 1.780(2) . ?
F3 C17 1.262(4) . ?
C10' C9' 1.382(4) . ?
C10' C6' 1.392(4) . ?
C10' H5' 0.93(3) . ?
F2 C17 1.260(4) . ?
C9' N2' 1.325(4) . ?
C9' H6' 0.9300 . ?
N2' C8' 1.331(4) . ?
N2 N1 1.363(3) . ?
N2 C3 1.369(3) . ?
N2 C11 1.438(3) . ?
C1 N1 1.326(3) . ?
C1 C2 1.388(3) . ?
C1 C17 1.485(4) . ?
C6' C7' 1.385(4) . ?
C6' C3' 1.487(3) . ?
C3' C2' 1.386(4) . ?
C3' C4' 1.386(4) . ?
C4' C5' 1.385(4) . ?
C4' H3' 0.9300 . ?
C5' N1' 1.326(4) . ?
C5' H4' 0.9300 . ?
N1' C1' 1.327(5) . ?
C1' C2' 1.387(4) . ?
C1' H1' 0.9300 . ?
C2' H2' 0.9300 . ?
C7' C8' 1.379(4) . ?
C7' H7' 0.9300 . ?
C8' H8' 0.9300 . ?
C14 C13 1.386(3) . ?
C14 C15 1.389(3) . ?
C15 C16 1.389(3) . ?
C15 H11 0.9300 . ?
C16 C11 1.385(3) . ?
C16 H12 0.9300 . ?
C11 C12 1.386(3) . ?
C3 C2 1.376(3) . ?
C3 C4 1.475(3) . ?
C4 C9 1.389(3) . ?
C4 C5 1.394(3) . ?
C9 C8 1.382(4) . ?
C9 H8 0.9300 . ?
C8 C7 1.387(4) . ?
C8 H7 0.9300 . ?
C7 C6 1.385(4) . ?
C7 C10 1.513(4) . ?
C10 H5 0.9600 . ?
C10 H4 0.9600 . ?
C10 H6 0.9600 . ?
C2 H1 0.9300 . ?
C5 C6 1.378(4) . ?
C5 H2 0.9300 . ?
C6 H3 0.9300 . ?
C17 F1 1.271(4) . ?
C12 C13 1.390(3) . ?
C12 H9 0.9300 . ?
C13 H10 0.9300 . ?
N3 H13 0.82(3) . ?
N3 H14 0.89(3) . ?

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
O2 S1 O1 120.43(13) . . ?
O2 S1 N3 106.83(14) . . ?
O1 S1 N3 107.95(14) . . ?
O2 S1 C14 106.78(11) . . ?
O1 S1 C14 106.15(11) . . ?
N3 S1 C14 108.23(12) . . ?
C9' C10' C6' 119.5(3) . . ?
C9' C10' H5' 120.2(19) . . ?
C6' C10' H5' 120.3(19) . . ?
N2' C9' C10' 123.7(3) . . ?
N2' C9' H6' 118.1 . . ?
C10' C9' H6' 118.1 . . ?
C9' N2' C8' 116.6(2) . . ?
N1 N2 C3 112.52(17) . . ?
N1 N2 C11 117.34(17) . . ?
C3 N2 C11 129.69(19) . . ?
N1 C1 C2 113.0(2) . . ?
N1 C1 C17 118.7(2) . . ?
C2 C1 C17 128.3(2) . . ?
C7' C6' C10' 116.9(2) . . ?
C7' C6' C3' 120.6(2) . . ?
C10' C6' C3' 122.5(2) . . ?
C2' C3' C4' 116.8(2) . . ?
C2' C3' C6' 122.5(2) . . ?
C4' C3' C6' 120.7(2) . . ?
C5' C4' C3' 118.8(3) . . ?
C5' C4' H3' 120.6 . . ?
C3' C4' H3' 120.6 . . ?
N1' C5' C4' 124.9(3) . . ?
N1' C5' H4' 117.6 . . ?
C4' C5' H4' 117.6 . . ?
C5' N1' C1' 115.9(3) . . ?
N1' C1' C2' 123.9(3) . . ?
N1' C1' H1' 118.1 . . ?
C2' C1' H1' 118.1 . . ?
C3' C2' C1' 119.7(3) . . ?
C3' C2' H2' 120.2 . . ?
C1' C2' H2' 120.2 . . ?
C8' C7' C6' 119.2(3) . . ?
C8' C7' H7' 120.4 . . ?
C6' C7' H7' 120.4 . . ?
N2' C8' C7' 124.1(3) . . ?
N2' C8' H8' 117.9 . . ?
C7' C8' H8' 117.9 . . ?
C13 C14 C15 121.4(2) . . ?
C13 C14 S1 118.47(18) . . ?
C15 C14 S1 120.09(17) . . ?
C14 C15 C16 119.2(2) . . ?
C14 C15 H11 120.4 . . ?
C16 C15 H11 120.4 . . ?
C11 C16 C15 119.4(2) . . ?
C11 C16 H12 120.3 . . ?
C15 C16 H12 120.3 . . ?
C16 C11 C12 121.3(2) . . ?
C16 C11 N2 118.5(2) . . ?
C12 C11 N2 120.14(19) . . ?
N2 C3 C2 105.7(2) . . ?
N2 C3 C4 126.01(19) . . ?
C2 C3 C4 127.9(2) . . ?
C9 C4 C5 118.4(2) . . ?
C9 C4 C3 122.1(2) . . ?
C5 C4 C3 119.1(2) . . ?
C8 C9 C4 120.2(2) . . ?
C8 C9 H8 119.9 . . ?
C4 C9 H8 119.9 . . ?
C9 C8 C7 121.8(3) . . ?
C9 C8 H7 119.1 . . ?
C7 C8 H7 119.1 . . ?
C6 C7 C8 117.5(2) . . ?
C6 C7 C10 121.3(3) . . ?
C8 C7 C10 121.1(3) . . ?
C7 C10 H5 109.5 . . ?
C7 C10 H4 109.5 . . ?
H5 C10 H4 109.5 . . ?
C7 C10 H6 109.5 . . ?
H5 C10 H6 109.5 . . ?
H4 C10 H6 109.5 . . ?
C1 N1 N2 103.53(18) . . ?
C3 C2 C1 105.3(2) . . ?
C3 C2 H1 127.3 . . ?
C1 C2 H1 127.3 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H2 119.7 . . ?
C4 C5 H2 119.7 . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H3 119.2 . . ?
C7 C6 H3 119.2 . . ?
F2 C17 F3 106.6(4) . . ?
F2 C17 F1 103.6(4) . . ?
F3 C17 F1 102.4(4) . . ?
F2 C17 C1 114.3(3) . . ?
F3 C17 C1 115.1(3) . . ?
F1 C17 C1 113.5(3) . . ?
C11 C12 C13 119.4(2) . . ?
C11 C12 H9 120.3 . . ?
C13 C12 H9 120.3 . . ?
C14 C13 C12 119.2(2) . . ?
C14 C13 H10 120.4 . . ?
C12 C13 H10 120.4 . . ?
S1 N3 H13 114(2) . . ?
S1 N3 H14 114(2) . . ?
H13 N3 H14 125(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
C6' C10' C9' N2' -0.7(5) . . . . ?
C10' C9' N2' C8' -0.4(5) . . . . ?
C9' C10' C6' C7' 1.6(4) . . . . ?
C9' C10' C6' C3' 179.5(3) . . . . ?
C7' C6' C3' C2' -26.1(4) . . . . ?
C10' C6' C3' C2' 156.1(3) . . . . ?
C7' C6' C3' C4' 152.7(3) . . . . ?
C10' C6' C3' C4' -25.0(4) . . . . ?
C2' C3' C4' C5' 0.9(4) . . . . ?
C6' C3' C4' C5' -178.0(3) . . . . ?
C3' C4' C5' N1' -0.2(5) . . . . ?
C4' C5' N1' C1' -0.9(5) . . . . ?
C5' N1' C1' C2' 1.2(5) . . . . ?
C4' C3' C2' C1' -0.6(4) . . . . ?
C6' C3' C2' C1' 178.2(3) . . . . ?
N1' C1' C2' C3' -0.4(5) . . . . ?
C10' C6' C7' C8' -1.5(4) . . . . ?
C3' C6' C7' C8' -179.4(3) . . . . ?
C9' N2' C8' C7' 0.6(5) . . . . ?
C6' C7' C8' N2' 0.4(5) . . . . ?
O2 S1 C14 C13 -153.1(2) . . . . ?
O1 S1 C14 C13 -23.5(2) . . . . ?
N3 S1 C14 C13 92.2(2) . . . . ?
O2 S1 C14 C15 25.8(2) . . . . ?
O1 S1 C14 C15 155.4(2) . . . . ?
N3 S1 C14 C15 -88.9(2) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
S1 C14 C15 C16 -178.28(18) . . . . ?
C14 C15 C16 C11 -0.3(4) . . . . ?
C15 C16 C11 C12 -0.1(4) . . . . ?
C15 C16 C11 N2 177.1(2) . . . . ?
N1 N2 C11 C16 -38.3(3) . . . . ?
C3 N2 C11 C16 150.0(2) . . . . ?
N1 N2 C11 C12 139.0(2) . . . . ?
C3 N2 C11 C12 -32.7(3) . . . . ?
N1 N2 C3 C2 -0.6(3) . . . . ?
C11 N2 C3 C2 171.3(2) . . . . ?
N1 N2 C3 C4 172.1(2) . . . . ?
C11 N2 C3 C4 -15.9(4) . . . . ?
N2 C3 C4 C9 -44.9(3) . . . . ?
C2 C3 C4 C9 126.2(3) . . . . ?
N2 C3 C4 C5 141.7(2) . . . . ?
C2 C3 C4 C5 -47.1(4) . . . . ?
C5 C4 C9 C8 0.3(3) . . . . ?
C3 C4 C9 C8 -173.0(2) . . . . ?
C4 C9 C8 C7 0.4(4) . . . . ?
C9 C8 C7 C6 -0.6(4) . . . . ?
C9 C8 C7 C10 178.9(3) . . . . ?
C2 C1 N1 N2 0.3(3) . . . . ?
C17 C1 N1 N2 -179.7(2) . . . . ?
C3 N2 N1 C1 0.2(3) . . . . ?
C11 N2 N1 C1 -172.9(2) . . . . ?
N2 C3 C2 C1 0.8(3) . . . . ?
C4 C3 C2 C1 -171.8(2) . . . . ?
N1 C1 C2 C3 -0.7(3) . . . . ?
C17 C1 C2 C3 179.3(3) . . . . ?
C9 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 C6 172.7(2) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C8 C7 C6 C5 0.1(4) . . . . ?
C10 C7 C6 C5 -179.4(3) . . . . ?
N1 C1 C17 F2 137.7(4) . . . . ?
C2 C1 C17 F2 -42.4(5) . . . . ?
N1 C1 C17 F3 13.8(5) . . . . ?
C2 C1 C17 F3 -166.3(4) . . . . ?
N1 C1 C17 F1 -103.8(4) . . . . ?
C2 C1 C17 F1 76.1(4) . . . . ?
C16 C11 C12 C13 0.2(4) . . . . ?
N2 C11 C12 C13 -177.0(2) . . . . ?
C15 C14 C13 C12 -0.5(4) . . . . ?
S1 C14 C13 C12 178.40(17) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.852
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 1010375'
#######################################################################
#
#                 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_mo_2014096_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H24 F3 N5 O2 S'
_chemical_formula_weight         563.60

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1324(2)
_cell_length_b                   11.6423(3)
_cell_length_c                   14.2374(3)
_cell_angle_alpha                92.939(2)
_cell_angle_beta                 99.316(2)
_cell_angle_gamma                110.239(2)
_cell_volume                     1392.12(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23871
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_sigmaI/netI    0.0981
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         27.59
_reflns_number_total             6447
_reflns_number_gt                2948
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0900P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6447
_refine_ls_number_parameters     368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1832
_refine_ls_wR_factor_gt          0.1430
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.37350(9) 0.32112(7) 0.40997(5) 0.0426(2) Uani 1 1 d . . .
F1 F 0.4743(6) 0.8735(3) -0.0197(3) 0.208(2) Uani 1 1 d . . .
F2 F 0.2651(5) 0.8298(3) -0.1130(4) 0.202(2) Uani 1 1 d . . .
O1 O 0.3078(2) 0.19013(18) 0.38685(15) 0.0541(6) Uani 1 1 d . . .
O2 O 0.5370(2) 0.37817(19) 0.45699(14) 0.0536(6) Uani 1 1 d . . .
N1' N -0.0864(3) 0.5858(3) 0.3491(2) 0.0640(8) Uani 1 1 d . . .
N2' N 0.9283(3) 1.1996(3) 0.3992(2) 0.0592(8) Uani 1 1 d . . .
N2 N 0.2973(3) 0.5272(2) 0.03960(17) 0.0481(7) Uani 1 1 d . . .
N3 N 0.2668(3) 0.3563(3) 0.47607(19) 0.0510(7) Uani 1 1 d . . .
H13 H 0.174(4) 0.326(3) 0.459(3) 0.076 Uiso 1 1 d . . .
H14 H 0.303(4) 0.437(3) 0.500(2) 0.076 Uiso 1 1 d . . .
N1 N 0.3705(3) 0.6505(3) 0.03679(19) 0.0568(7) Uani 1 1 d . . .
C10' C 0.9209(4) 1.0852(4) 0.4050(3) 0.0808(12) Uani 1 1 d . . .
H8' H 1.0163 1.0713 0.4140 0.097 Uiso 1 1 calc R . .
C9' C 0.7840(5) 0.9852(4) 0.3988(3) 0.0830(13) Uani 1 1 d . . .
H7' H 0.7887 0.9073 0.4045 0.100 Uiso 1 1 calc R . .
C8' C 0.6395(4) 1.0002(3) 0.3843(2) 0.0582(9) Uani 1 1 d . . .
C7' C 0.4915(4) 0.8913(4) 0.3780(3) 0.0688(10) Uani 1 1 d . . .
H6' H 0.5028 0.8152 0.3821 0.083 Uiso 1 1 calc R . .
C6' C 0.3496(4) 0.8919(3) 0.3674(2) 0.0628(10) Uani 1 1 d . . .
H5' H 0.3381 0.9679 0.3629 0.075 Uiso 1 1 calc R . .
C3' C 0.2028(4) 0.7836(3) 0.3617(2) 0.0531(9) Uani 1 1 d . . .
C2' C 0.1968(4) 0.6648(4) 0.3727(3) 0.0682(10) Uani 1 1 d . . .
H2' H 0.2902 0.6481 0.3843 0.082 Uiso 1 1 calc R . .
C1' C 0.0518(4) 0.5712(3) 0.3664(3) 0.0697(11) Uani 1 1 d . . .
H1' H 0.0516 0.4924 0.3748 0.084 Uiso 1 1 calc R . .
C12' C 0.6452(4) 1.1190(3) 0.3784(2) 0.0625(10) Uani 1 1 d . . .
H10' H 0.5513 1.1350 0.3685 0.075 Uiso 1 1 calc R . .
C11' C 0.7890(4) 1.2149(3) 0.3868(2) 0.0618(9) Uani 1 1 d . . .
H9' H 0.7885 1.2943 0.3838 0.074 Uiso 1 1 calc R . .
C4' C 0.0580(4) 0.7990(3) 0.3436(2) 0.0586(9) Uani 1 1 d . . .
H3' H 0.0536 0.8765 0.3352 0.070 Uiso 1 1 calc R . .
C5' C -0.0784(4) 0.6997(4) 0.3382(2) 0.0632(10) Uani 1 1 d . . .
H4' H -0.1739 0.7133 0.3259 0.076 Uiso 1 1 calc R . .
C10 C -0.1193(7) -0.0562(4) -0.1510(3) 0.136(2) Uani 1 1 d . . .
H5 H -0.0949 -0.0754 -0.2116 0.204 Uiso 1 1 calc R . .
H4 H -0.2322 -0.0790 -0.1571 0.204 Uiso 1 1 calc R . .
H6 H -0.0816 -0.1012 -0.1042 0.204 Uiso 1 1 calc R . .
C7 C -0.0382(7) 0.0817(4) -0.1191(3) 0.0841(14) Uani 1 1 d . . .
C6 C -0.1224(5) 0.1603(5) -0.1207(3) 0.0856(14) Uani 1 1 d . . .
H3 H -0.2327 0.1282 -0.1385 0.103 Uiso 1 1 calc R . .
C5 C -0.0448(4) 0.2864(4) -0.0962(2) 0.0695(11) Uani 1 1 d . . .
H2 H -0.1032 0.3381 -0.0990 0.083 Uiso 1 1 calc R . .
C4 C 0.1186(4) 0.3356(3) -0.0677(2) 0.0509(8) Uani 1 1 d . . .
C3 C 0.2016(4) 0.4694(3) -0.0460(2) 0.0470(8) Uani 1 1 d . . .
C11 C 0.3154(3) 0.4785(3) 0.1286(2) 0.0432(7) Uani 1 1 d . . .
C12 C 0.1843(4) 0.3984(3) 0.1575(2) 0.0476(8) Uani 1 1 d . . .
H9 H 0.0840 0.3759 0.1190 0.057 Uiso 1 1 calc R . .
C13 C 0.2029(3) 0.3517(3) 0.2438(2) 0.0445(8) Uani 1 1 d . . .
H10 H 0.1152 0.2969 0.2636 0.053 Uiso 1 1 calc R . .
C14 C 0.3521(3) 0.3865(3) 0.30092(19) 0.0379(7) Uani 1 1 d . . .
C1 C 0.3194(4) 0.6676(3) -0.0513(2) 0.0578(9) Uani 1 1 d . . .
C2 C 0.2150(4) 0.5599(3) -0.1054(2) 0.0602(9) Uani 1 1 d . . .
H1 H 0.1644 0.5507 -0.1690 0.072 Uiso 1 1 calc R . .
C8 C 0.1238(6) 0.1309(4) -0.0899(3) 0.0849(13) Uani 1 1 d . . .
H7 H 0.1822 0.0793 -0.0875 0.102 Uiso 1 1 calc R . .
C9 C 0.2013(5) 0.2562(3) -0.0641(2) 0.0649(10) Uani 1 1 d . . .
H8 H 0.3112 0.2875 -0.0439 0.078 Uiso 1 1 calc R . .
F3 F 0.4480(5) 0.7964(3) -0.1536(3) 0.1780(17) Uani 1 1 d . . .
C16 C 0.4643(4) 0.5132(3) 0.1856(2) 0.0554(9) Uani 1 1 d . . .
H12 H 0.5518 0.5681 0.1657 0.067 Uiso 1 1 calc R . .
C15 C 0.4837(4) 0.4666(3) 0.2720(2) 0.0521(9) Uani 1 1 d . . .
H11 H 0.5842 0.4889 0.3103 0.062 Uiso 1 1 calc R . .
C17 C 0.3752(7) 0.7915(4) -0.0818(4) 0.0874(13) 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 O1 1.430(2) . ?
S1 O2 1.436(2) . ?
S1 N3 1.593(3) . ?
S1 C14 1.776(3) . ?
F1 C17 1.252(5) . ?
F2 C17 1.262(5) . ?
N1' C5' 1.321(4) . ?
N1' C1' 1.317(4) . ?
N2' C10' 1.318(5) . ?
N2' C11' 1.329(4) . ?
N2 N1 1.363(3) . ?
N2 C3 1.366(4) . ?
N2 C11 1.423(4) . ?
N3 H13 0.79(4) . ?
N3 H14 0.91(4) . ?
N1 C1 1.315(4) . ?
C10' C9' 1.369(5) . ?
C10' H8' 0.9300 . ?
C9' C8' 1.374(5) . ?
C9' H7' 0.9300 . ?
C8' C12' 1.374(5) . ?
C8' C7' 1.485(5) . ?
C7' C6' 1.283(5) . ?
C7' H6' 0.9300 . ?
C6' C3' 1.476(5) . ?
C6' H5' 0.9300 . ?
C3' C4' 1.380(5) . ?
C3' C2' 1.383(5) . ?
C2' C1' 1.379(5) . ?
C2' H2' 0.9300 . ?
C1' H1' 0.9300 . ?
C12' C11' 1.380(4) . ?
C12' H10' 0.9300 . ?
C11' H9' 0.9300 . ?
C4' C5' 1.363(5) . ?
C4' H3' 0.9300 . ?
C5' H4' 0.9300 . ?
C10 C7 1.525(6) . ?
C10 H5 0.9600 . ?
C10 H4 0.9600 . ?
C10 H6 0.9600 . ?
C7 C8 1.371(6) . ?
C7 C6 1.383(6) . ?
C6 C5 1.388(6) . ?
C6 H3 0.9300 . ?
C5 C4 1.382(5) . ?
C5 H2 0.9300 . ?
C4 C9 1.380(5) . ?
C4 C3 1.468(4) . ?
C3 C2 1.369(4) . ?
C11 C12 1.378(4) . ?
C11 C16 1.379(4) . ?
C12 C13 1.378(4) . ?
C12 H9 0.9300 . ?
C13 C14 1.381(4) . ?
C13 H10 0.9300 . ?
C14 C15 1.381(4) . ?
C1 C2 1.382(5) . ?
C1 C17 1.470(5) . ?
C2 H1 0.9300 . ?
C8 C9 1.382(5) . ?
C8 H7 0.9300 . ?
C9 H8 0.9300 . ?
F3 C17 1.299(5) . ?
C16 C15 1.380(4) . ?
C16 H12 0.9300 . ?
C15 H11 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
O1 S1 O2 118.99(13) . . ?
O1 S1 N3 106.82(15) . . ?
O2 S1 N3 108.04(14) . . ?
O1 S1 C14 107.11(13) . . ?
O2 S1 C14 107.10(13) . . ?
N3 S1 C14 108.42(15) . . ?
C5' N1' C1' 115.0(3) . . ?
C10' N2' C11' 115.1(3) . . ?
N1 N2 C3 112.0(2) . . ?
N1 N2 C11 118.8(2) . . ?
C3 N2 C11 128.9(3) . . ?
S1 N3 H13 117(3) . . ?
S1 N3 H14 114(2) . . ?
H13 N3 H14 115(4) . . ?
C1 N1 N2 104.0(3) . . ?
N2' C10' C9' 125.2(4) . . ?
N2' C10' H8' 117.4 . . ?
C9' C10' H8' 117.4 . . ?
C10' C9' C8' 119.9(4) . . ?
C10' C9' H7' 120.1 . . ?
C8' C9' H7' 120.1 . . ?
C12' C8' C9' 115.7(3) . . ?
C12' C8' C7' 124.8(3) . . ?
C9' C8' C7' 119.5(4) . . ?
C6' C7' C8' 126.3(4) . . ?
C6' C7' H6' 116.8 . . ?
C8' C7' H6' 116.8 . . ?
C7' C6' C3' 126.2(4) . . ?
C7' C6' H5' 116.9 . . ?
C3' C6' H5' 116.9 . . ?
C4' C3' C2' 115.9(3) . . ?
C4' C3' C6' 118.9(3) . . ?
C2' C3' C6' 125.2(3) . . ?
C1' C2' C3' 119.7(4) . . ?
C1' C2' H2' 120.1 . . ?
C3' C2' H2' 120.1 . . ?
N1' C1' C2' 124.4(4) . . ?
N1' C1' H1' 117.8 . . ?
C2' C1' H1' 117.8 . . ?
C8' C12' C11' 120.7(3) . . ?
C8' C12' H10' 119.7 . . ?
C11' C12' H10' 119.7 . . ?
N2' C11' C12' 123.5(3) . . ?
N2' C11' H9' 118.3 . . ?
C12' C11' H9' 118.3 . . ?
C5' C4' C3' 119.5(4) . . ?
C5' C4' H3' 120.3 . . ?
C3' C4' H3' 120.3 . . ?
N1' C5' C4' 125.5(4) . . ?
N1' C5' H4' 117.3 . . ?
C4' C5' H4' 117.3 . . ?
C7 C10 H5 109.5 . . ?
C7 C10 H4 109.5 . . ?
H5 C10 H4 109.5 . . ?
C7 C10 H6 109.5 . . ?
H5 C10 H6 109.5 . . ?
H4 C10 H6 109.5 . . ?
C8 C7 C6 118.3(4) . . ?
C8 C7 C10 119.5(5) . . ?
C6 C7 C10 122.2(5) . . ?
C7 C6 C5 121.0(4) . . ?
C7 C6 H3 119.5 . . ?
C5 C6 H3 119.5 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H2 119.8 . . ?
C6 C5 H2 119.8 . . ?
C9 C4 C5 118.2(3) . . ?
C9 C4 C3 121.2(3) . . ?
C5 C4 C3 120.5(3) . . ?
N2 C3 C2 105.6(3) . . ?
N2 C3 C4 124.6(3) . . ?
C2 C3 C4 129.5(3) . . ?
C12 C11 C16 120.6(3) . . ?
C12 C11 N2 119.9(3) . . ?
C16 C11 N2 119.4(3) . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H9 120.2 . . ?
C11 C12 H9 120.2 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H10 120.1 . . ?
C14 C13 H10 120.1 . . ?
C13 C14 C15 120.8(3) . . ?
C13 C14 S1 118.8(2) . . ?
C15 C14 S1 120.4(2) . . ?
N1 C1 C2 112.7(3) . . ?
N1 C1 C17 119.8(3) . . ?
C2 C1 C17 127.5(3) . . ?
C3 C2 C1 105.7(3) . . ?
C3 C2 H1 127.1 . . ?
C1 C2 H1 127.1 . . ?
C7 C8 C9 120.9(4) . . ?
C7 C8 H7 119.6 . . ?
C9 C8 H7 119.6 . . ?
C4 C9 C8 121.2(4) . . ?
C4 C9 H8 119.4 . . ?
C8 C9 H8 119.4 . . ?
C11 C16 C15 120.1(3) . . ?
C11 C16 H12 120.0 . . ?
C15 C16 H12 120.0 . . ?
C16 C15 C14 119.2(3) . . ?
C16 C15 H11 120.4 . . ?
C14 C15 H11 120.4 . . ?
F1 C17 F2 107.5(5) . . ?
F1 C17 F3 103.6(5) . . ?
F2 C17 F3 102.9(4) . . ?
F1 C17 C1 115.1(4) . . ?
F2 C17 C1 114.0(4) . . ?
F3 C17 C1 112.5(4) . . ?

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
C3 N2 N1 C1 -0.2(4) . . . . ?
C11 N2 N1 C1 -174.3(3) . . . . ?
C11' N2' C10' C9' 0.3(6) . . . . ?
N2' C10' C9' C8' 0.9(7) . . . . ?
C10' C9' C8' C12' -1.0(6) . . . . ?
C10' C9' C8' C7' -179.8(4) . . . . ?
C12' C8' C7' C6' -0.9(6) . . . . ?
C9' C8' C7' C6' 177.8(4) . . . . ?
C8' C7' C6' C3' -179.6(3) . . . . ?
C7' C6' C3' C4' -175.6(4) . . . . ?
C7' C6' C3' C2' 4.0(6) . . . . ?
C4' C3' C2' C1' -0.7(5) . . . . ?
C6' C3' C2' C1' 179.6(3) . . . . ?
C5' N1' C1' C2' -0.4(5) . . . . ?
C3' C2' C1' N1' 0.8(6) . . . . ?
C9' C8' C12' C11' 0.0(5) . . . . ?
C7' C8' C12' C11' 178.8(3) . . . . ?
C10' N2' C11' C12' -1.4(5) . . . . ?
C8' C12' C11' N2' 1.3(5) . . . . ?
C2' C3' C4' C5' 0.3(5) . . . . ?
C6' C3' C4' C5' 180.0(3) . . . . ?
C1' N1' C5' C4' -0.1(5) . . . . ?
C3' C4' C5' N1' 0.1(5) . . . . ?
C8 C7 C6 C5 1.9(6) . . . . ?
C10 C7 C6 C5 -176.5(3) . . . . ?
C7 C6 C5 C4 -1.4(6) . . . . ?
C6 C5 C4 C9 -0.2(5) . . . . ?
C6 C5 C4 C3 177.2(3) . . . . ?
N1 N2 C3 C2 0.0(4) . . . . ?
C11 N2 C3 C2 173.4(3) . . . . ?
N1 N2 C3 C4 174.3(3) . . . . ?
C11 N2 C3 C4 -12.4(5) . . . . ?
C9 C4 C3 N2 -60.2(4) . . . . ?
C5 C4 C3 N2 122.5(4) . . . . ?
C9 C4 C3 C2 112.5(4) . . . . ?
C5 C4 C3 C2 -64.7(5) . . . . ?
N1 N2 C11 C12 133.3(3) . . . . ?
C3 N2 C11 C12 -39.6(5) . . . . ?
N1 N2 C11 C16 -46.0(4) . . . . ?
C3 N2 C11 C16 141.1(3) . . . . ?
C16 C11 C12 C13 -0.6(5) . . . . ?
N2 C11 C12 C13 -179.9(3) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C12 C13 C14 S1 -178.0(2) . . . . ?
O1 S1 C14 C13 54.6(3) . . . . ?
O2 S1 C14 C13 -176.7(2) . . . . ?
N3 S1 C14 C13 -60.4(3) . . . . ?
O1 S1 C14 C15 -122.7(3) . . . . ?
O2 S1 C14 C15 6.1(3) . . . . ?
N3 S1 C14 C15 122.4(3) . . . . ?
N2 N1 C1 C2 0.3(4) . . . . ?
N2 N1 C1 C17 -179.4(4) . . . . ?
N2 C3 C2 C1 0.2(4) . . . . ?
C4 C3 C2 C1 -173.7(3) . . . . ?
N1 C1 C2 C3 -0.3(4) . . . . ?
C17 C1 C2 C3 179.4(4) . . . . ?
C6 C7 C8 C9 -0.9(6) . . . . ?
C10 C7 C8 C9 177.6(3) . . . . ?
C5 C4 C9 C8 1.2(5) . . . . ?
C3 C4 C9 C8 -176.2(3) . . . . ?
C7 C8 C9 C4 -0.7(6) . . . . ?
C12 C11 C16 C15 0.7(5) . . . . ?
N2 C11 C16 C15 -179.9(3) . . . . ?
C11 C16 C15 C14 -0.9(5) . . . . ?
C13 C14 C15 C16 0.9(5) . . . . ?
S1 C14 C15 C16 178.1(3) . . . . ?
N1 C1 C17 F1 2.0(7) . . . . ?
C2 C1 C17 F1 -177.7(5) . . . . ?
N1 C1 C17 F2 -122.9(5) . . . . ?
C2 C1 C17 F2 57.3(7) . . . . ?
N1 C1 C17 F3 120.4(5) . . . . ?
C2 C1 C17 F3 -59.4(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 1010376'
#######################################################################
#
#                 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_2013377_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H26 F3 N5 O2 S'
_chemical_formula_weight         565.62

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9890(8)
_cell_length_b                   11.3277(11)
_cell_length_c                   15.7937(15)
_cell_angle_alpha                78.780(6)
_cell_angle_beta                 81.807(6)
_cell_angle_gamma                83.993(6)
_cell_volume                     1383.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             590
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23780
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         27.62
_reflns_number_total             6412
_reflns_number_gt                4292
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0824P)²+0.8915P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6412
_refine_ls_number_parameters     370
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1813
_refine_ls_wR_factor_gt          0.1597
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      4.042
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C6'' C 0.9100(17) 0.0246(11) 1.0072(12) 0.077(4) Uani 1 1 d . . .
H3'' H 0.8702 0.0076 1.0690 0.093 Uiso 1 1 calc R . .
H4'' H 0.8413 -0.0164 0.9779 0.093 Uiso 1 1 calc R . .
C6' C 0.933(2) 0.4977(12) 0.5384(10) 0.084(5) Uani 1 1 d . . .
H4' H 0.8429 0.5602 0.5248 0.101 Uiso 1 1 calc R . .
H3' H 0.9810 0.5140 0.5875 0.101 Uiso 1 1 calc R . .
S1 S 1.2873(3) 0.1781(3) 0.41650(18) 0.0484(8) Uani 1 1 d . . .
F1 F 0.3138(18) 0.2152(10) 0.0591(9) 0.159(6) Uani 1 1 d . . .
F2 F 0.5015(13) 0.0777(14) 0.0738(11) 0.174(7) Uani 1 1 d . . .
F3 F 0.3107(17) 0.0932(11) 0.1703(7) 0.133(5) Uani 1 1 d . . .
O1 O 1.2279(11) 0.1253(10) 0.5037(5) 0.076(3) Uani 1 1 d . . .
O2 O 1.3776(11) 0.2842(8) 0.3994(7) 0.074(3) Uani 1 1 d . . .
N3 N 1.4089(11) 0.0769(9) 0.3756(7) 0.049(2) Uani 1 1 d . . .
C2' C 0.739(2) 0.3450(14) 0.5179(10) 0.080(4) Uani 1 1 d . . .
H2' H 0.6985 0.4005 0.4724 0.096 Uiso 1 1 calc RD . .
C3' C 0.8586(17) 0.3774(11) 0.5633(8) 0.061(3) Uani 1 1 d . . .
C4' C 0.911(2) 0.2906(14) 0.6293(10) 0.084(4) Uani 1 1 d . . .
H5' H 0.9906 0.3065 0.6624 0.101 Uiso 1 1 calc R . .
C14 C 1.1085(12) 0.2116(9) 0.3585(6) 0.040(2) Uani 1 1 d . . .
C15 C 0.9790(13) 0.1348(10) 0.3781(7) 0.048(2) Uani 1 1 d . . .
H11 H 0.9849 0.0675 0.4222 0.057 Uiso 1 1 calc R . .
C16 C 0.8406(13) 0.1583(9) 0.3320(7) 0.046(2) Uani 1 1 d . . .
H12 H 0.7537 0.1067 0.3446 0.055 Uiso 1 1 calc R . .
C11 C 0.8329(11) 0.2592(8) 0.2671(6) 0.036(2) Uani 1 1 d . . .
N2 N 0.6898(10) 0.2814(7) 0.2189(5) 0.0382(18) Uani 1 1 d . . .
C3 C 0.6058(12) 0.3885(9) 0.1860(6) 0.041(2) Uani 1 1 d . . .
C4 C 0.6330(12) 0.5062(9) 0.2065(7) 0.043(2) Uani 1 1 d . . .
C9 C 0.6194(16) 0.5221(10) 0.2919(7) 0.057(3) Uani 1 1 d . . .
H8 H 0.5952 0.4575 0.3369 0.068 Uiso 1 1 calc R . .
C8 C 0.6413(17) 0.6332(10) 0.3112(8) 0.061(3) Uani 1 1 d . . .
H7 H 0.6330 0.6418 0.3691 0.073 Uiso 1 1 calc R . .
C7 C 0.6753(15) 0.7315(10) 0.2460(8) 0.055(3) Uani 1 1 d . . .
C10 C 0.697(2) 0.8530(11) 0.2673(10) 0.079(4) Uani 1 1 d . . .
H6 H 0.6802 0.8480 0.3292 0.119 Uiso 1 1 calc R . .
H4 H 0.6148 0.9121 0.2415 0.119 Uiso 1 1 calc R . .
H5 H 0.8090 0.8761 0.2446 0.119 Uiso 1 1 calc R . .
C13 C 1.1004(12) 0.3122(9) 0.2929(6) 0.042(2) Uani 1 1 d . . .
H10 H 1.1877 0.3636 0.2799 0.050 Uiso 1 1 calc R . .
C12 C 0.9620(12) 0.3358(9) 0.2466(6) 0.041(2) Uani 1 1 d . . .
H9 H 0.9561 0.4027 0.2022 0.049 Uiso 1 1 calc R . .
C6 C 0.6867(19) 0.7150(10) 0.1611(8) 0.065(3) Uani 1 1 d . . .
H3 H 0.7088 0.7800 0.1162 0.078 Uiso 1 1 calc R . .
C5 C 0.6663(17) 0.6043(10) 0.1409(8) 0.058(3) Uani 1 1 d . . .
H2 H 0.6750 0.5959 0.0830 0.070 Uiso 1 1 calc R . .
C2 C 0.4894(13) 0.3600(9) 0.1384(7) 0.046(2) Uani 1 1 d . . .
H1 H 0.4137 0.4128 0.1070 0.055 Uiso 1 1 calc R . .
C1 C 0.5095(12) 0.2353(9) 0.1474(6) 0.043(2) Uani 1 1 d . . .
N1 N 0.6305(10) 0.1857(7) 0.1971(5) 0.0414(19) Uani 1 1 d D . .
C17 C 0.4127(14) 0.1561(11) 0.1118(8) 0.054(3) Uani 1 1 d . . .
N1' N 0.7320(14) 0.1499(10) 0.6042(8) 0.068(3) Uani 1 1 d . . .
C1' C 0.6816(19) 0.2332(14) 0.5391(10) 0.078(4) Uani 1 1 d . . .
H1' H 0.6032 0.2139 0.5067 0.093 Uiso 1 1 calc RD . .
C5' C 0.846(2) 0.1802(14) 0.6465(11) 0.088(5) Uani 1 1 d . . .
H6' H 0.8854 0.1227 0.6913 0.105 Uiso 1 1 calc R . .
N1'' N 0.8382(19) 0.4092(11) 0.9179(11) 0.095(4) Uani 1 1 d . . .
C5'' C 0.800(2) 0.3314(17) 0.8729(13) 0.103(6) Uani 1 1 d . . .
H6'' H 0.7558 0.3620 0.8209 0.124 Uiso 1 1 calc R . .
C4'' C 0.822(2) 0.2062(14) 0.8978(11) 0.087(5) Uani 1 1 d . . .
H5'' H 0.7940 0.1557 0.8629 0.105 Uiso 1 1 calc R . .
C3'' C 0.8852(15) 0.1587(10) 0.9747(9) 0.060(3) Uani 1 1 d . . .
C1'' C 0.8969(19) 0.3605(13) 0.9923(12) 0.078(4) Uani 1 1 d . . .
H1'' H 0.9218 0.4125 1.0268 0.094 Uiso 1 1 calc R . .
C2'' C 0.9233(16) 0.2403(11) 1.0217(9) 0.062(3) Uani 1 1 d . . .
H2'' H 0.9674 0.2128 1.0741 0.075 Uiso 1 1 calc R . .
H13 H 1.457(18) 0.105(13) 0.323(9) 0.07(4) Uiso 1 1 d . . .
H14 H 1.365(19) 0.005(14) 0.383(9) 0.08(4) Uiso 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
C6'' C6'' 1.49(3) 2_757 ?
C6'' C3'' 1.507(17) . ?
C6'' H3'' 0.9700 . ?
C6'' H4'' 0.9700 . ?
C6' C6' 1.50(3) 2_766 ?
C6' C3' 1.502(17) . ?
C6' H4' 0.9700 . ?
C6' H3' 0.9700 . ?
S1 O1 1.425(9) . ?
S1 O2 1.427(9) . ?
S1 N3 1.597(10) . ?
S1 C14 1.774(9) . ?
F1 C17 1.276(14) . ?
F2 C17 1.268(15) . ?
F3 C17 1.295(15) . ?
N3 H13 0.88(15) . ?
N3 H14 0.90(15) . ?
C2' C1' 1.36(2) . ?
C2' C3' 1.388(19) . ?
C2' H2' 0.9300 . ?
C3' C4' 1.37(2) . ?
C4' C5' 1.37(2) . ?
C4' H5' 0.9300 . ?
C14 C15 1.384(14) . ?
C14 C13 1.386(14) . ?
C15 C16 1.384(13) . ?
C15 H11 0.9300 . ?
C16 C11 1.381(13) . ?
C16 H12 0.9300 . ?
C11 C12 1.380(13) . ?
C11 N2 1.437(11) . ?
N2 N1 1.347(10) . ?
N2 C3 1.370(12) . ?
C3 C2 1.375(13) . ?
C3 C4 1.476(13) . ?
C4 C9 1.384(15) . ?
C4 C5 1.384(15) . ?
C9 C8 1.385(15) . ?
C9 H8 0.9300 . ?
C8 C7 1.383(16) . ?
C8 H7 0.9300 . ?
C7 C6 1.378(17) . ?
C7 C10 1.510(16) . ?
C10 H6 0.9600 . ?
C10 H4 0.9600 . ?
C10 H5 0.9600 . ?
C13 C12 1.386(13) . ?
C13 H10 0.9300 . ?
C12 H9 0.9300 . ?
C6 C5 1.383(16) . ?
C6 H3 0.9300 . ?
C5 H2 0.9300 . ?
C2 C1 1.386(14) . ?
C2 H1 0.9300 . ?
C1 N1 1.340(12) . ?
C1 C17 1.478(14) . ?
N1' C5' 1.313(17) . ?
N1' C1' 1.330(18) . ?
C1' H1' 0.9300 . ?
C5' H6' 0.9300 . ?
N1'' C5'' 1.32(2) . ?
N1'' C1'' 1.32(2) . ?
C5'' C4'' 1.40(2) . ?
C5'' H6'' 0.9300 . ?
C4'' C3'' 1.37(2) . ?
C4'' H5'' 0.9300 . ?
C3'' C2'' 1.374(17) . ?
C1'' C2'' 1.355(19) . ?
C1'' H1'' 0.9300 . ?
C2'' H2'' 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
C6'' C6'' C3'' 113.2(14) 2_757 . ?
C6'' C6'' H3'' 108.9 2_757 . ?
C3'' C6'' H3'' 108.9 . . ?
C6'' C6'' H4'' 108.9 2_757 . ?
C3'' C6'' H4'' 108.9 . . ?
H3'' C6'' H4'' 107.7 . . ?
C6' C6' C3' 112.3(13) 2_766 . ?
C6' C6' H4' 109.1 2_766 . ?
C3' C6' H4' 109.1 . . ?
C6' C6' H3' 109.1 2_766 . ?
C3' C6' H3' 109.1 . . ?
H4' C6' H3' 107.9 . . ?
O1 S1 O2 120.3(6) . . ?
O1 S1 N3 107.0(6) . . ?
O2 S1 N3 106.9(6) . . ?
O1 S1 C14 107.2(5) . . ?
O2 S1 C14 107.2(5) . . ?
N3 S1 C14 107.7(5) . . ?
S1 N3 H13 112(9) . . ?
S1 N3 H14 115(9) . . ?
H13 N3 H14 116(10) . . ?
C1' C2' C3' 120.6(13) . . ?
C1' C2' H2' 119.7 . . ?
C3' C2' H2' 119.7 . . ?
C4' C3' C2' 115.8(12) . . ?
C4' C3' C6' 121.9(13) . . ?
C2' C3' C6' 122.1(13) . . ?
C3' C4' C5' 119.7(13) . . ?
C3' C4' H5' 120.1 . . ?
C5' C4' H5' 120.1 . . ?
C15 C14 C13 120.3(9) . . ?
C15 C14 S1 119.4(8) . . ?
C13 C14 S1 120.3(7) . . ?
C16 C15 C14 120.0(9) . . ?
C16 C15 H11 120.0 . . ?
C14 C15 H11 120.0 . . ?
C11 C16 C15 119.4(9) . . ?
C11 C16 H12 120.3 . . ?
C15 C16 H12 120.3 . . ?
C12 C11 C16 121.1(8) . . ?
C12 C11 N2 120.1(8) . . ?
C16 C11 N2 118.8(8) . . ?
N1 N2 C3 112.5(7) . . ?
N1 N2 C11 117.7(7) . . ?
C3 N2 C11 129.7(8) . . ?
N2 C3 C2 106.1(8) . . ?
N2 C3 C4 124.1(8) . . ?
C2 C3 C4 129.7(9) . . ?
C9 C4 C5 118.4(10) . . ?
C9 C4 C3 120.6(9) . . ?
C5 C4 C3 120.9(9) . . ?
C4 C9 C8 120.7(10) . . ?
C4 C9 H8 119.7 . . ?
C8 C9 H8 119.7 . . ?
C7 C8 C9 121.2(11) . . ?
C7 C8 H7 119.4 . . ?
C9 C8 H7 119.4 . . ?
C6 C7 C8 117.6(10) . . ?
C6 C7 C10 121.3(11) . . ?
C8 C7 C10 121.1(11) . . ?
C7 C10 H6 109.5 . . ?
C7 C10 H4 109.5 . . ?
H6 C10 H4 109.5 . . ?
C7 C10 H5 109.5 . . ?
H6 C10 H5 109.5 . . ?
H4 C10 H5 109.5 . . ?
C12 C13 C14 119.8(9) . . ?
C12 C13 H10 120.1 . . ?
C14 C13 H10 120.1 . . ?
C11 C12 C13 119.5(9) . . ?
C11 C12 H9 120.3 . . ?
C13 C12 H9 120.3 . . ?
C7 C6 C5 121.8(11) . . ?
C7 C6 H3 119.1 . . ?
C5 C6 H3 119.1 . . ?
C6 C5 C4 120.3(11) . . ?
C6 C5 H2 119.9 . . ?
C4 C5 H2 119.9 . . ?
C3 C2 C1 105.0(9) . . ?
C3 C2 H1 127.5 . . ?
C1 C2 H1 127.5 . . ?
N1 C1 C2 112.6(8) . . ?
N1 C1 C17 119.3(9) . . ?
C2 C1 C17 128.1(9) . . ?
C1 N1 N2 103.8(8) . . ?
F2 C17 F1 107.3(13) . . ?
F2 C17 F3 103.7(13) . . ?
F1 C17 F3 103.0(12) . . ?
F2 C17 C1 115.4(10) . . ?
F1 C17 C1 112.7(10) . . ?
F3 C17 C1 113.6(10) . . ?
C5' N1' C1' 116.2(12) . . ?
N1' C1' C2' 123.0(13) . . ?
N1' C1' H1' 118.5 . . ?
C2' C1' H1' 118.5 . . ?
N1' C5' C4' 124.5(14) . . ?
N1' C5' H6' 117.7 . . ?
C4' C5' H6' 117.7 . . ?
C5'' N1'' C1'' 115.1(14) . . ?
N1'' C5'' C4'' 124.4(16) . . ?
N1'' C5'' H6'' 117.8 . . ?
C4'' C5'' H6'' 117.8 . . ?
C3'' C4'' C5'' 118.9(15) . . ?
C3'' C4'' H5'' 120.5 . . ?
C5'' C4'' H5'' 120.5 . . ?
C4'' C3'' C2'' 116.3(12) . . ?
C4'' C3'' C6'' 122.4(13) . . ?
C2'' C3'' C6'' 121.3(13) . . ?
N1'' C1'' C2'' 124.7(15) . . ?
N1'' C1'' H1'' 117.6 . . ?
C2'' C1'' H1'' 117.6 . . ?
C1'' C2'' C3'' 120.4(14) . . ?
C1'' C2'' H2'' 119.8 . . ?
C3'' C2'' H2'' 119.8 . . ?

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
C1' C2' C3' C4' 0(2) . . . . ?
C1' C2' C3' C6' 176.4(14) . . . . ?
C6' C6' C3' C4' 98(2) 2_766 . . . ?
C6' C6' C3' C2' -78(2) 2_766 . . . ?
C2' C3' C4' C5' 0(2) . . . . ?
C6' C3' C4' C5' -176.6(15) . . . . ?
O1 S1 C14 C15 -35.4(10) . . . . ?
O2 S1 C14 C15 -165.9(9) . . . . ?
N3 S1 C14 C15 79.4(10) . . . . ?
O1 S1 C14 C13 146.1(9) . . . . ?
O2 S1 C14 C13 15.7(10) . . . . ?
N3 S1 C14 C13 -99.0(9) . . . . ?
C13 C14 C15 C16 0.0(16) . . . . ?
S1 C14 C15 C16 -178.5(8) . . . . ?
C14 C15 C16 C11 -0.5(16) . . . . ?
C15 C16 C11 C12 1.0(16) . . . . ?
C15 C16 C11 N2 179.0(9) . . . . ?
C12 C11 N2 N1 138.3(9) . . . . ?
C16 C11 N2 N1 -39.8(13) . . . . ?
C12 C11 N2 C3 -37.7(15) . . . . ?
C16 C11 N2 C3 144.2(10) . . . . ?
N1 N2 C3 C2 -1.8(11) . . . . ?
C11 N2 C3 C2 174.3(9) . . . . ?
N1 N2 C3 C4 173.9(9) . . . . ?
C11 N2 C3 C4 -9.9(16) . . . . ?
N2 C3 C4 C9 -53.9(15) . . . . ?
C2 C3 C4 C9 120.8(13) . . . . ?
N2 C3 C4 C5 128.6(11) . . . . ?
C2 C3 C4 C5 -56.7(16) . . . . ?
C5 C4 C9 C8 -1.0(18) . . . . ?
C3 C4 C9 C8 -178.6(11) . . . . ?
C4 C9 C8 C7 1(2) . . . . ?
C9 C8 C7 C6 0(2) . . . . ?
C9 C8 C7 C10 179.2(13) . . . . ?
C15 C14 C13 C12 0.0(15) . . . . ?
S1 C14 C13 C12 178.4(7) . . . . ?
C16 C11 C12 C13 -1.0(15) . . . . ?
N2 C11 C12 C13 -179.0(9) . . . . ?
C14 C13 C12 C11 0.5(15) . . . . ?
C8 C7 C6 C5 0(2) . . . . ?
C10 C7 C6 C5 -179.6(13) . . . . ?
C7 C6 C5 C4 0(2) . . . . ?
C9 C4 C5 C6 0.6(18) . . . . ?
C3 C4 C5 C6 178.1(11) . . . . ?
N2 C3 C2 C1 1.1(11) . . . . ?
C4 C3 C2 C1 -174.3(10) . . . . ?
C3 C2 C1 N1 -0.2(12) . . . . ?
C3 C2 C1 C17 177.9(10) . . . . ?
C2 C1 N1 N2 -0.9(11) . . . . ?
C17 C1 N1 N2 -179.2(9) . . . . ?
C3 N2 N1 C1 1.7(11) . . . . ?
C11 N2 N1 C1 -175.0(8) . . . . ?
N1 C1 C17 F2 -49.8(17) . . . . ?
C2 C1 C17 F2 132.2(15) . . . . ?
N1 C1 C17 F1 -173.6(12) . . . . ?
C2 C1 C17 F1 8.5(19) . . . . ?
N1 C1 C17 F3 69.8(15) . . . . ?
C2 C1 C17 F3 -108.2(15) . . . . ?
C5' N1' C1' C2' -2(2) . . . . ?
C3' C2' C1' N1' 1(3) . . . . ?
C1' N1' C5' C4' 2(3) . . . . ?
C3' C4' C5' N1' -1(3) . . . . ?
C1'' N1'' C5'' C4'' -2(3) . . . . ?
N1'' C5'' C4'' C3'' 1(3) . . . . ?
C5'' C4'' C3'' C2'' 0(2) . . . . ?
C5'' C4'' C3'' C6'' 179.0(15) . . . . ?
C6'' C6'' C3'' C4'' 102(2) 2_757 . . . ?
C6'' C6'' C3'' C2'' -79(2) 2_757 . . . ?
C5'' N1'' C1'' C2'' 2(2) . . . . ?
N1'' C1'' C2'' C3'' -2(2) . . . . ?
C4'' C3'' C2'' C1'' 0.6(19) . . . . ?
C6'' C3'' C2'' C1'' -178.7(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 1010377'
#######################################################################
#
#                 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_mo_2014084_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C57 H50 F6 N10 O5 S2'
_chemical_formula_weight         1133.21

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   21.710(4)
_cell_length_b                   9.5377(16)
_cell_length_c                   27.024(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.813(8)
_cell_angle_gamma                90.00
_cell_volume                     5588.9(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2264
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23381
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         27.54
_reflns_number_total             6405
_reflns_number_gt                4863
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0984P)²+5.6048P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6405
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1955
_refine_ls_wR_factor_gt          0.1760
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.07038(3) 0.29726(8) 0.13615(2) 0.0594(2) Uani 1 1 d . . .
F1 F 0.66290(12) 0.5029(5) 0.29449(10) 0.1794(18) Uani 1 1 d . . .
F2 F 0.7393(3) 0.5918(5) 0.32587(13) 0.233(2) Uani 1 1 d . . .
O1 O 1.09015(9) 0.1726(2) 0.16162(8) 0.0793(6) Uani 1 1 d . . .
F3 F 0.73310(14) 0.3865(4) 0.32901(9) 0.1696(16) Uani 1 1 d . . .
O2 O 1.06235(9) 0.2965(3) 0.08329(7) 0.0802(6) Uani 1 1 d . . .
C3 C 0.77126(9) 0.4824(2) 0.17321(7) 0.0464(5) Uani 1 1 d . . .
N2 N 0.82140(8) 0.4433(2) 0.20234(6) 0.0459(4) Uani 1 1 d . . .
N3 N 1.11781(10) 0.4188(3) 0.15005(9) 0.0692(7) Uani 1 1 d . . .
N1 N 0.80969(9) 0.4390(2) 0.25097(6) 0.0560(5) Uani 1 1 d . . .
O1A O 0.0000 0.9493(6) 0.2500 0.259(5) Uani 1 2 d S . .
N1' N 0.90654(13) 0.3408(4) -0.08388(10) 0.0907(9) Uani 1 1 d . . .
C1' C 0.92659(15) 0.3693(4) -0.03782(12) 0.0824(9) Uani 1 1 d . . .
H1' H 0.9366 0.4617 -0.0298 0.099 Uiso 1 1 calc R . .
C2' C 0.93338(14) 0.2687(3) -0.00102(10) 0.0719(7) Uani 1 1 d . . .
H2' H 0.9483 0.2943 0.0306 0.086 Uiso 1 1 calc R . .
C3' C 0.91821(10) 0.1310(3) -0.01089(9) 0.0593(6) Uani 1 1 d . . .
C6' C 0.92247(11) 0.0206(3) 0.02784(9) 0.0578(6) Uani 1 1 d . . .
C7' C 0.91572(15) -0.1193(4) 0.01691(12) 0.0813(9) Uani 1 1 d . . .
H8' H 0.9096 -0.1482 -0.0158 0.098 Uiso 1 1 calc R . .
C8' C 0.91810(19) -0.2163(4) 0.05444(16) 0.0934(10) Uani 1 1 d . . .
H7' H 0.9126 -0.3099 0.0457 0.112 Uiso 1 1 calc R . .
N2' N 0.92752(16) -0.1875(3) 0.10173(12) 0.0958(9) Uani 1 1 d . . .
C4' C 0.89808(18) 0.1015(5) -0.05903(11) 0.0988(12) Uani 1 1 d . . .
H3' H 0.8882 0.0100 -0.0682 0.119 Uiso 1 1 calc R . .
C5' C 0.8927(2) 0.2082(5) -0.09335(12) 0.1162(16) Uani 1 1 d . . .
H4' H 0.8785 0.1853 -0.1253 0.139 Uiso 1 1 calc R . .
C10' C 0.93000(18) 0.0542(4) 0.07735(11) 0.0869(10) Uani 1 1 d . . .
H5' H 0.9335 0.1473 0.0873 0.104 Uiso 1 1 calc R . .
C9' C 0.9322(2) -0.0522(4) 0.11189(13) 0.1052(13) Uani 1 1 d . . .
H6' H 0.9374 -0.0268 0.1451 0.126 Uiso 1 1 calc R . .
C10 C 0.75595(17) 0.5026(4) -0.04101(9) 0.0808(9) Uani 1 1 d . . .
H4 H 0.7216 0.5602 -0.0519 0.121 Uiso 1 1 calc R . .
H6 H 0.7502 0.4095 -0.0539 0.121 Uiso 1 1 calc R . .
H5 H 0.7933 0.5415 -0.0528 0.121 Uiso 1 1 calc R . .
C7 C 0.76026(12) 0.4976(3) 0.01490(8) 0.0577(6) Uani 1 1 d . . .
C8 C 0.78776(11) 0.3848(3) 0.03962(9) 0.0589(6) Uani 1 1 d . . .
H7 H 0.8037 0.3116 0.0215 0.071 Uiso 1 1 calc R . .
C9 C 0.79199(11) 0.3792(3) 0.09083(9) 0.0550(5) Uani 1 1 d . . .
H8 H 0.8104 0.3021 0.1066 0.066 Uiso 1 1 calc R . .
C4 C 0.76910(9) 0.4873(2) 0.11878(7) 0.0462(5) Uani 1 1 d . . .
C11 C 0.88259(9) 0.4112(2) 0.18803(7) 0.0432(4) Uani 1 1 d . . .
C16 C 0.91190(10) 0.2932(2) 0.20748(8) 0.0472(5) Uani 1 1 d . . .
H12 H 0.8929 0.2375 0.2305 0.057 Uiso 1 1 calc R . .
C15 C 0.97007(10) 0.2593(2) 0.19209(8) 0.0495(5) Uani 1 1 d . . .
H11 H 0.9903 0.1798 0.2045 0.059 Uiso 1 1 calc R . .
C14 C 0.99787(9) 0.3438(2) 0.15825(7) 0.0462(5) Uani 1 1 d . . .
C6 C 0.73640(12) 0.6037(3) 0.04333(8) 0.0579(6) Uani 1 1 d . . .
H3 H 0.7170 0.6795 0.0275 0.070 Uiso 1 1 calc R . .
C5 C 0.74061(11) 0.5999(3) 0.09442(8) 0.0527(5) Uani 1 1 d . . .
H2 H 0.7244 0.6728 0.1126 0.063 Uiso 1 1 calc R . .
C2 C 0.72489(11) 0.5061(3) 0.20485(9) 0.0607(6) Uani 1 1 d . . .
H1 H 0.6848 0.5354 0.1967 0.073 Uiso 1 1 calc R . .
C1 C 0.75062(12) 0.4767(3) 0.25173(9) 0.0633(7) Uani 1 1 d . . .
C17 C 0.72084(17) 0.4823(5) 0.29956(11) 0.0991(13) Uani 1 1 d . . .
C12 C 0.91064(10) 0.4984(2) 0.15517(8) 0.0499(5) Uani 1 1 d . . .
H9 H 0.8908 0.5789 0.1433 0.060 Uiso 1 1 calc R . .
C13 C 0.96871(10) 0.4643(3) 0.14014(9) 0.0535(5) Uani 1 1 d . . .
H10 H 0.9882 0.5219 0.1180 0.064 Uiso 1 1 calc R . .
C2A C 0.0000 0.8271(6) 0.2500 0.123(3) Uani 1 2 d S . .
C1A C 0.0487(4) 0.7418(10) 0.2290(3) 0.220(4) Uani 1 1 d . . .
H1A1 H 0.0509 0.7624 0.1944 0.329 Uiso 1 1 calc R . .
H1A2 H 0.0394 0.6442 0.2332 0.329 Uiso 1 1 calc R . .
H1A3 H 0.0876 0.7630 0.2458 0.329 Uiso 1 1 calc R . .
H14 H 1.1309(14) 0.424(3) 0.1809(12) 0.073(9) Uiso 1 1 d . . .
H13 H 1.1130(15) 0.498(4) 0.1331(13) 0.084(11) Uiso 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 O1 1.429(2) . ?
S1 O2 1.4305(19) . ?
S1 N3 1.583(3) . ?
S1 C14 1.767(2) . ?
F1 C17 1.274(4) . ?
F2 C17 1.315(6) . ?
F3 C17 1.233(4) . ?
C3 N2 1.363(3) . ?
C3 C2 1.371(3) . ?
C3 C4 1.470(3) . ?
N2 N1 1.352(2) . ?
N2 C11 1.435(3) . ?
N3 H14 0.87(3) . ?
N3 H13 0.89(3) . ?
N1 C1 1.333(3) . ?
O1A C2A 1.165(7) . ?
N1' C5' 1.322(5) . ?
N1' C1' 1.326(4) . ?
C1' C2' 1.385(4) . ?
C1' H1' 0.9300 . ?
C2' C3' 1.377(4) . ?
C2' H2' 0.9300 . ?
C3' C4' 1.381(4) . ?
C3' C6' 1.484(4) . ?
C6' C7' 1.373(4) . ?
C6' C10' 1.378(4) . ?
C7' C8' 1.372(5) . ?
C7' H8' 0.9300 . ?
C8' N2' 1.313(5) . ?
C8' H7' 0.9300 . ?
N2' C9' 1.322(5) . ?
C4' C5' 1.378(5) . ?
C4' H3' 0.9300 . ?
C5' H4' 0.9300 . ?
C10' C9' 1.378(5) . ?
C10' H5' 0.9300 . ?
C9' H6' 0.9300 . ?
C10 C7 1.510(3) . ?
C10 H4 0.9600 . ?
C10 H6 0.9600 . ?
C10 H5 0.9600 . ?
C7 C8 1.386(4) . ?
C7 C6 1.387(4) . ?
C8 C9 1.383(3) . ?
C8 H7 0.9300 . ?
C9 C4 1.385(3) . ?
C9 H8 0.9300 . ?
C4 C5 1.389(3) . ?
C11 C12 1.380(3) . ?
C11 C16 1.384(3) . ?
C16 C15 1.387(3) . ?
C16 H12 0.9300 . ?
C15 C14 1.380(3) . ?
C15 H11 0.9300 . ?
C14 C13 1.389(3) . ?
C6 C5 1.380(3) . ?
C6 H3 0.9300 . ?
C5 H2 0.9300 . ?
C2 C1 1.388(3) . ?
C2 H1 0.9300 . ?
C1 C17 1.474(4) . ?
C12 C13 1.382(3) . ?
C12 H9 0.9300 . ?
C13 H10 0.9300 . ?
C2A C1A 1.469(8) 2 ?
C2A C1A 1.470(8) . ?
C1A H1A1 0.9600 . ?
C1A H1A2 0.9600 . ?
C1A H1A3 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
O1 S1 O2 119.69(13) . . ?
O1 S1 N3 108.58(14) . . ?
O2 S1 N3 106.66(14) . . ?
O1 S1 C14 107.31(12) . . ?
O2 S1 C14 105.77(10) . . ?
N3 S1 C14 108.39(12) . . ?
N2 C3 C2 105.95(18) . . ?
N2 C3 C4 124.88(18) . . ?
C2 C3 C4 129.06(19) . . ?
N1 N2 C3 112.75(17) . . ?
N1 N2 C11 118.46(15) . . ?
C3 N2 C11 128.77(17) . . ?
S1 N3 H14 116(2) . . ?
S1 N3 H13 116(2) . . ?
H14 N3 H13 118(3) . . ?
C1 N1 N2 103.52(17) . . ?
C5' N1' C1' 116.0(3) . . ?
N1' C1' C2' 123.4(3) . . ?
N1' C1' H1' 118.3 . . ?
C2' C1' H1' 118.3 . . ?
C3' C2' C1' 120.4(3) . . ?
C3' C2' H2' 119.8 . . ?
C1' C2' H2' 119.8 . . ?
C2' C3' C4' 116.0(3) . . ?
C2' C3' C6' 122.3(2) . . ?
C4' C3' C6' 121.7(3) . . ?
C7' C6' C10' 116.2(3) . . ?
C7' C6' C3' 122.4(2) . . ?
C10' C6' C3' 121.4(3) . . ?
C8' C7' C6' 119.8(3) . . ?
C8' C7' H8' 120.1 . . ?
C6' C7' H8' 120.1 . . ?
N2' C8' C7' 125.2(3) . . ?
N2' C8' H7' 117.4 . . ?
C7' C8' H7' 117.4 . . ?
C8' N2' C9' 114.4(3) . . ?
C5' C4' C3' 119.8(4) . . ?
C5' C4' H3' 120.1 . . ?
C3' C4' H3' 120.1 . . ?
N1' C5' C4' 124.4(3) . . ?
N1' C5' H4' 117.8 . . ?
C4' C5' H4' 117.8 . . ?
C6' C10' C9' 119.0(3) . . ?
C6' C10' H5' 120.5 . . ?
C9' C10' H5' 120.5 . . ?
N2' C9' C10' 125.3(3) . . ?
N2' C9' H6' 117.3 . . ?
C10' C9' H6' 117.3 . . ?
C7 C10 H4 109.5 . . ?
C7 C10 H6 109.5 . . ?
H4 C10 H6 109.5 . . ?
C7 C10 H5 109.5 . . ?
H4 C10 H5 109.5 . . ?
H6 C10 H5 109.5 . . ?
C8 C7 C6 117.6(2) . . ?
C8 C7 C10 120.8(2) . . ?
C6 C7 C10 121.6(2) . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H7 119.4 . . ?
C7 C8 H7 119.4 . . ?
C8 C9 C4 120.6(2) . . ?
C8 C9 H8 119.7 . . ?
C4 C9 H8 119.7 . . ?
C9 C4 C5 118.7(2) . . ?
C9 C4 C3 121.80(19) . . ?
C5 C4 C3 119.41(19) . . ?
C12 C11 C16 121.69(19) . . ?
C12 C11 N2 119.26(18) . . ?
C16 C11 N2 119.05(19) . . ?
C11 C16 C15 119.0(2) . . ?
C11 C16 H12 120.5 . . ?
C15 C16 H12 120.5 . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 H11 120.1 . . ?
C16 C15 H11 120.1 . . ?
C15 C14 C13 120.67(19) . . ?
C15 C14 S1 120.18(17) . . ?
C13 C14 S1 119.12(18) . . ?
C5 C6 C7 121.8(2) . . ?
C5 C6 H3 119.1 . . ?
C7 C6 H3 119.1 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H2 120.0 . . ?
C4 C5 H2 120.0 . . ?
C3 C2 C1 105.1(2) . . ?
C3 C2 H1 127.4 . . ?
C1 C2 H1 127.4 . . ?
N1 C1 C2 112.6(2) . . ?
N1 C1 C17 119.1(2) . . ?
C2 C1 C17 128.2(2) . . ?
F3 C17 F1 111.4(4) . . ?
F3 C17 F2 100.9(4) . . ?
F1 C17 F2 102.1(4) . . ?
F3 C17 C1 116.7(3) . . ?
F1 C17 C1 112.6(3) . . ?
F2 C17 C1 111.6(4) . . ?
C11 C12 C13 119.0(2) . . ?
C11 C12 H9 120.5 . . ?
C13 C12 H9 120.5 . . ?
C12 C13 C14 119.8(2) . . ?
C12 C13 H10 120.1 . . ?
C14 C13 H10 120.1 . . ?
O1A C2A C1A 123.6(4) . 2 ?
O1A C2A C1A 123.6(4) . . ?
C1A C2A C1A 112.7(8) 2 . ?
C2A C1A H1A1 109.5 . . ?
C2A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
C2A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 N2 N1 0.7(3) . . . . ?
C4 C3 N2 N1 -175.8(2) . . . . ?
C2 C3 N2 C11 -177.7(2) . . . . ?
C4 C3 N2 C11 5.8(4) . . . . ?
C3 N2 N1 C1 -0.1(3) . . . . ?
C11 N2 N1 C1 178.4(2) . . . . ?
C5' N1' C1' C2' 0.2(5) . . . . ?
N1' C1' C2' C3' -1.0(5) . . . . ?
C1' C2' C3' C4' 1.7(4) . . . . ?
C1' C2' C3' C6' -177.6(3) . . . . ?
C2' C3' C6' C7' -170.7(3) . . . . ?
C4' C3' C6' C7' 9.9(4) . . . . ?
C2' C3' C6' C10' 13.0(4) . . . . ?
C4' C3' C6' C10' -166.3(3) . . . . ?
C10' C6' C7' C8' -1.4(5) . . . . ?
C3' C6' C7' C8' -177.8(3) . . . . ?
C6' C7' C8' N2' -1.1(6) . . . . ?
C7' C8' N2' C9' 2.9(6) . . . . ?
C2' C3' C4' C5' -1.7(5) . . . . ?
C6' C3' C4' C5' 177.7(3) . . . . ?
C1' N1' C5' C4' -0.2(6) . . . . ?
C3' C4' C5' N1' 1.0(7) . . . . ?
C7' C6' C10' C9' 2.0(5) . . . . ?
C3' C6' C10' C9' 178.5(3) . . . . ?
C8' N2' C9' C10' -2.2(7) . . . . ?
C6' C10' C9' N2' -0.2(7) . . . . ?
C6 C7 C8 C9 -0.8(4) . . . . ?
C10 C7 C8 C9 179.9(2) . . . . ?
C7 C8 C9 C4 -0.5(4) . . . . ?
C8 C9 C4 C5 1.4(3) . . . . ?
C8 C9 C4 C3 178.1(2) . . . . ?
N2 C3 C4 C9 45.6(3) . . . . ?
C2 C3 C4 C9 -130.1(3) . . . . ?
N2 C3 C4 C5 -137.7(2) . . . . ?
C2 C3 C4 C5 46.6(4) . . . . ?
N1 N2 C11 C12 -132.8(2) . . . . ?
C3 N2 C11 C12 45.4(3) . . . . ?
N1 N2 C11 C16 47.4(3) . . . . ?
C3 N2 C11 C16 -134.4(2) . . . . ?
C12 C11 C16 C15 -2.4(3) . . . . ?
N2 C11 C16 C15 177.45(18) . . . . ?
C11 C16 C15 C14 0.6(3) . . . . ?
C16 C15 C14 C13 1.3(3) . . . . ?
C16 C15 C14 S1 -177.02(16) . . . . ?
O1 S1 C14 C15 -3.1(2) . . . . ?
O2 S1 C14 C15 125.76(19) . . . . ?
N3 S1 C14 C15 -120.16(19) . . . . ?
O1 S1 C14 C13 178.56(18) . . . . ?
O2 S1 C14 C13 -52.6(2) . . . . ?
N3 S1 C14 C13 61.5(2) . . . . ?
C8 C7 C6 C5 1.2(4) . . . . ?
C10 C7 C6 C5 -179.5(2) . . . . ?
C7 C6 C5 C4 -0.3(4) . . . . ?
C9 C4 C5 C6 -1.0(3) . . . . ?
C3 C4 C5 C6 -177.8(2) . . . . ?
N2 C3 C2 C1 -1.0(3) . . . . ?
C4 C3 C2 C1 175.4(2) . . . . ?
N2 N1 C1 C2 -0.6(3) . . . . ?
N2 N1 C1 C17 179.2(3) . . . . ?
C3 C2 C1 N1 1.0(3) . . . . ?
C3 C2 C1 C17 -178.8(4) . . . . ?
N1 C1 C17 F3 -41.3(6) . . . . ?
C2 C1 C17 F3 138.5(4) . . . . ?
N1 C1 C17 F1 -171.9(4) . . . . ?
C2 C1 C17 F1 7.8(6) . . . . ?
N1 C1 C17 F2 74.0(4) . . . . ?
C2 C1 C17 F2 -106.3(5) . . . . ?
C16 C11 C12 C13 2.1(3) . . . . ?
N2 C11 C12 C13 -177.72(19) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C15 C14 C13 C12 -1.6(3) . . . . ?
S1 C14 C13 C12 176.77(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.083
_database_code_depnum_ccdc_archive 'CCDC 1010378'
#######################################################################
#
#                 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_mo_2014078_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C58 H52 F6 N10 O5 S2'
_chemical_formula_weight         1147.24

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'
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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   21.952(4)
_cell_length_b                   9.4776(17)
_cell_length_c                   27.112(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.885(12)
_cell_angle_gamma                90.00
_cell_volume                     5633.5(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2272
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20312
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4964
_reflns_number_gt                3146
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0521P)²+10.4486P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4964
_refine_ls_number_parameters     375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1529
_refine_ls_wR_factor_gt          0.1318
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H14 H 1.1287(16) 0.422(4) 0.1831(14) 0.079(12) Uiso 1 1 d . . .
S1 S 1.06967(4) 0.29066(10) 0.13672(3) 0.0565(3) Uani 1 1 d . . .
F2 F 0.67199(15) 0.5334(6) 0.29637(10) 0.203(2) Uani 1 1 d . . .
O1 O 1.06216(10) 0.2873(3) 0.08406(8) 0.0770(8) Uani 1 1 d . . .
O2 O 1.08868(10) 0.1667(3) 0.16311(9) 0.0742(7) Uani 1 1 d . . .
N2' N 0.92304(19) -0.1857(4) 0.10033(14) 0.0962(11) Uani 1 1 d . . .
N2 N 0.82409(10) 0.4473(3) 0.20173(8) 0.0464(6) Uani 1 1 d . . .
N3 N 1.11679(13) 0.4116(4) 0.15002(12) 0.0643(9) Uani 1 1 d . . .
N1 N 0.81335(11) 0.4474(3) 0.25052(9) 0.0567(7) Uani 1 1 d . . .
F3 F 0.73554(17) 0.3984(4) 0.32835(11) 0.1658(17) Uani 1 1 d . . .
N1' N 0.90676(15) 0.3481(4) -0.08307(12) 0.0834(10) Uani 1 1 d . . .
C1' C 0.92763(18) 0.3742(5) -0.03726(15) 0.0805(11) Uani 1 1 d . . .
H1' H 0.9389 0.4663 -0.0292 0.097 Uiso 1 1 calc R . .
C2' C 0.93362(17) 0.2734(4) -0.00091(13) 0.0701(10) Uani 1 1 d . . .
H2' H 0.9487 0.2983 0.0306 0.084 Uiso 1 1 calc R . .
C3' C 0.91744(13) 0.1362(4) -0.01094(11) 0.0554(9) Uani 1 1 d . . .
C6' C 0.92095(14) 0.0252(4) 0.02756(12) 0.0552(9) Uani 1 1 d . . .
C7' C 0.9258(2) 0.0568(4) 0.07686(13) 0.0819(12) Uani 1 1 d . . .
H8' H 0.9287 0.1502 0.0872 0.098 Uiso 1 1 calc R . .
C8' C 0.9265(2) -0.0501(6) 0.11097(16) 0.1029(16) Uani 1 1 d . . .
H7' H 0.9297 -0.0250 0.1442 0.123 Uiso 1 1 calc R . .
C9' C 0.9168(2) -0.2136(5) 0.05294(18) 0.0938(13) Uani 1 1 d . . .
H6' H 0.9129 -0.3078 0.0437 0.113 Uiso 1 1 calc R . .
C10' C 0.91578(18) -0.1148(5) 0.01579(14) 0.0775(11) Uani 1 1 d . . .
H5' H 0.9116 -0.1428 -0.0171 0.093 Uiso 1 1 calc R . .
C5' C 0.8925(2) 0.2164(6) -0.09294(15) 0.1004(16) Uani 1 1 d . . .
H4' H 0.8785 0.1944 -0.1250 0.120 Uiso 1 1 calc R . .
C4' C 0.89701(19) 0.1085(5) -0.05895(14) 0.0866(13) Uani 1 1 d . . .
H3' H 0.8863 0.0171 -0.0683 0.104 Uiso 1 1 calc R . .
C14 C 0.99766(12) 0.3399(3) 0.15789(10) 0.0435(7) Uani 1 1 d . . .
C13 C 0.96916(13) 0.4593(3) 0.13888(11) 0.0519(8) Uani 1 1 d . . .
H10 H 0.9884 0.5150 0.1161 0.062 Uiso 1 1 calc R . .
C12 C 0.91214(13) 0.4960(3) 0.15378(11) 0.0498(8) Uani 1 1 d . . .
H9 H 0.8929 0.5768 0.1414 0.060 Uiso 1 1 calc R . .
C11 C 0.88411(12) 0.4120(3) 0.18707(10) 0.0429(7) Uani 1 1 d . . .
C3 C 0.77394(13) 0.4878(3) 0.17310(11) 0.0483(8) Uani 1 1 d . . .
C4 C 0.77062(13) 0.4904(3) 0.11877(11) 0.0477(8) Uani 1 1 d . . .
C9 C 0.79275(14) 0.3819(4) 0.09102(12) 0.0570(9) Uani 1 1 d . . .
H8 H 0.8113 0.3048 0.1068 0.068 Uiso 1 1 calc R . .
C8 C 0.78779(15) 0.3862(4) 0.03999(12) 0.0616(9) Uani 1 1 d . . .
H7 H 0.8036 0.3123 0.0220 0.074 Uiso 1 1 calc R . .
C7 C 0.75994(15) 0.4975(4) 0.01523(12) 0.0596(9) Uani 1 1 d . . .
C10 C 0.7554(2) 0.5019(5) -0.04091(13) 0.0864(13) Uani 1 1 d . . .
H6 H 0.7887 0.5561 -0.0526 0.130 Uiso 1 1 calc R . .
H4 H 0.7175 0.5448 -0.0519 0.130 Uiso 1 1 calc R . .
H5 H 0.7572 0.4076 -0.0537 0.130 Uiso 1 1 calc R . .
C15 C 0.96996(13) 0.2581(3) 0.19216(10) 0.0470(8) Uani 1 1 d . . .
H11 H 0.9896 0.1785 0.2052 0.056 Uiso 1 1 calc R . .
C16 C 0.91254(13) 0.2947(3) 0.20717(10) 0.0461(7) Uani 1 1 d . . .
H12 H 0.8936 0.2406 0.2305 0.055 Uiso 1 1 calc R . .
C1 C 0.75585(15) 0.4891(4) 0.25178(12) 0.0635(10) Uani 1 1 d . . .
C2 C 0.72949(14) 0.5168(4) 0.20518(11) 0.0608(9) Uani 1 1 d . . .
H1 H 0.6900 0.5484 0.1974 0.073 Uiso 1 1 calc R . .
C6 C 0.73685(16) 0.6038(4) 0.04320(12) 0.0614(9) Uani 1 1 d . . .
H3 H 0.7172 0.6794 0.0274 0.074 Uiso 1 1 calc R . .
C5 C 0.74190(14) 0.6017(4) 0.09396(11) 0.0557(8) Uani 1 1 d . . .
H2 H 0.7259 0.6756 0.1118 0.067 Uiso 1 1 calc R . .
C17 C 0.7271(2) 0.4979(7) 0.29963(16) 0.1025(18) Uani 1 1 d . . .
F1 F 0.7529(3) 0.6001(6) 0.32741(15) 0.223(2) Uani 1 1 d . . .
O1A O 0.5000 0.4394(6) 0.2500 0.171(3) Uani 1 2 d S . .
C2A C 0.5443(4) 0.3559(9) 0.2313(3) 0.196(3) Uani 1 1 d . . .
H2'1 H 0.5475 0.3755 0.1964 0.236 Uiso 1 1 calc R . .
H2'2 H 0.5833 0.3761 0.2481 0.236 Uiso 1 1 calc R . .
C1A C 0.5298(4) 0.2201(8) 0.2376(4) 0.217(5) Uani 1 1 d . . .
H1'1 H 0.5611 0.1729 0.2581 0.260 Uiso 1 1 calc R . .
H1'2 H 0.5257 0.1720 0.2060 0.260 Uiso 1 1 calc R . .
H13 H 1.1116(16) 0.493(4) 0.1346(14) 0.071(13) Uiso 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 O2 1.427(3) . ?
S1 O1 1.429(2) . ?
S1 N3 1.574(3) . ?
S1 C14 1.771(3) . ?
F2 C17 1.254(5) . ?
N2' C9' 1.312(5) . ?
N2' C8' 1.319(5) . ?
N2 N1 1.355(3) . ?
N2 C3 1.370(3) . ?
N2 C11 1.435(3) . ?
N3 H14 0.93(4) . ?
N3 H13 0.88(4) . ?
N1 C1 1.325(4) . ?
F3 C17 1.231(5) . ?
N1' C5' 1.312(6) . ?
N1' C1' 1.325(5) . ?
C1' C2' 1.374(5) . ?
C1' H1' 0.9300 . ?
C2' C3' 1.372(5) . ?
C2' H2' 0.9300 . ?
C3' C4' 1.380(5) . ?
C3' C6' 1.481(5) . ?
C6' C10' 1.368(5) . ?
C6' C7' 1.369(5) . ?
C7' C8' 1.371(5) . ?
C7' H8' 0.9300 . ?
C8' H7' 0.9300 . ?
C9' C10' 1.375(5) . ?
C9' H6' 0.9300 . ?
C10' H5' 0.9300 . ?
C5' C4' 1.376(6) . ?
C5' H4' 0.9300 . ?
C4' H3' 0.9300 . ?
C14 C15 1.375(4) . ?
C14 C13 1.380(4) . ?
C13 C12 1.379(4) . ?
C13 H10 0.9300 . ?
C12 C11 1.372(4) . ?
C12 H9 0.9300 . ?
C11 C16 1.374(4) . ?
C3 C2 1.367(4) . ?
C3 C4 1.471(4) . ?
C4 C9 1.377(4) . ?
C4 C5 1.386(4) . ?
C9 C8 1.383(4) . ?
C9 H8 0.9300 . ?
C8 C7 1.377(5) . ?
C8 H7 0.9300 . ?
C7 C6 1.373(5) . ?
C7 C10 1.521(5) . ?
C10 H6 0.9600 . ?
C10 H4 0.9600 . ?
C10 H5 0.9600 . ?
C15 C16 1.388(4) . ?
C15 H11 0.9300 . ?
C16 H12 0.9300 . ?
C1 C2 1.388(4) . ?
C1 C17 1.473(5) . ?
C2 H1 0.9300 . ?
C6 C5 1.375(4) . ?
C6 H3 0.9300 . ?
C5 H2 0.9300 . ?
C17 F1 1.335(7) . ?
O1A C2A 1.370(7) 2_655 ?
O1A C2A 1.370(7) . ?
C2A C1A 1.339(9) . ?
C2A H2'1 0.9700 . ?
C2A H2'2 0.9700 . ?
C1A C1A 1.502(15) 2_655 ?
C1A H1'1 0.9700 . ?
C1A H1'2 0.9700 . ?

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
O2 S1 O1 119.91(16) . . ?
O2 S1 N3 108.23(18) . . ?
O1 S1 N3 106.65(18) . . ?
O2 S1 C14 107.33(15) . . ?
O1 S1 C14 105.63(13) . . ?
N3 S1 C14 108.70(16) . . ?
C9' N2' C8' 114.4(4) . . ?
N1 N2 C3 112.3(2) . . ?
N1 N2 C11 118.5(2) . . ?
C3 N2 C11 129.2(2) . . ?
S1 N3 H14 117(2) . . ?
S1 N3 H13 117(2) . . ?
H14 N3 H13 113(3) . . ?
C1 N1 N2 103.8(2) . . ?
C5' N1' C1' 115.9(4) . . ?
N1' C1' C2' 124.0(4) . . ?
N1' C1' H1' 118.0 . . ?
C2' C1' H1' 118.0 . . ?
C3' C2' C1' 120.2(4) . . ?
C3' C2' H2' 119.9 . . ?
C1' C2' H2' 119.9 . . ?
C2' C3' C4' 115.8(3) . . ?
C2' C3' C6' 122.0(3) . . ?
C4' C3' C6' 122.2(3) . . ?
C10' C6' C7' 116.2(3) . . ?
C10' C6' C3' 121.6(3) . . ?
C7' C6' C3' 122.1(3) . . ?
C6' C7' C8' 119.7(4) . . ?
C6' C7' H8' 120.2 . . ?
C8' C7' H8' 120.2 . . ?
N2' C8' C7' 125.0(4) . . ?
N2' C8' H7' 117.5 . . ?
C7' C8' H7' 117.5 . . ?
N2' C9' C10' 125.2(4) . . ?
N2' C9' H6' 117.4 . . ?
C10' C9' H6' 117.4 . . ?
C6' C10' C9' 119.5(4) . . ?
C6' C10' H5' 120.3 . . ?
C9' C10' H5' 120.3 . . ?
N1' C5' C4' 124.2(4) . . ?
N1' C5' H4' 117.9 . . ?
C4' C5' H4' 117.9 . . ?
C5' C4' C3' 120.0(4) . . ?
C5' C4' H3' 120.0 . . ?
C3' C4' H3' 120.0 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 S1 120.1(2) . . ?
C13 C14 S1 119.4(2) . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H10 120.1 . . ?
C14 C13 H10 120.1 . . ?
C11 C12 C13 119.4(3) . . ?
C11 C12 H9 120.3 . . ?
C13 C12 H9 120.3 . . ?
C12 C11 C16 121.4(3) . . ?
C12 C11 N2 119.7(3) . . ?
C16 C11 N2 119.0(3) . . ?
C2 C3 N2 106.0(3) . . ?
C2 C3 C4 129.2(3) . . ?
N2 C3 C4 124.7(3) . . ?
C9 C4 C5 117.9(3) . . ?
C9 C4 C3 122.3(3) . . ?
C5 C4 C3 119.8(3) . . ?
C4 C9 C8 120.8(3) . . ?
C4 C9 H8 119.6 . . ?
C8 C9 H8 119.6 . . ?
C7 C8 C9 121.4(3) . . ?
C7 C8 H7 119.3 . . ?
C9 C8 H7 119.3 . . ?
C6 C7 C8 117.4(3) . . ?
C6 C7 C10 121.7(3) . . ?
C8 C7 C10 120.9(3) . . ?
C7 C10 H6 109.5 . . ?
C7 C10 H4 109.5 . . ?
H6 C10 H4 109.5 . . ?
C7 C10 H5 109.5 . . ?
H6 C10 H5 109.5 . . ?
H4 C10 H5 109.5 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H11 120.2 . . ?
C16 C15 H11 120.2 . . ?
C11 C16 C15 119.2(3) . . ?
C11 C16 H12 120.4 . . ?
C15 C16 H12 120.4 . . ?
N1 C1 C2 112.8(3) . . ?
N1 C1 C17 119.4(3) . . ?
C2 C1 C17 127.8(3) . . ?
C3 C2 C1 105.2(3) . . ?
C3 C2 H1 127.4 . . ?
C1 C2 H1 127.4 . . ?
C7 C6 C5 121.9(3) . . ?
C7 C6 H3 119.0 . . ?
C5 C6 H3 119.0 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H2 119.7 . . ?
C4 C5 H2 119.7 . . ?
F3 C17 F2 111.3(5) . . ?
F3 C17 F1 98.8(4) . . ?
F2 C17 F1 103.0(5) . . ?
F3 C17 C1 117.1(4) . . ?
F2 C17 C1 114.0(4) . . ?
F1 C17 C1 110.5(5) . . ?
C2A O1A C2A 109.4(8) 2_655 . ?
C1A C2A O1A 109.3(7) . . ?
C1A C2A H2'1 109.8 . . ?
O1A C2A H2'1 109.8 . . ?
C1A C2A H2'2 109.8 . . ?
O1A C2A H2'2 109.8 . . ?
H2'1 C2A H2'2 108.3 . . ?
C2A C1A C1A 105.9(5) . 2_655 ?
C2A C1A H1'1 110.5 . . ?
C1A C1A H1'1 110.5 2_655 . ?
C2A C1A H1'2 110.5 . . ?
C1A C1A H1'2 110.5 2_655 . ?
H1'1 C1A H1'2 108.7 . . ?

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
C3 N2 N1 C1 -0.2(4) . . . . ?
C11 N2 N1 C1 177.5(3) . . . . ?
C5' N1' C1' C2' -1.3(6) . . . . ?
N1' C1' C2' C3' -0.2(6) . . . . ?
C1' C2' C3' C4' 1.6(5) . . . . ?
C1' C2' C3' C6' -177.7(3) . . . . ?
C2' C3' C6' C10' -167.7(4) . . . . ?
C4' C3' C6' C10' 13.1(5) . . . . ?
C2' C3' C6' C7' 16.3(5) . . . . ?
C4' C3' C6' C7' -162.9(4) . . . . ?
C10' C6' C7' C8' 1.3(6) . . . . ?
C3' C6' C7' C8' 177.5(4) . . . . ?
C9' N2' C8' C7' -1.9(8) . . . . ?
C6' C7' C8' N2' 0.3(8) . . . . ?
C8' N2' C9' C10' 2.1(7) . . . . ?
C7' C6' C10' C9' -1.2(6) . . . . ?
C3' C6' C10' C9' -177.4(4) . . . . ?
N2' C9' C10' C6' -0.6(7) . . . . ?
C1' N1' C5' C4' 1.2(7) . . . . ?
N1' C5' C4' C3' 0.2(7) . . . . ?
C2' C3' C4' C5' -1.6(6) . . . . ?
C6' C3' C4' C5' 177.7(4) . . . . ?
O2 S1 C14 C15 -2.6(3) . . . . ?
O1 S1 C14 C15 126.4(2) . . . . ?
N3 S1 C14 C15 -119.5(3) . . . . ?
O2 S1 C14 C13 178.8(2) . . . . ?
O1 S1 C14 C13 -52.2(3) . . . . ?
N3 S1 C14 C13 61.9(3) . . . . ?
C15 C14 C13 C12 -0.9(4) . . . . ?
S1 C14 C13 C12 177.7(2) . . . . ?
C14 C13 C12 C11 -0.7(5) . . . . ?
C13 C12 C11 C16 2.3(4) . . . . ?
C13 C12 C11 N2 -178.3(3) . . . . ?
N1 N2 C11 C12 -132.0(3) . . . . ?
C3 N2 C11 C12 45.3(4) . . . . ?
N1 N2 C11 C16 47.4(4) . . . . ?
C3 N2 C11 C16 -135.3(3) . . . . ?
N1 N2 C3 C2 0.8(4) . . . . ?
C11 N2 C3 C2 -176.6(3) . . . . ?
N1 N2 C3 C4 -176.4(3) . . . . ?
C11 N2 C3 C4 6.2(5) . . . . ?
C2 C3 C4 C9 -132.5(4) . . . . ?
N2 C3 C4 C9 44.0(5) . . . . ?
C2 C3 C4 C5 44.4(5) . . . . ?
N2 C3 C4 C5 -139.1(3) . . . . ?
C5 C4 C9 C8 1.7(5) . . . . ?
C3 C4 C9 C8 178.6(3) . . . . ?
C4 C9 C8 C7 -0.9(5) . . . . ?
C9 C8 C7 C6 -0.5(5) . . . . ?
C9 C8 C7 C10 179.2(3) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
S1 C14 C15 C16 -177.7(2) . . . . ?
C12 C11 C16 C15 -2.2(4) . . . . ?
N2 C11 C16 C15 178.4(3) . . . . ?
C14 C15 C16 C11 0.6(4) . . . . ?
N2 N1 C1 C2 -0.5(4) . . . . ?
N2 N1 C1 C17 178.2(4) . . . . ?
N2 C3 C2 C1 -1.0(4) . . . . ?
C4 C3 C2 C1 176.0(3) . . . . ?
N1 C1 C2 C3 1.0(4) . . . . ?
C17 C1 C2 C3 -177.6(5) . . . . ?
C8 C7 C6 C5 1.1(5) . . . . ?
C10 C7 C6 C5 -178.6(3) . . . . ?
C7 C6 C5 C4 -0.3(5) . . . . ?
C9 C4 C5 C6 -1.1(5) . . . . ?
C3 C4 C5 C6 -178.1(3) . . . . ?
N1 C1 C17 F3 -44.9(8) . . . . ?
C2 C1 C17 F3 133.5(5) . . . . ?
N1 C1 C17 F2 -177.5(5) . . . . ?
C2 C1 C17 F2 1.0(9) . . . . ?
N1 C1 C17 F1 67.0(6) . . . . ?
C2 C1 C17 F1 -114.5(5) . . . . ?
C2A O1A C2A C1A -0.2(7) 2_655 . . . ?
O1A C2A C1A C1A 0.5(15) . . . 2_655 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 1010379'
#######################################################################
#
#                 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.
#
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#  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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_mo_2014118_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H26 F3 N5 O3 S'
_chemical_formula_weight         581.62

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   21.9683(5)
_cell_length_b                   9.4685(2)
_cell_length_c                   27.2121(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.4200(10)
_cell_angle_gamma                90.00
_cell_volume                     5650.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2272
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23895
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         27.53
_reflns_number_total             6498
_reflns_number_gt                3901
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0952P)²+4.6136P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6498
_refine_ls_number_parameters     380
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.2000
_refine_ls_wR_factor_gt          0.1725
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.56940(3) 0.78530(9) 0.13710(2) 0.0511(2) Uani 1 1 d . A 4
F1 F 0.23622(15) 0.8992(4) 0.32691(10) 0.1530(15) Uani 1 1 d . A 4
F2 F 0.2549(3) 1.1038(5) 0.32640(14) 0.213(2) Uani 1 1 d . A 4
F3 F 0.17274(14) 1.0342(5) 0.29447(10) 0.192(2) Uani 1 1 d . A 4
O1 O 0.58805(9) 0.6609(2) 0.16365(9) 0.0695(6) Uani 1 1 d . A 4
O1S O 0.5000 0.4301(4) 0.2500 0.1127(15) Uani 1 2 d S . 4
O2 O 0.56175(10) 0.7813(3) 0.08458(7) 0.0699(7) Uani 1 1 d . A 4
N2' N 0.42183(18) 0.3193(4) 0.10079(12) 0.0924(10) Uani 1 1 d . B 4
C4 C 0.27148(11) 0.9916(3) 0.11830(9) 0.0457(6) Uani 1 1 d . A 4
N2 N 0.32524(9) 0.9493(3) 0.20129(7) 0.0435(5) Uani 1 1 d . A 4
N3 N 0.61748(11) 0.9055(4) 0.15019(10) 0.0595(7) Uani 1 1 d . A 4
N1 N 0.31472(10) 0.9494(3) 0.24982(8) 0.0527(6) Uani 1 1 d . A 4
N1' N 0.40609(14) 0.8512(4) -0.08351(10) 0.0796(9) Uani 1 1 d . B 4
C5' C 0.3910(2) 0.7185(5) -0.09282(13) 0.0928(13) Uani 1 1 d . B 4
H4' H 0.3764 0.6963 -0.1247 0.111 Uiso 1 1 calc R B 4
C4' C 0.39541(18) 0.6105(4) -0.05886(11) 0.0777(11) Uani 1 1 d . B 4
H3' H 0.3838 0.5193 -0.0680 0.093 Uiso 1 1 calc R B 4
C3' C 0.41733(12) 0.6389(4) -0.01093(10) 0.0538(7) Uani 1 1 d . B 4
C6' C 0.42027(13) 0.5289(3) 0.02755(10) 0.0536(7) Uani 1 1 d . B 4
O2S O 0.5000 0.1390(6) 0.2500 0.147(3) Uani 1 2 d S . 4
C7' C 0.42301(18) 0.5622(4) 0.07731(11) 0.0734(10) Uani 1 1 d . B 4
H8' H 0.4242 0.6561 0.0874 0.088 Uiso 1 1 calc R B 4
C8' C 0.4240(2) 0.4563(5) 0.11149(13) 0.0898(13) Uani 1 1 d . B 4
H7' H 0.4264 0.4819 0.1445 0.108 Uiso 1 1 calc R B 4
C9' C 0.4175(2) 0.2883(4) 0.05346(15) 0.0873(12) Uani 1 1 d . B 4
H6' H 0.4145 0.1936 0.0446 0.105 Uiso 1 1 calc R B 4
C10' C 0.41707(18) 0.3868(4) 0.01639(12) 0.0743(10) Uani 1 1 d . B 4
H5' H 0.4146 0.3577 -0.0163 0.089 Uiso 1 1 calc R B 4
C1' C 0.42792(17) 0.8781(4) -0.03767(13) 0.0750(10) Uani 1 1 d . B 4
H1' H 0.4396 0.9702 -0.0299 0.090 Uiso 1 1 calc R B 4
C2' C 0.43419(15) 0.7776(4) -0.00112(11) 0.0651(9) Uani 1 1 d . B 4
H2' H 0.4498 0.8028 0.0302 0.078 Uiso 1 1 calc R B 4
C10 C 0.2550(2) 1.0014(4) -0.04078(11) 0.0816(11) Uani 1 1 d . A 4
H6 H 0.2512 0.9069 -0.0533 0.122 Uiso 1 1 calc R A 4
H5 H 0.2909 1.0446 -0.0526 0.122 Uiso 1 1 calc R A 4
H4 H 0.2197 1.0553 -0.0518 0.122 Uiso 1 1 calc R A 4
C7 C 0.25991(14) 0.9975(4) 0.01492(10) 0.0570(8) Uani 1 1 d . A 4
C8 C 0.28819(14) 0.8865(4) 0.03985(11) 0.0597(8) Uani 1 1 d . A 4
H7 H 0.3040 0.8127 0.0220 0.072 Uiso 1 1 calc R A 4
C9 C 0.29356(13) 0.8823(3) 0.09081(10) 0.0538(7) Uani 1 1 d . A 4
H8 H 0.3122 0.8052 0.1067 0.065 Uiso 1 1 calc R A 4
C3 C 0.27511(12) 0.9905(3) 0.17251(9) 0.0452(6) Uani 1 1 d . A 4
C11 C 0.38494(11) 0.9120(3) 0.18706(8) 0.0394(6) Uani 1 1 d . A 4
C16 C 0.41301(11) 0.7939(3) 0.20729(9) 0.0435(6) Uani 1 1 d . A 4
H12 H 0.3940 0.7405 0.2306 0.052 Uiso 1 1 calc R A 4
C15 C 0.47023(12) 0.7554(3) 0.19247(9) 0.0438(6) Uani 1 1 d . A 4
H11 H 0.4897 0.6755 0.2056 0.053 Uiso 1 1 calc R A 4
C14 C 0.49795(11) 0.8365(3) 0.15812(8) 0.0407(6) Uani 1 1 d . A 4
C1 C 0.25706(14) 0.9926(4) 0.25094(11) 0.0592(8) Uani 1 1 d . A 4
C2 C 0.23060(13) 1.0196(4) 0.20426(10) 0.0583(8) Uani 1 1 d . A 4
H1 H 0.1911 1.0508 0.1962 0.070 Uiso 1 1 calc R A 4
C6 C 0.23643(15) 1.1053(3) 0.04261(10) 0.0585(8) Uani 1 1 d . A 4
H3 H 0.2165 1.1804 0.0265 0.070 Uiso 1 1 calc R A 4
C5 C 0.24182(13) 1.1040(3) 0.09357(10) 0.0538(7) Uani 1 1 d . A 4
H2 H 0.2258 1.1777 0.1113 0.065 Uiso 1 1 calc R A 4
C17 C 0.22919(18) 1.0030(5) 0.29877(13) 0.0882(14) Uani 1 1 d . A 4
C12 C 0.41306(12) 0.9955(3) 0.15358(10) 0.0473(6) Uani 1 1 d . A 4
H9 H 0.3938 1.0763 0.1409 0.057 Uiso 1 1 calc R A 4
C13 C 0.47005(12) 0.9584(3) 0.13895(10) 0.0490(7) Uani 1 1 d . A 4
H10 H 0.4896 1.0141 0.1166 0.059 Uiso 1 1 calc R A 4
C1S C 0.5468(4) 0.3598(7) 0.2304(4) 0.209(4) Uani 1 1 d D C 4
H1S1 H 0.5846 0.3900 0.2475 0.250 Uiso 1 1 calc R C 4
H1S2 H 0.5484 0.3882 0.1962 0.250 Uiso 1 1 calc R C 4
C2S C 0.5443(5) 0.2070(7) 0.2321(4) 0.234(5) Uani 1 1 d D C 4
H2S1 H 0.5470 0.1741 0.1985 0.280 Uiso 1 1 calc R C 4
H2S2 H 0.5813 0.1761 0.2502 0.280 Uiso 1 1 calc R C 4
H14 H 0.6110(16) 0.984(4) 0.1342(13) 0.071(12) Uiso 1 1 d . D 4
H13 H 0.6329(15) 0.915(4) 0.1823(13) 0.074(10) Uiso 1 1 d . E 4


_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 O1 1.429(2) . ?
S1 O2 1.429(2) . ?
S1 N3 1.579(3) . ?
S1 C14 1.770(2) . ?
F1 C17 1.250(5) . ?
F2 C17 1.321(6) . ?
F3 C17 1.274(4) . ?
O1S C1S 1.361(7) . ?
O1S C1S 1.361(7) 2_655 ?
N2' C9' 1.319(5) . ?
N2' C8' 1.330(5) . ?
C4 C9 1.382(4) . ?
C4 C5 1.399(4) . ?
C4 C3 1.472(3) . ?
N2 N1 1.354(3) . ?
N2 C3 1.369(3) . ?
N2 C11 1.434(3) . ?
N3 H14 0.86(4) . ?
N3 H13 0.92(4) . ?
N1 C1 1.333(4) . ?
N1' C5' 1.320(5) . ?
N1' C1' 1.334(4) . ?
C5' C4' 1.378(5) . ?
C5' H4' 0.9300 . ?
C4' C3' 1.389(4) . ?
C4' H3' 0.9300 . ?
C3' C2' 1.386(4) . ?
C3' C6' 1.475(4) . ?
C6' C10' 1.380(5) . ?
C6' C7' 1.388(4) . ?
O2S C2S 1.288(8) . ?
O2S C2S 1.288(8) 2_655 ?
C7' C8' 1.367(5) . ?
C7' H8' 0.9300 . ?
C8' H7' 0.9300 . ?
C9' C10' 1.374(5) . ?
C9' H6' 0.9300 . ?
C10' H5' 0.9300 . ?
C1' C2' 1.378(5) . ?
C1' H1' 0.9300 . ?
C2' H2' 0.9300 . ?
C10 C7 1.514(4) . ?
C10 H6 0.9600 . ?
C10 H5 0.9600 . ?
C10 H4 0.9600 . ?
C7 C8 1.378(4) . ?
C7 C6 1.386(4) . ?
C8 C9 1.385(4) . ?
C8 H7 0.9300 . ?
C9 H8 0.9300 . ?
C3 C2 1.371(4) . ?
C11 C16 1.376(4) . ?
C11 C12 1.380(4) . ?
C16 C15 1.391(3) . ?
C16 H12 0.9300 . ?
C15 C14 1.379(4) . ?
C15 H11 0.9300 . ?
C14 C13 1.393(4) . ?
C1 C2 1.389(4) . ?
C1 C17 1.474(4) . ?
C2 H1 0.9300 . ?
C6 C5 1.385(4) . ?
C6 H3 0.9300 . ?
C5 H2 0.9300 . ?
C12 C13 1.381(4) . ?
C12 H9 0.9300 . ?
C13 H10 0.9300 . ?
C1S C2S 1.4479(10) . ?
C1S H1S1 0.9700 . ?
C1S H1S2 0.9700 . ?
C2S H2S1 0.9700 . ?
C2S H2S2 0.9700 . ?

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
O1 S1 O2 119.78(14) . . ?
O1 S1 N3 108.20(15) . . ?
O2 S1 N3 106.38(15) . . ?
O1 S1 C14 107.18(13) . . ?
O2 S1 C14 106.07(12) . . ?
N3 S1 C14 108.88(14) . . ?
C1S O1S C1S 121.4(7) . 2_655 ?
C9' N2' C8' 115.5(3) . . ?
C9 C4 C5 118.5(2) . . ?
C9 C4 C3 122.5(2) . . ?
C5 C4 C3 118.9(2) . . ?
N1 N2 C3 112.3(2) . . ?
N1 N2 C11 118.40(19) . . ?
C3 N2 C11 129.3(2) . . ?
S1 N3 H14 114(2) . . ?
S1 N3 H13 119(2) . . ?
H14 N3 H13 116(3) . . ?
C1 N1 N2 103.9(2) . . ?
C5' N1' C1' 115.7(3) . . ?
N1' C5' C4' 124.8(3) . . ?
N1' C5' H4' 117.6 . . ?
C4' C5' H4' 117.6 . . ?
C5' C4' C3' 119.5(4) . . ?
C5' C4' H3' 120.2 . . ?
C3' C4' H3' 120.2 . . ?
C2' C3' C4' 116.0(3) . . ?
C2' C3' C6' 122.1(3) . . ?
C4' C3' C6' 121.9(3) . . ?
C10' C6' C7' 115.8(3) . . ?
C10' C6' C3' 122.2(3) . . ?
C7' C6' C3' 122.0(3) . . ?
C2S O2S C2S 119.9(8) . 2_655 ?
C8' C7' C6' 119.7(3) . . ?
C8' C7' H8' 120.2 . . ?
C6' C7' H8' 120.2 . . ?
N2' C8' C7' 124.6(4) . . ?
N2' C8' H7' 117.7 . . ?
C7' C8' H7' 117.7 . . ?
N2' C9' C10' 124.2(4) . . ?
N2' C9' H6' 117.9 . . ?
C10' C9' H6' 117.9 . . ?
C9' C10' C6' 120.2(3) . . ?
C9' C10' H5' 119.9 . . ?
C6' C10' H5' 119.9 . . ?
N1' C1' C2' 123.9(4) . . ?
N1' C1' H1' 118.0 . . ?
C2' C1' H1' 118.0 . . ?
C1' C2' C3' 120.1(3) . . ?
C1' C2' H2' 120.0 . . ?
C3' C2' H2' 120.0 . . ?
C8 C7 C6 117.7(3) . . ?
C8 C7 C10 121.0(3) . . ?
C6 C7 C10 121.3(3) . . ?
C7 C8 C9 121.6(3) . . ?
C7 C8 H7 119.2 . . ?
C9 C8 H7 119.2 . . ?
C4 C9 C8 120.6(3) . . ?
C4 C9 H8 119.7 . . ?
C8 C9 H8 119.7 . . ?
N2 C3 C2 106.0(2) . . ?
N2 C3 C4 124.7(2) . . ?
C2 C3 C4 129.2(2) . . ?
C16 C11 C12 121.5(2) . . ?
C16 C11 N2 119.2(2) . . ?
C12 C11 N2 119.3(2) . . ?
C11 C16 C15 119.2(2) . . ?
C11 C16 H12 120.4 . . ?
C15 C16 H12 120.4 . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H11 120.2 . . ?
C16 C15 H11 120.2 . . ?
C15 C14 C13 120.8(2) . . ?
C15 C14 S1 120.2(2) . . ?
C13 C14 S1 119.0(2) . . ?
N1 C1 C2 112.5(3) . . ?
N1 C1 C17 119.1(3) . . ?
C2 C1 C17 128.5(3) . . ?
C3 C2 C1 105.3(2) . . ?
C3 C2 H1 127.3 . . ?
C1 C2 H1 127.3 . . ?
C5 C6 C7 121.7(3) . . ?
C5 C6 H3 119.1 . . ?
C7 C6 H3 119.1 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H2 120.1 . . ?
C4 C5 H2 120.1 . . ?
F1 C17 F3 108.8(4) . . ?
F1 C17 F2 100.7(4) . . ?
F3 C17 F2 105.4(4) . . ?
F1 C17 C1 116.5(3) . . ?
F3 C17 C1 112.8(3) . . ?
F2 C17 C1 111.4(4) . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H9 120.2 . . ?
C13 C12 H9 120.2 . . ?
C12 C13 C14 119.3(2) . . ?
C12 C13 H10 120.4 . . ?
C14 C13 H10 120.4 . . ?
O1S C1S C2S 116.5(6) . . ?
O1S C1S H1S1 108.2 . . ?
C2S C1S H1S1 108.2 . . ?
O1S C1S H1S2 108.2 . . ?
C2S C1S H1S2 108.2 . . ?
H1S1 C1S H1S2 107.3 . . ?
O2S C2S C1S 122.9(7) . . ?
O2S C2S H2S1 106.6 . . ?
C1S C2S H2S1 106.6 . . ?
O2S C2S H2S2 106.6 . . ?
C1S C2S H2S2 106.6 . . ?
H2S1 C2S H2S2 106.6 . . ?

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
C3 N2 N1 C1 -0.5(3) . . . . ?
C11 N2 N1 C1 177.9(2) . . . . ?
C1' N1' C5' C4' 1.2(6) . . . . ?
N1' C5' C4' C3' -0.3(7) . . . . ?
C5' C4' C3' C2' -0.8(5) . . . . ?
C5' C4' C3' C6' 177.1(3) . . . . ?
C2' C3' C6' C10' -165.0(3) . . . . ?
C4' C3' C6' C10' 17.3(5) . . . . ?
C2' C3' C6' C7' 18.7(5) . . . . ?
C4' C3' C6' C7' -159.0(3) . . . . ?
C10' C6' C7' C8' 1.7(5) . . . . ?
C3' C6' C7' C8' 178.2(4) . . . . ?
C9' N2' C8' C7' -1.1(7) . . . . ?
C6' C7' C8' N2' -0.8(7) . . . . ?
C8' N2' C9' C10' 2.0(7) . . . . ?
N2' C9' C10' C6' -1.1(7) . . . . ?
C7' C6' C10' C9' -0.8(5) . . . . ?
C3' C6' C10' C9' -177.3(3) . . . . ?
C5' N1' C1' C2' -1.0(6) . . . . ?
N1' C1' C2' C3' -0.1(6) . . . . ?
C4' C3' C2' C1' 0.9(5) . . . . ?
C6' C3' C2' C1' -176.9(3) . . . . ?
C6 C7 C8 C9 -0.4(5) . . . . ?
C10 C7 C8 C9 179.4(3) . . . . ?
C5 C4 C9 C8 2.1(4) . . . . ?
C3 C4 C9 C8 178.8(3) . . . . ?
C7 C8 C9 C4 -1.2(5) . . . . ?
N1 N2 C3 C2 0.6(3) . . . . ?
C11 N2 C3 C2 -177.5(3) . . . . ?
N1 N2 C3 C4 -175.8(3) . . . . ?
C11 N2 C3 C4 6.1(5) . . . . ?
C9 C4 C3 N2 43.3(4) . . . . ?
C5 C4 C3 N2 -140.1(3) . . . . ?
C9 C4 C3 C2 -132.2(3) . . . . ?
C5 C4 C3 C2 44.4(5) . . . . ?
N1 N2 C11 C16 47.0(3) . . . . ?
C3 N2 C11 C16 -134.9(3) . . . . ?
N1 N2 C11 C12 -132.7(3) . . . . ?
C3 N2 C11 C12 45.4(4) . . . . ?
C12 C11 C16 C15 -2.1(4) . . . . ?
N2 C11 C16 C15 178.2(2) . . . . ?
C11 C16 C15 C14 0.5(4) . . . . ?
C16 C15 C14 C13 1.6(4) . . . . ?
C16 C15 C14 S1 -177.57(19) . . . . ?
O1 S1 C14 C15 -2.6(2) . . . . ?
O2 S1 C14 C15 126.4(2) . . . . ?
N3 S1 C14 C15 -119.5(2) . . . . ?
O1 S1 C14 C13 178.2(2) . . . . ?
O2 S1 C14 C13 -52.7(2) . . . . ?
N3 S1 C14 C13 61.4(2) . . . . ?
N2 N1 C1 C2 0.1(4) . . . . ?
N2 N1 C1 C17 178.9(4) . . . . ?
N2 C3 C2 C1 -0.5(4) . . . . ?
C4 C3 C2 C1 175.7(3) . . . . ?
N1 C1 C2 C3 0.2(4) . . . . ?
C17 C1 C2 C3 -178.4(4) . . . . ?
C8 C7 C6 C5 1.1(5) . . . . ?
C10 C7 C6 C5 -178.7(3) . . . . ?
C7 C6 C5 C4 -0.2(5) . . . . ?
C9 C4 C5 C6 -1.5(4) . . . . ?
C3 C4 C5 C6 -178.2(3) . . . . ?
N1 C1 C17 F1 -47.7(6) . . . . ?
C2 C1 C17 F1 130.8(4) . . . . ?
N1 C1 C17 F3 -174.7(4) . . . . ?
C2 C1 C17 F3 3.9(7) . . . . ?
N1 C1 C17 F2 67.0(5) . . . . ?
C2 C1 C17 F2 -114.5(5) . . . . ?
C16 C11 C12 C13 1.7(4) . . . . ?
N2 C11 C12 C13 -178.7(2) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C15 C14 C13 C12 -2.0(4) . . . . ?
S1 C14 C13 C12 177.1(2) . . . . ?
C1S O1S C1S C2S -0.7(7) 2_655 . . . ?
C2S O2S C2S C1S -0.8(8) 2_655 . . . ?
O1S C1S C2S O2S 1.6(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 1010380'
#######################################################################
#
#                 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_mo_2014077_0ma

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C61 H54 F6 N10 O5 S2'
_chemical_formula_weight         1185.28

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   21.3705(11)
_cell_length_b                   10.0269(4)
_cell_length_c                   27.7028(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.927(4)
_cell_angle_gamma                90.00
_cell_volume                     5932.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2348
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21794
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5205
_reflns_number_gt                3905
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0848P)²+7.8216P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5205
_refine_ls_number_parameters     390
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1899
_refine_ls_wR_factor_gt          0.1728
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.409
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.06788(4) 0.29350(10) 0.14038(3) 0.0488(3) Uani 1 1 d . . .
O1A O 0.0000 0.6435(10) 0.2500 0.244(7) Uani 1 2 d S . .
F3 F 0.65457(17) 0.0799(5) 0.29944(14) 0.1370(16) Uani 1 1 d . . .
O1 O 1.08584(13) 0.4147(3) 0.16407(11) 0.0668(8) Uani 1 1 d . . .
C11 C 0.7581(2) -0.0075(6) -0.02651(16) 0.0835(15) Uani 1 1 d . . .
H5 H 0.7609 0.0753 -0.0437 0.125 Uiso 1 1 calc R . .
H4 H 0.7192 -0.0507 -0.0353 0.125 Uiso 1 1 calc R . .
H6 H 0.7924 -0.0641 -0.0347 0.125 Uiso 1 1 calc R . .
O2 O 1.05953(14) 0.2905(3) 0.08892(10) 0.0673(8) Uani 1 1 d . . .
N2 N 0.81589(13) 0.1402(3) 0.20685(11) 0.0492(8) Uani 1 1 d . . .
C5 C 0.76654(16) 0.0673(4) 0.12712(13) 0.0491(9) Uani 1 1 d . . .
N3 N 1.11843(16) 0.1835(4) 0.15419(15) 0.0588(9) Uani 1 1 d . . .
N1 N 0.80204(15) 0.1535(4) 0.25390(12) 0.0628(9) Uani 1 1 d . . .
F1 F 0.7214(4) 0.2000(9) 0.3283(3) 0.298(4) Uani 1 1 d U . .
N2' N 0.9347(2) 0.7984(4) 0.11169(16) 0.0802(12) Uani 1 1 d . . .
C10' C 0.9547(3) 0.6768(5) 0.11944(18) 0.0859(16) Uani 1 1 d . . .
H9' H 0.9741 0.6587 0.1493 0.103 Uiso 1 1 calc R . .
C9' C 0.9493(2) 0.5741(5) 0.08707(17) 0.0752(13) Uani 1 1 d . . .
H10' H 0.9641 0.4897 0.0954 0.090 Uiso 1 1 calc R . .
C8' C 0.92196(17) 0.5958(4) 0.04239(14) 0.0520(9) Uani 1 1 d . . .
C7' C 0.91314(19) 0.4948(5) 0.00431(16) 0.0644(11) Uani 1 1 d . . .
H6' H 0.8964 0.5234 -0.0253 0.077 Uiso 1 1 calc R . .
C6' C 0.9266(2) 0.3706(5) 0.00857(17) 0.0675(12) Uani 1 1 d . . .
H5' H 0.9443 0.3425 0.0380 0.081 Uiso 1 1 calc R . .
C3' C 0.91649(18) 0.2676(4) -0.02948(15) 0.0584(10) Uani 1 1 d . . .
C4' C 0.8892(2) 0.2897(5) -0.07459(18) 0.0735(13) Uani 1 1 d . . .
H3' H 0.8767 0.3753 -0.0835 0.088 Uiso 1 1 calc R . .
C5' C 0.8805(2) 0.1847(5) -0.10674(18) 0.0760(13) Uani 1 1 d . . .
H4' H 0.8612 0.2022 -0.1366 0.091 Uiso 1 1 calc R . .
N1' N 0.89838(17) 0.0604(4) -0.09694(14) 0.0665(10) Uani 1 1 d . . .
C11' C 0.9081(3) 0.8195(5) 0.0686(2) 0.0813(14) Uani 1 1 d . . .
H8' H 0.8931 0.9047 0.0617 0.098 Uiso 1 1 calc R . .
C12' C 0.9012(2) 0.7239(5) 0.03342(18) 0.0722(12) Uani 1 1 d . . .
H7' H 0.8825 0.7454 0.0036 0.087 Uiso 1 1 calc R . .
C2' C 0.9341(2) 0.1391(5) -0.01993(17) 0.0667(11) Uani 1 1 d . . .
H2' H 0.9531 0.1179 0.0098 0.080 Uiso 1 1 calc R . .
C1' C 0.9240(2) 0.0415(5) -0.05364(18) 0.0686(12) Uani 1 1 d . . .
H1' H 0.9361 -0.0448 -0.0454 0.082 Uiso 1 1 calc R . .
C2A C 0.0000 0.7602(14) 0.2500 0.137(5) Uani 1 2 d S . .
C15 C 0.99473(15) 0.2449(4) 0.16319(12) 0.0427(8) Uani 1 1 d . . .
C14 C 0.96857(17) 0.1244(4) 0.14825(14) 0.0502(9) Uani 1 1 d . . .
H10 H 0.9905 0.0678 0.1283 0.060 Uiso 1 1 calc R . .
C13 C 0.90981(17) 0.0889(4) 0.16316(14) 0.0508(9) Uani 1 1 d . . .
H9 H 0.8920 0.0081 0.1535 0.061 Uiso 1 1 calc R . .
C12 C 0.87772(15) 0.1747(4) 0.19250(13) 0.0445(8) Uani 1 1 d . . .
C3 C 0.76657(17) 0.0899(4) 0.17955(14) 0.0518(9) Uani 1 1 d . . .
C10 C 0.78969(18) 0.1603(4) 0.09480(15) 0.0559(10) Uani 1 1 d . . .
H8 H 0.8074 0.2394 0.1064 0.067 Uiso 1 1 calc R . .
C9 C 0.78648(18) 0.1357(4) 0.04587(15) 0.0603(11) Uani 1 1 d . . .
H7 H 0.8020 0.1991 0.0249 0.072 Uiso 1 1 calc R . .
C8 C 0.76073(18) 0.0193(5) 0.02701(15) 0.0590(10) Uani 1 1 d . . .
C16 C 0.96342(16) 0.3275(4) 0.19407(13) 0.0467(9) Uani 1 1 d . . .
H11 H 0.9818 0.4067 0.2048 0.056 Uiso 1 1 calc R . .
C17 C 0.90439(17) 0.2919(4) 0.20895(13) 0.0483(9) Uani 1 1 d . . .
H12 H 0.8830 0.3468 0.2299 0.058 Uiso 1 1 calc R . .
C1 C 0.7434(2) 0.1103(5) 0.25582(16) 0.0727(13) Uani 1 1 d . . .
C2 C 0.7193(2) 0.0701(5) 0.21084(16) 0.0685(12) Uani 1 1 d . . .
H1 H 0.6794 0.0369 0.2036 0.082 Uiso 1 1 calc R . .
C7 C 0.73714(19) -0.0712(4) 0.05940(15) 0.0613(11) Uani 1 1 d . . .
H3 H 0.7191 -0.1497 0.0477 0.074 Uiso 1 1 calc R . .
C6 C 0.73965(18) -0.0483(4) 0.10866(15) 0.0565(10) Uani 1 1 d . . .
H2 H 0.7232 -0.1109 0.1295 0.068 Uiso 1 1 calc R . .
C4 C 0.7102(3) 0.1169(11) 0.3008(2) 0.144(3) Uani 1 1 d U . .
F2 F 0.7337(4) 0.0175(12) 0.3298(2) 0.285(4) Uani 1 1 d U . .
C1A C 0.0518(6) 0.8378(14) 0.2326(4) 0.214(5) Uani 1 1 d . . .
H1A1 H 0.0877 0.8262 0.2540 0.321 Uiso 1 1 calc R . .
H1A2 H 0.0403 0.9304 0.2315 0.321 Uiso 1 1 calc R . .
H1A3 H 0.0616 0.8083 0.2008 0.321 Uiso 1 1 calc R . .
H14 H 1.133(2) 0.184(5) 0.1832(18) 0.072(14) Uiso 1 1 d . . .
H13 H 1.118(2) 0.107(5) 0.1382(17) 0.077(15) Uiso 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 O1 1.428(3) . ?
S1 O2 1.431(3) . ?
S1 N3 1.582(4) . ?
S1 C15 1.774(4) . ?
O1A C2A 1.170(13) . ?
F3 C4 1.245(6) . ?
C11 C8 1.506(6) . ?
C11 H5 0.9600 . ?
C11 H4 0.9600 . ?
C11 H6 0.9600 . ?
N2 N1 1.353(4) . ?
N2 C3 1.372(4) . ?
N2 C12 1.435(4) . ?
C5 C6 1.384(5) . ?
C5 C10 1.395(5) . ?
C5 C3 1.470(5) . ?
N3 H14 0.85(5) . ?
N3 H13 0.89(5) . ?
N1 C1 1.330(5) . ?
F1 C4 1.148(8) . ?
N2' C10' 1.308(6) . ?
N2' C11' 1.322(7) . ?
C10' C9' 1.368(6) . ?
C10' H9' 0.9300 . ?
C9' C8' 1.368(6) . ?
C9' H10' 0.9300 . ?
C8' C12' 1.380(6) . ?
C8' C7' 1.469(6) . ?
C7' C6' 1.283(6) . ?
C7' H6' 0.9300 . ?
C6' C3' 1.486(6) . ?
C6' H5' 0.9300 . ?
C3' C2' 1.366(6) . ?
C3' C4' 1.379(6) . ?
C4' C5' 1.387(6) . ?
C4' H3' 0.9300 . ?
C5' N1' 1.329(6) . ?
C5' H4' 0.9300 . ?
N1' C1' 1.315(6) . ?
C11' C12' 1.371(7) . ?
C11' H8' 0.9300 . ?
C12' H7' 0.9300 . ?
C2' C1' 1.365(6) . ?
C2' H2' 0.9300 . ?
C1' H1' 0.9300 . ?
C2A C1A 1.448(12) . ?
C2A C1A 1.448(12) 2 ?
C15 C16 1.380(5) . ?
C15 C14 1.389(5) . ?
C14 C13 1.382(5) . ?
C14 H10 0.9300 . ?
C13 C12 1.382(5) . ?
C13 H9 0.9300 . ?
C12 C17 1.377(5) . ?
C3 C2 1.368(6) . ?
C10 C9 1.377(6) . ?
C10 H8 0.9300 . ?
C9 C8 1.386(6) . ?
C9 H7 0.9300 . ?
C8 C7 1.383(6) . ?
C16 C17 1.387(5) . ?
C16 H11 0.9300 . ?
C17 H12 0.9300 . ?
C1 C2 1.392(6) . ?
C1 C4 1.457(8) . ?
C2 H1 0.9300 . ?
C7 C6 1.383(6) . ?
C7 H3 0.9300 . ?
C6 H2 0.9300 . ?
C4 F2 1.364(12) . ?
C1A H1A1 0.9600 . ?
C1A H1A2 0.9600 . ?
C1A H1A3 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
O1 S1 O2 119.88(19) . . ?
O1 S1 N3 108.2(2) . . ?
O2 S1 N3 106.7(2) . . ?
O1 S1 C15 107.25(17) . . ?
O2 S1 C15 105.50(16) . . ?
N3 S1 C15 108.97(19) . . ?
C8 C11 H5 109.5 . . ?
C8 C11 H4 109.5 . . ?
H5 C11 H4 109.5 . . ?
C8 C11 H6 109.5 . . ?
H5 C11 H6 109.5 . . ?
H4 C11 H6 109.5 . . ?
N1 N2 C3 112.2(3) . . ?
N1 N2 C12 118.4(3) . . ?
C3 N2 C12 129.3(3) . . ?
C6 C5 C10 118.3(4) . . ?
C6 C5 C3 118.7(3) . . ?
C10 C5 C3 122.9(3) . . ?
S1 N3 H14 117(3) . . ?
S1 N3 H13 119(3) . . ?
H14 N3 H13 119(4) . . ?
C1 N1 N2 104.1(3) . . ?
C10' N2' C11' 115.2(4) . . ?
N2' C10' C9' 125.1(5) . . ?
N2' C10' H9' 117.5 . . ?
C9' C10' H9' 117.5 . . ?
C10' C9' C8' 119.8(4) . . ?
C10' C9' H10' 120.1 . . ?
C8' C9' H10' 120.1 . . ?
C9' C8' C12' 115.9(4) . . ?
C9' C8' C7' 125.5(4) . . ?
C12' C8' C7' 118.7(4) . . ?
C6' C7' C8' 125.4(4) . . ?
C6' C7' H6' 117.3 . . ?
C8' C7' H6' 117.3 . . ?
C7' C6' C3' 125.6(4) . . ?
C7' C6' H5' 117.2 . . ?
C3' C6' H5' 117.2 . . ?
C2' C3' C4' 115.6(4) . . ?
C2' C3' C6' 119.0(4) . . ?
C4' C3' C6' 125.3(4) . . ?
C3' C4' C5' 120.2(4) . . ?
C3' C4' H3' 119.9 . . ?
C5' C4' H3' 119.9 . . ?
N1' C5' C4' 123.3(4) . . ?
N1' C5' H4' 118.3 . . ?
C4' C5' H4' 118.3 . . ?
C1' N1' C5' 115.4(4) . . ?
N2' C11' C12' 124.3(5) . . ?
N2' C11' H8' 117.9 . . ?
C12' C11' H8' 117.9 . . ?
C11' C12' C8' 119.8(4) . . ?
C11' C12' H7' 120.1 . . ?
C8' C12' H7' 120.1 . . ?
C1' C2' C3' 120.5(4) . . ?
C1' C2' H2' 119.7 . . ?
C3' C2' H2' 119.7 . . ?
N1' C1' C2' 124.9(4) . . ?
N1' C1' H1' 117.6 . . ?
C2' C1' H1' 117.6 . . ?
O1A C2A C1A 122.5(7) . . ?
O1A C2A C1A 122.5(7) . 2 ?
C1A C2A C1A 115.0(14) . 2 ?
C16 C15 C14 120.6(3) . . ?
C16 C15 S1 120.5(3) . . ?
C14 C15 S1 118.9(3) . . ?
C13 C14 C15 119.7(3) . . ?
C13 C14 H10 120.1 . . ?
C15 C14 H10 120.1 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H9 120.3 . . ?
C12 C13 H9 120.3 . . ?
C17 C12 C13 121.2(3) . . ?
C17 C12 N2 119.3(3) . . ?
C13 C12 N2 119.5(3) . . ?
C2 C3 N2 105.9(3) . . ?
C2 C3 C5 128.9(3) . . ?
N2 C3 C5 125.1(3) . . ?
C9 C10 C5 120.3(4) . . ?
C9 C10 H8 119.8 . . ?
C5 C10 H8 119.8 . . ?
C10 C9 C8 121.9(4) . . ?
C10 C9 H7 119.1 . . ?
C8 C9 H7 119.1 . . ?
C7 C8 C9 117.2(4) . . ?
C7 C8 C11 121.3(4) . . ?
C9 C8 C11 121.5(4) . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H11 120.2 . . ?
C17 C16 H11 120.2 . . ?
C12 C17 C16 119.5(3) . . ?
C12 C17 H12 120.3 . . ?
C16 C17 H12 120.3 . . ?
N1 C1 C2 112.3(4) . . ?
N1 C1 C4 120.4(4) . . ?
C2 C1 C4 127.2(4) . . ?
C3 C2 C1 105.5(4) . . ?
C3 C2 H1 127.3 . . ?
C1 C2 H1 127.3 . . ?
C8 C7 C6 121.9(4) . . ?
C8 C7 H3 119.1 . . ?
C6 C7 H3 119.1 . . ?
C7 C6 C5 120.4(4) . . ?
C7 C6 H2 119.8 . . ?
C5 C6 H2 119.8 . . ?
F1 C4 F3 114.4(8) . . ?
F1 C4 F2 94.4(8) . . ?
F3 C4 F2 97.7(7) . . ?
F1 C4 C1 120.3(6) . . ?
F3 C4 C1 116.8(5) . . ?
F2 C4 C1 106.8(8) . . ?
C2A C1A H1A1 109.5 . . ?
C2A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
C2A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 N1 C1 0.3(5) . . . . ?
C12 N2 N1 C1 -178.0(4) . . . . ?
C11' N2' C10' C9' -0.7(9) . . . . ?
N2' C10' C9' C8' 1.0(9) . . . . ?
C10' C9' C8' C12' -0.3(7) . . . . ?
C10' C9' C8' C7' -180.0(5) . . . . ?
C9' C8' C7' C6' 4.2(7) . . . . ?
C12' C8' C7' C6' -175.6(4) . . . . ?
C8' C7' C6' C3' 178.6(4) . . . . ?
C7' C6' C3' C2' 179.0(5) . . . . ?
C7' C6' C3' C4' -2.1(7) . . . . ?
C2' C3' C4' C5' 0.8(7) . . . . ?
C6' C3' C4' C5' -178.1(4) . . . . ?
C3' C4' C5' N1' -1.4(8) . . . . ?
C4' C5' N1' C1' 1.6(7) . . . . ?
C10' N2' C11' C12' -0.2(8) . . . . ?
N2' C11' C12' C8' 0.9(8) . . . . ?
C9' C8' C12' C11' -0.6(7) . . . . ?
C7' C8' C12' C11' 179.1(4) . . . . ?
C4' C3' C2' C1' -0.6(6) . . . . ?
C6' C3' C2' C1' 178.3(4) . . . . ?
C5' N1' C1' C2' -1.5(7) . . . . ?
C3' C2' C1' N1' 1.0(7) . . . . ?
O1 S1 C15 C16 6.3(3) . . . . ?
O2 S1 C15 C16 -122.6(3) . . . . ?
N3 S1 C15 C16 123.1(3) . . . . ?
O1 S1 C15 C14 -175.8(3) . . . . ?
O2 S1 C15 C14 55.3(3) . . . . ?
N3 S1 C15 C14 -58.9(3) . . . . ?
C16 C15 C14 C13 2.1(5) . . . . ?
S1 C15 C14 C13 -175.8(3) . . . . ?
C15 C14 C13 C12 0.5(6) . . . . ?
C14 C13 C12 C17 -3.0(6) . . . . ?
C14 C13 C12 N2 178.1(3) . . . . ?
N1 N2 C12 C17 -45.8(5) . . . . ?
C3 N2 C12 C17 136.3(4) . . . . ?
N1 N2 C12 C13 133.1(4) . . . . ?
C3 N2 C12 C13 -44.8(6) . . . . ?
N1 N2 C3 C2 -0.1(5) . . . . ?
C12 N2 C3 C2 177.9(4) . . . . ?
N1 N2 C3 C5 178.3(4) . . . . ?
C12 N2 C3 C5 -3.7(6) . . . . ?
C6 C5 C3 C2 -43.5(6) . . . . ?
C10 C5 C3 C2 133.3(5) . . . . ?
C6 C5 C3 N2 138.4(4) . . . . ?
C10 C5 C3 N2 -44.8(6) . . . . ?
C6 C5 C10 C9 -1.0(6) . . . . ?
C3 C5 C10 C9 -177.8(4) . . . . ?
C5 C10 C9 C8 -0.2(6) . . . . ?
C10 C9 C8 C7 1.1(6) . . . . ?
C10 C9 C8 C11 -179.3(4) . . . . ?
C14 C15 C16 C17 -2.2(5) . . . . ?
S1 C15 C16 C17 175.7(3) . . . . ?
C13 C12 C17 C16 2.9(5) . . . . ?
N2 C12 C17 C16 -178.2(3) . . . . ?
C15 C16 C17 C12 -0.3(5) . . . . ?
N2 N1 C1 C2 -0.3(6) . . . . ?
N2 N1 C1 C4 -176.3(7) . . . . ?
N2 C3 C2 C1 -0.1(5) . . . . ?
C5 C3 C2 C1 -178.4(4) . . . . ?
N1 C1 C2 C3 0.3(6) . . . . ?
C4 C1 C2 C3 175.8(7) . . . . ?
C9 C8 C7 C6 -0.9(6) . . . . ?
C11 C8 C7 C6 179.6(4) . . . . ?
C8 C7 C6 C5 -0.3(6) . . . . ?
C10 C5 C6 C7 1.2(6) . . . . ?
C3 C5 C6 C7 178.1(4) . . . . ?
N1 C1 C4 F1 30.7(16) . . . . ?
C2 C1 C4 F1 -144.6(10) . . . . ?
N1 C1 C4 F3 177.0(7) . . . . ?
C2 C1 C4 F3 1.8(14) . . . . ?
N1 C1 C4 F2 -75.0(9) . . . . ?
C2 C1 C4 F2 109.8(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.961
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 1010381'
#######################################################################
#
#                 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_mo_2014081_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C62 H56 F6 N10 O5 S2'
_chemical_formula_weight         1199.31

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   21.606(3)
_cell_length_b                   10.0057(16)
_cell_length_c                   27.794(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.919(6)
_cell_angle_gamma                90.00
_cell_volume                     6005.2(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2640
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25985
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_av_sigmaI/netI    0.1082
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         27.45
_reflns_number_total             6831
_reflns_number_gt                2641
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1485P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6831
_refine_ls_number_parameters     393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2142
_refine_ls_R_factor_gt           0.0823
_refine_ls_wR_factor_ref         0.2987
_refine_ls_wR_factor_gt          0.2226
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.56744(5) 0.20014(12) 0.14092(4) 0.0554(4) Uani 1 1 d . . .
O1 O 0.56074(16) 0.1988(4) 0.09004(12) 0.0750(10) Uani 1 1 d . . .
C10 C 0.2575(3) 0.5034(7) -0.0269(2) 0.0916(19) Uani 1 1 d . . .
H6 H 0.2850 0.5752 -0.0345 0.137 Uiso 1 1 calc R . .
H4 H 0.2159 0.5273 -0.0365 0.137 Uiso 1 1 calc R . .
H5 H 0.2694 0.4241 -0.0437 0.137 Uiso 1 1 calc R . .
O2 O 0.58464(15) 0.0799(3) 0.16580(13) 0.0736(10) Uani 1 1 d . . .
F1 F 0.2309(5) 0.3245(10) 0.3303(3) 0.323(8) Uani 1 1 d . . .
N1 N 0.30842(19) 0.3593(4) 0.25379(16) 0.0698(12) Uani 1 1 d . . .
C1 C 0.2505(3) 0.4067(6) 0.2558(2) 0.0811(17) Uani 1 1 d . . .
F3 F 0.1651(2) 0.4442(6) 0.30121(16) 0.169(2) Uani 1 1 d . . .
N3 N 0.61708(18) 0.3117(4) 0.15412(19) 0.0618(11) Uani 1 1 d . . .
N1' N 0.3998(2) 0.4441(5) -0.09760(18) 0.0745(13) Uani 1 1 d . . .
C1A C 0.4705(7) 0.6356(11) 0.2628(5) 0.223(7) Uani 1 1 d . . .
H1A H 0.4399 0.5799 0.2462 0.267 Uiso 1 1 calc R . .
H1B H 0.4767 0.6031 0.2955 0.267 Uiso 1 1 calc R . .
C2A C 0.4517(6) 0.7704(13) 0.2626(4) 0.185(5) Uani 1 1 d . . .
H2A H 0.4172 0.7828 0.2398 0.222 Uiso 1 1 calc R . .
H2B H 0.4383 0.7958 0.2943 0.222 Uiso 1 1 calc R . .
O1A O 0.5000 0.8475(9) 0.2500 0.156(3) Uani 1 2 d S . .
C14 C 0.49536(19) 0.2513(4) 0.16231(15) 0.0464(11) Uani 1 1 d . . .
C13 C 0.4695(2) 0.3709(5) 0.14637(17) 0.0575(13) Uani 1 1 d . . .
H10 H 0.4912 0.4251 0.1256 0.069 Uiso 1 1 calc R . .
C12 C 0.4122(2) 0.4102(4) 0.16087(18) 0.0598(13) Uani 1 1 d . . .
H9 H 0.3950 0.4905 0.1502 0.072 Uiso 1 1 calc R . .
C11 C 0.3806(2) 0.3285(4) 0.19151(17) 0.0501(11) Uani 1 1 d . . .
N2 N 0.31965(16) 0.3668(4) 0.20603(15) 0.0558(10) Uani 1 1 d . . .
C3 C 0.2709(2) 0.4183(5) 0.17902(18) 0.0571(12) Uani 1 1 d . . .
C4 C 0.2689(2) 0.4363(5) 0.12686(17) 0.0548(12) Uani 1 1 d . . .
C5 C 0.2422(2) 0.5510(5) 0.1078(2) 0.0690(14) Uani 1 1 d . . .
H2 H 0.2267 0.6153 0.1284 0.083 Uiso 1 1 calc R . .
C6 C 0.2383(2) 0.5717(6) 0.0581(2) 0.0738(15) Uani 1 1 d . . .
H3 H 0.2201 0.6495 0.0460 0.089 Uiso 1 1 calc R . .
C7 C 0.2611(2) 0.4780(6) 0.02646(19) 0.0664(14) Uani 1 1 d . . .
C17 C 0.2203(4) 0.4104(13) 0.3028(3) 0.147(4) Uani 1 1 d . . .
F2 F 0.2450(4) 0.5050(14) 0.3287(3) 0.325(8) Uani 1 1 d . . .
C2 C 0.2255(2) 0.4449(6) 0.2109(2) 0.0741(16) Uani 1 1 d . . .
H1 H 0.1865 0.4808 0.2040 0.089 Uiso 1 1 calc R . .
C9 C 0.2912(2) 0.3429(5) 0.09522(19) 0.0621(13) Uani 1 1 d . . .
H8 H 0.3093 0.2646 0.1071 0.074 Uiso 1 1 calc R . .
C8 C 0.2868(2) 0.3649(5) 0.0455(2) 0.0664(14) Uani 1 1 d . . .
H7 H 0.3018 0.3002 0.0249 0.080 Uiso 1 1 calc R . .
C16 C 0.4064(2) 0.2117(4) 0.20938(16) 0.0499(11) Uani 1 1 d . . .
H12 H 0.3853 0.1598 0.2312 0.060 Uiso 1 1 calc R . .
C15 C 0.4639(2) 0.1732(4) 0.19437(16) 0.0511(12) Uani 1 1 d . . .
H11 H 0.4816 0.0942 0.2059 0.061 Uiso 1 1 calc R . .
C5' C 0.3837(3) 0.3205(6) -0.1089(2) 0.0861(18) Uani 1 1 d . . .
H4' H 0.3666 0.3050 -0.1395 0.103 Uiso 1 1 calc R . .
C4' C 0.3907(3) 0.2132(6) -0.0783(3) 0.0873(18) Uani 1 1 d . . .
H3' H 0.3788 0.1280 -0.0883 0.105 Uiso 1 1 calc R . .
C3' C 0.4155(3) 0.2338(7) -0.0328(3) 0.0847(18) Uani 1 1 d . . .
C6' C 0.4260(3) 0.1297(8) 0.0081(3) 0.101(2) Uani 1 1 d . . .
H5' H 0.4429 0.1589 0.0375 0.121 Uiso 1 1 calc R . .
C7' C 0.4136(3) 0.0144(7) 0.0038(3) 0.101(2) Uani 1 1 d . . .
H6' H 0.3982 -0.0124 -0.0264 0.121 Uiso 1 1 calc R . .
C8' C 0.4200(2) -0.0922(5) 0.04146(19) 0.0643(14) Uani 1 1 d . . .
C12' C 0.4422(3) -0.0716(6) 0.0866(2) 0.099(2) Uani 1 1 d . . .
H7' H 0.4550 0.0135 0.0960 0.118 Uiso 1 1 calc R . .
C11' C 0.4462(4) -0.1756(7) 0.1191(2) 0.113(3) Uani 1 1 d . . .
H8' H 0.4627 -0.1589 0.1498 0.136 Uiso 1 1 calc R . .
N2' N 0.4277(3) -0.2974(6) 0.1084(2) 0.1028(18) Uani 1 1 d . . .
C1' C 0.4239(3) 0.4596(6) -0.0544(3) 0.0826(17) Uani 1 1 d . . .
H1' H 0.4353 0.5460 -0.0455 0.099 Uiso 1 1 calc R . .
C2' C 0.4341(3) 0.3612(6) -0.0207(2) 0.0865(18) Uani 1 1 d . . .
H2' H 0.4527 0.3799 0.0091 0.104 Uiso 1 1 calc R . .
C9' C 0.4017(3) -0.2171(6) 0.0309(2) 0.0814(17) Uani 1 1 d . . .
H10' H 0.3860 -0.2362 0.0001 0.098 Uiso 1 1 calc R . .
C10' C 0.4057(3) -0.3168(6) 0.0642(3) 0.094(2) Uani 1 1 d . . .
H9' H 0.3923 -0.4020 0.0554 0.113 Uiso 1 1 calc R . .
H14 H 0.632(3) 0.323(6) 0.189(2) 0.11(2) Uiso 1 1 d . . .
H13 H 0.610(3) 0.386(6) 0.131(2) 0.092(19) Uiso 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 O1 1.417(3) . ?
S1 O2 1.431(3) . ?
S1 N3 1.582(4) . ?
S1 C14 1.761(4) . ?
C10 C7 1.504(7) . ?
C10 H6 0.9600 . ?
C10 H4 0.9600 . ?
C10 H5 0.9600 . ?
F1 C17 1.166(10) . ?
N1 C1 1.342(6) . ?
N1 N2 1.360(5) . ?
C1 C2 1.398(7) . ?
C1 C17 1.479(9) . ?
F3 C17 1.240(8) . ?
N3 H14 1.02(6) . ?
N3 H13 0.98(6) . ?
N1' C1' 1.301(7) . ?
N1' C5' 1.319(7) . ?
C1A C2A 1.409(14) . ?
C1A C1A 1.48(2) 2_655 ?
C1A H1A 0.9700 . ?
C1A H1B 0.9700 . ?
C2A O1A 1.353(11) . ?
C2A H2A 0.9700 . ?
C2A H2B 0.9700 . ?
O1A C2A 1.353(11) 2_655 ?
C14 C15 1.381(6) . ?
C14 C13 1.388(6) . ?
C13 C12 1.372(6) . ?
C13 H10 0.9300 . ?
C12 C11 1.378(6) . ?
C12 H9 0.9300 . ?
C11 C16 1.380(6) . ?
C11 N2 1.442(5) . ?
N2 C3 1.373(6) . ?
C3 C2 1.369(7) . ?
C3 C4 1.460(6) . ?
C4 C9 1.381(7) . ?
C4 C5 1.382(6) . ?
C5 C6 1.398(7) . ?
C5 H2 0.9300 . ?
C6 C7 1.387(7) . ?
C6 H3 0.9300 . ?
C7 C8 1.360(7) . ?
C17 F2 1.293(13) . ?
C2 H1 0.9300 . ?
C9 C8 1.399(7) . ?
C9 H8 0.9300 . ?
C8 H7 0.9300 . ?
C16 C15 1.379(6) . ?
C16 H12 0.9300 . ?
C15 H11 0.9300 . ?
C5' C4' 1.375(8) . ?
C5' H4' 0.9300 . ?
C4' C3' 1.372(9) . ?
C4' H3' 0.9300 . ?
C3' C2' 1.374(8) . ?
C3' C6' 1.554(9) . ?
C6' C7' 1.189(8) . ?
C6' H5' 0.9300 . ?
C7' C8' 1.498(8) . ?
C7' H6' 0.9300 . ?
C8' C9' 1.340(7) . ?
C8' C12' 1.345(7) . ?
C12' C11' 1.378(8) . ?
C12' H7' 0.9300 . ?
C11' N2' 1.314(8) . ?
C11' H8' 0.9300 . ?
N2' C10' 1.316(8) . ?
C1' C2' 1.372(8) . ?
C1' H1' 0.9300 . ?
C2' H2' 0.9300 . ?
C9' C10' 1.362(8) . ?
C9' H10' 0.9300 . ?
C10' H9' 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
O1 S1 O2 119.4(2) . . ?
O1 S1 N3 106.5(3) . . ?
O2 S1 N3 108.5(2) . . ?
O1 S1 C14 106.1(2) . . ?
O2 S1 C14 107.4(2) . . ?
N3 S1 C14 108.5(2) . . ?
C7 C10 H6 109.5 . . ?
C7 C10 H4 109.5 . . ?
H6 C10 H4 109.5 . . ?
C7 C10 H5 109.5 . . ?
H6 C10 H5 109.5 . . ?
H4 C10 H5 109.5 . . ?
C1 N1 N2 102.6(4) . . ?
N1 C1 C2 113.0(5) . . ?
N1 C1 C17 119.0(5) . . ?
C2 C1 C17 127.9(5) . . ?
S1 N3 H14 119(3) . . ?
S1 N3 H13 107(3) . . ?
H14 N3 H13 125(5) . . ?
C1' N1' C5' 115.2(5) . . ?
C2A C1A C1A 104.5(6) . 2_655 ?
C2A C1A H1A 110.8 . . ?
C1A C1A H1A 110.8 2_655 . ?
C2A C1A H1B 110.8 . . ?
C1A C1A H1B 110.8 2_655 . ?
H1A C1A H1B 108.9 . . ?
O1A C2A C1A 108.8(11) . . ?
O1A C2A H2A 109.9 . . ?
C1A C2A H2A 109.9 . . ?
O1A C2A H2B 109.9 . . ?
C1A C2A H2B 109.9 . . ?
H2A C2A H2B 108.3 . . ?
C2A O1A C2A 110.5(12) 2_655 . ?
C15 C14 C13 119.5(4) . . ?
C15 C14 S1 120.9(3) . . ?
C13 C14 S1 119.6(4) . . ?
C12 C13 C14 120.7(4) . . ?
C12 C13 H10 119.6 . . ?
C14 C13 H10 119.6 . . ?
C13 C12 C11 118.8(4) . . ?
C13 C12 H9 120.6 . . ?
C11 C12 H9 120.6 . . ?
C12 C11 C16 121.5(4) . . ?
C12 C11 N2 119.4(4) . . ?
C16 C11 N2 119.1(4) . . ?
N1 N2 C3 113.4(4) . . ?
N1 N2 C11 116.9(4) . . ?
C3 N2 C11 129.6(4) . . ?
C2 C3 N2 105.8(4) . . ?
C2 C3 C4 128.3(4) . . ?
N2 C3 C4 125.9(4) . . ?
C9 C4 C5 117.9(5) . . ?
C9 C4 C3 123.4(4) . . ?
C5 C4 C3 118.7(5) . . ?
C4 C5 C6 120.9(5) . . ?
C4 C5 H2 119.6 . . ?
C6 C5 H2 119.6 . . ?
C7 C6 C5 121.0(5) . . ?
C7 C6 H3 119.5 . . ?
C5 C6 H3 119.5 . . ?
C8 C7 C6 117.7(5) . . ?
C8 C7 C10 122.1(5) . . ?
C6 C7 C10 120.2(5) . . ?
F1 C17 F3 113.1(11) . . ?
F1 C17 F2 96.1(9) . . ?
F3 C17 F2 101.4(9) . . ?
F1 C17 C1 118.4(7) . . ?
F3 C17 C1 115.3(6) . . ?
F2 C17 C1 109.0(11) . . ?
C3 C2 C1 105.2(4) . . ?
C3 C2 H1 127.4 . . ?
C1 C2 H1 127.4 . . ?
C4 C9 C8 120.6(5) . . ?
C4 C9 H8 119.7 . . ?
C8 C9 H8 119.7 . . ?
C7 C8 C9 121.9(5) . . ?
C7 C8 H7 119.0 . . ?
C9 C8 H7 119.0 . . ?
C15 C16 C11 119.1(4) . . ?
C15 C16 H12 120.5 . . ?
C11 C16 H12 120.5 . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H11 119.9 . . ?
C14 C15 H11 119.9 . . ?
N1' C5' C4' 124.2(6) . . ?
N1' C5' H4' 117.9 . . ?
C4' C5' H4' 117.9 . . ?
C3' C4' C5' 118.9(6) . . ?
C3' C4' H3' 120.5 . . ?
C5' C4' H3' 120.5 . . ?
C4' C3' C2' 117.8(5) . . ?
C4' C3' C6' 128.1(6) . . ?
C2' C3' C6' 114.1(7) . . ?
C7' C6' C3' 123.3(8) . . ?
C7' C6' H5' 118.4 . . ?
C3' C6' H5' 118.4 . . ?
C6' C7' C8' 127.1(8) . . ?
C6' C7' H6' 116.4 . . ?
C8' C7' H6' 116.4 . . ?
C9' C8' C12' 116.1(5) . . ?
C9' C8' C7' 119.4(6) . . ?
C12' C8' C7' 124.4(6) . . ?
C8' C12' C11' 120.5(6) . . ?
C8' C12' H7' 119.7 . . ?
C11' C12' H7' 119.7 . . ?
N2' C11' C12' 122.7(7) . . ?
N2' C11' H8' 118.6 . . ?
C12' C11' H8' 118.6 . . ?
C11' N2' C10' 116.5(5) . . ?
N1' C1' C2' 126.4(6) . . ?
N1' C1' H1' 116.8 . . ?
C2' C1' H1' 116.8 . . ?
C1' C2' C3' 117.4(6) . . ?
C1' C2' H2' 121.3 . . ?
C3' C2' H2' 121.3 . . ?
C8' C9' C10' 121.6(6) . . ?
C8' C9' H10' 119.2 . . ?
C10' C9' H10' 119.2 . . ?
N2' C10' C9' 122.6(6) . . ?
N2' C10' H9' 118.7 . . ?
C9' C10' H9' 118.7 . . ?

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
N2 N1 C1 C2 -0.7(6) . . . . ?
N2 N1 C1 C17 178.1(8) . . . . ?
C1A C1A C2A O1A -14(2) 2_655 . . . ?
C1A C2A O1A C2A 5.8(8) . . . 2_655 ?
O1 S1 C14 C15 123.9(4) . . . . ?
O2 S1 C14 C15 -4.8(4) . . . . ?
N3 S1 C14 C15 -122.0(4) . . . . ?
O1 S1 C14 C13 -55.4(4) . . . . ?
O2 S1 C14 C13 175.9(3) . . . . ?
N3 S1 C14 C13 58.7(4) . . . . ?
C15 C14 C13 C12 -2.1(7) . . . . ?
S1 C14 C13 C12 177.2(4) . . . . ?
C14 C13 C12 C11 -0.2(7) . . . . ?
C13 C12 C11 C16 2.8(7) . . . . ?
C13 C12 C11 N2 -178.4(4) . . . . ?
C1 N1 N2 C3 0.6(6) . . . . ?
C1 N1 N2 C11 177.1(4) . . . . ?
C12 C11 N2 N1 -132.3(5) . . . . ?
C16 C11 N2 N1 46.6(6) . . . . ?
C12 C11 N2 C3 43.5(7) . . . . ?
C16 C11 N2 C3 -137.7(5) . . . . ?
N1 N2 C3 C2 -0.3(6) . . . . ?
C11 N2 C3 C2 -176.2(5) . . . . ?
N1 N2 C3 C4 -178.9(4) . . . . ?
C11 N2 C3 C4 5.3(8) . . . . ?
C2 C3 C4 C9 -136.4(6) . . . . ?
N2 C3 C4 C9 41.8(7) . . . . ?
C2 C3 C4 C5 42.1(7) . . . . ?
N2 C3 C4 C5 -139.7(5) . . . . ?
C9 C4 C5 C6 -0.3(7) . . . . ?
C3 C4 C5 C6 -178.9(5) . . . . ?
C4 C5 C6 C7 -0.1(8) . . . . ?
C5 C6 C7 C8 0.7(8) . . . . ?
C5 C6 C7 C10 -178.8(5) . . . . ?
N1 C1 C17 F1 -35.4(18) . . . . ?
C2 C1 C17 F1 143.1(13) . . . . ?
N1 C1 C17 F3 -173.9(9) . . . . ?
C2 C1 C17 F3 4.7(16) . . . . ?
N1 C1 C17 F2 72.9(12) . . . . ?
C2 C1 C17 F2 -108.5(10) . . . . ?
N2 C3 C2 C1 -0.1(6) . . . . ?
C4 C3 C2 C1 178.4(5) . . . . ?
N1 C1 C2 C3 0.5(7) . . . . ?
C17 C1 C2 C3 -178.1(9) . . . . ?
C5 C4 C9 C8 0.2(7) . . . . ?
C3 C4 C9 C8 178.7(4) . . . . ?
C6 C7 C8 C9 -0.9(8) . . . . ?
C10 C7 C8 C9 178.7(5) . . . . ?
C4 C9 C8 C7 0.4(8) . . . . ?
C12 C11 C16 C15 -3.1(7) . . . . ?
N2 C11 C16 C15 178.1(4) . . . . ?
C11 C16 C15 C14 0.7(6) . . . . ?
C13 C14 C15 C16 1.9(7) . . . . ?
S1 C14 C15 C16 -177.4(3) . . . . ?
C1' N1' C5' C4' 0.3(9) . . . . ?
N1' C5' C4' C3' 0.5(10) . . . . ?
C5' C4' C3' C2' -2.0(9) . . . . ?
C5' C4' C3' C6' 178.1(6) . . . . ?
C4' C3' C6' C7' 1.0(11) . . . . ?
C2' C3' C6' C7' -178.9(7) . . . . ?
C3' C6' C7' C8' -177.8(5) . . . . ?
C6' C7' C8' C9' 177.8(7) . . . . ?
C6' C7' C8' C12' -1.0(11) . . . . ?
C9' C8' C12' C11' 0.9(10) . . . . ?
C7' C8' C12' C11' 179.7(6) . . . . ?
C8' C12' C11' N2' -1.5(13) . . . . ?
C12' C11' N2' C10' 1.2(12) . . . . ?
C5' N1' C1' C2' 0.5(9) . . . . ?
N1' C1' C2' C3' -2.1(10) . . . . ?
C4' C3' C2' C1' 2.7(9) . . . . ?
C6' C3' C2' C1' -177.4(5) . . . . ?
C12' C8' C9' C10' 0.0(9) . . . . ?
C7' C8' C9' C10' -178.9(6) . . . . ?
C11' N2' C10' C9' -0.3(11) . . . . ?
C8' C9' C10' N2' -0.3(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 1010382'
#######################################################################
#
#                 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_mo_2014263_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H28 F3 N5 O3 S'
_chemical_formula_weight         607.65

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   21.5985(15)
_cell_length_b                   9.9370(7)
_cell_length_c                   28.061(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.248(3)
_cell_angle_gamma                90.00
_cell_volume                     6017.9(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2392
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25216
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         27.58
_reflns_number_total             6910
_reflns_number_gt                4044
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1400P)²+8.5793P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6910
_refine_ls_number_parameters     398
_refine_ls_number_restraints     397
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0818
_refine_ls_wR_factor_ref         0.2803
_refine_ls_wR_factor_gt          0.2448
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.195
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.06877(4) 0.80485(10) 0.14192(4) 0.0510(3) Uani 1 1 d U . .
C10 C 0.7581(3) 0.4967(6) -0.02675(17) 0.0856(15) Uani 1 1 d U . .
H5 H 0.7731 0.5746 -0.0429 0.128 Uiso 1 1 calc R . .
H4 H 0.7158 0.4800 -0.0369 0.128 Uiso 1 1 calc R . .
H6 H 0.7830 0.4201 -0.0343 0.128 Uiso 1 1 calc R . .
O2 O 1.06299(15) 0.8048(3) 0.09099(10) 0.0701(9) Uani 1 1 d U . .
O2S O 0.0000 0.4515(10) 0.2500 0.207(5) Uani 1 2 d SU . .
O1 O 1.08541(13) 0.9252(3) 0.16674(12) 0.0677(8) Uani 1 1 d U . .
F3 F 0.66329(18) 0.5670(6) 0.29631(15) 0.1510(18) Uani 1 1 d U . .
N3 N 1.11881(16) 0.6938(4) 0.15553(15) 0.0586(9) Uani 1 1 d U . .
N1 N 0.80825(15) 0.6429(4) 0.25091(13) 0.0631(9) Uani 1 1 d U . .
C1 C 0.7511(2) 0.5946(5) 0.25322(18) 0.0731(13) Uani 1 1 d U . .
F2 F 0.7346(3) 0.6737(7) 0.32842(18) 0.218(3) Uani 1 1 d U . .
N2' N 0.89869(19) 0.5529(4) -0.09840(15) 0.0706(10) Uani 1 1 d U . .
C14 C 0.99604(16) 0.7531(4) 0.16232(13) 0.0451(8) Uani 1 1 d U . .
C13 C 0.96484(17) 0.8311(4) 0.19418(13) 0.0473(9) Uani 1 1 d U . .
H11 H 0.9826 0.9099 0.2063 0.057 Uiso 1 1 calc R . .
C12 C 0.90666(17) 0.7912(4) 0.20810(14) 0.0489(9) Uani 1 1 d U . .
H12 H 0.8853 0.8426 0.2298 0.059 Uiso 1 1 calc R . .
C11 C 0.88075(16) 0.6750(4) 0.18961(14) 0.0468(8) Uani 1 1 d U . .
N2 N 0.82041(14) 0.6348(3) 0.20413(12) 0.0518(8) Uani 1 1 d U . .
O1S O 0.0000 0.1767(7) 0.2500 0.120(2) Uani 1 2 d SU . .
C3 C 0.77183(17) 0.5833(4) 0.17708(15) 0.0553(10) Uani 1 1 d U . .
C4 C 0.77002(17) 0.5641(4) 0.12553(15) 0.0532(9) Uani 1 1 d U . .
C9 C 0.79165(19) 0.6588(4) 0.09389(16) 0.0602(10) Uani 1 1 d U . .
H8 H 0.8091 0.7384 0.1055 0.072 Uiso 1 1 calc R . .
C8 C 0.78758(19) 0.6362(5) 0.04541(17) 0.0643(11) Uani 1 1 d U . .
H7 H 0.8027 0.7011 0.0250 0.077 Uiso 1 1 calc R . .
C7 C 0.7618(2) 0.5205(5) 0.02627(16) 0.0642(11) Uani 1 1 d U . .
C16 C 0.91269(17) 0.5944(4) 0.15904(15) 0.0551(10) Uani 1 1 d U . .
H9 H 0.8954 0.5139 0.1480 0.066 Uiso 1 1 calc R . .
C15 C 0.97021(17) 0.6335(4) 0.14493(15) 0.0552(10) Uani 1 1 d U . .
H10 H 0.9918 0.5805 0.1239 0.066 Uiso 1 1 calc R . .
C17 C 0.7204(4) 0.5950(12) 0.2982(3) 0.147(2) Uani 1 1 d U . .
F1 F 0.7407(3) 0.4824(10) 0.3233(2) 0.218(2) Uani 1 1 d U . .
C2 C 0.7264(2) 0.5566(5) 0.20869(16) 0.0683(12) Uani 1 1 d U . .
H1 H 0.6874 0.5207 0.2018 0.082 Uiso 1 1 calc R . .
C6 C 0.7389(2) 0.4272(5) 0.05823(17) 0.0672(12) Uani 1 1 d U . .
H3 H 0.7204 0.3488 0.0465 0.081 Uiso 1 1 calc R . .
C5 C 0.7430(2) 0.4477(5) 0.10634(16) 0.0625(11) Uani 1 1 d U . .
H2 H 0.7276 0.3830 0.1266 0.075 Uiso 1 1 calc R . .
C11' C 0.8816(3) 0.6769(6) -0.1090(2) 0.0838(15) Uani 1 1 d U . .
H8' H 0.8629 0.6936 -0.1389 0.101 Uiso 1 1 calc R . .
C12' C 0.8903(3) 0.7848(5) -0.0773(2) 0.0844(15) Uani 1 1 d U . .
H7' H 0.8786 0.8714 -0.0865 0.101 Uiso 1 1 calc R . .
C8' C 0.9163(2) 0.7624(5) -0.03249(19) 0.0701(12) Uani 1 1 d U . .
C7' C 0.9256(2) 0.8657(6) 0.0062(2) 0.0814(14) Uani 1 1 d U . .
H6' H 0.9422 0.8361 0.0354 0.098 Uiso 1 1 calc R . .
C6' C 0.9131(2) 0.9876(6) 0.0025(2) 0.0804(14) Uani 1 1 d U . .
H5' H 0.8980 1.0173 -0.0272 0.096 Uiso 1 1 calc R . .
C3' C 0.9199(2) 1.0894(5) 0.04059(16) 0.0633(11) Uani 1 1 d U . .
C4' C 0.9019(3) 1.2185(5) 0.03000(19) 0.0755(13) Uani 1 1 d U . .
H3' H 0.8870 1.2401 -0.0006 0.091 Uiso 1 1 calc R . .
C5' C 0.9058(3) 1.3150(5) 0.0644(2) 0.0858(15) Uani 1 1 d U . .
H4' H 0.8927 1.4014 0.0562 0.103 Uiso 1 1 calc R . .
N1' N 0.9271(3) 1.2939(5) 0.10871(18) 0.0925(14) Uani 1 1 d U . .
C10' C 0.9239(2) 0.5342(5) -0.0555(2) 0.0766(13) Uani 1 1 d U . .
H9' H 0.9364 0.4476 -0.0471 0.092 Uiso 1 1 calc R . .
C9' C 0.9329(2) 0.6333(6) -0.02252(19) 0.0772(13) Uani 1 1 d U . .
H10' H 0.9507 0.6124 0.0073 0.093 Uiso 1 1 calc R . .
C2' C 0.9414(3) 1.0674(6) 0.0866(2) 0.0935(17) Uani 1 1 d U . .
H2' H 0.9540 0.9817 0.0960 0.112 Uiso 1 1 calc R . .
C1' C 0.9442(4) 1.1707(7) 0.1182(2) 0.108(2) Uani 1 1 d U . .
H1' H 0.9595 1.1521 0.1490 0.130 Uiso 1 1 calc R . .
C1S C 0.0494(5) 0.2447(12) 0.2353(5) 0.185(4) Uani 1 1 d U . .
H1S1 H 0.0555 0.2191 0.2025 0.222 Uiso 1 1 calc R . .
H1S2 H 0.0853 0.2130 0.2539 0.222 Uiso 1 1 calc R . .
C2S C 0.0497(8) 0.3808(14) 0.2372(6) 0.235(5) Uani 1 1 d U . .
H2S1 H 0.0838 0.4063 0.2589 0.282 Uiso 1 1 calc R . .
H2S2 H 0.0602 0.4125 0.2059 0.282 Uiso 1 1 calc R . .
H14 H 1.129(3) 0.675(6) 0.186(2) 0.10(2) Uiso 1 1 d . . .
H13 H 1.1155(19) 0.610(5) 0.1403(15) 0.054(12) Uiso 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 O1 1.423(3) . ?
S1 O2 1.430(3) . ?
S1 N3 1.581(4) . ?
S1 C14 1.769(4) . ?
C10 C7 1.505(6) . ?
C10 H5 0.9600 . ?
C10 H4 0.9600 . ?
C10 H6 0.9600 . ?
O2S C2S 1.344(15) 2 ?
O2S C2S 1.344(15) . ?
F3 C17 1.263(8) . ?
N3 H14 0.89(6) . ?
N3 H13 0.93(5) . ?
N1 C1 1.328(5) . ?
N1 N2 1.351(5) . ?
C1 C2 1.391(6) . ?
C1 C17 1.450(8) . ?
F2 C17 1.184(8) . ?
N2' C10' 1.316(6) . ?
N2' C11' 1.318(7) . ?
C14 C13 1.379(5) . ?
C14 C15 1.393(5) . ?
C13 C12 1.388(5) . ?
C13 H11 0.9300 . ?
C12 C11 1.375(5) . ?
C12 H12 0.9300 . ?
C11 C16 1.378(5) . ?
C11 N2 1.437(5) . ?
N2 C3 1.370(5) . ?
O1S C1S 1.341(10) 2 ?
O1S C1S 1.341(10) . ?
C3 C2 1.373(6) . ?
C3 C4 1.458(6) . ?
C4 C9 1.387(6) . ?
C4 C5 1.394(6) . ?
C9 C8 1.378(6) . ?
C9 H8 0.9300 . ?
C8 C7 1.378(6) . ?
C8 H7 0.9300 . ?
C7 C6 1.393(7) . ?
C16 C15 1.375(5) . ?
C16 H9 0.9300 . ?
C15 H10 0.9300 . ?
C17 F1 1.384(13) . ?
C2 H1 0.9300 . ?
C6 C5 1.365(6) . ?
C6 H3 0.9300 . ?
C5 H2 0.9300 . ?
C11' C12' 1.403(7) . ?
C11' H8' 0.9300 . ?
C12' C8' 1.373(8) . ?
C12' H7' 0.9300 . ?
C8' C9' 1.358(7) . ?
C8' C7' 1.502(7) . ?
C7' C6' 1.245(7) . ?
C7' H6' 0.9300 . ?
C6' C3' 1.476(7) . ?
C6' H5' 0.9300 . ?
C3' C4' 1.370(7) . ?
C3' C2' 1.371(7) . ?
C4' C5' 1.360(7) . ?
C4' H3' 0.9300 . ?
C5' N1' 1.326(7) . ?
C5' H4' 0.9300 . ?
N1' C1' 1.304(8) . ?
C10' C9' 1.359(7) . ?
C10' H9' 0.9300 . ?
C9' H10' 0.9300 . ?
C2' C1' 1.357(8) . ?
C2' H2' 0.9300 . ?
C1' H1' 0.9300 . ?
C1S C2S 1.353(17) . ?
C1S H1S1 0.9700 . ?
C1S H1S2 0.9700 . ?
C2S H2S1 0.9700 . ?
C2S H2S2 0.9700 . ?

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
O1 S1 O2 120.0(2) . . ?
O1 S1 N3 108.1(2) . . ?
O2 S1 N3 105.9(2) . . ?
O1 S1 C14 107.24(18) . . ?
O2 S1 C14 106.24(18) . . ?
N3 S1 C14 109.04(19) . . ?
C7 C10 H5 109.5 . . ?
C7 C10 H4 109.5 . . ?
H5 C10 H4 109.5 . . ?
C7 C10 H6 109.5 . . ?
H5 C10 H6 109.5 . . ?
H4 C10 H6 109.5 . . ?
C2S O2S C2S 117.0(14) 2 . ?
S1 N3 H14 121(4) . . ?
S1 N3 H13 118(3) . . ?
H14 N3 H13 106(5) . . ?
C1 N1 N2 104.0(3) . . ?
N1 C1 C2 112.2(4) . . ?
N1 C1 C17 120.0(5) . . ?
C2 C1 C17 127.7(5) . . ?
C10' N2' C11' 116.2(4) . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 S1 120.6(3) . . ?
C15 C14 S1 118.9(3) . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H11 120.3 . . ?
C12 C13 H11 120.3 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C11 C16 121.1(3) . . ?
C12 C11 N2 119.1(3) . . ?
C16 C11 N2 119.8(3) . . ?
N1 N2 C3 112.7(3) . . ?
N1 N2 C11 118.2(3) . . ?
C3 N2 C11 129.1(3) . . ?
C1S O1S C1S 119.5(12) 2 . ?
N2 C3 C2 105.4(4) . . ?
N2 C3 C4 126.1(4) . . ?
C2 C3 C4 128.6(4) . . ?
C9 C4 C5 117.5(4) . . ?
C9 C4 C3 123.4(4) . . ?
C5 C4 C3 119.1(4) . . ?
C8 C9 C4 120.8(4) . . ?
C8 C9 H8 119.6 . . ?
C4 C9 H8 119.6 . . ?
C7 C8 C9 122.0(4) . . ?
C7 C8 H7 119.0 . . ?
C9 C8 H7 119.0 . . ?
C8 C7 C6 116.9(4) . . ?
C8 C7 C10 121.4(5) . . ?
C6 C7 C10 121.7(4) . . ?
C15 C16 C11 119.6(4) . . ?
C15 C16 H9 120.2 . . ?
C11 C16 H9 120.2 . . ?
C16 C15 C14 119.7(4) . . ?
C16 C15 H10 120.2 . . ?
C14 C15 H10 120.2 . . ?
F2 C17 F3 113.7(8) . . ?
F2 C17 F1 95.8(8) . . ?
F3 C17 F1 97.7(7) . . ?
F2 C17 C1 120.7(6) . . ?
F3 C17 C1 116.2(6) . . ?
F1 C17 C1 107.0(9) . . ?
C3 C2 C1 105.7(4) . . ?
C3 C2 H1 127.2 . . ?
C1 C2 H1 127.2 . . ?
C5 C6 C7 121.8(4) . . ?
C5 C6 H3 119.1 . . ?
C7 C6 H3 119.1 . . ?
C6 C5 C4 121.1(4) . . ?
C6 C5 H2 119.5 . . ?
C4 C5 H2 119.5 . . ?
N2' C11' C12' 122.8(5) . . ?
N2' C11' H8' 118.6 . . ?
C12' C11' H8' 118.6 . . ?
C8' C12' C11' 119.8(5) . . ?
C8' C12' H7' 120.1 . . ?
C11' C12' H7' 120.1 . . ?
C9' C8' C12' 115.9(5) . . ?
C9' C8' C7' 118.0(5) . . ?
C12' C8' C7' 126.0(5) . . ?
C6' C7' C8' 125.6(6) . . ?
C6' C7' H6' 117.2 . . ?
C8' C7' H6' 117.2 . . ?
C7' C6' C3' 126.2(6) . . ?
C7' C6' H5' 116.9 . . ?
C3' C6' H5' 116.9 . . ?
C4' C3' C2' 115.9(4) . . ?
C4' C3' C6' 117.7(5) . . ?
C2' C3' C6' 126.4(5) . . ?
C5' C4' C3' 119.8(5) . . ?
C5' C4' H3' 120.1 . . ?
C3' C4' H3' 120.1 . . ?
N1' C5' C4' 124.3(5) . . ?
N1' C5' H4' 117.8 . . ?
C4' C5' H4' 117.8 . . ?
C1' N1' C5' 115.2(5) . . ?
N2' C10' C9' 124.3(5) . . ?
N2' C10' H9' 117.8 . . ?
C9' C10' H9' 117.8 . . ?
C8' C9' C10' 120.9(5) . . ?
C8' C9' H10' 119.5 . . ?
C10' C9' H10' 119.5 . . ?
C1' C2' C3' 120.0(5) . . ?
C1' C2' H2' 120.0 . . ?
C3' C2' H2' 120.0 . . ?
N1' C1' C2' 124.8(6) . . ?
N1' C1' H1' 117.6 . . ?
C2' C1' H1' 117.6 . . ?
O1S C1S C2S 119.7(12) . . ?
O1S C1S H1S1 107.4 . . ?
C2S C1S H1S1 107.4 . . ?
O1S C1S H1S2 107.4 . . ?
C2S C1S H1S2 107.4 . . ?
H1S1 C1S H1S2 106.9 . . ?
O2S C2S C1S 122.0(14) . . ?
O2S C2S H2S1 106.8 . . ?
C1S C2S H2S1 106.8 . . ?
O2S C2S H2S2 106.8 . . ?
C1S C2S H2S2 106.8 . . ?
H2S1 C2S H2S2 106.7 . . ?

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
N2 N1 C1 C2 -0.4(6) . . . . ?
N2 N1 C1 C17 -176.2(7) . . . . ?
O1 S1 C14 C13 3.9(4) . . . . ?
O2 S1 C14 C13 -125.5(3) . . . . ?
N3 S1 C14 C13 120.8(3) . . . . ?
O1 S1 C14 C15 -177.4(3) . . . . ?
O2 S1 C14 C15 53.2(4) . . . . ?
N3 S1 C14 C15 -60.5(4) . . . . ?
C15 C14 C13 C12 -1.4(6) . . . . ?
S1 C14 C13 C12 177.3(3) . . . . ?
C14 C13 C12 C11 -0.6(6) . . . . ?
C13 C12 C11 C16 2.8(6) . . . . ?
C13 C12 C11 N2 -179.8(3) . . . . ?
C1 N1 N2 C3 0.4(5) . . . . ?
C1 N1 N2 C11 -177.5(4) . . . . ?
C12 C11 N2 N1 -44.0(5) . . . . ?
C16 C11 N2 N1 133.4(4) . . . . ?
C12 C11 N2 C3 138.5(4) . . . . ?
C16 C11 N2 C3 -44.1(6) . . . . ?
N1 N2 C3 C2 -0.3(5) . . . . ?
C11 N2 C3 C2 177.3(4) . . . . ?
N1 N2 C3 C4 178.8(4) . . . . ?
C11 N2 C3 C4 -3.5(7) . . . . ?
N2 C3 C4 C9 -43.1(6) . . . . ?
C2 C3 C4 C9 135.8(5) . . . . ?
N2 C3 C4 C5 139.6(4) . . . . ?
C2 C3 C4 C5 -41.5(7) . . . . ?
C5 C4 C9 C8 -1.3(6) . . . . ?
C3 C4 C9 C8 -178.7(4) . . . . ?
C4 C9 C8 C7 0.5(7) . . . . ?
C9 C8 C7 C6 0.9(7) . . . . ?
C9 C8 C7 C10 -179.5(4) . . . . ?
C12 C11 C16 C15 -3.1(6) . . . . ?
N2 C11 C16 C15 179.5(4) . . . . ?
C11 C16 C15 C14 1.1(6) . . . . ?
C13 C14 C15 C16 1.1(6) . . . . ?
S1 C14 C15 C16 -177.6(3) . . . . ?
N1 C1 C17 F2 25.2(15) . . . . ?
C2 C1 C17 F2 -149.9(9) . . . . ?
N1 C1 C17 F3 169.5(8) . . . . ?
C2 C1 C17 F3 -5.5(15) . . . . ?
N1 C1 C17 F1 -82.6(8) . . . . ?
C2 C1 C17 F1 102.3(8) . . . . ?
N2 C3 C2 C1 0.0(5) . . . . ?
C4 C3 C2 C1 -179.1(4) . . . . ?
N1 C1 C2 C3 0.3(6) . . . . ?
C17 C1 C2 C3 175.6(8) . . . . ?
C8 C7 C6 C5 -1.3(7) . . . . ?
C10 C7 C6 C5 179.0(4) . . . . ?
C7 C6 C5 C4 0.5(7) . . . . ?
C9 C4 C5 C6 0.9(6) . . . . ?
C3 C4 C5 C6 178.3(4) . . . . ?
C10' N2' C11' C12' 1.1(8) . . . . ?
N2' C11' C12' C8' -1.7(9) . . . . ?
C11' C12' C8' C9' 1.1(8) . . . . ?
C11' C12' C8' C7' -176.7(5) . . . . ?
C9' C8' C7' C6' 179.6(6) . . . . ?
C12' C8' C7' C6' -2.7(9) . . . . ?
C8' C7' C6' C3' 177.7(4) . . . . ?
C7' C6' C3' C4' -178.1(6) . . . . ?
C7' C6' C3' C2' 0.2(9) . . . . ?
C2' C3' C4' C5' -0.2(8) . . . . ?
C6' C3' C4' C5' 178.3(5) . . . . ?
C3' C4' C5' N1' 0.8(9) . . . . ?
C4' C5' N1' C1' -0.7(10) . . . . ?
C11' N2' C10' C9' 0.0(8) . . . . ?
C12' C8' C9' C10' 0.0(8) . . . . ?
C7' C8' C9' C10' 178.0(5) . . . . ?
N2' C10' C9' C8' -0.6(8) . . . . ?
C4' C3' C2' C1' -0.6(9) . . . . ?
C6' C3' C2' C1' -178.9(6) . . . . ?
C5' N1' C1' C2' -0.1(12) . . . . ?
C3' C2' C1' N1' 0.8(12) . . . . ?
C1S O1S C1S C2S 2.6(12) 2 . . . ?
C2S O2S C2S C1S 2.6(12) 2 . . . ?
O1S C1S C2S O2S -5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.023
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.066
_database_code_depnum_ccdc_archive 'CCDC 1010383'
