# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


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#                 Cambridge Crystallographic Data Centre
#                                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. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
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#  except for the purpose of generating routine backup copies 
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data_Compd2a
_database_code_depnum_ccdc_archive 'CCDC 883533'
#TrackingRef 'web_deposit_cif_file_0_Yih-ChernHorng_1341977221.Crystal Structures_revised.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H42 F9 N3 O9 S3'
_chemical_formula_weight         927.94

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   P2(1)/m


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

_cell_length_a                   9.8069(12)
_cell_length_b                   20.416(2)
_cell_length_c                   10.8597(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.450(5)
_cell_angle_gamma                90.00
_cell_volume                     2138.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7726
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.10

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1098
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  'Bruker SMART APEXII'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32985
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         28.74
_reflns_number_total             5678
_reflns_number_gt                4399
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 2006)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1000P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5678
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1438
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_restrained_S_all      0.901
_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 0.08885(7) 0.7500 0.47744(5) 0.02226(15) Uani 1 2 d S . .
S2 S 0.26576(4) 0.56597(2) 0.12432(4) 0.02230(12) Uani 1 1 d . . .
C4 C 0.9828(2) 0.7500 -0.0374(2) 0.0188(4) Uani 1 2 d S . .
C3 C 0.93518(17) 0.69011(8) 0.00314(15) 0.0184(3) Uani 1 1 d . . .
C1 C 0.8127(2) 0.7500 0.1446(2) 0.0184(4) Uani 1 2 d S . .
C2 C 0.85098(17) 0.69047(8) 0.09479(15) 0.0190(3) Uani 1 1 d . . .
C17 C 1.3425(3) 0.7500 -0.1212(2) 0.0240(5) Uani 1 2 d S . .
C10 C 0.86781(18) 0.54794(8) 0.32331(15) 0.0211(3) Uani 1 1 d . . .
C9 C 0.80499(18) 0.62650(8) 0.14471(15) 0.0211(3) Uani 1 1 d . . .
H9A H 0.7896 0.5934 0.0769 0.025 Uiso 1 1 calc R . .
H9B H 0.7164 0.6331 0.1747 0.025 Uiso 1 1 calc R . .
C7 C 0.96250(19) 0.62681(8) -0.06213(16) 0.0223(3) Uani 1 1 d . . .
H7A H 0.9565 0.5892 -0.0059 0.027 Uiso 1 1 calc R . .
H7B H 1.0570 0.6277 -0.0821 0.027 Uiso 1 1 calc R . .
C16 C 1.0881(3) 0.7500 -0.1230(2) 0.0209(5) Uani 1 2 d S . .
H16A H 1.0752 0.7893 -0.1773 0.025 Uiso 0.50 1 calc PR . .
H16B H 1.0752 0.7107 -0.1773 0.025 Uiso 0.50 1 calc PR . .
C5 C 0.7226(3) 0.7500 0.2450(2) 0.0233(5) Uani 1 2 d S . .
H5B H 0.7446 0.7892 0.2986 0.028 Uiso 0.50 1 calc PR . .
H5A H 0.7446 0.7108 0.2986 0.028 Uiso 0.50 1 calc PR . .
C18 C 1.3894(2) 0.69082(10) -0.15938(19) 0.0330(4) Uani 1 1 d . . .
H18 H 1.3568 0.6506 -0.1315 0.040 Uiso 1 1 calc R . .
C8 C 0.8558(2) 0.61881(10) -0.18267(19) 0.0322(4) Uani 1 1 d . . .
H8A H 0.7623 0.6181 -0.1626 0.048 Uiso 1 1 calc R . .
H8C H 0.8730 0.5776 -0.2237 0.048 Uiso 1 1 calc R . .
H8B H 0.8636 0.6556 -0.2390 0.048 Uiso 1 1 calc R . .
C11 C 0.8685(2) 0.48497(9) 0.27781(18) 0.0310(4) Uani 1 1 d . . .
H11 H 0.8980 0.4764 0.2008 0.037 Uiso 1 1 calc R . .
C12 C 0.8251(3) 0.43425(9) 0.3470(2) 0.0388(5) Uani 1 1 d . . .
H12 H 0.8263 0.3904 0.3179 0.047 Uiso 1 1 calc R . .
C15 C 0.8241(2) 0.56222(9) 0.43355(17) 0.0309(4) Uani 1 1 d . . .
H15 H 0.8241 0.6060 0.4630 0.037 Uiso 1 1 calc R . .
C6 C 0.5672(3) 0.7500 0.1890(3) 0.0318(6) Uani 1 2 d S . .
H6A H 0.5456 0.7123 0.1331 0.048 Uiso 0.50 1 calc PR . .
H6B H 0.5434 0.7905 0.1416 0.048 Uiso 0.50 1 calc PR . .
H6C H 0.5135 0.7472 0.2566 0.048 Uiso 0.50 1 calc PR . .
C13 C 0.7804(2) 0.44741(10) 0.4574(2) 0.0384(5) Uani 1 1 d . . .
H13 H 0.7499 0.4127 0.5039 0.046 Uiso 1 1 calc R . .
C14 C 0.7797(3) 0.51092(11) 0.5009(2) 0.0398(5) Uani 1 1 d . . .
H14 H 0.7487 0.5197 0.5773 0.048 Uiso 1 1 calc R . .
C19 C 1.4854(3) 0.69138(14) -0.2397(2) 0.0480(6) Uani 1 1 d . . .
H19 H 1.5189 0.6513 -0.2672 0.058 Uiso 1 1 calc R . .
C20 C 1.5315(4) 0.7500 -0.2790(4) 0.0548(10) Uani 1 2 d S . .
H20 H 1.5963 0.7500 -0.3342 0.066 Uiso 1 2 calc SR . .
N2 N 1.2339(2) 0.7500 -0.04438(19) 0.0212(4) Uani 1 2 d S . .
H2A H 1.2444 0.7864 0.0064 0.025 Uiso 0.50 1 calc PR . .
H2B H 1.2444 0.7136 0.0064 0.025 Uiso 0.50 1 calc PR . .
N1 N 0.91533(15) 0.60204(7) 0.25198(13) 0.0203(3) Uani 1 1 d . . .
H1A H 0.9912 0.5882 0.2201 0.024 Uiso 1 1 calc R . .
H1B H 0.9432 0.6363 0.3056 0.024 Uiso 1 1 calc R . .
O2 O 0.17315(15) 0.56086(8) 0.21259(14) 0.0391(4) Uani 1 1 d . . .
O3 O 0.29059(17) 0.63204(7) 0.08838(16) 0.0437(4) Uani 1 1 d . . .
O1 O 0.24150(17) 0.51962(8) 0.02472(14) 0.0429(4) Uani 1 1 d . . .
C21 C 0.4332(2) 0.54198(10) 0.2162(2) 0.0334(4) Uani 1 1 d . . .
F2 F 0.42815(14) 0.48206(6) 0.26213(15) 0.0503(4) Uani 1 1 d . . .
F1 F 0.53021(14) 0.54260(9) 0.14624(16) 0.0607(4) Uani 1 1 d . . .
F3 F 0.47245(18) 0.58217(8) 0.31073(16) 0.0684(5) Uani 1 1 d . . .
O4 O 0.01392(17) 0.69077(7) 0.43681(15) 0.0384(4) Uani 1 1 d . . .
O5 O 0.1559(2) 0.7500 0.60533(18) 0.0403(5) Uani 1 2 d S . .
C22 C 0.2287(3) 0.7500 0.3875(3) 0.0316(6) Uani 1 2 d S . .
F5 F 0.30985(16) 0.69789(6) 0.41270(16) 0.0544(4) Uani 1 1 d . . .
F4 F 0.1778(3) 0.7500 0.26519(19) 0.0660(7) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0273(3) 0.0192(3) 0.0186(3) 0.000 -0.0004(2) 0.000
S2 0.0219(2) 0.0211(2) 0.0233(2) 0.00333(15) 0.00249(16) 0.00087(15)
C4 0.0188(11) 0.0204(10) 0.0162(10) 0.000 0.0009(8) 0.000
C3 0.0186(8) 0.0175(7) 0.0178(7) 0.0002(6) -0.0002(6) 0.0010(6)
C1 0.0162(10) 0.0199(10) 0.0183(10) 0.000 0.0006(8) 0.000
C2 0.0196(8) 0.0175(7) 0.0183(7) 0.0018(6) -0.0006(6) -0.0011(6)
C17 0.0190(11) 0.0306(12) 0.0217(11) 0.000 0.0020(9) 0.000
C10 0.0218(8) 0.0199(7) 0.0205(8) 0.0050(6) 0.0006(6) -0.0010(6)
C9 0.0217(8) 0.0186(7) 0.0221(8) 0.0032(6) 0.0019(6) -0.0011(6)
C7 0.0265(9) 0.0171(7) 0.0228(8) -0.0025(6) 0.0030(7) 0.0018(6)
C16 0.0220(11) 0.0211(11) 0.0189(10) 0.000 0.0021(9) 0.000
C5 0.0235(12) 0.0241(11) 0.0234(11) 0.000 0.0074(9) 0.000
C18 0.0290(10) 0.0365(10) 0.0332(10) -0.0013(8) 0.0052(8) 0.0081(8)
C8 0.0342(10) 0.0264(9) 0.0325(10) -0.0098(7) -0.0030(8) 0.0000(8)
C11 0.0406(11) 0.0225(9) 0.0293(9) 0.0011(7) 0.0045(8) 0.0023(8)
C12 0.0523(13) 0.0175(9) 0.0430(12) 0.0043(8) -0.0003(10) -0.0026(8)
C15 0.0429(11) 0.0269(9) 0.0252(9) -0.0021(7) 0.0120(8) -0.0078(8)
C6 0.0206(12) 0.0389(15) 0.0364(14) 0.000 0.0070(11) 0.000
C13 0.0448(12) 0.0319(10) 0.0355(11) 0.0155(8) -0.0009(9) -0.0106(9)
C14 0.0515(13) 0.0421(11) 0.0277(10) 0.0065(8) 0.0123(9) -0.0117(10)
C19 0.0338(12) 0.0638(16) 0.0481(14) -0.0068(11) 0.0122(10) 0.0166(11)
C20 0.0302(17) 0.089(3) 0.050(2) 0.000 0.0192(15) 0.000
N2 0.0245(10) 0.0181(9) 0.0204(9) 0.000 0.0024(8) 0.000
N1 0.0215(7) 0.0187(6) 0.0207(6) 0.0022(5) 0.0036(5) -0.0011(5)
O2 0.0289(7) 0.0567(10) 0.0341(8) 0.0149(7) 0.0124(6) 0.0150(7)
O3 0.0387(8) 0.0285(7) 0.0580(10) 0.0190(7) -0.0066(7) -0.0051(6)
O1 0.0437(9) 0.0444(9) 0.0369(8) -0.0142(7) -0.0028(7) 0.0057(7)
C21 0.0245(9) 0.0285(9) 0.0447(11) 0.0050(8) -0.0006(8) -0.0010(7)
F2 0.0337(7) 0.0385(7) 0.0745(10) 0.0260(7) -0.0012(7) 0.0065(5)
F1 0.0240(7) 0.0770(11) 0.0837(12) 0.0203(9) 0.0172(7) 0.0013(7)
F3 0.0610(10) 0.0606(10) 0.0666(10) -0.0171(8) -0.0337(8) 0.0104(8)
O4 0.0424(9) 0.0279(7) 0.0443(9) -0.0076(6) 0.0061(7) -0.0101(6)
O5 0.0400(12) 0.0601(14) 0.0181(9) 0.000 -0.0018(8) 0.000
C22 0.0408(16) 0.0222(12) 0.0329(14) 0.000 0.0096(12) 0.000
F5 0.0537(9) 0.0333(7) 0.0841(11) 0.0074(7) 0.0334(8) 0.0132(6)
F4 0.0721(16) 0.1012(19) 0.0284(10) 0.000 0.0185(10) 0.000

_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 O5 1.425(2) . ?
S1 O4 1.4420(14) . ?
S1 O4 1.4421(14) 4_575 ?
S1 C22 1.822(3) . ?
S2 O1 1.4243(15) . ?
S2 O3 1.4371(14) . ?
S2 O2 1.4390(15) . ?
S2 C21 1.827(2) . ?
C4 C3 1.4076(19) . ?
C4 C3 1.4076(19) 4_575 ?
C4 C16 1.510(3) . ?
C3 C2 1.404(2) . ?
C3 C7 1.521(2) . ?
C1 C2 1.408(2) 4_575 ?
C1 C2 1.408(2) . ?
C1 C5 1.523(3) . ?
C2 C9 1.514(2) . ?
C17 C18 1.383(2) 4_575 ?
C17 C18 1.383(2) . ?
C17 N2 1.467(3) . ?
C10 C15 1.374(2) . ?
C10 C11 1.378(2) . ?
C10 N1 1.473(2) . ?
C9 N1 1.523(2) . ?
C7 C8 1.529(2) . ?
C16 N2 1.527(3) . ?
C5 C6 1.535(4) . ?
C18 C19 1.395(3) . ?
C11 C12 1.391(3) . ?
C12 C13 1.376(3) . ?
C15 C14 1.392(3) . ?
C13 C14 1.381(3) . ?
C19 C20 1.374(3) . ?
C20 C19 1.374(3) 4_575 ?
C21 F3 1.316(3) . ?
C21 F1 1.321(3) . ?
C21 F2 1.325(2) . ?
C22 F5 1.327(2) . ?
C22 F5 1.327(2) 4_575 ?
C22 F4 1.331(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
O5 S1 O4 114.69(8) . . ?
O5 S1 O4 114.69(8) . 4_575 ?
O4 S1 O4 113.98(14) . 4_575 ?
O5 S1 C22 105.28(14) . . ?
O4 S1 C22 103.13(8) . . ?
O4 S1 C22 103.13(9) 4_575 . ?
O1 S2 O3 115.50(10) . . ?
O1 S2 O2 114.77(10) . . ?
O3 S2 O2 114.05(10) . . ?
O1 S2 C21 104.27(10) . . ?
O3 S2 C21 102.72(9) . . ?
O2 S2 C21 103.30(9) . . ?
C3 C4 C3 120.6(2) . 4_575 ?
C3 C4 C16 119.69(11) . . ?
C3 C4 C16 119.69(11) 4_575 . ?
C2 C3 C4 119.23(15) . . ?
C2 C3 C7 120.72(14) . . ?
C4 C3 C7 119.73(15) . . ?
C2 C1 C2 119.3(2) 4_575 . ?
C2 C1 C5 120.30(11) 4_575 . ?
C2 C1 C5 120.29(11) . . ?
C3 C2 C1 120.57(15) . . ?
C3 C2 C9 120.07(14) . . ?
C1 C2 C9 119.31(16) . . ?
C18 C17 C18 121.8(3) 4_575 . ?
C18 C17 N2 119.04(13) 4_575 . ?
C18 C17 N2 119.04(13) . . ?
C15 C10 C11 122.21(17) . . ?
C15 C10 N1 118.54(15) . . ?
C11 C10 N1 119.25(16) . . ?
C2 C9 N1 109.89(13) . . ?
C3 C7 C8 109.79(14) . . ?
C4 C16 N2 109.34(18) . . ?
C1 C5 C6 112.3(2) . . ?
C17 C18 C19 118.6(2) . . ?
C10 C11 C12 118.63(19) . . ?
C13 C12 C11 120.17(19) . . ?
C10 C15 C14 118.36(18) . . ?
C12 C13 C14 120.27(18) . . ?
C13 C14 C15 120.4(2) . . ?
C20 C19 C18 119.9(2) . . ?
C19 C20 C19 121.1(3) 4_575 . ?
C17 N2 C16 112.62(18) . . ?
C10 N1 C9 113.55(13) . . ?
F3 C21 F1 107.68(18) . . ?
F3 C21 F2 107.92(19) . . ?
F1 C21 F2 107.78(18) . . ?
F3 C21 S2 111.44(15) . . ?
F1 C21 S2 110.66(15) . . ?
F2 C21 S2 111.19(14) . . ?
F5 C22 F5 106.5(3) . 4_575 ?
F5 C22 F4 107.95(17) . . ?
F5 C22 F4 107.95(17) 4_575 . ?
F5 C22 S1 111.77(14) . . ?
F5 C22 S1 111.77(14) 4_575 . ?
F4 C22 S1 110.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.74
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.067