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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  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_oa166

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H7 F3 O4 S'
_chemical_formula_weight         328.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

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'

_cell_length_a                   13.4040(4)
_cell_length_b                   25.1954(6)
_cell_length_c                   12.1027(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.642(3)
_cell_angle_gamma                90.00
_cell_volume                     4003.2(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5372
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      25.6

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1992
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9169
_exptl_absorpt_correction_T_max  0.9797
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            16213
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         25.70
_reflns_number_total             6944
_reflns_number_gt                5682
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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 > 2σ(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)+(0.0328P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00033(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_number_reflns         6944
_refine_ls_number_parameters     596
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
C1 C -0.0105(3) 0.05907(17) -0.1183(5) 0.0683(14) Uani 1 1 d . . .
C3 C 0.2291(2) 0.12140(12) -0.0148(3) 0.0283(7) Uani 1 1 d . . .
C4 C 0.1836(2) 0.16814(13) -0.0636(3) 0.0328(8) Uani 1 1 d . . .
H4 H 0.1232 0.1667 -0.1201 0.039 Uiso 1 1 calc R . .
C5 C 0.2272(2) 0.21580(13) -0.0290(3) 0.0310(8) Uani 1 1 d . . .
H5 H 0.1954 0.2477 -0.0600 0.037 Uiso 1 1 calc R . .
C6 C 0.3186(2) 0.21855(12) 0.0518(3) 0.0281(7) Uani 1 1 d . . .
C7 C 0.3667(3) 0.26782(13) 0.0857(3) 0.0338(8) Uani 1 1 d . . .
H7 H 0.3357 0.3000 0.0553 0.041 Uiso 1 1 calc R . .
C8 C 0.4572(3) 0.26945(14) 0.1617(3) 0.0373(8) Uani 1 1 d . . .
H8 H 0.4888 0.3026 0.1836 0.045 Uiso 1 1 calc R . .
C9 C 0.5031(3) 0.22253(13) 0.2072(3) 0.0349(8) Uani 1 1 d . . .
H9 H 0.5667 0.2243 0.2588 0.042 Uiso 1 1 calc R . .
C10 C 0.4586(2) 0.17344(13) 0.1792(3) 0.0302(8) Uani 1 1 d . . .
C11 C 0.3642(2) 0.17084(11) 0.0996(3) 0.0259(7) Uani 1 1 d . . .
C12 C 0.3167(2) 0.12089(12) 0.0680(3) 0.0259(7) Uani 1 1 d . . .
C13 C 0.3621(2) 0.07179(13) 0.1244(3) 0.0317(8) Uani 1 1 d . . .
C14 C 0.4600(2) 0.07758(13) 0.2014(3) 0.0326(8) Uani 1 1 d . . .
H14 H 0.4939 0.0465 0.2342 0.039 Uiso 1 1 calc R . .
C15 C 0.5045(2) 0.12463(13) 0.2282(3) 0.0324(8) Uani 1 1 d . . .
H15 H 0.5677 0.1261 0.2806 0.039 Uiso 1 1 calc R . .
C16 C 0.8843(3) 0.10785(14) 0.3247(4) 0.0510(11) Uani 1 1 d . . .
C18 C 0.9140(2) 0.24613(12) 0.2796(3) 0.0293(7) Uani 1 1 d . . .
C19 C 1.0027(2) 0.24643(13) 0.3637(3) 0.0321(8) Uani 1 1 d . . .
H19 H 1.0378 0.2142 0.3865 0.039 Uiso 1 1 calc R . .
C20 C 1.0383(2) 0.29345(13) 0.4126(3) 0.0333(8) Uani 1 1 d . . .
H20 H 1.0985 0.2937 0.4697 0.040 Uiso 1 1 calc R . .
C21 C 0.9877(2) 0.34137(12) 0.3803(3) 0.0286(7) Uani 1 1 d . . .
C22 C 1.0254(3) 0.39110(14) 0.4253(3) 0.0385(9) Uani 1 1 d . . .
H22 H 1.0866 0.3924 0.4809 0.046 Uiso 1 1 calc R . .
C23 C 0.9752(3) 0.43705(14) 0.3900(3) 0.0418(9) Uani 1 1 d . . .
H23 H 1.0018 0.4701 0.4206 0.050 Uiso 1 1 calc R . .
C24 C 0.8850(3) 0.43569(13) 0.3091(3) 0.0380(9) Uani 1 1 d . . .
H24 H 0.8510 0.4681 0.2852 0.046 Uiso 1 1 calc R . .
C25 C 0.8440(2) 0.38883(12) 0.2632(3) 0.0308(7) Uani 1 1 d . . .
C26 C 0.8955(2) 0.34018(12) 0.2963(3) 0.0273(7) Uani 1 1 d . . .
C27 C 0.8574(2) 0.29124(12) 0.2459(3) 0.0260(7) Uani 1 1 d . . .
C28 C 0.7608(2) 0.29107(14) 0.1589(3) 0.0329(8) Uani 1 1 d . . .
C29 C 0.7131(3) 0.34243(14) 0.1295(3) 0.0361(8) Uani 1 1 d . . .
H29 H 0.6522 0.3438 0.0736 0.043 Uiso 1 1 calc R . .
C30 C 0.7512(2) 0.38797(14) 0.1779(3) 0.0359(8) Uani 1 1 d . . .
H30 H 0.7167 0.4203 0.1556 0.043 Uiso 1 1 calc R . .
C31 C 0.2042(3) 0.45990(18) 0.1433(5) 0.0646(13) Uani 1 1 d . . .
C33 C -0.0194(2) 0.38431(13) 0.0556(3) 0.0290(7) Uani 1 1 d . . .
C34 C -0.0724(2) 0.43105(13) 0.0258(3) 0.0322(8) Uani 1 1 d . . .
H34 H -0.0484 0.4636 0.0608 0.039 Uiso 1 1 calc R . .
C35 C -0.1606(2) 0.42952(13) -0.0557(3) 0.0326(8) Uani 1 1 d . . .
H35 H -0.1973 0.4614 -0.0772 0.039 Uiso 1 1 calc R . .
C36 C -0.1971(2) 0.38139(13) -0.1074(3) 0.0291(7) Uani 1 1 d . . .
C37 C -0.2882(2) 0.37899(14) -0.1895(3) 0.0348(8) Uani 1 1 d . . .
H37 H -0.3254 0.4106 -0.2119 0.042 Uiso 1 1 calc R . .
C38 C -0.3233(2) 0.33174(15) -0.2371(3) 0.0393(9) Uani 1 1 d . . .
H38 H -0.3840 0.3308 -0.2933 0.047 Uiso 1 1 calc R . .
C39 C -0.2703(2) 0.28454(14) -0.2035(3) 0.0368(8) Uani 1 1 d . . .
H39 H -0.2959 0.2519 -0.2369 0.044 Uiso 1 1 calc R . .
C40 C -0.1819(2) 0.28493(13) -0.1227(3) 0.0304(8) Uani 1 1 d . . .
C41 C -0.1423(2) 0.33382(13) -0.0744(3) 0.0282(7) Uani 1 1 d . . .
C42 C -0.0502(2) 0.33546(12) 0.0091(3) 0.0272(7) Uani 1 1 d . . .
C43 C 0.0053(3) 0.28463(13) 0.0446(3) 0.0332(8) Uani 1 1 d . . .
C44 C -0.0425(3) 0.23613(13) -0.0063(3) 0.0348(8) Uani 1 1 d . . .
H44 H -0.0111 0.2030 0.0165 0.042 Uiso 1 1 calc R . .
C45 C -0.1289(3) 0.23655(14) -0.0838(3) 0.0364(8) Uani 1 1 d . . .
H45 H -0.1564 0.2037 -0.1145 0.044 Uiso 1 1 calc R . .
F1 F 0.0023(3) 0.04508(15) -0.2172(3) 0.1175(13) Uani 1 1 d . . .
F2 F -0.08794(19) 0.03262(11) -0.0943(3) 0.0992(11) Uani 1 1 d . . .
F3 F -0.02933(19) 0.11010(10) -0.1156(4) 0.1248(15) Uani 1 1 d . . .
F4 F 0.9472(2) 0.08670(9) 0.2667(3) 0.0774(8) Uani 1 1 d . . .
F5 F 0.82285(19) 0.06957(8) 0.3481(2) 0.0721(8) Uani 1 1 d . . .
F6 F 0.93627(19) 0.12688(9) 0.4204(2) 0.0662(7) Uani 1 1 d . . .
F7 F 0.1460(2) 0.48594(10) 0.0606(3) 0.0962(10) Uani 1 1 d . . .
F8 F 0.30065(17) 0.46761(11) 0.1376(3) 0.0863(9) Uani 1 1 d . . .
F9 F 0.1883(2) 0.47739(11) 0.2407(3) 0.0929(10) Uani 1 1 d . . .
O1 O 0.31779(18) 0.02877(9) 0.1102(2) 0.0438(6) Uani 1 1 d . . .
O2 O 0.18431(16) 0.07315(8) -0.06251(19) 0.0335(5) Uani 1 1 d . . .
O3 O 0.0895(2) 0.06468(12) 0.0899(2) 0.0709(9) Uani 1 1 d . . .
O4 O 0.1174(2) -0.01283(9) -0.0268(3) 0.0581(7) Uani 1 1 d . . .
O5 O 0.72215(17) 0.25014(10) 0.1159(2) 0.0421(6) Uani 1 1 d . . .
O6 O 0.89191(17) 0.19682(8) 0.22287(19) 0.0358(5) Uani 1 1 d . . .
O7 O 0.7603(2) 0.13454(10) 0.1398(2) 0.0560(7) Uani 1 1 d . . .
O8 O 0.74743(16) 0.18166(8) 0.31664(19) 0.0370(6) Uani 1 1 d . . .
O9 O 0.08661(19) 0.28384(9) 0.1125(2) 0.0448(6) Uani 1 1 d . . .
O10 O 0.06549(16) 0.38900(9) 0.14698(18) 0.0360(5) Uani 1 1 d . . .
O11 O 0.18280(18) 0.37467(11) 0.0168(2) 0.0540(7) Uani 1 1 d . . .
O12 O 0.24036(19) 0.36505(10) 0.2242(2) 0.0540(7) Uani 1 1 d . . .
S1 S 0.10312(7) 0.04194(3) -0.01160(8) 0.0402(2) Uani 1 1 d . . .
S2 S 0.80468(7) 0.15879(3) 0.24290(8) 0.0379(2) Uani 1 1 d . . .
S3 S 0.17801(7) 0.38830(4) 0.12874(8) 0.0411(2) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 F1 1.292(6) . ?
C1 F3 1.312(5) . ?
C1 F2 1.315(5) . ?
C1 S1 1.838(5) . ?
C3 C12 1.381(4) . ?
C3 C4 1.401(4) . ?
C3 O2 1.425(4) . ?
C4 C5 1.364(4) . ?
C5 C6 1.407(4) . ?
C6 C11 1.418(4) . ?
C6 C7 1.421(4) . ?
C7 C8 1.367(5) . ?
C8 C9 1.394(5) . ?
C9 C10 1.385(4) . ?
C10 C11 1.428(4) . ?
C10 C15 1.448(4) . ?
C11 C12 1.428(4) . ?
C12 C13 1.483(4) . ?
C13 O1 1.231(4) . ?
C13 C14 1.456(5) . ?
C14 C15 1.337(5) . ?
C16 F4 1.314(4) . ?
C16 F6 1.315(5) . ?
C16 F5 1.335(4) . ?
C16 S2 1.828(4) . ?
C18 C27 1.381(4) . ?
C18 C19 1.401(4) . ?
C18 O6 1.422(4) . ?
C19 C20 1.367(5) . ?
C20 C21 1.401(4) . ?
C21 C22 1.418(4) . ?
C21 C26 1.433(4) . ?
C22 C23 1.363(5) . ?
C23 C24 1.395(5) . ?
C24 C25 1.372(4) . ?
C25 C26 1.424(4) . ?
C25 C30 1.447(5) . ?
C26 C27 1.424(4) . ?
C27 C28 1.496(5) . ?
C28 O5 1.222(4) . ?
C28 C29 1.455(5) . ?
C29 C30 1.341(5) . ?
C31 F7 1.313(5) . ?
C31 F9 1.315(5) . ?
C31 F8 1.323(5) . ?
C31 S3 1.839(5) . ?
C33 C42 1.381(4) . ?
C33 C34 1.385(4) . ?
C33 O10 1.422(4) . ?
C34 C35 1.379(5) . ?
C35 C36 1.406(4) . ?
C36 C37 1.411(5) . ?
C36 C41 1.420(4) . ?
C37 C38 1.364(5) . ?
C38 C39 1.402(5) . ?
C39 C40 1.376(5) . ?
C40 C41 1.420(4) . ?
C40 C45 1.441(5) . ?
C41 C42 1.430(4) . ?
C42 C43 1.500(4) . ?
C43 O9 1.225(4) . ?
C43 C44 1.458(5) . ?
C44 C45 1.335(5) . ?
O2 S1 1.566(2) . ?
O3 S1 1.400(3) . ?
O4 S1 1.410(2) . ?
O6 S2 1.568(2) . ?
O7 S2 1.409(3) . ?
O8 S2 1.412(2) . ?
O10 S3 1.568(2) . ?
O11 S3 1.412(3) . ?
O12 S3 1.409(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
F1 C1 F3 110.7(5) . . ?
F1 C1 F2 108.9(4) . . ?
F3 C1 F2 109.0(4) . . ?
F1 C1 S1 110.0(3) . . ?
F3 C1 S1 110.4(3) . . ?
F2 C1 S1 107.7(4) . . ?
C12 C3 C4 123.2(3) . . ?
C12 C3 O2 120.8(3) . . ?
C4 C3 O2 115.8(3) . . ?
C5 C4 C3 119.2(3) . . ?
C4 C5 C6 121.0(3) . . ?
C5 C6 C11 119.1(3) . . ?
C5 C6 C7 121.7(3) . . ?
C11 C6 C7 119.3(3) . . ?
C8 C7 C6 120.7(3) . . ?
C7 C8 C9 120.1(3) . . ?
C10 C9 C8 121.8(3) . . ?
C9 C10 C11 119.0(3) . . ?
C9 C10 C15 122.1(3) . . ?
C11 C10 C15 118.9(3) . . ?
C6 C11 C12 120.3(3) . . ?
C6 C11 C10 119.1(3) . . ?
C12 C11 C10 120.5(3) . . ?
C3 C12 C11 117.0(3) . . ?
C3 C12 C13 123.5(3) . . ?
C11 C12 C13 119.5(3) . . ?
O1 C13 C14 121.7(3) . . ?
O1 C13 C12 121.9(3) . . ?
C14 C13 C12 116.4(3) . . ?
C15 C14 C13 123.0(3) . . ?
C14 C15 C10 121.4(3) . . ?
F4 C16 F6 109.6(4) . . ?
F4 C16 F5 108.1(3) . . ?
F6 C16 F5 108.5(4) . . ?
F4 C16 S2 111.3(3) . . ?
F6 C16 S2 111.6(2) . . ?
F5 C16 S2 107.7(3) . . ?
C27 C18 C19 123.0(3) . . ?
C27 C18 O6 121.9(3) . . ?
C19 C18 O6 114.8(3) . . ?
C20 C19 C18 119.4(3) . . ?
C19 C20 C21 121.2(3) . . ?
C20 C21 C22 122.6(3) . . ?
C20 C21 C26 118.7(3) . . ?
C22 C21 C26 118.7(3) . . ?
C23 C22 C21 121.0(3) . . ?
C22 C23 C24 120.2(3) . . ?
C25 C24 C23 121.7(3) . . ?
C24 C25 C26 119.7(3) . . ?
C24 C25 C30 121.2(3) . . ?
C26 C25 C30 119.1(3) . . ?
C27 C26 C25 120.9(3) . . ?
C27 C26 C21 120.3(3) . . ?
C25 C26 C21 118.8(3) . . ?
C18 C27 C26 117.3(3) . . ?
C18 C27 C28 123.4(3) . . ?
C26 C27 C28 119.3(3) . . ?
O5 C28 C29 121.3(3) . . ?
O5 C28 C27 122.3(3) . . ?
C29 C28 C27 116.4(3) . . ?
C30 C29 C28 123.0(3) . . ?
C29 C30 C25 121.4(3) . . ?
F7 C31 F9 109.7(4) . . ?
F7 C31 F8 108.8(4) . . ?
F9 C31 F8 109.5(4) . . ?
F7 C31 S3 110.1(3) . . ?
F9 C31 S3 110.6(3) . . ?
F8 C31 S3 108.0(3) . . ?
C42 C33 C34 123.8(3) . . ?
C42 C33 O10 121.1(3) . . ?
C34 C33 O10 114.9(3) . . ?
C35 C34 C33 118.9(3) . . ?
C34 C35 C36 120.9(3) . . ?
C35 C36 C37 121.6(3) . . ?
C35 C36 C41 119.3(3) . . ?
C37 C36 C41 119.1(3) . . ?
C38 C37 C36 120.7(3) . . ?
C37 C38 C39 120.4(3) . . ?
C40 C39 C38 120.9(3) . . ?
C39 C40 C41 119.7(3) . . ?
C39 C40 C45 121.6(3) . . ?
C41 C40 C45 118.7(3) . . ?
C40 C41 C36 119.2(3) . . ?
C40 C41 C42 120.9(3) . . ?
C36 C41 C42 119.9(3) . . ?
C33 C42 C41 117.3(3) . . ?
C33 C42 C43 123.6(3) . . ?
C41 C42 C43 119.0(3) . . ?
O9 C43 C44 121.7(3) . . ?
O9 C43 C42 121.9(3) . . ?
C44 C43 C42 116.4(3) . . ?
C45 C44 C43 122.4(3) . . ?
C44 C45 C40 122.5(3) . . ?
C3 O2 S1 122.55(19) . . ?
C18 O6 S2 123.26(19) . . ?
C33 O10 S3 122.1(2) . . ?
O3 S1 O4 124.0(2) . . ?
O3 S1 O2 111.34(14) . . ?
O4 S1 O2 108.47(15) . . ?
O3 S1 C1 106.5(2) . . ?
O4 S1 C1 104.65(19) . . ?
O2 S1 C1 98.53(19) . . ?
O7 S2 O8 123.40(16) . . ?
O7 S2 O6 108.85(16) . . ?
O8 S2 O6 111.46(13) . . ?
O7 S2 C16 105.73(19) . . ?
O8 S2 C16 106.06(17) . . ?
O6 S2 C16 98.08(16) . . ?
O12 S3 O11 123.44(16) . . ?
O12 S3 O10 108.51(15) . . ?
O11 S3 O10 111.66(14) . . ?
O12 S3 C31 105.01(19) . . ?
O11 S3 C31 106.6(2) . . ?
O10 S3 C31 98.37(17) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.70
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.24
_refine_diff_density_rms         0.05
_database_code_depnum_ccdc_archive 'CCDC 943186'
#######################################################################
#
#                 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_oa157

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20.50 H15 F3 N O4.50 S'
_chemical_formula_weight         436.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   23.961(5)
_cell_length_b                   23.211(5)
_cell_length_c                   6.8908(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3832.3(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    845
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      18.2

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1792
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_process_details   SADABS

_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 ApexII Quasar CCD'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            23837
_diffrn_reflns_av_R_equivalents  0.1786
_diffrn_reflns_av_sigmaI/netI    0.2376
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.43
_reflns_number_total             6873
_reflns_number_gt                3094
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       Apex2
_computing_cell_refinement       Apex2
_computing_data_reduction        Apex2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    Diamond3
_computing_publication_material  WinGX

_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 > 2σ(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)+(0.0481P)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     SHELXL
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.17(17)
_refine_ls_number_reflns         6873
_refine_ls_number_parameters     540
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2125
_refine_ls_R_factor_gt           0.0736
_refine_ls_wR_factor_ref         0.1668
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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
C1 C 0.3475(4) 0.2935(4) 0.2817(15) 0.047(2) Uani 1 1 d . . .
C2 C 1.0063(4) 0.7158(5) 0.235(2) 0.072(3) Uiso 1 1 d . . .
C3 C 0.2538(3) 0.8787(3) 0.4422(12) 0.028(2) Uani 1 1 d . . .
H3 H 0.2409 0.9005 0.5500 0.034 Uiso 1 1 calc R . .
C4 C 0.3062(3) 0.8558(3) 0.4463(13) 0.027(2) Uani 1 1 d . . .
H4 H 0.3289 0.8601 0.5584 0.033 Uiso 1 1 calc R . .
C5 C 0.3260(3) 0.8265(3) 0.2870(13) 0.028(2) Uani 1 1 d . . .
H5 H 0.3630 0.8118 0.2855 0.033 Uiso 1 1 calc R . .
C6 C 0.2907(3) 0.8188(3) 0.1273(12) 0.0234(19) Uani 1 1 d . . .
H6 H 0.3032 0.7980 0.0169 0.028 Uiso 1 1 calc R . .
C7 C 0.2380(3) 0.8417(3) 0.1321(12) 0.026(2) Uani 1 1 d . . .
H7 H 0.2139 0.8367 0.0239 0.032 Uiso 1 1 calc R . .
C9 C 0.1629(3) 0.8935(3) 0.2948(12) 0.0230(19) Uani 1 1 d . . .
C10 C 0.1213(3) 0.8505(3) 0.2769(12) 0.026(2) Uani 1 1 d . . .
H10 H 0.1308 0.8110 0.2605 0.031 Uiso 1 1 calc R . .
C11 C 0.0676(3) 0.8679(3) 0.2842(12) 0.031(2) Uani 1 1 d . . .
H11 H 0.0389 0.8400 0.2676 0.037 Uiso 1 1 calc R . .
C12 C 0.0524(3) 0.9251(3) 0.3151(11) 0.0234(19) Uani 1 1 d . . .
C13 C -0.0037(3) 0.9436(3) 0.3310(11) 0.031(2) Uani 1 1 d . . .
H13 H -0.0329 0.9164 0.3146 0.037 Uiso 1 1 calc R . .
C14 C -0.0166(3) 0.9991(4) 0.3690(12) 0.037(2) Uani 1 1 d . . .
H14 H -0.0546 1.0105 0.3792 0.045 Uiso 1 1 calc R . .
C15 C 0.0256(3) 1.0400(3) 0.3932(11) 0.033(2) Uani 1 1 d . . .
H15 H 0.0160 1.0785 0.4249 0.040 Uiso 1 1 calc R . .
C16 C 0.0808(3) 1.0254(3) 0.3719(11) 0.025(2) Uani 1 1 d . . .
C17 C 0.1246(3) 1.0670(3) 0.3927(12) 0.031(2) Uani 1 1 d . . .
H17 H 0.1154 1.1054 0.4278 0.038 Uiso 1 1 calc R . .
C18 C 0.1777(3) 1.0532(3) 0.3640(12) 0.032(2) Uani 1 1 d . . .
H18 H 0.2051 1.0824 0.3801 0.038 Uiso 1 1 calc R . .
C19 C 0.1962(3) 0.9960(3) 0.3095(12) 0.0237(18) Uani 1 1 d . . .
C20 C 0.1517(3) 0.9498(3) 0.3172(11) 0.0231(19) Uani 1 1 d . . .
C21 C 0.0958(3) 0.9668(3) 0.3368(11) 0.0239(19) Uani 1 1 d . . .
C22 C 0.8576(3) 0.8659(3) 0.9504(13) 0.030(2) Uani 1 1 d . . .
H22 H 0.8711 0.8839 1.0650 0.036 Uiso 1 1 calc R . .
C23 C 0.8048(3) 0.8438(3) 0.9456(13) 0.031(2) Uani 1 1 d . . .
H23 H 0.7814 0.8457 1.0568 0.037 Uiso 1 1 calc R . .
C24 C 0.7863(3) 0.8188(3) 0.7777(15) 0.037(2) Uani 1 1 d . . .
H24 H 0.7497 0.8033 0.7725 0.044 Uiso 1 1 calc R . .
C25 C 0.8197(3) 0.8159(3) 0.6182(14) 0.034(2) Uani 1 1 d . . .
H25 H 0.8064 0.7989 0.5015 0.041 Uiso 1 1 calc R . .
C26 C 0.8730(3) 0.8381(3) 0.6288(13) 0.029(2) Uani 1 1 d . . .
H26 H 0.8969 0.8361 0.5192 0.035 Uiso 1 1 calc R . .
C28 C 0.9470(2) 0.8869(3) 0.8006(11) 0.0235(19) Uani 1 1 d . . .
C29 C 0.9907(3) 0.8469(3) 0.7799(12) 0.029(2) Uani 1 1 d . . .
H29 H 0.9831 0.8070 0.7628 0.034 Uiso 1 1 calc R . .
C30 C 1.0442(3) 0.8664(3) 0.7849(12) 0.033(2) Uani 1 1 d . . .
H30 H 1.0740 0.8400 0.7662 0.039 Uiso 1 1 calc R . .
C31 C 1.0563(3) 0.9246(3) 0.8171(11) 0.0234(19) Uani 1 1 d . . .
C32 C 1.1118(3) 0.9459(3) 0.8202(12) 0.029(2) Uani 1 1 d . . .
H32 H 1.1420 0.9203 0.7964 0.034 Uiso 1 1 calc R . .
C33 C 1.1223(3) 1.0018(4) 0.8564(12) 0.034(2) Uani 1 1 d . . .
H33 H 1.1598 1.0150 0.8623 0.041 Uiso 1 1 calc R . .
C34 C 1.0786(3) 1.0407(3) 0.8854(11) 0.033(2) Uani 1 1 d . . .
H34 H 1.0865 1.0800 0.9127 0.040 Uiso 1 1 calc R . .
C35 C 1.0238(3) 1.0222(3) 0.8743(11) 0.024(2) Uani 1 1 d . . .
C36 C 0.9780(3) 1.0630(3) 0.8947(12) 0.034(2) Uani 1 1 d . . .
H36 H 0.9858 1.1023 0.9215 0.040 Uiso 1 1 calc R . .
C37 C 0.9250(3) 1.0459(3) 0.8762(12) 0.034(2) Uani 1 1 d . . .
H37 H 0.8963 1.0737 0.8924 0.041 Uiso 1 1 calc R . .
C38 C 0.9091(3) 0.9877(3) 0.8331(12) 0.028(2) Uani 1 1 d . . .
C39 C 0.9560(3) 0.9439(3) 0.8249(11) 0.0223(18) Uani 1 1 d . . .
C40 C 1.0118(3) 0.9640(3) 0.8402(11) 0.0207(18) Uani 1 1 d . . .
C41 C 0.8228(3) 1.0479(3) 1.3935(16) 0.067(3) Uani 1 1 d . . .
H41A H 0.8522 1.0631 1.3089 0.100 Uiso 1 1 calc R . .
H41B H 0.8326 1.0552 1.5293 0.100 Uiso 1 1 calc R . .
H41C H 0.7874 1.0670 1.3631 0.100 Uiso 1 1 calc R . .
C42 C 0.8171(3) 0.9851(4) 1.3619(14) 0.044(3) Uani 1 1 d . . .
C43 C 0.7650(3) 0.9566(4) 1.4387(14) 0.060(3) Uani 1 1 d . . .
H43A H 0.7601 0.9191 1.3755 0.090 Uiso 1 1 calc R . .
H43B H 0.7326 0.9810 1.4112 0.090 Uiso 1 1 calc R . .
H43C H 0.7685 0.9511 1.5792 0.090 Uiso 1 1 calc R . .
F1 F 0.32901(19) 0.34681(19) 0.2408(10) 0.0745(19) Uani 1 1 d . . .
F2 F 0.39914(18) 0.2895(2) 0.2233(9) 0.0698(17) Uani 1 1 d . . .
F3 F 0.34617(19) 0.2884(2) 0.4751(9) 0.0691(17) Uani 1 1 d . . .
F4 F 1.0130(3) 0.6628(2) 0.2204(16) 0.158(4) Uani 1 1 d . . .
F5 F 1.03656(18) 0.7433(2) 0.1009(10) 0.086(2) Uani 1 1 d . . .
F6 F 1.0250(3) 0.7347(3) 0.4061(11) 0.120(3) Uani 1 1 d . . .
N1 N 0.2201(2) 0.8710(2) 0.2888(10) 0.0226(15) Uani 1 1 d . . .
N2 N 0.8909(2) 0.8623(2) 0.7916(10) 0.0226(15) Uani 1 1 d . . .
O1 O 0.24345(18) 0.98660(19) 0.2536(8) 0.0314(14) Uani 1 1 d . . .
O2 O 0.86081(19) 0.9747(2) 0.7933(9) 0.0381(16) Uani 1 1 d . . .
O3 O 0.24824(16) 0.25368(19) 0.2572(7) 0.0327(13) Uani 1 1 d . . .
O4 O 0.32609(17) 0.18711(18) 0.2341(9) 0.0348(15) Uani 1 1 d . . .
O5 O 0.30627(18) 0.2524(2) -0.0330(8) 0.0388(14) Uani 1 1 d . . .
O6 O 0.9059(3) 0.7061(3) 0.3541(13) 0.118(3) Uani 1 1 d . . .
O7 O 0.9197(2) 0.7218(3) 0.0123(10) 0.078(2) Uani 1 1 d . . .
O8 O 0.93585(19) 0.8002(2) 0.2387(9) 0.0500(18) Uani 1 1 d . . .
O9 O 0.8534(2) 0.9576(2) 1.2820(10) 0.060(2) Uani 1 1 d . . .
S1 S 0.30187(7) 0.24093(8) 0.1709(3) 0.0284(5) Uani 1 1 d . . .
S2 S 0.93286(8) 0.73871(11) 0.2056(4) 0.0481(7) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 F2 1.305(9) . ?
C1 F3 1.338(11) . ?
C1 F1 1.344(9) . ?
C1 S1 1.808(9) . ?
C2 F4 1.243(11) . ?
C2 F6 1.336(13) . ?
C2 F5 1.338(12) . ?
C2 S2 1.850(10) . ?
C3 N1 1.342(9) . ?
C3 C4 1.364(9) . ?
C4 C5 1.375(10) . ?
C5 C6 1.399(10) . ?
C6 C7 1.370(9) . ?
C7 N1 1.347(8) . ?
C9 C20 1.342(8) . ?
C9 C10 1.416(8) . ?
C9 N1 1.467(8) . ?
C10 C11 1.350(8) . ?
C11 C12 1.394(9) . ?
C12 C13 1.414(8) . ?
C12 C21 1.428(9) . ?
C13 C14 1.351(10) . ?
C14 C15 1.396(10) . ?
C15 C16 1.373(9) . ?
C16 C21 1.429(9) . ?
C16 C17 1.433(9) . ?
C17 C18 1.328(9) . ?
C18 C19 1.448(9) . ?
C19 O1 1.216(7) . ?
C19 C20 1.512(9) . ?
C20 C21 1.403(8) . ?
C22 N2 1.356(9) . ?
C22 C23 1.366(9) . ?
C23 C24 1.368(11) . ?
C24 C25 1.361(11) . ?
C25 C26 1.380(9) . ?
C26 N2 1.325(9) . ?
C28 C39 1.352(9) . ?
C28 C29 1.407(8) . ?
C28 N2 1.461(8) . ?
C29 C30 1.360(8) . ?
C30 C31 1.399(9) . ?
C31 C40 1.413(9) . ?
C31 C32 1.419(8) . ?
C32 C33 1.346(9) . ?
C33 C34 1.398(9) . ?
C34 C35 1.384(9) . ?
C35 C40 1.401(9) . ?
C35 C36 1.457(9) . ?
C36 C37 1.336(9) . ?
C37 C38 1.436(9) . ?
C38 O2 1.226(7) . ?
C38 C39 1.516(9) . ?
C39 C40 1.420(8) . ?
C41 C42 1.480(10) . ?
C42 O9 1.211(9) . ?
C42 C43 1.509(11) . ?
O3 S1 1.447(4) . ?
O4 S1 1.445(5) . ?
O5 S1 1.434(6) . ?
O6 S2 1.428(7) . ?
O7 S2 1.424(6) . ?
O8 S2 1.447(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 C1 F3 108.9(7) . . ?
F2 C1 F1 108.3(8) . . ?
F3 C1 F1 106.5(8) . . ?
F2 C1 S1 113.3(6) . . ?
F3 C1 S1 110.3(7) . . ?
F1 C1 S1 109.5(6) . . ?
F4 C2 F6 110.7(11) . . ?
F4 C2 F5 110.3(11) . . ?
F6 C2 F5 105.6(9) . . ?
F4 C2 S2 113.5(8) . . ?
F6 C2 S2 108.8(8) . . ?
F5 C2 S2 107.6(8) . . ?
N1 C3 C4 121.2(8) . . ?
C3 C4 C5 119.6(8) . . ?
C4 C5 C6 118.9(7) . . ?
C7 C6 C5 119.2(7) . . ?
N1 C7 C6 120.6(7) . . ?
C20 C9 C10 123.8(6) . . ?
C20 C9 N1 122.4(6) . . ?
C10 C9 N1 113.8(6) . . ?
C11 C10 C9 117.2(6) . . ?
C10 C11 C12 122.6(6) . . ?
C11 C12 C13 123.3(6) . . ?
C11 C12 C21 118.1(6) . . ?
C13 C12 C21 118.6(6) . . ?
C14 C13 C12 121.5(7) . . ?
C13 C14 C15 120.3(7) . . ?
C16 C15 C14 121.2(7) . . ?
C15 C16 C21 119.7(6) . . ?
C15 C16 C17 121.9(7) . . ?
C21 C16 C17 118.3(6) . . ?
C18 C17 C16 121.6(7) . . ?
C17 C18 C19 123.6(7) . . ?
O1 C19 C18 122.1(6) . . ?
O1 C19 C20 122.6(6) . . ?
C18 C19 C20 115.2(6) . . ?
C9 C20 C21 118.3(6) . . ?
C9 C20 C19 123.1(6) . . ?
C21 C20 C19 118.4(6) . . ?
C20 C21 C12 119.7(6) . . ?
C20 C21 C16 121.6(6) . . ?
C12 C21 C16 118.6(6) . . ?
N2 C22 C23 120.1(8) . . ?
C22 C23 C24 118.7(8) . . ?
C25 C24 C23 121.0(7) . . ?
C24 C25 C26 118.8(8) . . ?
N2 C26 C25 120.2(8) . . ?
C39 C28 C29 122.6(6) . . ?
C39 C28 N2 122.3(6) . . ?
C29 C28 N2 115.1(6) . . ?
C30 C29 C28 118.7(6) . . ?
C29 C30 C31 121.3(7) . . ?
C30 C31 C40 119.1(6) . . ?
C30 C31 C32 122.1(6) . . ?
C40 C31 C32 118.7(6) . . ?
C33 C32 C31 120.9(7) . . ?
C32 C33 C34 120.6(7) . . ?
C35 C34 C33 120.2(7) . . ?
C34 C35 C40 120.2(7) . . ?
C34 C35 C36 120.6(7) . . ?
C40 C35 C36 119.2(6) . . ?
C37 C36 C35 120.9(7) . . ?
C36 C37 C38 123.5(7) . . ?
O2 C38 C37 121.9(6) . . ?
O2 C38 C39 121.8(6) . . ?
C37 C38 C39 116.1(6) . . ?
C28 C39 C40 118.8(6) . . ?
C28 C39 C38 122.8(6) . . ?
C40 C39 C38 118.4(6) . . ?
C35 C40 C31 119.2(6) . . ?
C35 C40 C39 121.5(6) . . ?
C31 C40 C39 119.3(6) . . ?
O9 C42 C41 121.3(9) . . ?
O9 C42 C43 121.5(8) . . ?
C41 C42 C43 117.2(8) . . ?
C3 N1 C7 120.4(6) . . ?
C3 N1 C9 119.5(6) . . ?
C7 N1 C9 120.1(6) . . ?
C26 N2 C22 121.3(6) . . ?
C26 N2 C28 119.9(6) . . ?
C22 N2 C28 118.8(6) . . ?
O5 S1 O4 115.2(3) . . ?
O5 S1 O3 115.5(3) . . ?
O4 S1 O3 114.2(3) . . ?
O5 S1 C1 104.1(4) . . ?
O4 S1 C1 102.3(4) . . ?
O3 S1 C1 103.0(4) . . ?
O7 S2 O6 115.0(4) . . ?
O7 S2 O8 115.5(5) . . ?
O6 S2 O8 115.6(4) . . ?
O7 S2 C2 103.5(5) . . ?
O6 S2 C2 101.5(5) . . ?
O8 S2 C2 102.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.43
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.35
_refine_diff_density_rms         0.08
_database_code_depnum_ccdc_archive 'CCDC 943187'
#######################################################################
#
#                 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_oa196

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H7 I O'
_chemical_formula_weight         306.09

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   12.8997(18)
_cell_length_b                   12.184(2)
_cell_length_c                   13.1411(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.649(10)
_cell_angle_gamma                90.00
_cell_volume                     2022.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2370
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      25.4

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    2.010
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    3.131
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6026
_exptl_absorpt_correction_T_max  0.7878
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_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  'Oxford Gemini Ultra A'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean 10.4383
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8018
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         25.47
_reflns_number_total             1872
_reflns_number_gt                1480
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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 > 2σ(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)+(0.0163P)²+7.6282P] 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       none
_refine_ls_number_reflns         1872
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0712
_refine_ls_wR_factor_gt          0.0652
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_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
C1 C 0.3503(3) 0.2145(4) 0.2366(3) 0.0238(10) Uani 1 1 d . . .
C2 C 0.3500(4) 0.1022(4) 0.2157(3) 0.0279(11) Uani 1 1 d . . .
H2 H 0.3365 0.0516 0.2665 0.033 Uiso 1 1 calc R . .
C3 C 0.3688(4) 0.0639(4) 0.1235(4) 0.0308(12) Uani 1 1 d . . .
H3 H 0.3706 -0.0129 0.1118 0.037 Uiso 1 1 calc R . .
C4 C 0.3855(3) 0.1374(4) 0.0455(3) 0.0245(10) Uani 1 1 d . . .
C5 C 0.4038(4) 0.1008(4) -0.0519(4) 0.0297(11) Uani 1 1 d . . .
H5 H 0.4078 0.0243 -0.0646 0.036 Uiso 1 1 calc R . .
C6 C 0.4159(4) 0.1739(5) -0.1281(3) 0.0307(12) Uani 1 1 d . . .
H6 H 0.4290 0.1481 -0.1925 0.037 Uiso 1 1 calc R . .
C7 C 0.4088(4) 0.2860(4) -0.1107(3) 0.0298(12) Uani 1 1 d . . .
H7 H 0.4145 0.3362 -0.1647 0.036 Uiso 1 1 calc R . .
C8 C 0.3935(3) 0.3256(4) -0.0164(3) 0.0239(10) Uani 1 1 d . . .
C9 C 0.3869(4) 0.4432(4) 0.0010(4) 0.0290(11) Uani 1 1 d . . .
H9 H 0.3906 0.4928 -0.0540 0.035 Uiso 1 1 calc R . .
C10 C 0.3756(4) 0.4825(4) 0.0934(3) 0.0292(11) Uani 1 1 d . . .
H10 H 0.3718 0.5598 0.1017 0.035 Uiso 1 1 calc R . .
C11 C 0.3688(3) 0.4130(4) 0.1817(4) 0.0262(11) Uani 1 1 d . . .
C12 C 0.3666(3) 0.2920(4) 0.1641(3) 0.0209(10) Uani 1 1 d . . .
C13 C 0.3832(3) 0.2512(4) 0.0646(3) 0.0199(9) Uani 1 1 d . . .
O1 O 0.3658(3) 0.4529(3) 0.2663(3) 0.0404(9) Uani 1 1 d . . .
I1 I 0.31540(3) 0.25443(3) 0.38237(2) 0.03475(14) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C12 1.388(6) . ?
C1 C2 1.395(7) . ?
C1 I1 2.110(4) . ?
C2 C3 1.365(7) . ?
C3 C4 1.410(6) . ?
C4 C13 1.411(6) . ?
C4 C5 1.421(6) . ?
C5 C6 1.373(7) . ?
C6 C7 1.391(8) . ?
C7 C8 1.380(6) . ?
C8 C13 1.425(6) . ?
C8 C9 1.457(7) . ?
C9 C10 1.341(6) . ?
C10 C11 1.452(7) . ?
C11 O1 1.221(5) . ?
C11 C12 1.492(6) . ?
C12 C13 1.454(6) . ?

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
C12 C1 C2 121.8(4) . . ?
C12 C1 I1 123.8(3) . . ?
C2 C1 I1 114.3(3) . . ?
C3 C2 C1 121.1(4) . . ?
C2 C3 C4 120.6(5) . . ?
C3 C4 C13 118.9(4) . . ?
C3 C4 C5 122.2(5) . . ?
C13 C4 C5 118.9(4) . . ?
C6 C5 C4 121.2(5) . . ?
C5 C6 C7 119.8(4) . . ?
C8 C7 C6 121.1(4) . . ?
C7 C8 C13 120.1(4) . . ?
C7 C8 C9 120.5(4) . . ?
C13 C8 C9 119.4(4) . . ?
C10 C9 C8 120.9(4) . . ?
C9 C10 C11 123.4(5) . . ?
O1 C11 C10 120.9(4) . . ?
O1 C11 C12 122.0(4) . . ?
C10 C11 C12 117.1(4) . . ?
C1 C12 C13 117.1(4) . . ?
C1 C12 C11 124.6(4) . . ?
C13 C12 C11 118.4(4) . . ?
C4 C13 C8 118.9(4) . . ?
C4 C13 C12 120.5(4) . . ?
C8 C13 C12 120.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.47
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.56
_refine_diff_density_rms         0.10
_database_code_depnum_ccdc_archive 'CCDC 943188'
#######################################################################
#
#                 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_oa306a4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H7 N O'
_chemical_formula_weight         193.20

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.5727(9)
_cell_length_b                   8.2341(9)
_cell_length_c                   14.4327(19)
_cell_angle_alpha                100.949(10)
_cell_angle_beta                 96.440(10)
_cell_angle_gamma                94.028(9)
_cell_volume                     874.11(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1305
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      24.3

_exptl_crystal_description       block
_exptl_crystal_colour            'pale pink'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean 10.4383
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8715
_diffrn_reflns_av_R_equivalents  0.105
_diffrn_reflns_av_sigmaI/netI    0.0773
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         24.47
_reflns_number_total             4372
_reflns_number_gt                2139
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    Diamond3
_computing_publication_material  WinGX

_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 > 2σ(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)+(0.1714P)²+0.0890P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         4372
_refine_ls_number_parameters     270
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1768
_refine_ls_R_factor_gt           0.0976
_refine_ls_wR_factor_ref         0.3178
_refine_ls_wR_factor_gt          0.2800
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8072(8) 0.8874(7) 0.5467(5) 0.0512(17) Uani 1 1 d D . .
C2 C 0.9448(8) 0.8982(6) 0.6223(5) 0.0491(15) Uani 1 1 d . . .
H2 H 0.9362 0.9629 0.6833 0.059 Uiso 1 1 calc R . .
C3 C 1.0907(8) 0.8138(7) 0.6063(4) 0.0497(16) Uani 1 1 d D . .
C4 C 1.1039(9) 0.7176(7) 0.5150(5) 0.0580(18) Uani 1 1 d . . .
C5 C 1.2578(8) 0.6361(7) 0.5013(5) 0.0541(18) Uani 1 1 d D . .
C6 C 1.2676(9) 0.5399(7) 0.4090(5) 0.0517(16) Uani 1 1 d . . .
H6 H 1.3702 0.4823 0.3984 0.062 Uiso 1 1 calc R . .
C7 C 1.1330(8) 0.5281(6) 0.3352(5) 0.0535(17) Uani 1 1 d . . .
H7 H 1.1429 0.4625 0.2747 0.064 Uiso 1 1 calc R . .
C8 C 0.9792(8) 0.6138(6) 0.3494(5) 0.0494(16) Uani 1 1 d . . .
C9 C 0.8367(8) 0.6117(7) 0.2791(5) 0.0570(17) Uani 1 1 d . . .
H9 H 0.8401 0.5501 0.2167 0.068 Uiso 1 1 calc R . .
C10 C 0.6866(8) 0.7001(7) 0.2990(5) 0.0518(16) Uani 1 1 d . . .
H10 H 0.5923 0.6969 0.2492 0.062 Uiso 1 1 calc R . .
C11 C 0.6733(8) 0.7900(6) 0.3880(5) 0.0492(16) Uani 1 1 d D . .
C12 C 0.8245(9) 0.7933(7) 0.4598(5) 0.0553(17) Uani 1 1 d . . .
C13 C 0.9659(8) 0.7046(6) 0.4387(5) 0.0445(15) Uani 1 1 d . . .
C14 C 0.1654(10) 0.9161(10) -0.0985(5) 0.074(2) Uani 1 1 d D . .
C15 C 0.2133(9) 1.0616(8) -0.1189(5) 0.0620(18) Uani 1 1 d D . .
H15 H 0.1882 1.0805 -0.1818 0.074 Uiso 1 1 calc R . .
C16 C 0.3038(9) 1.1900(11) -0.0441(5) 0.076(2) Uani 1 1 d D . .
C17 C 0.3428(11) 1.1710(12) 0.0466(6) 0.100(3) Uani 1 1 d D . .
C18 C 0.4345(9) 1.3035(9) 0.1193(7) 0.076(3) Uani 1 1 d D . .
C19 C 0.4682(10) 1.2744(8) 0.2088(6) 0.073(2) Uani 1 1 d D . .
H19 H 0.5297 1.3597 0.2578 0.087 Uiso 1 1 calc R . .
C20 C 0.4119(9) 1.1149(9) 0.2309(6) 0.077(2) Uani 1 1 d . . .
H20 H 0.4378 1.0994 0.2944 0.092 Uiso 1 1 calc R . .
C21 C 0.3284(9) 0.9942(9) 0.1678(6) 0.074(2) Uani 1 1 d . . .
C22 C 0.2719(8) 0.8341(7) 0.1836(6) 0.0547(17) Uani 1 1 d . . .
H22 H 0.2939 0.8093 0.2453 0.066 Uiso 1 1 calc R . .
C23 C 0.1818(11) 0.7108(12) 0.1060(7) 0.085(3) Uani 1 1 d D . .
H23 H 0.1444 0.6048 0.1177 0.102 Uiso 1 1 calc R . .
C24 C 0.1454(9) 0.7411(12) 0.0105(8) 0.118(4) Uani 1 1 d D . .
C25 C 0.2055(9) 0.8909(10) 0.0031(6) 0.073(2) Uani 1 1 d D . .
C26 C 0.2929(8) 1.0229(8) 0.0687(5) 0.0491(16) Uani 1 1 d . . .
N1' N 1.3501(15) 0.6723(12) 0.5792(8) 0.060(3) Uiso 0.481(8) 1 d PD . .
N1 N 0.5780(12) 0.8876(10) 0.4340(7) 0.046(3) Uiso 0.519(8) 1 d PD . .
N2 N 0.0735(13) 0.6598(11) -0.0695(7) 0.066(3) Uiso 0.607(9) 1 d PD . .
N2' N 0.4505(18) 1.3992(16) 0.0649(10) 0.061(4) Uiso 0.393(9) 1 d PD . .
O1 O 0.6594(12) 0.9535(9) 0.5392(6) 0.069(3) Uiso 0.519(8) 1 d PD . .
O1' O 1.2392(14) 0.7897(12) 0.6496(8) 0.083(4) Uiso 0.481(8) 1 d PD . .
O2 O 0.0856(12) 0.7858(11) -0.1420(7) 0.087(3) Uiso 0.607(9) 1 d PD . .
O2' O 0.3665(19) 1.3336(16) -0.0405(11) 0.096(5) Uiso 0.393(9) 1 d PD . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 O1 1.282(9) . ?
C1 C12 1.368(9) . ?
C1 C2 1.407(8) . ?
C2 C3 1.365(8) . ?
C3 O1' 1.270(10) . ?
C3 C4 1.420(9) . ?
C4 C5 1.399(8) . ?
C4 C13 1.413(9) . ?
C5 N1' 1.228(11) . ?
C5 C6 1.427(8) . ?
C6 C7 1.374(9) . ?
C7 C8 1.418(8) . ?
C8 C13 1.379(8) . ?
C8 C9 1.393(9) . ?
C9 C10 1.420(8) . ?
C10 C11 1.373(8) . ?
C11 N1 1.263(9) . ?
C11 C12 1.451(9) . ?
C12 C13 1.368(8) . ?
C14 O2 1.216(9) . ?
C14 C15 1.322(9) . ?
C14 C25 1.520(9) . ?
C15 C16 1.433(9) . ?
C16 O2' 1.232(12) . ?
C16 C17 1.351(9) . ?
C17 C26 1.356(10) . ?
C17 C18 1.438(11) . ?
C17 N2' 1.953(17) . ?
C18 N2' 1.222(12) . ?
C18 C19 1.358(9) . ?
C19 C20 1.456(9) . ?
C20 C21 1.287(10) . ?
C21 C22 1.425(9) . ?
C21 C26 1.492(10) . ?
C22 C23 1.432(11) . ?
C23 C24 1.447(11) . ?
C24 N2 1.261(11) . ?
C24 C25 1.312(10) . ?
C25 C26 1.372(10) . ?
N1' O1' 1.614(14) . ?
N1 O1 1.553(12) . ?
N2 O2 1.613(12) . ?
N2' O2' 1.560(18) . ?

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 C1 C12 108.0(7) . . ?
O1 C1 C2 133.0(7) . . ?
C12 C1 C2 119.0(6) . . ?
C3 C2 C1 118.7(6) . . ?
O1' C3 C2 140.2(8) . . ?
O1' C3 C4 99.2(7) . . ?
C2 C3 C4 120.7(6) . . ?
C5 C4 C13 120.1(6) . . ?
C5 C4 C3 118.7(7) . . ?
C13 C4 C3 121.2(6) . . ?
N1' C5 C4 104.3(8) . . ?
N1' C5 C6 138.1(8) . . ?
C4 C5 C6 117.6(7) . . ?
C7 C6 C5 121.9(6) . . ?
C6 C7 C8 120.0(7) . . ?
C13 C8 C9 116.7(6) . . ?
C13 C8 C7 118.8(7) . . ?
C9 C8 C7 124.5(7) . . ?
C8 C9 C10 121.1(7) . . ?
C11 C10 C9 122.1(6) . . ?
N1 C11 C10 143.1(7) . . ?
N1 C11 C12 100.8(7) . . ?
C10 C11 C12 115.9(5) . . ?
C13 C12 C1 125.6(7) . . ?
C13 C12 C11 120.5(6) . . ?
C1 C12 C11 113.9(6) . . ?
C12 C13 C8 123.6(7) . . ?
C12 C13 C4 114.9(6) . . ?
C8 C13 C4 121.5(5) . . ?
O2 C14 C15 135.8(9) . . ?
O2 C14 C25 104.8(8) . . ?
C15 C14 C25 119.3(8) . . ?
C14 C15 C16 118.5(7) . . ?
O2' C16 C17 102.5(10) . . ?
O2' C16 C15 134.0(10) . . ?
C17 C16 C15 123.6(8) . . ?
C16 C17 C26 118.5(10) . . ?
C16 C17 C18 121.5(9) . . ?
C26 C17 C18 120.0(8) . . ?
C16 C17 N2' 82.9(7) . . ?
C26 C17 N2' 158.6(9) . . ?
C18 C17 N2' 38.6(6) . . ?
N2' C18 C19 148.0(9) . . ?
N2' C18 C17 94.1(10) . . ?
C19 C18 C17 117.8(8) . . ?
C18 C19 C20 121.2(8) . . ?
C21 C20 C19 122.5(8) . . ?
C20 C21 C22 125.8(8) . . ?
C20 C21 C26 117.0(7) . . ?
C22 C21 C26 117.2(7) . . ?
C21 C22 C23 119.6(7) . . ?
C22 C23 C24 122.6(8) . . ?
N2 C24 C25 110.2(11) . . ?
N2 C24 C23 136.8(11) . . ?
C25 C24 C23 113.0(9) . . ?
C24 C25 C26 132.1(9) . . ?
C24 C25 C14 111.0(9) . . ?
C26 C25 C14 116.9(7) . . ?
C17 C26 C25 123.2(7) . . ?
C17 C26 C21 121.4(7) . . ?
C25 C26 C21 115.4(7) . . ?
C5 N1' O1' 106.9(9) . . ?
C11 N1 O1 113.1(7) . . ?
C24 N2 O2 105.7(8) . . ?
C18 N2' O2' 116.2(11) . . ?
C18 N2' C17 47.2(6) . . ?
O2' N2' C17 69.0(7) . . ?
C1 O1 N1 104.1(7) . . ?
C3 O1' N1' 111.0(9) . . ?
C14 O2 N2 108.2(8) . . ?
C16 O2' N2' 105.6(11) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        24.47
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.75
_refine_diff_density_min         -0.22
_refine_diff_density_rms         0.07
_database_code_depnum_ccdc_archive 'CCDC 943189'
