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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_13dab4b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 N2 O10 Se'
_chemical_formula_weight         567.40

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'
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'
Se Se -0.0929 2.2259 '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                   10.0929(6)
_cell_length_b                   11.5641(7)
_cell_length_c                   11.7886(7)
_cell_angle_alpha                67.9280(10)
_cell_angle_beta                 77.7760(10)
_cell_angle_gamma                67.5130(10)
_cell_volume                     1174.40(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3800
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      25.21

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    1.661
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.5710
_exptl_absorpt_correction_T_max  0.8786
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15681
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4797
_reflns_number_gt                3989
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0328P)²+0.6157P] 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       ?
_refine_ls_number_reflns         4797
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0809
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Se Se 0.77755(3) 0.43122(2) 0.41930(2) 0.01920(9) Uani 1 1 d . . .
N1 N 0.6674(2) 0.5158(2) 0.61633(19) 0.0213(5) Uani 1 1 d . . .
N2 N 1.1753(2) 0.9214(2) 0.10375(18) 0.0159(4) Uani 1 1 d . . .
O1 O 0.89939(18) 0.64130(16) 0.35946(15) 0.0173(4) Uani 1 1 d . . .
O2 O 1.10038(18) 1.04190(16) 0.28948(17) 0.0205(4) Uani 1 1 d . . .
O3 O 0.6915(2) 0.19393(18) 0.45427(17) 0.0261(4) Uani 1 1 d . . .
O4 O 0.55525(19) 0.18665(17) 0.63315(15) 0.0199(4) Uani 1 1 d . . .
O5 O 1.2203(2) 1.22706(17) 0.21969(17) 0.0237(4) Uani 1 1 d . . .
O6 O 1.0082(2) 1.39000(17) 0.17982(17) 0.0261(4) Uani 1 1 d . . .
O7 O 1.3723(2) 0.68445(17) 0.06301(16) 0.0254(4) Uani 1 1 d . . .
O8 O 1.3012(2) 0.75735(18) -0.12672(16) 0.0258(4) Uani 1 1 d . . .
O9 O 1.12169(18) 1.19161(16) -0.01348(16) 0.0199(4) Uani 1 1 d . . .
O10 O 1.35613(18) 1.16193(17) -0.02349(16) 0.0204(4) Uani 1 1 d . . .
C1 C 0.8129(3) 0.6426(2) 0.4680(2) 0.0180(5) Uani 1 1 d . . .
C2 C 0.8119(3) 0.7389(2) 0.5069(2) 0.0188(5) Uani 1 1 d . . .
H2A H 0.7612 0.7583 0.5788 0.023 Uiso 1 1 calc R . .
C3 C 0.9027(3) 0.8063(2) 0.4183(2) 0.0167(5) Uani 1 1 d . . .
C4 C 0.9518(3) 0.9102(2) 0.4028(2) 0.0175(5) Uani 1 1 d . . .
H4A H 0.9220 0.9560 0.4608 0.021 Uiso 1 1 calc R . .
C5 C 1.0442(3) 0.9443(2) 0.3017(2) 0.0160(5) Uani 1 1 d . . .
C6 C 1.0926(3) 0.8792(2) 0.2120(2) 0.0138(5) Uani 1 1 d . . .
C7 C 1.0468(3) 0.7734(2) 0.2300(2) 0.0158(5) Uani 1 1 d . . .
H7A H 1.0788 0.7246 0.1743 0.019 Uiso 1 1 calc R . .
C8 C 0.9537(3) 0.7421(2) 0.3311(2) 0.0152(5) Uani 1 1 d . . .
C9 C 0.7468(3) 0.5410(2) 0.5127(2) 0.0172(5) Uani 1 1 d . . .
C10 C 0.6645(3) 0.3510(2) 0.5470(2) 0.0176(5) Uani 1 1 d . . .
C11 C 0.6235(3) 0.4108(2) 0.6340(2) 0.0214(6) Uani 1 1 d . . .
H11A H 0.5657 0.3808 0.7058 0.026 Uiso 1 1 calc R . .
C12 C 0.6402(3) 0.2369(2) 0.5383(2) 0.0183(5) Uani 1 1 d . . .
C13 C 1.0030(3) 1.1738(2) 0.2585(2) 0.0199(6) Uani 1 1 d . . .
H13A H 0.9364 1.1882 0.3306 0.024 Uiso 1 1 calc R . .
H13B H 0.9456 1.1919 0.1915 0.024 Uiso 1 1 calc R . .
C14 C 1.0922(3) 1.2632(2) 0.2177(2) 0.0188(6) Uani 1 1 d . . .
C15 C 1.1739(3) 0.8892(2) -0.0026(2) 0.0159(5) Uani 1 1 d . . .
H15A H 1.1805 0.9647 -0.0770 0.019 Uiso 1 1 calc R . .
H15B H 1.0805 0.8781 0.0005 0.019 Uiso 1 1 calc R . .
C16 C 1.2943(3) 0.7646(2) -0.0151(2) 0.0172(5) Uani 1 1 d . . .
C17 C 1.2846(3) 0.9776(2) 0.0936(2) 0.0164(5) Uani 1 1 d . . .
H17A H 1.3761 0.9271 0.0577 0.020 Uiso 1 1 calc R . .
H17B H 1.3007 0.9700 0.1764 0.020 Uiso 1 1 calc R . .
C18 C 1.2414(3) 1.1217(2) 0.0139(2) 0.0164(5) Uani 1 1 d . . .
C19 C 0.5308(3) 0.0729(3) 0.6261(2) 0.0224(6) Uani 1 1 d . . .
H19A H 0.6227 -0.0013 0.6292 0.027 Uiso 1 1 calc R . .
H19B H 0.4889 0.0970 0.5483 0.027 Uiso 1 1 calc R . .
C20 C 0.4281(3) 0.0330(3) 0.7344(2) 0.0272(6) Uani 1 1 d . . .
H20A H 0.4091 -0.0432 0.7324 0.041 Uiso 1 1 calc R . .
H20B H 0.3376 0.1072 0.7303 0.041 Uiso 1 1 calc R . .
H20C H 0.4709 0.0091 0.8108 0.041 Uiso 1 1 calc R . .
C21 C 1.0821(3) 1.4851(3) 0.1463(3) 0.0315(7) Uani 1 1 d . . .
H21A H 1.0126 1.5751 0.1210 0.047 Uiso 1 1 calc R . .
H21B H 1.1548 1.4726 0.0782 0.047 Uiso 1 1 calc R . .
H21C H 1.1291 1.4721 0.2170 0.047 Uiso 1 1 calc R . .
C22 C 1.3256(3) 1.2988(3) -0.1029(3) 0.0274(7) Uani 1 1 d . . .
H22A H 1.4147 1.3203 -0.1257 0.041 Uiso 1 1 calc R . .
H22B H 1.2557 1.3573 -0.0595 0.041 Uiso 1 1 calc R . .
H22C H 1.2859 1.3110 -0.1772 0.041 Uiso 1 1 calc R . .
C23 C 1.4163(3) 0.6469(3) -0.1549(3) 0.0388(8) Uani 1 1 d . . .
H23A H 1.4108 0.6515 -0.2386 0.058 Uiso 1 1 calc R . .
H23B H 1.4063 0.5635 -0.0966 0.058 Uiso 1 1 calc R . .
H23C H 1.5094 0.6513 -0.1485 0.058 Uiso 1 1 calc R . .


_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
Se C10 1.860(2) . ?
Se C9 1.877(3) . ?
N1 C9 1.310(3) . ?
N1 C11 1.378(3) . ?
N2 C6 1.398(3) . ?
N2 C15 1.440(3) . ?
N2 C17 1.446(3) . ?
O1 C8 1.375(3) . ?
O1 C1 1.390(3) . ?
O2 C5 1.397(3) . ?
O2 C13 1.419(3) . ?
O3 C12 1.205(3) . ?
O4 C12 1.345(3) . ?
O4 C19 1.462(3) . ?
O5 C14 1.200(3) . ?
O6 C14 1.336(3) . ?
O6 C21 1.449(3) . ?
O7 C16 1.198(3) . ?
O8 C16 1.335(3) . ?
O8 C23 1.453(3) . ?
O9 C18 1.200(3) . ?
O10 C18 1.339(3) . ?
O10 C22 1.453(3) . ?
C1 C2 1.351(4) . ?
C1 C9 1.445(3) . ?
C2 C3 1.438(3) . ?
C3 C8 1.389(3) . ?
C3 C4 1.405(3) . ?
C4 C5 1.379(3) . ?
C5 C6 1.421(3) . ?
C6 C7 1.398(3) . ?
C7 C8 1.377(3) . ?
C10 C11 1.355(4) . ?
C10 C12 1.474(4) . ?
C13 C14 1.506(4) . ?
C15 C16 1.523(3) . ?
C17 C18 1.513(3) . ?
C19 C20 1.510(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 Se C9 84.08(11) . . ?
C9 N1 C11 111.3(2) . . ?
C6 N2 C15 120.4(2) . . ?
C6 N2 C17 124.7(2) . . ?
C15 N2 C17 114.10(19) . . ?
C8 O1 C1 105.35(18) . . ?
C5 O2 C13 116.10(18) . . ?
C12 O4 C19 113.7(2) . . ?
C14 O6 C21 115.0(2) . . ?
C16 O8 C23 116.6(2) . . ?
C18 O10 C22 114.7(2) . . ?
C2 C1 O1 111.6(2) . . ?
C2 C1 C9 135.3(2) . . ?
O1 C1 C9 113.1(2) . . ?
C1 C2 C3 106.6(2) . . ?
C8 C3 C4 117.3(2) . . ?
C8 C3 C2 105.6(2) . . ?
C4 C3 C2 137.1(2) . . ?
C5 C4 C3 118.7(2) . . ?
C4 C5 O2 119.1(2) . . ?
C4 C5 C6 123.2(2) . . ?
O2 C5 C6 117.6(2) . . ?
C7 C6 N2 118.8(2) . . ?
C7 C6 C5 117.8(2) . . ?
N2 C6 C5 123.3(2) . . ?
C8 C7 C6 117.8(2) . . ?
O1 C8 C7 123.9(2) . . ?
O1 C8 C3 110.8(2) . . ?
C7 C8 C3 125.2(2) . . ?
N1 C9 C1 125.4(2) . . ?
N1 C9 Se 115.68(18) . . ?
C1 C9 Se 118.96(18) . . ?
C11 C10 C12 132.6(2) . . ?
C11 C10 Se 110.30(19) . . ?
C12 C10 Se 117.10(18) . . ?
C10 C11 N1 118.7(2) . . ?
O3 C12 O4 123.9(2) . . ?
O3 C12 C10 122.9(2) . . ?
O4 C12 C10 113.1(2) . . ?
O2 C13 C14 106.8(2) . . ?
O5 C14 O6 124.2(2) . . ?
O5 C14 C13 125.4(2) . . ?
O6 C14 C13 110.4(2) . . ?
N2 C15 C16 114.7(2) . . ?
O7 C16 O8 124.5(2) . . ?
O7 C16 C15 125.4(2) . . ?
O8 C16 C15 110.1(2) . . ?
N2 C17 C18 111.4(2) . . ?
O9 C18 O10 123.8(2) . . ?
O9 C18 C17 125.5(2) . . ?
O10 C18 C17 110.7(2) . . ?
O4 C19 C20 107.3(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.073
_database_code_depnum_ccdc_archive 'CCDC 1007936'
#######################################################################
#
#                 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_db_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 N2 O10 S'
_chemical_formula_weight         520.50

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'

_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                   10.0940(14)
_cell_length_b                   11.5565(16)
_cell_length_c                   11.7894(17)
_cell_angle_alpha                67.376(2)
_cell_angle_beta                 77.489(2)
_cell_angle_gamma                67.165(2)
_cell_volume                     1166.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5743
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      28.12

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.8972
_exptl_absorpt_correction_T_max  0.9762
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21799
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         28.44
_reflns_number_total             5877
_reflns_number_gt                4657
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0560P)²+0.4232P] 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       ?
_refine_ls_number_reflns         5877
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
S S 0.77322(4) 0.43290(4) 0.43428(4) 0.02117(11) Uani 1 1 d . . .
N1 N 0.66295(16) 0.51832(14) 0.61913(13) 0.0248(3) Uani 1 1 d . . .
N2 N 1.17678(14) 0.92060(14) 0.10322(12) 0.0201(3) Uani 1 1 d . . .
O1 O 0.89984(12) 0.63872(11) 0.35964(10) 0.0199(2) Uani 1 1 d . . .
O2 O 1.10029(12) 1.04008(11) 0.28987(11) 0.0243(3) Uani 1 1 d . . .
O3 O 0.69807(14) 0.20032(12) 0.45143(11) 0.0282(3) Uani 1 1 d . . .
O4 O 0.55824(12) 0.19044(11) 0.63022(10) 0.0228(3) Uani 1 1 d . . .
O5 O 1.22030(13) 1.22551(12) 0.22099(12) 0.0270(3) Uani 1 1 d . . .
O6 O 1.00680(14) 1.38981(12) 0.18417(12) 0.0304(3) Uani 1 1 d . . .
O7 O 1.37566(14) 0.68396(12) 0.06146(11) 0.0301(3) Uani 1 1 d . . .
O8 O 1.30223(14) 0.75844(13) -0.12826(11) 0.0313(3) Uani 1 1 d . . .
O9 O 1.11968(12) 1.19319(11) -0.01360(11) 0.0251(3) Uani 1 1 d . . .
O10 O 1.35434(13) 1.16468(12) -0.02470(11) 0.0257(3) Uani 1 1 d . . .
C1 C 0.81331(17) 0.63931(16) 0.46842(14) 0.0206(3) Uani 1 1 d . . .
C2 C 0.81121(18) 0.73595(16) 0.50765(15) 0.0216(3) Uani 1 1 d . . .
H2A H 0.7593 0.7554 0.5793 0.026 Uiso 1 1 calc R . .
C3 C 0.90334(17) 0.80336(16) 0.41913(15) 0.0195(3) Uani 1 1 d . . .
C4 C 0.95175(17) 0.90746(16) 0.40330(15) 0.0211(3) Uani 1 1 d . . .
H4A H 0.9208 0.9533 0.4613 0.025 Uiso 1 1 calc R . .
C5 C 1.04499(17) 0.94254(15) 0.30238(15) 0.0197(3) Uani 1 1 d . . .
C6 C 1.09359(16) 0.87772(15) 0.21171(14) 0.0180(3) Uani 1 1 d . . .
C7 C 1.04811(17) 0.77176(15) 0.22995(14) 0.0189(3) Uani 1 1 d . . .
H7A H 1.0807 0.7232 0.1741 0.023 Uiso 1 1 calc R . .
C8 C 0.95469(16) 0.73955(15) 0.33112(14) 0.0178(3) Uani 1 1 d . . .
C9 C 0.74589(17) 0.53845(16) 0.51483(14) 0.0199(3) Uani 1 1 d . . .
C10 C 0.66683(17) 0.35496(15) 0.54826(14) 0.0195(3) Uani 1 1 d . . .
C11 C 0.61972(18) 0.41414(17) 0.63684(15) 0.0241(4) Uani 1 1 d . . .
H11A H 0.5597 0.3841 0.7074 0.029 Uiso 1 1 calc R . .
C12 C 0.64469(17) 0.24155(16) 0.53628(15) 0.0211(3) Uani 1 1 d . . .
C13 C 1.00220(18) 1.17253(16) 0.26012(16) 0.0235(3) Uani 1 1 d . . .
H13A H 0.9356 1.1854 0.3328 0.028 Uiso 1 1 calc R . .
H13B H 0.9446 1.1924 0.1926 0.028 Uiso 1 1 calc R . .
C14 C 1.09130(19) 1.26252(16) 0.22025(15) 0.0225(3) Uani 1 1 d . . .
C15 C 1.17490(17) 0.89033(16) -0.00440(15) 0.0196(3) Uani 1 1 d . . .
H15A H 1.1815 0.9669 -0.0788 0.024 Uiso 1 1 calc R . .
H15B H 1.0814 0.8797 -0.0013 0.024 Uiso 1 1 calc R . .
C16 C 1.29639(17) 0.76484(16) -0.01671(15) 0.0214(3) Uani 1 1 d . . .
C17 C 1.28555(17) 0.97707(16) 0.09249(15) 0.0210(3) Uani 1 1 d . . .
H17A H 1.3772 0.9271 0.0559 0.025 Uiso 1 1 calc R . .
H17B H 1.3022 0.9683 0.1756 0.025 Uiso 1 1 calc R . .
C18 C 1.24080(17) 1.12282(16) 0.01292(14) 0.0196(3) Uani 1 1 d . . .
C19 C 0.53443(19) 0.07705(17) 0.62184(17) 0.0268(4) Uani 1 1 d . . .
H19A H 0.6269 0.0027 0.6243 0.032 Uiso 1 1 calc R . .
H19B H 0.4923 0.1029 0.5436 0.032 Uiso 1 1 calc R . .
C20 C 0.4321(2) 0.03492(19) 0.73028(17) 0.0309(4) Uani 1 1 d . . .
H20A H 0.4139 -0.0412 0.7274 0.046 Uiso 1 1 calc R . .
H20B H 0.3410 0.1092 0.7268 0.046 Uiso 1 1 calc R . .
H20C H 0.4751 0.0094 0.8071 0.046 Uiso 1 1 calc R . .
C21 C 1.0818(2) 1.48493(18) 0.1499(2) 0.0354(4) Uani 1 1 d . . .
H21A H 1.0123 1.5757 0.1244 0.053 Uiso 1 1 calc R . .
H21B H 1.1544 1.4723 0.0816 0.053 Uiso 1 1 calc R . .
H21C H 1.1290 1.4709 0.2208 0.053 Uiso 1 1 calc R . .
C22 C 1.3213(2) 1.30343(18) -0.10222(18) 0.0332(4) Uani 1 1 d . . .
H22A H 1.4098 1.3259 -0.1255 0.050 Uiso 1 1 calc R . .
H22B H 1.2515 1.3601 -0.0568 0.050 Uiso 1 1 calc R . .
H22C H 1.2803 1.3179 -0.1767 0.050 Uiso 1 1 calc R . .
C23 C 1.4176(2) 0.6475(2) -0.1567(2) 0.0454(6) Uani 1 1 d . . .
H23A H 1.4115 0.6527 -0.2404 0.068 Uiso 1 1 calc R . .
H23B H 1.4081 0.5634 -0.0978 0.068 Uiso 1 1 calc R . .
H23C H 1.5110 0.6517 -0.1509 0.068 Uiso 1 1 calc R . .


_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
S C10 1.7218(16) . ?
S C9 1.7270(17) . ?
N1 C9 1.324(2) . ?
N1 C11 1.363(2) . ?
N2 C6 1.399(2) . ?
N2 C17 1.442(2) . ?
N2 C15 1.445(2) . ?
O1 C8 1.3770(19) . ?
O1 C1 1.3873(19) . ?
O2 C5 1.3887(19) . ?
O2 C13 1.4168(19) . ?
O3 C12 1.205(2) . ?
O4 C12 1.3472(19) . ?
O4 C19 1.463(2) . ?
O5 C14 1.203(2) . ?
O6 C14 1.332(2) . ?
O6 C21 1.455(2) . ?
O7 C16 1.200(2) . ?
O8 C16 1.333(2) . ?
O8 C23 1.454(2) . ?
O9 C18 1.2051(19) . ?
O10 C18 1.3376(19) . ?
O10 C22 1.452(2) . ?
C1 C2 1.355(2) . ?
C1 C9 1.444(2) . ?
C2 C3 1.441(2) . ?
C3 C8 1.396(2) . ?
C3 C4 1.402(2) . ?
C4 C5 1.381(2) . ?
C5 C6 1.431(2) . ?
C6 C7 1.396(2) . ?
C7 C8 1.376(2) . ?
C10 C11 1.366(2) . ?
C10 C12 1.473(2) . ?
C13 C14 1.509(2) . ?
C15 C16 1.527(2) . ?
C17 C18 1.516(2) . ?
C19 C20 1.509(2) . ?

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
C10 S C9 88.81(8) . . ?
C9 N1 C11 109.10(14) . . ?
C6 N2 C17 125.05(14) . . ?
C6 N2 C15 120.32(13) . . ?
C17 N2 C15 113.92(13) . . ?
C8 O1 C1 105.45(12) . . ?
C5 O2 C13 116.34(12) . . ?
C12 O4 C19 113.90(13) . . ?
C14 O6 C21 114.65(14) . . ?
C16 O8 C23 116.45(14) . . ?
C18 O10 C22 114.68(13) . . ?
C2 C1 O1 111.84(14) . . ?
C2 C1 C9 134.14(15) . . ?
O1 C1 C9 114.02(14) . . ?
C1 C2 C3 106.43(14) . . ?
C8 C3 C4 117.26(15) . . ?
C8 C3 C2 105.57(14) . . ?
C4 C3 C2 137.16(16) . . ?
C5 C4 C3 119.14(15) . . ?
C4 C5 O2 119.52(15) . . ?
C4 C5 C6 122.62(15) . . ?
O2 C5 C6 117.79(14) . . ?
C7 C6 N2 118.95(14) . . ?
C7 C6 C5 117.86(14) . . ?
N2 C6 C5 123.08(14) . . ?
C8 C7 C6 118.09(15) . . ?
C7 C8 O1 124.33(14) . . ?
C7 C8 C3 124.97(15) . . ?
O1 C8 C3 110.70(14) . . ?
N1 C9 C1 124.16(15) . . ?
N1 C9 S 115.66(12) . . ?
C1 C9 S 120.18(12) . . ?
C11 C10 C12 132.30(15) . . ?
C11 C10 S 109.61(13) . . ?
C12 C10 S 118.09(12) . . ?
N1 C11 C10 116.83(15) . . ?
O3 C12 O4 124.36(16) . . ?
O3 C12 C10 123.30(15) . . ?
O4 C12 C10 112.34(14) . . ?
O2 C13 C14 106.75(13) . . ?
O5 C14 O6 124.39(16) . . ?
O5 C14 C13 125.25(15) . . ?
O6 C14 C13 110.37(14) . . ?
N2 C15 C16 114.15(13) . . ?
O7 C16 O8 124.67(16) . . ?
O7 C16 C15 125.55(15) . . ?
O8 C16 C15 109.78(13) . . ?
N2 C17 C18 111.38(13) . . ?
O9 C18 O10 123.69(15) . . ?
O9 C18 C17 125.33(15) . . ?
O10 C18 C17 110.98(13) . . ?
O4 C19 C20 107.39(15) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.44
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 1007937'
