# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_dm12521

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 N2 O5'
_chemical_formula_weight         393.41

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   10.1723(8)
_cell_length_b                   19.9258(16)
_cell_length_c                   10.4443(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.467(2)
_cell_angle_gamma                90.00
_cell_volume                     2116.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      32.09

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             828
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_T_max  0.9723
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(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_reflns_number            14743
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         26.00
_reflns_number_total             7730
_reflns_number_gt                7379
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1531P)²+0.0738P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7730
_refine_ls_number_parameters     525
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1910
_refine_ls_wR_factor_gt          0.1872
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.133 0.871 0.166 119 33 ' '
2 0.133 0.371 0.834 118 34 ' '
_platon_squeeze_details          
;
;


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
N1 N 0.5455(2) 0.00134(10) 0.40479(19) 0.0206(4) Uani 1 1 d . . .
N2 N 0.5393(2) 0.03789(11) 0.62690(19) 0.0212(4) Uani 1 1 d . . .
N3 N 0.7142(2) 0.21715(13) 0.6632(2) 0.0297(5) Uani 1 1 d . . .
N4 N 0.8048(2) 0.10488(12) 0.6343(2) 0.0249(4) Uani 1 1 d . . .
O1 O 0.56776(19) -0.01323(11) 0.81989(17) 0.0297(4) Uani 1 1 d . . .
O2 O 0.65394(17) -0.05722(9) 0.63926(17) 0.0240(4) Uani 1 1 d . . .
O3 O 0.2904(2) 0.02334(11) 0.7338(2) 0.0347(5) Uani 1 1 d . . .
O4 O 0.29389(18) 0.13081(12) 0.79939(19) 0.0337(5) Uani 1 1 d . . .
O5 O 0.8992(2) 0.02788(13) 0.7666(2) 0.0415(6) Uani 1 1 d . . .
O6 O 0.7697(2) 0.11137(15) 0.84434(18) 0.0427(6) Uani 1 1 d . . .
O7 O 1.07132(18) 0.10414(10) 0.5544(2) 0.0301(4) Uani 1 1 d . . .
O8 O 1.02710(19) 0.00915(11) 0.4457(2) 0.0351(5) Uani 1 1 d . . .
C1 C 0.5154(2) 0.04067(12) 0.2934(2) 0.0210(5) Uani 1 1 d . . .
C2 C 0.4885(3) 0.01461(14) 0.1722(2) 0.0282(5) Uani 1 1 d . . .
H2 H 0.5009 -0.0316 0.1536 0.034 Uiso 1 1 calc R . .
C3 C 0.4424(3) 0.05928(16) 0.0795(2) 0.0316(6) Uani 1 1 d . . .
H3 H 0.4251 0.0433 -0.0047 0.038 Uiso 1 1 calc R . .
C4 C 0.4213(3) 0.12596(16) 0.1070(3) 0.0309(6) Uani 1 1 d . . .
H4 H 0.3869 0.1547 0.0424 0.037 Uiso 1 1 calc R . .
C5 C 0.4498(3) 0.15220(14) 0.2290(2) 0.0251(5) Uani 1 1 d . . .
H5 H 0.4354 0.1983 0.2476 0.030 Uiso 1 1 calc R . .
C6 C 0.4990(2) 0.10933(12) 0.3208(2) 0.0195(5) Uani 1 1 d . . .
C7 C 0.5414(2) 0.11877(12) 0.4590(2) 0.0176(4) Uani 1 1 d . . .
C8 C 0.4440(2) 0.14236(12) 0.5611(2) 0.0194(4) Uani 1 1 d . . .
H8A H 0.3523 0.1370 0.5305 0.023 Uiso 1 1 calc R . .
H8B H 0.4591 0.1901 0.5829 0.023 Uiso 1 1 calc R . .
C9 C 0.4715(2) 0.09646(12) 0.6794(2) 0.0202(5) Uani 1 1 d . . .
H9 H 0.5294 0.1202 0.7428 0.024 Uiso 1 1 calc R . .
C10 C 0.5516(2) 0.04491(12) 0.4953(2) 0.0182(5) Uani 1 1 d . . .
C11 C 0.3414(2) 0.07720(15) 0.7410(2) 0.0247(5) Uani 1 1 d . . .
C12 C 0.1640(3) 0.1236(2) 0.8542(3) 0.0486(9) Uani 1 1 d . . .
H12A H 0.0987 0.1189 0.7852 0.073 Uiso 1 1 calc R . .
H12B H 0.1435 0.1634 0.9055 0.073 Uiso 1 1 calc R . .
H12C H 0.1620 0.0836 0.9088 0.073 Uiso 1 1 calc R . .
C13 C 0.5860(2) -0.01266(12) 0.7057(2) 0.0213(5) Uani 1 1 d . . .
C14 C 0.7151(3) -0.11068(14) 0.7165(3) 0.0306(6) Uani 1 1 d . . .
H14A H 0.6468 -0.1404 0.7528 0.037 Uiso 1 1 calc R . .
H14B H 0.7670 -0.0911 0.7879 0.037 Uiso 1 1 calc R . .
C15 C 0.8019(3) -0.14921(14) 0.6296(3) 0.0300(6) Uani 1 1 d . . .
C16 C 0.9370(3) -0.13599(16) 0.6254(3) 0.0377(7) Uani 1 1 d . . .
H16 H 0.9733 -0.1012 0.6768 0.045 Uiso 1 1 calc R . .
C17 C 1.0180(3) -0.17330(18) 0.5467(4) 0.0454(8) Uani 1 1 d . . .
H17 H 1.1097 -0.1642 0.5458 0.054 Uiso 1 1 calc R . .
C18 C 0.9681(3) -0.22333(17) 0.4699(4) 0.0448(8) Uani 1 1 d . . .
H18 H 1.0250 -0.2487 0.4169 0.054 Uiso 1 1 calc R . .
C19 C 0.8325(3) -0.23680(18) 0.4700(4) 0.0458(8) Uani 1 1 d . . .
H19 H 0.7969 -0.2707 0.4160 0.055 Uiso 1 1 calc R . .
C20 C 0.7506(3) -0.19992(15) 0.5503(3) 0.0339(6) Uani 1 1 d . . .
H20 H 0.6591 -0.2092 0.5513 0.041 Uiso 1 1 calc R . .
C21 C 0.6663(2) 0.26070(15) 0.5650(3) 0.0290(6) Uani 1 1 d . . .
C22 C 0.6401(3) 0.32846(16) 0.5805(4) 0.0409(8) Uani 1 1 d . . .
H22 H 0.6389 0.3486 0.6629 0.049 Uiso 1 1 calc R . .
C23 C 0.6157(3) 0.36569(15) 0.4699(4) 0.0477(9) Uani 1 1 d . . .
H23 H 0.5954 0.4121 0.4775 0.057 Uiso 1 1 calc R . .
C24 C 0.6200(3) 0.33694(16) 0.3488(4) 0.0434(8) Uani 1 1 d . . .
H24 H 0.6085 0.3644 0.2751 0.052 Uiso 1 1 calc R . .
C25 C 0.6410(2) 0.26807(14) 0.3343(3) 0.0298(6) Uani 1 1 d . . .
H25 H 0.6409 0.2480 0.2518 0.036 Uiso 1 1 calc R . .
C26 C 0.6621(2) 0.23007(12) 0.4429(3) 0.0222(5) Uani 1 1 d . . .
C27 C 0.6813(2) 0.15588(12) 0.4665(2) 0.0174(4) Uani 1 1 d . . .
C28 C 0.7943(2) 0.11590(12) 0.4061(2) 0.0194(5) Uani 1 1 d . . .
H28A H 0.8646 0.1463 0.3762 0.023 Uiso 1 1 calc R . .
H28B H 0.7621 0.0888 0.3328 0.023 Uiso 1 1 calc R . .
C29 C 0.8452(2) 0.06992(12) 0.5161(2) 0.0205(5) Uani 1 1 d . . .
H29 H 0.8037 0.0245 0.5106 0.025 Uiso 1 1 calc R . .
C30 C 0.7298(2) 0.16118(13) 0.6046(2) 0.0225(5) Uani 1 1 d . . .
C31 C 0.9949(2) 0.06439(13) 0.5108(2) 0.0238(5) Uani 1 1 d . . .
C32 C 1.1675(3) -0.0034(2) 0.4336(4) 0.0483(9) Uani 1 1 d . . .
H32A H 1.2083 0.0337 0.3867 0.072 Uiso 1 1 calc R . .
H32B H 1.1812 -0.0454 0.3869 0.072 Uiso 1 1 calc R . .
H32C H 1.2075 -0.0068 0.5190 0.072 Uiso 1 1 calc R . .
C33 C 0.8318(3) 0.07631(17) 0.7531(3) 0.0320(6) Uani 1 1 d . . .
C34 C 0.7843(4) 0.0849(2) 0.9740(3) 0.0559(11) Uani 1 1 d . . .
H34A H 0.8111 0.0372 0.9699 0.067 Uiso 1 1 calc R . .
H34B H 0.6986 0.0872 1.0182 0.067 Uiso 1 1 calc R . .
C35 C 0.8840(3) 0.12348(17) 1.0486(2) 0.0330(6) Uani 1 1 d . . .
C36 C 0.8790(5) 0.1915(3) 1.0518(7) 0.0786(16) Uani 1 1 d . . .
H36 H 0.8112 0.2140 1.0057 0.094 Uiso 1 1 calc R . .
C37 C 0.9685(7) 0.2285(4) 1.1193(9) 0.111(3) Uani 1 1 d . . .
H37 H 0.9628 0.2761 1.1170 0.133 Uiso 1 1 calc R . .
C38 C 1.0609(6) 0.2006(4) 1.1864(5) 0.0786(16) Uani 1 1 d . . .
H38 H 1.1211 0.2280 1.2327 0.094 Uiso 1 1 calc R . .
C39 C 1.0732(3) 0.1342(4) 1.1917(3) 0.0687(16) Uani 1 1 d . . .
H39 H 1.1402 0.1141 1.2427 0.082 Uiso 1 1 calc R . .
C40 C 0.9812(3) 0.0925(2) 1.1173(3) 0.0476(9) Uani 1 1 d . . .
H40 H 0.9892 0.0450 1.1171 0.057 Uiso 1 1 calc R . .
C2S C 0.4750(7) 0.8101(6) 0.0345(8) 0.119(4) Uani 1 1 d . . .
O2S O 0.3771(8) 0.8530(3) 0.0726(6) 0.1228(19) Uani 1 1 d . . .
C1S C 0.5542(12) 0.7869(6) 0.1290(12) 0.139(3) Uani 1 1 d U . .
H1SA H 0.6211 0.7573 0.0924 0.208 Uiso 1 1 calc R . .
H1SB H 0.5019 0.7618 0.1911 0.208 Uiso 1 1 calc R . .
H1SC H 0.5973 0.8248 0.1719 0.208 Uiso 1 1 calc R . .
C3S C 0.2965(11) 0.8855(6) -0.0197(10) 0.133(3) Uani 1 1 d . . .
H3SA H 0.2763 0.8524 -0.0877 0.159 Uiso 1 1 calc R . .
H3SB H 0.3499 0.9213 -0.0595 0.159 Uiso 1 1 calc R . .
O1S O 0.4932(13) 0.7982(9) -0.0722(12) 0.240(7) Uani 1 1 d . . .
C4S C 0.1648(15) 0.9175(7) 0.021(3) 0.260(12) Uani 1 1 d . . .
H4SA H 0.1228 0.9388 -0.0535 0.390 Uiso 1 1 calc R . .
H4SB H 0.1814 0.9514 0.0871 0.390 Uiso 1 1 calc R . .
H4SC H 0.1068 0.8827 0.0550 0.390 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
N1 C10 1.284(3) . ?
N1 C1 1.434(3) . ?
N2 C13 1.382(3) . ?
N2 C10 1.388(3) . ?
N2 C9 1.464(3) . ?
N3 C30 1.283(4) . ?
N3 C21 1.427(4) . ?
N4 C30 1.390(4) . ?
N4 C33 1.391(3) . ?
N4 C29 1.479(3) . ?
O1 C13 1.208(3) . ?
O2 C13 1.325(3) . ?
O2 C14 1.471(3) . ?
O3 C11 1.194(4) . ?
O4 C11 1.323(4) . ?
O4 C12 1.452(3) . ?
O5 C33 1.191(4) . ?
O6 C33 1.344(4) . ?
O6 C34 1.460(4) . ?
O7 C31 1.197(3) . ?
O8 C31 1.336(3) . ?
O8 C32 1.456(4) . ?
C1 C2 1.393(3) . ?
C1 C6 1.408(4) . ?
C2 C3 1.394(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.405(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.514(3) . ?
C7 C10 1.523(3) . ?
C7 C8 1.535(3) . ?
C7 C27 1.605(3) . ?
C8 C9 1.561(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C11 1.526(3) . ?
C9 H9 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C15 1.486(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.400(4) . ?
C15 C20 1.404(4) . ?
C16 C17 1.385(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.374(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.405(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.396(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.386(4) . ?
C21 C26 1.413(4) . ?
C22 C23 1.394(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.397(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.379(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.511(3) . ?
C27 C30 1.524(3) . ?
C27 C28 1.538(3) . ?
C28 C29 1.555(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C31 1.528(3) . ?
C29 H29 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C34 C35 1.488(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.357(6) . ?
C35 C40 1.365(5) . ?
C36 C37 1.364(8) . ?
C36 H36 0.9500 . ?
C37 C38 1.294(11) . ?
C37 H37 0.9500 . ?
C38 C39 1.330(9) . ?
C38 H38 0.9500 . ?
C39 C40 1.469(7) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C2S O1S 1.155(13) . ?
C2S C1S 1.351(14) . ?
C2S O2S 1.374(10) . ?
O2S C3S 1.417(13) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C3S C4S 1.546(18) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 0.9800 . ?

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 N1 C1 103.7(2) . . ?
C13 N2 C10 129.0(2) . . ?
C13 N2 C9 121.2(2) . . ?
C10 N2 C9 109.70(18) . . ?
C30 N3 C21 103.2(2) . . ?
C30 N4 C33 129.3(2) . . ?
C30 N4 C29 110.45(19) . . ?
C33 N4 C29 119.9(2) . . ?
C13 O2 C14 114.7(2) . . ?
C11 O4 C12 116.0(3) . . ?
C33 O6 C34 115.2(3) . . ?
C31 O8 C32 115.5(2) . . ?
C2 C1 C6 121.6(2) . . ?
C2 C1 N1 124.9(2) . . ?
C6 C1 N1 113.0(2) . . ?
C1 C2 C3 117.1(3) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 C7 133.3(2) . . ?
C1 C6 C7 106.3(2) . . ?
C6 C7 C10 97.80(18) . . ?
C6 C7 C8 121.35(19) . . ?
C10 C7 C8 99.55(18) . . ?
C6 C7 C27 110.43(18) . . ?
C10 C7 C27 111.98(18) . . ?
C8 C7 C27 113.67(18) . . ?
C7 C8 C9 104.97(18) . . ?
C7 C8 H8A 110.8 . . ?
C9 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
C9 C8 H8B 110.8 . . ?
H8A C8 H8B 108.8 . . ?
N2 C9 C11 111.7(2) . . ?
N2 C9 C8 104.61(17) . . ?
C11 C9 C8 109.31(19) . . ?
N2 C9 H9 110.3 . . ?
C11 C9 H9 110.3 . . ?
C8 C9 H9 110.3 . . ?
N1 C10 N2 131.0(2) . . ?
N1 C10 C7 117.8(2) . . ?
N2 C10 C7 109.72(19) . . ?
O3 C11 O4 126.5(2) . . ?
O3 C11 C9 125.3(2) . . ?
O4 C11 C9 108.2(2) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 O2 126.5(2) . . ?
O1 C13 N2 122.7(2) . . ?
O2 C13 N2 110.8(2) . . ?
O2 C14 C15 106.9(2) . . ?
O2 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O2 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.6 . . ?
C16 C15 C20 118.5(3) . . ?
C16 C15 C14 120.7(3) . . ?
C20 C15 C14 120.8(2) . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 121.1(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 119.7(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C15 120.8(3) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C22 C21 C26 121.5(3) . . ?
C22 C21 N3 125.0(3) . . ?
C26 C21 N3 113.2(2) . . ?
C21 C22 C23 117.0(3) . . ?
C21 C22 H22 121.5 . . ?
C23 C22 H22 121.5 . . ?
C24 C23 C22 121.9(3) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C23 C24 C25 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 118.2(3) . . ?
C26 C25 H25 120.9 . . ?
C24 C25 H25 120.9 . . ?
C25 C26 C21 120.5(3) . . ?
C25 C26 C27 133.6(2) . . ?
C21 C26 C27 105.8(2) . . ?
C26 C27 C30 97.27(19) . . ?
C26 C27 C28 122.4(2) . . ?
C30 C27 C28 100.75(18) . . ?
C26 C27 C7 109.22(18) . . ?
C30 C27 C7 111.00(18) . . ?
C28 C27 C7 113.99(19) . . ?
C27 C28 C29 104.37(18) . . ?
C27 C28 H28A 110.9 . . ?
C29 C28 H28A 110.9 . . ?
C27 C28 H28B 110.9 . . ?
C29 C28 H28B 110.9 . . ?
H28A C28 H28B 108.9 . . ?
N4 C29 C31 110.37(19) . . ?
N4 C29 C28 104.23(19) . . ?
C31 C29 C28 110.01(19) . . ?
N4 C29 H29 110.7 . . ?
C31 C29 H29 110.7 . . ?
C28 C29 H29 110.7 . . ?
N3 C30 N4 131.7(2) . . ?
N3 C30 C27 118.1(2) . . ?
N4 C30 C27 109.2(2) . . ?
O7 C31 O8 125.3(2) . . ?
O7 C31 C29 125.6(2) . . ?
O8 C31 C29 109.0(2) . . ?
O8 C32 H32A 109.5 . . ?
O8 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O8 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O5 C33 O6 127.6(3) . . ?
O5 C33 N4 123.2(3) . . ?
O6 C33 N4 109.2(3) . . ?
O6 C34 C35 111.3(3) . . ?
O6 C34 H34A 109.4 . . ?
C35 C34 H34A 109.4 . . ?
O6 C34 H34B 109.4 . . ?
C35 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?
C36 C35 C40 117.8(4) . . ?
C36 C35 C34 120.2(4) . . ?
C40 C35 C34 122.0(4) . . ?
C35 C36 C37 121.8(6) . . ?
C35 C36 H36 119.1 . . ?
C37 C36 H36 119.1 . . ?
C38 C37 C36 121.7(7) . . ?
C38 C37 H37 119.1 . . ?
C36 C37 H37 119.1 . . ?
C37 C38 C39 121.3(5) . . ?
C37 C38 H38 119.4 . . ?
C39 C38 H38 119.4 . . ?
C38 C39 C40 118.7(4) . . ?
C38 C39 H39 120.6 . . ?
C40 C39 H39 120.6 . . ?
C35 C40 C39 118.6(4) . . ?
C35 C40 H40 120.7 . . ?
C39 C40 H40 120.7 . . ?
O1S C2S C1S 122.3(10) . . ?
O1S C2S O2S 121.9(10) . . ?
C1S C2S O2S 115.6(8) . . ?
C2S O2S C3S 120.3(7) . . ?
C2S C1S H1SA 109.5 . . ?
C2S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
C2S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
O2S C3S C4S 120.0(13) . . ?
O2S C3S H3SA 107.3 . . ?
C4S C3S H3SA 107.3 . . ?
O2S C3S H3SB 107.3 . . ?
C4S C3S H3SB 107.3 . . ?
H3SA C3S H3SB 106.9 . . ?
C3S C4S H4SA 109.5 . . ?
C3S C4S H4SB 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
C3S C4S H4SC 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C1 C2 -174.5(2) . . . . ?
C10 N1 C1 C6 -2.1(3) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
N1 C1 C2 C3 170.8(2) . . . . ?
C1 C2 C3 C4 -1.5(4) . . . . ?
C2 C3 C4 C5 2.2(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C1 -2.3(4) . . . . ?
C4 C5 C6 C7 179.5(2) . . . . ?
C2 C1 C6 C5 3.0(4) . . . . ?
N1 C1 C6 C5 -169.7(2) . . . . ?
C2 C1 C6 C7 -178.4(2) . . . . ?
N1 C1 C6 C7 8.9(3) . . . . ?
C5 C6 C7 C10 167.8(3) . . . . ?
C1 C6 C7 C10 -10.7(2) . . . . ?
C5 C6 C7 C8 61.5(4) . . . . ?
C1 C6 C7 C8 -116.9(2) . . . . ?
C5 C6 C7 C27 -75.2(3) . . . . ?
C1 C6 C7 C27 106.3(2) . . . . ?
C6 C7 C8 C9 136.2(2) . . . . ?
C10 C7 C8 C9 30.9(2) . . . . ?
C27 C7 C8 C9 -88.3(2) . . . . ?
C13 N2 C9 C11 -65.3(3) . . . . ?
C10 N2 C9 C11 117.5(2) . . . . ?
C13 N2 C9 C8 176.50(19) . . . . ?
C10 N2 C9 C8 -0.7(2) . . . . ?
C7 C8 C9 N2 -20.1(2) . . . . ?
C7 C8 C9 C11 -139.9(2) . . . . ?
C1 N1 C10 N2 158.7(2) . . . . ?
C1 N1 C10 C7 -6.1(3) . . . . ?
C13 N2 C10 N1 39.3(4) . . . . ?
C9 N2 C10 N1 -143.8(3) . . . . ?
C13 N2 C10 C7 -154.9(2) . . . . ?
C9 N2 C10 C7 22.0(2) . . . . ?
C6 C7 C10 N1 11.0(2) . . . . ?
C8 C7 C10 N1 134.7(2) . . . . ?
C27 C7 C10 N1 -104.8(2) . . . . ?
C6 C7 C10 N2 -156.93(18) . . . . ?
C8 C7 C10 N2 -33.2(2) . . . . ?
C27 C7 C10 N2 87.3(2) . . . . ?
C12 O4 C11 O3 -3.2(4) . . . . ?
C12 O4 C11 C9 174.7(2) . . . . ?
N2 C9 C11 O3 -9.4(3) . . . . ?
C8 C9 C11 O3 105.9(3) . . . . ?
N2 C9 C11 O4 172.60(18) . . . . ?
C8 C9 C11 O4 -72.1(2) . . . . ?
C14 O2 C13 O1 -2.0(4) . . . . ?
C14 O2 C13 N2 176.1(2) . . . . ?
C10 N2 C13 O1 -179.5(2) . . . . ?
C9 N2 C13 O1 4.0(3) . . . . ?
C10 N2 C13 O2 2.3(3) . . . . ?
C9 N2 C13 O2 -174.3(2) . . . . ?
C13 O2 C14 C15 -171.8(2) . . . . ?
O2 C14 C15 C16 97.6(3) . . . . ?
O2 C14 C15 C20 -82.7(3) . . . . ?
C20 C15 C16 C17 -1.4(4) . . . . ?
C14 C15 C16 C17 178.3(3) . . . . ?
C15 C16 C17 C18 0.9(5) . . . . ?
C16 C17 C18 C19 0.4(6) . . . . ?
C17 C18 C19 C20 -1.2(6) . . . . ?
C18 C19 C20 C15 0.7(5) . . . . ?
C16 C15 C20 C19 0.6(4) . . . . ?
C14 C15 C20 C19 -179.0(3) . . . . ?
C30 N3 C21 C22 -176.9(3) . . . . ?
C30 N3 C21 C26 -4.0(3) . . . . ?
C26 C21 C22 C23 -3.0(4) . . . . ?
N3 C21 C22 C23 169.3(2) . . . . ?
C21 C22 C23 C24 -1.4(4) . . . . ?
C22 C23 C24 C25 4.1(5) . . . . ?
C23 C24 C25 C26 -2.3(4) . . . . ?
C24 C25 C26 C21 -2.0(4) . . . . ?
C24 C25 C26 C27 176.5(3) . . . . ?
C22 C21 C26 C25 4.8(4) . . . . ?
N3 C21 C26 C25 -168.3(2) . . . . ?
C22 C21 C26 C27 -174.1(2) . . . . ?
N3 C21 C26 C27 12.8(3) . . . . ?
C25 C26 C27 C30 167.0(3) . . . . ?
C21 C26 C27 C30 -14.2(2) . . . . ?
C25 C26 C27 C28 59.4(4) . . . . ?
C21 C26 C27 C28 -121.9(2) . . . . ?
C25 C26 C27 C7 -77.7(3) . . . . ?
C21 C26 C27 C7 101.0(2) . . . . ?
C6 C7 C27 C26 78.0(2) . . . . ?
C10 C7 C27 C26 -174.15(19) . . . . ?
C8 C7 C27 C26 -62.3(2) . . . . ?
C6 C7 C27 C30 -175.89(19) . . . . ?
C10 C7 C27 C30 -68.0(2) . . . . ?
C8 C7 C27 C30 43.8(3) . . . . ?
C6 C7 C27 C28 -63.0(2) . . . . ?
C10 C7 C27 C28 44.9(3) . . . . ?
C8 C7 C27 C28 156.74(19) . . . . ?
C26 C27 C28 C29 137.8(2) . . . . ?
C30 C27 C28 C29 31.9(2) . . . . ?
C7 C27 C28 C29 -87.0(2) . . . . ?
C30 N4 C29 C31 122.6(2) . . . . ?
C33 N4 C29 C31 -63.7(3) . . . . ?
C30 N4 C29 C28 4.5(2) . . . . ?
C33 N4 C29 C28 178.3(2) . . . . ?
C27 C28 C29 N4 -23.5(2) . . . . ?
C27 C28 C29 C31 -141.8(2) . . . . ?
C21 N3 C30 N4 159.9(3) . . . . ?
C21 N3 C30 C27 -7.0(3) . . . . ?
C33 N4 C30 N3 36.1(4) . . . . ?
C29 N4 C30 N3 -151.0(3) . . . . ?
C33 N4 C30 C27 -156.1(2) . . . . ?
C29 N4 C30 C27 16.8(3) . . . . ?
C26 C27 C30 N3 13.9(3) . . . . ?
C28 C27 C30 N3 139.0(2) . . . . ?
C7 C27 C30 N3 -99.9(3) . . . . ?
C26 C27 C30 N4 -155.74(19) . . . . ?
C28 C27 C30 N4 -30.7(2) . . . . ?
C7 C27 C30 N4 90.4(2) . . . . ?
C32 O8 C31 O7 2.8(4) . . . . ?
C32 O8 C31 C29 -179.4(3) . . . . ?
N4 C29 C31 O7 -31.8(3) . . . . ?
C28 C29 C31 O7 82.7(3) . . . . ?
N4 C29 C31 O8 150.4(2) . . . . ?
C28 C29 C31 O8 -95.1(2) . . . . ?
C34 O6 C33 O5 -2.1(4) . . . . ?
C34 O6 C33 N4 177.2(2) . . . . ?
C30 N4 C33 O5 -179.2(3) . . . . ?
C29 N4 C33 O5 8.4(4) . . . . ?
C30 N4 C33 O6 1.4(4) . . . . ?
C29 N4 C33 O6 -170.9(2) . . . . ?
C33 O6 C34 C35 101.1(4) . . . . ?
O6 C34 C35 C36 49.4(6) . . . . ?
O6 C34 C35 C40 -131.9(4) . . . . ?
C40 C35 C36 C37 1.1(9) . . . . ?
C34 C35 C36 C37 179.8(6) . . . . ?
C35 C36 C37 C38 -1.8(12) . . . . ?
C36 C37 C38 C39 0.5(12) . . . . ?
C37 C38 C39 C40 1.4(9) . . . . ?
C36 C35 C40 C39 0.7(5) . . . . ?
C34 C35 C40 C39 -178.0(3) . . . . ?
C38 C39 C40 C35 -2.0(5) . . . . ?
O1S C2S O2S C3S -1.4(17) . . . . ?
C1S C2S O2S C3S 173.8(10) . . . . ?
C2S O2S C3S C4S 163.1(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.315
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.085
_database_code_depnum_ccdc_archive 'CCDC 1012367'
#######################################################################
#
#                 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_dm11689

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H25 N6 O8 S2'
_chemical_formula_weight         685.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   I-4

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

_cell_length_a                   21.9204(5)
_cell_length_b                   21.9204(5)
_cell_length_c                   14.1057(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6777.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3620
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      65.58

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2840
_exptl_absorpt_coefficient_mu    1.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4703
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            19057
_diffrn_reflns_av_R_equivalents  0.1803
_diffrn_reflns_av_sigmaI/netI    0.1717
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         64.93
_reflns_number_total             5494
_reflns_number_gt                4627
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1797P)²+2.1923P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5494
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0941
_refine_ls_wR_factor_ref         0.2633
_refine_ls_wR_factor_gt          0.2457
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.003

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 44 12 ' '
2 0.000 0.500 -0.166 451 130 ' '
3 0.500 0.000 0.157 451 130 ' '
4 0.500 0.500 0.000 12 3 ' '
5 0.500 0.500 0.500 44 12 ' '
6 0.000 0.000 0.500 12 3 ' '
_platon_squeeze_details          
;
;


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 0.24486(6) 0.84718(5) -0.00601(10) 0.0277(4) Uani 1 1 d . . .
S2 S 0.15478(9) 0.97050(7) 0.16673(12) 0.0495(5) Uani 1 1 d . . .
N1 N 0.27999(19) 0.91302(17) -0.0061(3) 0.0235(9) Uani 1 1 d . . .
N2 N 0.26963(18) 0.94401(18) -0.1695(3) 0.0237(9) Uani 1 1 d . . .
N3 N 0.1896(3) 1.0038(2) 0.0792(4) 0.0417(13) Uani 1 1 d . . .
N4 N 0.2611(3) 1.0692(2) 0.1614(4) 0.0450(14) Uani 1 1 d . . .
N5 N 0.3520(3) 0.7572(3) 0.0467(6) 0.0569(18) Uani 1 1 d . . .
N6 N 0.1326(6) 0.9684(5) 0.3863(6) 0.104(4) Uani 1 1 d . . .
O1 O 0.18701(19) 0.8574(2) -0.0489(4) 0.0423(11) Uani 1 1 d . . .
O2 O 0.2502(2) 0.82502(18) 0.0894(3) 0.0372(10) Uani 1 1 d . . .
O3 O 0.1989(3) 0.9415(3) 0.2226(4) 0.0709(18) Uani 1 1 d . . .
O4 O 0.1075(3) 0.9342(2) 0.1238(4) 0.0598(15) Uani 1 1 d . . .
O5 O 0.3836(2) 0.7988(2) 0.0745(5) 0.0653(18) Uani 1 1 d . . .
O6 O 0.3357(4) 0.7139(3) 0.1019(6) 0.087(2) Uani 1 1 d . . .
O7 O 0.1025(6) 0.9216(4) 0.3585(8) 0.123(4) Uani 1 1 d . . .
O8 O 0.1680(8) 0.9728(8) 0.4515(7) 0.179(7) Uani 1 1 d . . .
C1 C 0.2645(2) 1.0600(2) -0.0096(4) 0.0280(11) Uani 1 1 d . . .
C2 C 0.2032(2) 1.0624(2) -0.0643(4) 0.0261(11) Uani 1 1 d . . .
H2A H 0.1845 1.1024 -0.0586 0.031 Uiso 1 1 calc R . .
H2B H 0.2094 1.0534 -0.1310 0.031 Uiso 1 1 calc R . .
C3 C 0.1627(3) 1.0130(3) -0.0170(4) 0.0364(13) Uani 1 1 d . . .
H3A H 0.1208 1.0267 -0.0124 0.044 Uiso 1 1 calc R . .
H3B H 0.1637 0.9754 -0.0532 0.044 Uiso 1 1 calc R . .
C4 C 0.2407(3) 1.0416(3) 0.0870(4) 0.0352(13) Uani 1 1 d . . .
C5 C 0.2976(3) 1.1173(3) 0.0194(5) 0.0371(14) Uani 1 1 d . . .
C6 C 0.2985(4) 1.1164(3) 0.1217(5) 0.0499(19) Uani 1 1 d . . .
C7 C 0.3283(4) 1.1597(3) 0.1745(6) 0.058(2) Uani 1 1 d . . .
H7 H 0.3296 1.1579 0.2403 0.070 Uiso 1 1 calc R . .
C8 C 0.3573(4) 1.2081(3) 0.1221(7) 0.062(2) Uani 1 1 d . . .
H8 H 0.3795 1.2376 0.1544 0.074 Uiso 1 1 calc R . .
C9 C 0.3526(4) 1.2111(3) 0.0249(7) 0.056(2) Uani 1 1 d . . .
H9 H 0.3689 1.2447 -0.0065 0.068 Uiso 1 1 calc R . .
C10 C 0.3245(3) 1.1657(3) -0.0279(5) 0.0415(15) Uani 1 1 d . . .
H10 H 0.3236 1.1678 -0.0938 0.050 Uiso 1 1 calc R . .
C11 C 0.1193(3) 1.0301(3) 0.2310(5) 0.0434(15) Uani 1 1 d . . .
H11 H 0.0780 1.0144 0.2205 0.052 Uiso 1 1 calc R . .
C12 C 0.1161(4) 1.0236(4) 0.3324(6) 0.059(2) Uani 1 1 d . . .
C13 C 0.0956(4) 1.0719(4) 0.3885(6) 0.062(2) Uani 1 1 d . . .
H13 H 0.0947 1.0688 0.4542 0.074 Uiso 1 1 calc R . .
C14 C 0.0766(6) 1.1256(4) 0.3425(8) 0.085(3) Uani 1 1 d . . .
H14 H 0.0583 1.1571 0.3763 0.101 Uiso 1 1 calc R . .
C15 C 0.0854(6) 1.1302(4) 0.2487(9) 0.091(4) Uani 1 1 d . . .
H15 H 0.0758 1.1671 0.2198 0.109 Uiso 1 1 calc R . .
C16 C 0.1079(5) 1.0834(4) 0.1916(7) 0.076(3) Uani 1 1 d . . .
H16 H 0.1148 1.0896 0.1272 0.092 Uiso 1 1 calc R . .
C17 C 0.3122(2) 1.0130(2) -0.0527(4) 0.0228(10) Uani 1 1 d . . .
C18 C 0.3576(3) 0.9878(2) 0.0212(4) 0.0283(11) Uani 1 1 d . . .
H18A H 0.3951 0.9747 -0.0091 0.034 Uiso 1 1 calc R . .
H18B H 0.3672 1.0186 0.0683 0.034 Uiso 1 1 calc R . .
C19 C 0.3245(3) 0.9333(3) 0.0671(4) 0.0325(12) Uani 1 1 d . . .
H19A H 0.3531 0.9009 0.0822 0.039 Uiso 1 1 calc R . .
H19B H 0.3037 0.9457 0.1247 0.039 Uiso 1 1 calc R . .
C20 C 0.2809(2) 0.9528(2) -0.0803(4) 0.0205(10) Uani 1 1 d . . .
C21 C 0.3315(2) 1.0316(2) -0.1517(4) 0.0255(11) Uani 1 1 d . . .
C22 C 0.2999(2) 0.9948(2) -0.2154(4) 0.0221(10) Uani 1 1 d . . .
C23 C 0.3051(2) 1.0017(3) -0.3118(4) 0.0299(11) Uani 1 1 d . . .
H23 H 0.2834 0.9773 -0.3539 0.036 Uiso 1 1 calc R . .
C24 C 0.3445(3) 1.0473(3) -0.3433(5) 0.0395(14) Uani 1 1 d . . .
H24 H 0.3482 1.0544 -0.4081 0.047 Uiso 1 1 calc R . .
C25 C 0.3780(3) 1.0820(3) -0.2819(6) 0.0479(17) Uani 1 1 d . . .
H25 H 0.4049 1.1110 -0.3057 0.057 Uiso 1 1 calc R . .
C26 C 0.3724(3) 1.0748(3) -0.1855(5) 0.0357(13) Uani 1 1 d . . .
H26 H 0.3955 1.0982 -0.1439 0.043 Uiso 1 1 calc R . .
C27 C 0.2847(3) 0.7978(2) -0.0821(4) 0.0326(13) Uani 1 1 d . . .
C28 C 0.3299(3) 0.7575(3) -0.0503(6) 0.0413(15) Uani 1 1 d . . .
C29 C 0.3557(4) 0.7155(3) -0.1088(8) 0.064(3) Uani 1 1 d . . .
H29 H 0.3840 0.6879 -0.0849 0.077 Uiso 1 1 calc R . .
C30 C 0.3398(5) 0.7136(4) -0.2041(9) 0.074(3) Uani 1 1 d . . .
H30 H 0.3587 0.6859 -0.2444 0.089 Uiso 1 1 calc R . .
C31 C 0.2960(5) 0.7526(4) -0.2389(6) 0.073(3) Uani 1 1 d . . .
H31 H 0.2851 0.7510 -0.3026 0.087 Uiso 1 1 calc R . .
C32 C 0.2669(3) 0.7961(3) -0.1765(4) 0.0416(16) Uani 1 1 d . . .
H32 H 0.2368 0.8223 -0.1991 0.050 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
S1 O1 1.423(4) . ?
S1 O2 1.436(4) . ?
S1 N1 1.636(4) . ?
S1 C27 1.758(6) . ?
S2 O3 1.401(6) . ?
S2 O4 1.440(6) . ?
S2 N3 1.624(5) . ?
S2 C11 1.769(6) . ?
N1 C20 1.362(7) . ?
N1 C19 1.489(7) . ?
N2 C20 1.297(7) . ?
N2 C22 1.449(6) . ?
N3 C4 1.399(9) . ?
N3 C3 1.493(9) . ?
N4 C4 1.292(9) . ?
N4 C6 1.435(11) . ?
N5 O5 1.210(8) . ?
N5 O6 1.278(10) . ?
N5 C28 1.452(12) . ?
N6 O8 1.207(19) . ?
N6 O7 1.280(17) . ?
N6 C12 1.474(13) . ?
C1 C5 1.505(8) . ?
C1 C4 1.515(8) . ?
C1 C2 1.552(7) . ?
C1 C17 1.590(7) . ?
C2 C3 1.551(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C10 1.385(10) . ?
C5 C6 1.445(10) . ?
C6 C7 1.369(10) . ?
C7 C8 1.442(14) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(9) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.318(11) . ?
C11 C12 1.440(11) . ?
C11 H11 0.9800 . ?
C12 C13 1.396(11) . ?
C13 C14 1.407(14) . ?
C13 H13 0.9300 . ?
C14 C15 1.341(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.397(13) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C21 1.515(7) . ?
C17 C20 1.538(6) . ?
C17 C18 1.543(7) . ?
C18 C19 1.540(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C21 C26 1.390(8) . ?
C21 C22 1.391(8) . ?
C22 C23 1.374(7) . ?
C23 C24 1.395(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.366(11) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(11) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C32 1.388(9) . ?
C27 C28 1.400(10) . ?
C28 C29 1.359(11) . ?
C29 C30 1.389(17) . ?
C29 H29 0.9300 . ?
C30 C31 1.377(16) . ?
C30 H30 0.9300 . ?
C31 C32 1.446(11) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 121.6(3) . . ?
O1 S1 N1 106.3(2) . . ?
O2 S1 N1 105.1(3) . . ?
O1 S1 C27 106.3(3) . . ?
O2 S1 C27 108.9(3) . . ?
N1 S1 C27 108.0(2) . . ?
O3 S2 O4 118.9(4) . . ?
O3 S2 N3 107.9(3) . . ?
O4 S2 N3 105.4(3) . . ?
O3 S2 C11 110.5(4) . . ?
O4 S2 C11 107.9(4) . . ?
N3 S2 C11 105.4(3) . . ?
C20 N1 C19 109.4(4) . . ?
C20 N1 S1 124.9(4) . . ?
C19 N1 S1 124.9(4) . . ?
C20 N2 C22 103.5(4) . . ?
C4 N3 C3 107.9(5) . . ?
C4 N3 S2 125.6(5) . . ?
C3 N3 S2 124.5(5) . . ?
C4 N4 C6 102.7(6) . . ?
O5 N5 O6 121.6(8) . . ?
O5 N5 C28 119.5(7) . . ?
O6 N5 C28 118.9(6) . . ?
O8 N6 O7 129.0(13) . . ?
O8 N6 C12 119.0(14) . . ?
O7 N6 C12 111.9(11) . . ?
C5 C1 C4 98.4(5) . . ?
C5 C1 C2 121.6(4) . . ?
C4 C1 C2 99.1(4) . . ?
C5 C1 C17 109.2(4) . . ?
C4 C1 C17 113.4(4) . . ?
C2 C1 C17 113.6(4) . . ?
C3 C2 C1 105.0(4) . . ?
C3 C2 H2A 110.7 . . ?
C1 C2 H2A 110.7 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.8 . . ?
N3 C3 C2 105.1(5) . . ?
N3 C3 H3A 110.7 . . ?
C2 C3 H3A 110.7 . . ?
N3 C3 H3B 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
N4 C4 N3 128.3(6) . . ?
N4 C4 C1 119.1(6) . . ?
N3 C4 C1 111.3(5) . . ?
C10 C5 C6 119.0(6) . . ?
C10 C5 C1 135.5(6) . . ?
C6 C5 C1 105.5(6) . . ?
C7 C6 N4 124.0(8) . . ?
C7 C6 C5 122.7(8) . . ?
N4 C6 C5 113.0(6) . . ?
C6 C7 C8 116.2(8) . . ?
C6 C7 H7 121.9 . . ?
C8 C7 H7 121.9 . . ?
C9 C8 C7 120.9(7) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 122.2(9) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C5 C10 C9 118.7(7) . . ?
C5 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C16 C11 C12 119.9(7) . . ?
C16 C11 S2 121.4(6) . . ?
C12 C11 S2 117.3(5) . . ?
C16 C11 H11 94.1 . . ?
C12 C11 H11 94.1 . . ?
S2 C11 H11 94.1 . . ?
C13 C12 C11 120.2(7) . . ?
C13 C12 N6 114.2(8) . . ?
C11 C12 N6 125.6(7) . . ?
C12 C13 C14 118.0(8) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
C15 C14 C13 118.4(7) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C16 124.4(9) . . ?
C14 C15 H15 117.8 . . ?
C16 C15 H15 117.8 . . ?
C11 C16 C15 118.4(9) . . ?
C11 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C21 C17 C20 97.0(4) . . ?
C21 C17 C18 122.6(4) . . ?
C20 C17 C18 98.8(4) . . ?
C21 C17 C1 111.2(4) . . ?
C20 C17 C1 111.1(4) . . ?
C18 C17 C1 113.4(4) . . ?
C19 C18 C17 104.9(4) . . ?
C19 C18 H18A 110.8 . . ?
C17 C18 H18A 110.8 . . ?
C19 C18 H18B 110.8 . . ?
C17 C18 H18B 110.8 . . ?
H18A C18 H18B 108.8 . . ?
N1 C19 C18 104.4(4) . . ?
N1 C19 H19A 110.9 . . ?
C18 C19 H19A 110.9 . . ?
N1 C19 H19B 110.9 . . ?
C18 C19 H19B 110.9 . . ?
H19A C19 H19B 108.9 . . ?
N2 C20 N1 130.4(4) . . ?
N2 C20 C17 117.2(5) . . ?
N1 C20 C17 111.1(4) . . ?
C26 C21 C22 119.6(5) . . ?
C26 C21 C17 132.8(5) . . ?
C22 C21 C17 107.5(4) . . ?
C23 C22 C21 122.3(5) . . ?
C23 C22 N2 124.4(5) . . ?
C21 C22 N2 112.6(4) . . ?
C22 C23 C24 116.5(6) . . ?
C22 C23 H23 121.8 . . ?
C24 C23 H23 121.8 . . ?
C25 C24 C23 122.0(6) . . ?
C25 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
C24 C25 C26 121.0(6) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C21 118.4(6) . . ?
C25 C26 H26 120.8 . . ?
C21 C26 H26 120.8 . . ?
C32 C27 C28 119.4(6) . . ?
C32 C27 S1 117.5(5) . . ?
C28 C27 S1 123.0(5) . . ?
C29 C28 C27 121.7(8) . . ?
C29 C28 N5 115.6(8) . . ?
C27 C28 N5 122.7(6) . . ?
C28 C29 C30 120.3(9) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C31 C30 C29 120.1(7) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 120.0(8) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 118.5(8) . . ?
C27 C32 H32 120.8 . . ?
C31 C32 H32 120.8 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        64.93
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.801
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.118
_database_code_depnum_ccdc_archive 'CCDC 1012368'
#######################################################################
#
#                 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_cu_dm11686_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H28 Cl4 N6 O8 S2'
_chemical_formula_weight         854.54

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

_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                   11.2563(3)
_cell_length_b                   13.0650(3)
_cell_length_c                   14.4176(4)
_cell_angle_alpha                87.383(2)
_cell_angle_beta                 69.786(2)
_cell_angle_gamma                66.9080(10)
_cell_volume                     1820.34(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    132(2)
_cell_measurement_reflns_used    4162
_cell_measurement_theta_min      4.57
_cell_measurement_theta_max      65.51

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             876
_exptl_absorpt_coefficient_mu    4.554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5483
_exptl_absorpt_correction_T_max  0.9144
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      132(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            11661
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.57
_diffrn_reflns_theta_max         65.00
_reflns_number_total             5898
_reflns_number_gt                5060
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0838P)²+0.4413P] 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         5898
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.02690(6) 0.24270(5) 0.35206(4) 0.01372(17) Uani 1 1 d . . .
S2 S 0.47542(6) 0.76209(5) 0.14519(4) 0.01377(17) Uani 1 1 d . . .
N1 N 0.9092(2) 0.36093(16) 0.34177(16) 0.0149(4) Uani 1 1 d . . .
N2 N 0.7431(2) 0.30119(18) 0.31615(16) 0.0166(5) Uani 1 1 d . . .
N3 N 0.5972(2) 0.64594(17) 0.15354(16) 0.0149(4) Uani 1 1 d . . .
N4 N 0.7640(2) 0.70727(17) 0.17755(17) 0.0166(5) Uani 1 1 d . . .
N6 N 1.0662(2) 0.26309(19) 0.55787(17) 0.0193(5) Uani 1 1 d . . .
N7 N 0.4138(2) 0.72821(19) -0.05198(18) 0.0223(5) Uani 1 1 d . . .
O1 O 1.13664(18) 0.26765(15) 0.35776(14) 0.0197(4) Uani 1 1 d . . .
O2 O 1.05082(18) 0.16390(15) 0.27530(13) 0.0194(4) Uani 1 1 d . . .
O3 O 0.35979(18) 0.73737(15) 0.15276(14) 0.0201(4) Uani 1 1 d . . .
O4 O 0.46177(18) 0.84462(14) 0.21461(13) 0.0178(4) Uani 1 1 d . . .
O5 O 1.0143(2) 0.36453(16) 0.55964(16) 0.0272(5) Uani 1 1 d . . .
O6 O 1.1774(2) 0.20951(19) 0.56659(18) 0.0357(5) Uani 1 1 d . . .
O7 O 0.4611(2) 0.62955(17) -0.03817(17) 0.0323(5) Uani 1 1 d . . .
O8 O 0.3083(2) 0.77402(19) -0.07113(19) 0.0370(5) Uani 1 1 d . . .
C1 C 0.7980(3) 0.3708(2) 0.31517(18) 0.0138(5) Uani 1 1 d . . .
C2 C 0.8840(3) 0.4723(2) 0.3874(2) 0.0174(5) Uani 1 1 d . . .
H2A H 0.9572 0.4978 0.3489 0.021 Uiso 1 1 calc R . .
H2B H 0.8803 0.4683 0.4570 0.021 Uiso 1 1 calc R . .
C3 C 0.7414(3) 0.5518(2) 0.38235(19) 0.0171(5) Uani 1 1 d . . .
H3A H 0.6668 0.5641 0.4477 0.021 Uiso 1 1 calc R . .
H3B H 0.7422 0.6250 0.3622 0.021 Uiso 1 1 calc R . .
C4 C 0.7202(3) 0.4916(2) 0.30414(19) 0.0145(5) Uani 1 1 d . . .
C5 C 0.5814(3) 0.4863(2) 0.32274(19) 0.0165(5) Uani 1 1 d . . .
C6 C 0.6065(3) 0.3719(2) 0.31852(19) 0.0170(5) Uani 1 1 d . . .
C7 C 0.5026(3) 0.3364(2) 0.3265(2) 0.0222(6) Uani 1 1 d . . .
H7 H 0.5204 0.2590 0.3228 0.027 Uiso 1 1 calc R . .
C8 C 0.3712(3) 0.4178(3) 0.3400(2) 0.0256(6) Uani 1 1 d . . .
H8 H 0.2990 0.3957 0.3433 0.031 Uiso 1 1 calc R . .
C9 C 0.3443(3) 0.5313(3) 0.3486(2) 0.0259(6) Uani 1 1 d . . .
H9 H 0.2533 0.5852 0.3599 0.031 Uiso 1 1 calc R . .
C10 C 0.4489(3) 0.5671(2) 0.3411(2) 0.0212(6) Uani 1 1 d . . .
H10 H 0.4298 0.6445 0.3482 0.025 Uiso 1 1 calc R . .
C11 C 0.9518(2) 0.19600(19) 0.46612(19) 0.0143(5) Uani 1 1 d . . .
C12 C 0.8666(3) 0.1421(2) 0.4680(2) 0.0190(5) Uani 1 1 d . . .
H12 H 0.8435 0.1374 0.4114 0.023 Uiso 1 1 calc R . .
C13 C 0.8151(3) 0.0952(2) 0.5530(2) 0.0244(6) Uani 1 1 d . . .
H13 H 0.7546 0.0604 0.5548 0.029 Uiso 1 1 calc R . .
C14 C 0.8510(3) 0.0985(2) 0.6352(2) 0.0250(6) Uani 1 1 d . . .
H14 H 0.8173 0.0643 0.6922 0.030 Uiso 1 1 calc R . .
C15 C 0.9364(3) 0.1520(2) 0.6339(2) 0.0221(6) Uani 1 1 d . . .
H15 H 0.9620 0.1545 0.6898 0.027 Uiso 1 1 calc R . .
C16 C 0.9835(3) 0.2014(2) 0.5508(2) 0.0161(5) Uani 1 1 d . . .
C18 C 0.7088(3) 0.6371(2) 0.17940(18) 0.0141(5) Uani 1 1 d . . .
C19 C 0.6234(3) 0.5338(2) 0.10956(19) 0.0164(5) Uani 1 1 d . . .
H19A H 0.6256 0.5368 0.0403 0.020 Uiso 1 1 calc R . .
H19B H 0.5510 0.5079 0.1491 0.020 Uiso 1 1 calc R . .
C20 C 0.7658(3) 0.4559(2) 0.11333(19) 0.0162(5) Uani 1 1 d . . .
H20A H 0.8395 0.4444 0.0476 0.019 Uiso 1 1 calc R . .
H20B H 0.7663 0.3822 0.1332 0.019 Uiso 1 1 calc R . .
C21 C 0.7876(2) 0.51646(19) 0.19164(18) 0.0128(5) Uani 1 1 d . . .
C22 C 0.9255(3) 0.5225(2) 0.17352(19) 0.0161(5) Uani 1 1 d . . .
C23 C 1.0567(3) 0.4422(2) 0.1566(2) 0.0207(6) Uani 1 1 d . . .
H23 H 1.0761 0.3648 0.1486 0.025 Uiso 1 1 calc R . .
C24 C 1.1607(3) 0.4782(2) 0.1514(2) 0.0238(6) Uani 1 1 d . . .
H24 H 1.2512 0.4242 0.1418 0.029 Uiso 1 1 calc R . .
C25 C 1.1341(3) 0.5910(3) 0.1600(2) 0.0249(6) Uani 1 1 d . . .
H25 H 1.2061 0.6130 0.1577 0.030 Uiso 1 1 calc R . .
C26 C 1.0028(3) 0.6728(2) 0.1721(2) 0.0208(6) Uani 1 1 d . . .
H26 H 0.9847 0.7502 0.1764 0.025 Uiso 1 1 calc R . .
C27 C 0.9001(3) 0.6368(2) 0.17773(19) 0.0163(5) Uani 1 1 d . . .
C28 C 0.5380(2) 0.8023(2) 0.02472(19) 0.0149(5) Uani 1 1 d . . .
C29 C 0.6266(3) 0.8567(2) 0.0116(2) 0.0180(5) Uani 1 1 d . . .
H29 H 0.6585 0.8632 0.0631 0.022 Uiso 1 1 calc R . .
C30 C 0.6680(3) 0.9012(2) -0.0775(2) 0.0225(6) Uani 1 1 d . . .
H30 H 0.7302 0.9365 -0.0870 0.027 Uiso 1 1 calc R . .
C31 C 0.6204(3) 0.8948(2) -0.1521(2) 0.0221(6) Uani 1 1 d . . .
H31 H 0.6479 0.9273 -0.2119 0.026 Uiso 1 1 calc R . .
C32 C 0.5323(3) 0.8411(2) -0.1401(2) 0.0229(6) Uani 1 1 d . . .
H32 H 0.4982 0.8368 -0.1909 0.027 Uiso 1 1 calc R . .
C33 C 0.4949(3) 0.7939(2) -0.0528(2) 0.0178(5) Uani 1 1 d . . .
C34 C 0.0413(3) 0.9135(2) 0.8831(2) 0.0236(6) Uani 1 1 d . . .
H34A H 0.1101 0.9276 0.9026 0.028 Uiso 1 1 calc R . .
H34B H 0.0900 0.8694 0.8171 0.028 Uiso 1 1 calc R . .
C35 C 0.3965(3) 0.0558(2) 0.6647(2) 0.0271(6) Uani 1 1 d . . .
H35A H 0.3993 0.1018 0.7160 0.032 Uiso 1 1 calc R . .
H35B H 0.3726 0.1045 0.6135 0.032 Uiso 1 1 calc R . .
Cl1 Cl -0.08620(7) 1.04269(5) 0.87464(5) 0.02559(18) Uani 1 1 d . . .
Cl2 Cl -0.03135(7) 0.83540(6) 0.97071(6) 0.0312(2) Uani 1 1 d . . .
Cl3 Cl 0.56066(7) -0.05391(6) 0.60947(5) 0.02891(19) Uani 1 1 d . . .
Cl4 Cl 0.26902(8) 0.00341(8) 0.71943(9) 0.0577(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4240(18) . ?
S1 O2 1.4276(18) . ?
S1 N1 1.635(2) . ?
S1 C11 1.773(2) . ?
S2 O3 1.4278(18) . ?
S2 O4 1.4319(18) . ?
S2 N3 1.632(2) . ?
S2 C28 1.775(3) . ?
N1 C1 1.389(3) . ?
N1 C2 1.505(3) . ?
N2 C1 1.282(3) . ?
N2 C6 1.439(3) . ?
N3 C18 1.391(3) . ?
N3 C19 1.501(3) . ?
N4 C18 1.288(3) . ?
N4 C27 1.446(3) . ?
N6 O5 1.218(3) . ?
N6 O6 1.219(3) . ?
N6 C16 1.479(3) . ?
N7 O7 1.223(3) . ?
N7 O8 1.224(3) . ?
N7 C33 1.476(3) . ?
C1 C4 1.507(3) . ?
C2 C3 1.557(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.537(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.520(3) . ?
C4 C21 1.615(4) . ?
C5 C10 1.388(4) . ?
C5 C6 1.408(3) . ?
C6 C7 1.388(4) . ?
C7 C8 1.394(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.387(3) . ?
C11 C16 1.398(4) . ?
C12 C13 1.391(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(4) . ?
C15 H15 0.9500 . ?
C18 C21 1.513(3) . ?
C19 C20 1.544(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.545(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.516(3) . ?
C22 C23 1.379(4) . ?
C22 C27 1.407(4) . ?
C23 C24 1.402(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.399(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(4) . ?
C26 H26 0.9500 . ?
C28 C33 1.387(4) . ?
C28 C29 1.395(3) . ?
C29 C30 1.391(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.376(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.387(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.381(4) . ?
C32 H32 0.9500 . ?
C34 Cl1 1.768(3) . ?
C34 Cl2 1.769(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 Cl4 1.758(3) . ?
C35 Cl3 1.764(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.88(11) . . ?
O1 S1 N1 106.56(10) . . ?
O2 S1 N1 106.50(11) . . ?
O1 S1 C11 108.76(12) . . ?
O2 S1 C11 106.36(11) . . ?
N1 S1 C11 107.07(11) . . ?
O3 S2 O4 120.43(11) . . ?
O3 S2 N3 107.27(10) . . ?
O4 S2 N3 106.18(11) . . ?
O3 S2 C28 108.36(12) . . ?
O4 S2 C28 106.89(11) . . ?
N3 S2 C28 107.02(11) . . ?
C1 N1 C2 109.7(2) . . ?
C1 N1 S1 124.94(16) . . ?
C2 N1 S1 123.24(17) . . ?
C1 N2 C6 103.1(2) . . ?
C18 N3 C19 109.35(19) . . ?
C18 N3 S2 125.99(17) . . ?
C19 N3 S2 123.04(17) . . ?
C18 N4 C27 103.1(2) . . ?
O5 N6 O6 125.0(2) . . ?
O5 N6 C16 117.1(2) . . ?
O6 N6 C16 117.8(2) . . ?
O7 N7 O8 124.3(2) . . ?
O7 N7 C33 117.6(2) . . ?
O8 N7 C33 117.9(2) . . ?
N2 C1 N1 130.6(2) . . ?
N2 C1 C4 118.7(2) . . ?
N1 C1 C4 109.5(2) . . ?
N1 C2 C3 103.73(19) . . ?
N1 C2 H2A 111.0 . . ?
C3 C2 H2A 111.0 . . ?
N1 C2 H2B 111.0 . . ?
C3 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C4 C3 C2 105.16(19) . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C1 C4 C5 97.48(19) . . ?
C1 C4 C3 101.3(2) . . ?
C5 C4 C3 120.7(2) . . ?
C1 C4 C21 109.1(2) . . ?
C5 C4 C21 111.7(2) . . ?
C3 C4 C21 113.96(19) . . ?
C10 C5 C6 120.4(2) . . ?
C10 C5 C4 133.5(2) . . ?
C6 C5 C4 106.1(2) . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 N2 125.4(2) . . ?
C5 C6 N2 112.8(2) . . ?
C6 C7 C8 117.8(2) . . ?
C6 C7 H7 121.1 . . ?
C8 C7 H7 121.1 . . ?
C7 C8 C9 120.9(2) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C10 121.2(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C5 C10 C9 118.0(2) . . ?
C5 C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
C12 C11 C16 118.5(2) . . ?
C12 C11 S1 117.7(2) . . ?
C16 C11 S1 123.60(18) . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.7(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 119.2(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C11 121.8(2) . . ?
C15 C16 N6 115.9(2) . . ?
C11 C16 N6 122.3(2) . . ?
N4 C18 N3 130.9(2) . . ?
N4 C18 C21 118.3(2) . . ?
N3 C18 C21 109.64(19) . . ?
N3 C19 C20 104.21(19) . . ?
N3 C19 H19A 110.9 . . ?
C20 C19 H19A 110.9 . . ?
N3 C19 H19B 110.9 . . ?
C20 C19 H19B 110.9 . . ?
H19A C19 H19B 108.9 . . ?
C19 C20 C21 105.30(19) . . ?
C19 C20 H20A 110.7 . . ?
C21 C20 H20A 110.7 . . ?
C19 C20 H20B 110.7 . . ?
C21 C20 H20B 110.7 . . ?
H20A C20 H20B 108.8 . . ?
C18 C21 C22 97.74(18) . . ?
C18 C21 C20 100.4(2) . . ?
C22 C21 C20 121.3(2) . . ?
C18 C21 C4 109.5(2) . . ?
C22 C21 C4 111.6(2) . . ?
C20 C21 C4 113.76(19) . . ?
C23 C22 C27 120.5(2) . . ?
C23 C22 C21 133.2(2) . . ?
C27 C22 C21 106.3(2) . . ?
C22 C23 C24 118.0(2) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
C25 C24 C23 121.4(3) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C24 C25 C26 120.8(2) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C27 C26 C25 117.6(2) . . ?
C27 C26 H26 121.2 . . ?
C25 C26 H26 121.2 . . ?
C26 C27 C22 121.5(2) . . ?
C26 C27 N4 125.6(2) . . ?
C22 C27 N4 112.6(2) . . ?
C33 C28 C29 118.3(2) . . ?
C33 C28 S2 124.97(19) . . ?
C29 C28 S2 116.4(2) . . ?
C30 C29 C28 119.6(3) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C31 C30 C29 121.1(2) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 C32 119.9(3) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C33 C32 C31 118.8(3) . . ?
C33 C32 H32 120.6 . . ?
C31 C32 H32 120.6 . . ?
C32 C33 C28 122.3(2) . . ?
C32 C33 N7 114.4(2) . . ?
C28 C33 N7 123.2(2) . . ?
Cl1 C34 Cl2 111.73(15) . . ?
Cl1 C34 H34A 109.3 . . ?
Cl2 C34 H34A 109.3 . . ?
Cl1 C34 H34B 109.3 . . ?
Cl2 C34 H34B 109.3 . . ?
H34A C34 H34B 107.9 . . ?
Cl4 C35 Cl3 111.09(15) . . ?
Cl4 C35 H35A 109.4 . . ?
Cl3 C35 H35A 109.4 . . ?
Cl4 C35 H35B 109.4 . . ?
Cl3 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        65.00
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.101
_database_code_depnum_ccdc_archive 'CCDC 1012369'
