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

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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H37 Ca2 N5 O15 S2'
_chemical_formula_weight         815.90

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'
Ca Ca 0.2262 0.3064 '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           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                   14.4784(15)
_cell_length_b                   13.8157(15)
_cell_length_c                   19.3044(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.539(2)
_cell_angle_gamma                90.00
_cell_volume                     3737.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2110
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      22.41

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1704
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            10847
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0758
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         25.27
_reflns_number_total             3392
_reflns_number_gt                1996
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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)+(0.0350P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3392
_refine_ls_number_parameters     341
_refine_ls_number_restraints     451
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.256
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ca1 Ca 0.09796(6) 0.45358(7) 0.19342(5) 0.0441(3) Uani 1 1 d . . .
S1 S 0.05363(9) 0.24547(11) 0.07124(7) 0.0530(4) Uani 1 1 d . . .
O1 O 0.0342(3) 0.4563(3) -0.15127(19) 0.0725(11) Uani 1 1 d . . .
O2 O 0.1469(3) 0.4435(3) -0.20887(17) 0.0751(11) Uani 1 1 d . . .
O3 O 0.0570(7) 0.3378(8) 0.1004(5) 0.062(3) Uani 0.614(8) 1 d PU A 1
O4 O 0.0445(5) 0.1693(6) 0.1258(5) 0.085(3) Uani 0.614(8) 1 d PU A 1
O5 O -0.0125(5) 0.2300(5) 0.0059(3) 0.067(2) Uani 0.614(8) 1 d PU A 1
O3B O 0.0882(13) 0.3127(13) 0.1301(8) 0.066(4) Uani 0.386(8) 1 d PU A 2
O4B O 0.0544(8) 0.1510(7) 0.0834(6) 0.059(3) Uani 0.386(8) 1 d PU A 2
O5B O -0.0442(7) 0.2861(11) 0.0274(7) 0.087(4) Uani 0.386(8) 1 d PU A 2
C1 C 0.1722(5) 0.2195(5) 0.0614(3) 0.0382(19) Uani 0.614(8) 1 d PDU . 1
C2 C 0.2040(7) 0.2613(9) 0.0046(5) 0.034(3) Uani 0.614(8) 1 d PDU . 1
C3 C 0.1446(7) 0.3242(6) -0.0443(4) 0.047(2) Uani 0.614(8) 1 d PDU A 1
H3A H 0.0865 0.3418 -0.0357 0.056 Uiso 0.614(8) 1 calc PR A 1
C5 C 0.2667(6) 0.3409(6) -0.1121(5) 0.044(2) Uani 0.614(8) 1 d PDU . 1
C1B C 0.1278(8) 0.2778(8) 0.0102(5) 0.034(3) Uani 0.386(8) 1 d PDU A 2
C2B C 0.0973(9) 0.3378(10) -0.0522(6) 0.039(3) Uani 0.386(8) 1 d PDU A 2
H2BA H 0.0362 0.3640 -0.0636 0.047 Uiso 0.386(8) 1 calc PR A 2
C3B C 0.2228(10) 0.2418(15) 0.0253(7) 0.035(4) Uani 0.386(8) 1 d PDU . 2
C5B C 0.2450(9) 0.3143(9) -0.0879(6) 0.036(3) Uani 0.386(8) 1 d PDU . 2
C4 C 0.1661(4) 0.3593(3) -0.1011(2) 0.0535(13) Uani 1 1 d D . .
C6 C 0.1116(4) 0.4248(3) -0.1582(2) 0.0481(12) Uani 1 1 d . A .
O6 O 0.1786(3) 0.5280(3) 0.1195(2) 0.0924(14) Uani 1 1 d . A .
N1 N 0.2363(4) 0.5702(4) 0.0263(3) 0.0902(17) Uani 1 1 d . A .
C7 C 0.1716(5) 0.5642(5) 0.0603(4) 0.092(2) Uani 1 1 d . . .
H7A H 0.1124 0.5903 0.0377 0.111 Uiso 1 1 calc R A .
C8 C 0.3241(6) 0.5227(7) 0.0515(5) 0.146(4) Uani 1 1 d . . .
H8A H 0.3263 0.4934 0.0969 0.219 Uiso 1 1 calc R A .
H8B H 0.3751 0.5686 0.0567 0.219 Uiso 1 1 calc R . .
H8C H 0.3309 0.4736 0.0179 0.219 Uiso 1 1 calc R . .
C9 C 0.2224(6) 0.6187(6) -0.0432(3) 0.150(4) Uani 1 1 d . . .
H9A H 0.1607 0.6490 -0.0556 0.224 Uiso 1 1 calc R A .
H9B H 0.2263 0.5720 -0.0791 0.224 Uiso 1 1 calc R . .
H9C H 0.2709 0.6669 -0.0403 0.224 Uiso 1 1 calc R . .
O7 O 0.2386(4) 0.3768(4) 0.2501(3) 0.126(2) Uani 1 1 d . A .
N2 N 0.3844(4) 0.3525(5) 0.3198(3) 0.0948(18) Uani 1 1 d . . .
C10 C 0.3101(7) 0.4097(7) 0.2914(5) 0.090(3) Uani 0.766(10) 1 d PU A 1
H10A H 0.3128 0.4751 0.3031 0.108 Uiso 0.766(10) 1 calc PR A 1
C11 C 0.4649(8) 0.3985(8) 0.3754(6) 0.123(4) Uani 0.766(10) 1 d PU A 1
H11A H 0.4426 0.4570 0.3925 0.184 Uiso 0.766(10) 1 calc PR A 1
H11B H 0.5167 0.4131 0.3543 0.184 Uiso 0.766(10) 1 calc PR A 1
H11C H 0.4864 0.3544 0.4146 0.184 Uiso 0.766(10) 1 calc PR A 1
C12 C 0.3836(10) 0.2541(8) 0.3136(7) 0.162(6) Uani 0.766(10) 1 d PU A 1
H12A H 0.3201 0.2305 0.3097 0.242 Uiso 0.766(10) 1 calc PR A 1
H12B H 0.4263 0.2265 0.3551 0.242 Uiso 0.766(10) 1 calc PR A 1
H12C H 0.4037 0.2362 0.2716 0.242 Uiso 0.766(10) 1 calc PR A 1
C10B C 0.313(3) 0.327(3) 0.263(2) 0.127(9) Uani 0.234(10) 1 d PU A 2
H10B H 0.3193 0.2744 0.2344 0.153 Uiso 0.234(10) 1 calc PR A 2
C11B C 0.473(3) 0.279(3) 0.313(2) 0.145(11) Uani 0.234(10) 1 d PU A 2
H11D H 0.4477 0.2287 0.2792 0.218 Uiso 0.234(10) 1 calc PR A 2
H11E H 0.5011 0.2511 0.3588 0.218 Uiso 0.234(10) 1 calc PR A 2
H11F H 0.5197 0.3153 0.2967 0.218 Uiso 0.234(10) 1 calc PR A 2
C12B C 0.398(3) 0.420(3) 0.350(3) 0.134(11) Uani 0.234(10) 1 d PU A 2
H12D H 0.3390 0.4559 0.3424 0.201 Uiso 0.234(10) 1 calc PR A 2
H12E H 0.4436 0.4578 0.3333 0.201 Uiso 0.234(10) 1 calc PR A 2
H12F H 0.4215 0.4064 0.3997 0.201 Uiso 0.234(10) 1 calc PR A 2
O8 O 0.0000 0.3548(3) 0.2500 0.0601(13) Uani 1 2 d S . .
N3 N 0.031(3) 0.1937(9) 0.254(2) 0.138(18) Uani 0.50 1 d P . .
C13 C -0.0223(17) 0.2702(9) 0.245(2) 0.083(6) Uani 0.50 1 d PU . .
H13A H -0.0772 0.2574 0.2068 0.099 Uiso 0.50 1 d PR A .
C14 C 0.1314(14) 0.2028(15) 0.2911(12) 0.167(9) Uani 0.50 1 d PU . .
H14A H 0.1529 0.2683 0.2896 0.251 Uiso 0.50 1 d PR A .
H14B H 0.1402 0.1830 0.3400 0.251 Uiso 0.50 1 d PR . .
H14C H 0.1675 0.1610 0.2679 0.251 Uiso 0.50 1 d PR . .
C15 C 0.0336(14) 0.0980(10) 0.2616(16) 0.146(7) Uani 0.50 1 d PU . .
H15A H -0.0314 0.0806 0.2398 0.219 Uiso 0.50 1 d PR . .
H15B H 0.0754 0.0617 0.2398 0.219 Uiso 0.50 1 d PR . .
H15C H 0.0481 0.0836 0.3119 0.219 Uiso 0.50 1 d PR . .


_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
Ca1 O1 2.257(4) 5_565 ?
Ca1 O3B 2.284(18) . ?
Ca1 O6 2.300(4) . ?
Ca1 O7 2.313(5) . ?
Ca1 O2 2.326(3) 6_566 ?
Ca1 O3 2.366(12) . ?
Ca1 O8 2.418(3) . ?
Ca1 C13 3.11(2) 2 ?
Ca1 C10 3.235(10) . ?
Ca1 Ca1 3.9912(17) 2 ?
S1 O4B 1.326(10) . ?
S1 O3 1.390(12) . ?
S1 O5 1.396(6) . ?
S1 O3B 1.455(18) . ?
S1 O4 1.517(7) . ?
S1 O5B 1.560(10) . ?
S1 C1 1.810(7) . ?
S1 C1B 1.838(10) . ?
O1 C6 1.240(5) . ?
O1 Ca1 2.257(4) 5_565 ?
O2 C6 1.239(5) . ?
O2 Ca1 2.326(3) 6_565 ?
C1 C2 1.415(9) . ?
C1 C5 1.415(9) 7 ?
C2 C3 1.406(11) . ?
C2 C2 1.421(17) 7 ?
C3 C4 1.306(9) . ?
C3 H3A 0.9300 . ?
C5 C1 1.415(9) 7 ?
C5 C4 1.545(9) . ?
C1B C3B 1.424(12) . ?
C1B C2B 1.437(12) . ?
C2B C4 1.563(12) . ?
C2B H2BA 0.9300 . ?
C3B C5B 1.412(13) 7 ?
C3B C3B 1.417(16) 7 ?
C5B C4 1.270(11) . ?
C5B C3B 1.412(13) 7 ?
C4 C6 1.489(6) . ?
O6 C7 1.229(7) . ?
N1 C7 1.274(7) . ?
N1 C8 1.405(9) . ?
N1 C9 1.467(8) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O7 C10 1.225(11) . ?
O7 C10B 1.25(3) . ?
N2 C12B 1.09(4) . ?
N2 C10 1.336(10) . ?
N2 C10B 1.35(4) . ?
N2 C12 1.365(11) . ?
N2 C11 1.511(12) . ?
N2 C11B 1.66(3) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C10B H10B 0.9300 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
O8 C13 1.210(13) . ?
O8 C13 1.210(13) 2 ?
O8 Ca1 2.418(3) 2 ?
N3 N3 0.88(7) 2 ?
N3 C13 1.065(14) 2 ?
N3 C13 1.30(3) . ?
N3 C15 1.331(16) . ?
N3 C14 1.45(5) . ?
N3 C15 1.61(3) 2 ?
C13 C13 0.63(5) 2 ?
C13 N3 1.065(14) 2 ?
C13 C14 1.82(3) 2 ?
C13 Ca1 3.11(2) 2 ?
C13 H13A 0.9599 . ?
C14 C13 1.82(3) 2 ?
C14 C15 2.00(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9599 . ?
C14 H14C 0.9600 . ?
C15 C15 0.96(4) 2 ?
C15 N3 1.61(3) 2 ?
C15 H15A 0.9600 . ?
C15 H15B 0.9598 . ?
C15 H15C 0.9601 . ?

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 Ca1 O3B 110.1(4) 5_565 . ?
O1 Ca1 O6 92.65(15) 5_565 . ?
O3B Ca1 O6 91.2(4) . . ?
O1 Ca1 O7 171.79(18) 5_565 . ?
O3B Ca1 O7 78.0(4) . . ?
O6 Ca1 O7 88.57(19) . . ?
O1 Ca1 O2 90.76(14) 5_565 6_566 ?
O3B Ca1 O2 157.0(4) . 6_566 ?
O6 Ca1 O2 97.54(15) . 6_566 ?
O7 Ca1 O2 81.03(17) . 6_566 ?
O1 Ca1 O3 94.1(2) 5_565 . ?
O3B Ca1 O3 17.8(4) . . ?
O6 Ca1 O3 84.3(3) . . ?
O7 Ca1 O3 94.1(3) . . ?
O2 Ca1 O3 174.7(2) 6_566 . ?
O1 Ca1 O8 86.20(12) 5_565 . ?
O3B Ca1 O8 78.2(4) . . ?
O6 Ca1 O8 168.27(13) . . ?
O7 Ca1 O8 94.24(17) . . ?
O2 Ca1 O8 94.15(12) 6_566 . ?
O3 Ca1 O8 84.1(3) . . ?
O1 Ca1 C13 103.8(4) 5_565 2 ?
O3B Ca1 C13 61.9(7) . 2 ?
O6 Ca1 C13 151.9(5) . 2 ?
O7 Ca1 C13 78.4(5) . 2 ?
O2 Ca1 C13 104.8(7) 6_566 2 ?
O3 Ca1 C13 72.1(7) . 2 ?
O8 Ca1 C13 20.9(4) . 2 ?
O1 Ca1 C10 155.4(2) 5_565 . ?
O3B Ca1 C10 94.3(5) . . ?
O6 Ca1 C10 83.75(19) . . ?
O7 Ca1 C10 17.0(2) . . ?
O2 Ca1 C10 65.7(2) 6_566 . ?
O3 Ca1 C10 109.7(3) . . ?
O8 Ca1 C10 102.05(16) . . ?
C13 Ca1 C10 89.9(6) 2 . ?
O1 Ca1 Ca1 62.76(10) 5_565 2 ?
O3B Ca1 Ca1 109.6(4) . 2 ?
O6 Ca1 Ca1 151.70(11) . 2 ?
O7 Ca1 Ca1 113.79(15) . 2 ?
O2 Ca1 Ca1 70.71(10) 6_566 2 ?
O3 Ca1 Ca1 109.8(3) . 2 ?
O8 Ca1 Ca1 34.38(10) . 2 ?
C13 Ca1 Ca1 54.9(5) 2 2 ?
C10 Ca1 Ca1 112.40(15) . 2 ?
O4B S1 O3 146.5(6) . . ?
O4B S1 O5 89.0(6) . . ?
O3 S1 O5 117.0(4) . . ?
O4B S1 O3B 120.3(7) . . ?
O3 S1 O3B 29.3(6) . . ?
O5 S1 O3B 145.8(7) . . ?
O4B S1 O4 36.1(4) . . ?
O3 S1 O4 110.8(5) . . ?
O5 S1 O4 111.2(4) . . ?
O3B S1 O4 88.5(7) . . ?
O4B S1 O5B 114.6(7) . . ?
O3 S1 O5B 79.9(6) . . ?
O5 S1 O5B 40.6(5) . . ?
O3B S1 O5B 106.4(8) . . ?
O4 S1 O5B 113.6(5) . . ?
O4B S1 C1 81.8(5) . . ?
O3 S1 C1 106.6(5) . . ?
O5 S1 C1 109.2(4) . . ?
O3B S1 C1 93.4(7) . . ?
O4 S1 C1 100.7(4) . . ?
O5B S1 C1 140.3(5) . . ?
O4B S1 C1B 111.9(6) . . ?
O3 S1 C1B 94.0(6) . . ?
O5 S1 C1B 80.6(4) . . ?
O3B S1 C1B 101.8(8) . . ?
O4 S1 C1B 141.3(4) . . ?
O5B S1 C1B 99.3(5) . . ?
C1 S1 C1B 42.2(3) . . ?
C6 O1 Ca1 149.6(3) . 5_565 ?
C6 O2 Ca1 131.8(3) . 6_565 ?
S1 O3 Ca1 154.7(6) . . ?
S1 O3B Ca1 157.6(10) . . ?
C2 C1 C5 120.6(7) . 7 ?
C2 C1 S1 120.1(6) . . ?
C5 C1 S1 119.2(5) 7 . ?
C3 C2 C1 120.6(8) . . ?
C3 C2 C2 119.1(10) . 7 ?
C1 C2 C2 120.3(10) . 7 ?
C4 C3 C2 124.0(8) . . ?
C4 C3 H3A 118.0 . . ?
C2 C3 H3A 118.0 . . ?
C1 C5 C4 116.6(7) 7 . ?
C3B C1B C2B 116.8(9) . . ?
C3B C1B S1 118.3(7) . . ?
C2B C1B S1 124.9(8) . . ?
C1B C2B C4 120.5(9) . . ?
C1B C2B H2BA 119.7 . . ?
C4 C2B H2BA 119.7 . . ?
C5B C3B C3B 123.8(15) 7 7 ?
C5B C3B C1B 117.4(9) 7 . ?
C3B C3B C1B 118.6(14) 7 . ?
C4 C5B C3B 121.9(11) . 7 ?
C5B C4 C3 92.3(7) . . ?
C5B C4 C6 136.9(7) . . ?
C3 C4 C6 130.8(6) . . ?
C5B C4 C5 27.8(5) . . ?
C3 C4 C5 119.1(6) . . ?
C6 C4 C5 109.9(5) . . ?
C5B C4 C2B 117.6(8) . . ?
C3 C4 C2B 25.9(4) . . ?
C6 C4 C2B 105.2(6) . . ?
C5 C4 C2B 144.9(6) . . ?
O2 C6 O1 125.0(5) . . ?
O2 C6 C4 117.7(5) . . ?
O1 C6 C4 117.3(5) . . ?
C7 O6 Ca1 145.4(4) . . ?
C7 N1 C8 120.7(7) . . ?
C7 N1 C9 123.4(7) . . ?
C8 N1 C9 115.7(6) . . ?
O6 C7 N1 127.3(7) . . ?
O6 C7 H7A 116.3 . . ?
N1 C7 H7A 116.3 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 O7 C10B 61.9(18) . . ?
C10 O7 Ca1 129.6(6) . . ?
C10B O7 Ca1 163.5(18) . . ?
C12B N2 C10 74(3) . . ?
C12B N2 C10B 131(3) . . ?
C10 N2 C10B 56.6(14) . . ?
C12B N2 C12 154(3) . . ?
C10 N2 C12 124.4(9) . . ?
C10B N2 C12 71.4(16) . . ?
C12B N2 C11 43(2) . . ?
C10 N2 C11 116.1(9) . . ?
C10B N2 C11 169.1(18) . . ?
C12 N2 C11 118.0(7) . . ?
C12B N2 C11B 122(3) . . ?
C10 N2 C11B 152.0(14) . . ?
C10B N2 C11B 103(2) . . ?
C12 N2 C11B 51.3(15) . . ?
C11 N2 C11B 80.9(13) . . ?
O7 C10 N2 120.6(10) . . ?
O7 C10 Ca1 33.4(4) . . ?
N2 C10 Ca1 154.0(8) . . ?
O7 C10 H10A 119.7 . . ?
N2 C10 H10A 119.7 . . ?
Ca1 C10 H10A 86.3 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O7 C10B N2 118(3) . . ?
O7 C10B H10B 121.2 . . ?
N2 C10B H10B 121.2 . . ?
N2 C11B H11D 109.5 . . ?
N2 C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N2 C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
N2 C12B H12D 109.5 . . ?
N2 C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
N2 C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C13 O8 C13 30(2) . 2 ?
C13 O8 Ca1 113.7(13) . 2 ?
C13 O8 Ca1 133.5(15) 2 2 ?
C13 O8 Ca1 133.5(15) . . ?
C13 O8 Ca1 113.7(13) 2 . ?
Ca1 O8 Ca1 111.24(19) 2 . ?
N3 N3 C13 83(2) 2 2 ?
N3 N3 C13 54.5(17) 2 . ?
C13 N3 C13 29(2) 2 . ?
N3 N3 C15 90.8(16) 2 . ?
C13 N3 C15 170(4) 2 . ?
C13 N3 C15 145(3) . . ?
N3 N3 C14 160(7) 2 . ?
C13 N3 C14 91(3) 2 . ?
C13 N3 C14 119(3) . . ?
C15 N3 C14 92(2) . . ?
N3 N3 C15 55.9(16) 2 2 ?
C13 N3 C15 139(4) 2 2 ?
C13 N3 C15 110(3) . 2 ?
C15 N3 C15 36.8(15) . 2 ?
C14 N3 C15 129(2) . 2 ?
C13 C13 N3 97(3) 2 2 ?
C13 C13 O8 75.0(11) 2 . ?
N3 C13 O8 171(4) 2 . ?
C13 C13 N3 54.6(18) 2 . ?
N3 C13 N3 43(3) 2 . ?
O8 C13 N3 130(2) . . ?
C13 C13 C14 148(2) 2 2 ?
N3 C13 C14 53(3) 2 2 ?
O8 C13 C14 136(2) . 2 ?
N3 C13 C14 94(2) . 2 ?
C13 C13 Ca1 109(4) 2 2 ?
N3 C13 Ca1 138(3) 2 2 ?
O8 C13 Ca1 45.4(9) . 2 ?
N3 C13 Ca1 151(3) . 2 ?
C14 C13 Ca1 102.1(11) 2 2 ?
C13 C13 H13A 144.6 2 . ?
N3 C13 H13A 75.4 2 . ?
O8 C13 H13A 112.8 . . ?
N3 C13 H13A 107.6 . . ?
C14 C13 H13A 30.1 2 . ?
Ca1 C13 H13A 98.2 2 . ?
N3 C14 C13 35.9(8) . 2 ?
N3 C14 C15 41.6(9) . . ?
C13 C14 C15 77.1(11) 2 . ?
N3 C14 H14A 111.0 . . ?
C13 C14 H14A 76.3 2 . ?
C15 C14 H14A 152.1 . . ?
N3 C14 H14B 109.4 . . ?
C13 C14 H14B 114.5 2 . ?
C15 C14 H14B 89.0 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 108.0 . . ?
C13 C14 H14C 130.5 2 . ?
C15 C14 H14C 82.1 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 C15 N3 87(2) 2 . ?
C15 C15 N3 55.8(15) 2 2 ?
N3 C15 N3 33(3) . 2 ?
C15 C15 C14 133.7(8) 2 . ?
N3 C15 C14 46(2) . . ?
N3 C15 C14 78.3(15) 2 . ?
C15 C15 H15A 14.5 2 . ?
N3 C15 H15A 101.9 . . ?
N3 C15 H15A 70.1 2 . ?
C14 C15 H15A 148.2 . . ?
C15 C15 H15B 118.0 2 . ?
N3 C15 H15B 118.0 . . ?
N3 C15 H15B 138.8 2 . ?
C14 C15 H15B 91.3 . . ?
H15A C15 H15B 109.5 . . ?
C15 C15 H15C 114.1 2 . ?
N3 C15 H15C 108.2 . . ?
N3 C15 H15C 109.1 2 . ?
C14 C15 H15C 84.4 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.27
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 1005216'
#######################################################################
#
#                 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_Cd

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 Cd N2 O7 S'
_chemical_formula_weight         456.74

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnnm

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

_cell_length_a                   13.3226(4)
_cell_length_b                   16.3848(5)
_cell_length_c                   6.9437(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1515.73(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6859
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.09

_exptl_crystal_description       block
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.001
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    1.620
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_T_max  0.750
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            9173
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         26.09
_reflns_number_total             1643
_reflns_number_gt                1562
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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)+(0.0657P)²+3.1595P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1643
_refine_ls_number_parameters     139
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.191
_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
C2 C 0.4782(4) 0.1135(3) 0.5000 0.0282(11) Uani 1 2 d S . .
H2 H 0.5152 0.1616 0.5000 0.034 Uiso 1 2 calc SR . .
C6 C 0.6234(4) -0.1172(3) 0.5000 0.0283(11) Uani 1 2 d S . .
C10 C 0.8492(6) -0.0005(5) 1.0824(14) 0.101(2) Uani 1 1 d U . .
C11 C 0.9325(7) -0.1044(8) 0.8291(17) 0.130(3) Uani 1 1 d U . .
H11A H 0.9079 -0.0732 0.7219 0.196 Uiso 1 1 calc R . .
H11B H 0.9051 -0.1585 0.8239 0.196 Uiso 1 1 calc R . .
H11C H 1.0044 -0.1072 0.8234 0.196 Uiso 1 1 calc R . .
H7 H 0.425(11) 0.060(9) 1.0000 0.15(6) Uiso 1 2 d S . .
C1 C 0.8229(4) 0.3014(3) 1.0000 0.0266(11) Uani 1 2 d S . .
C3 C 0.5296(4) 0.0366(3) 0.5000 0.0252(10) Uani 1 2 d S . .
C4 C 0.6360(4) 0.0300(3) 0.5000 0.0263(11) Uani 1 2 d S . .
C5 C 0.6819(4) -0.0445(3) 0.5000 0.0291(11) Uani 1 2 d S . .
H5 H 0.7516 -0.0477 0.5000 0.035 Uiso 1 2 calc SR . .
C7 C 0.4837(4) 0.1002(4) 1.0000 0.0361(13) Uani 1 2 d S . .
C8 C 0.4801(7) 0.2457(5) 1.0000 0.089(4) Uani 1 2 d S . .
H8A H 0.4300 0.2879 1.0000 0.134 Uiso 1 2 calc SR . .
H8B H 0.5212 0.2508 0.8871 0.134 Uiso 0.50 1 calc PR . .
H8C H 0.5212 0.2508 1.1129 0.134 Uiso 0.50 1 calc PR . .
C9 C 0.3227(5) 0.1663(5) 1.0000 0.0482(17) Uani 1 2 d S . .
H9A H 0.2977 0.2213 1.0000 0.072 Uiso 1 2 calc SR . .
H9B H 0.2991 0.1384 1.1129 0.072 Uiso 0.50 1 calc PR . .
H9C H 0.2991 0.1384 0.8871 0.072 Uiso 0.50 1 calc PR . .
N1 N 0.4320(4) 0.1676(3) 1.0000 0.0353(12) Uani 1 2 d S . .
N2 N 0.9035(5) -0.0670(4) 1.0000 0.0702(19) Uani 1 2 d SU . .
O1 O 0.8729(3) 0.2367(2) 1.0000 0.0410(10) Uani 1 2 d S . .
O2 O 0.7290(3) 0.3013(2) 1.0000 0.0337(10) Uani 1 2 d S . .
O3 O 0.6905(3) 0.16550(17) 0.6713(5) 0.0390(7) Uani 1 1 d . . .
O4 O 0.8167(3) 0.0873(3) 0.5000 0.0468(11) Uani 1 2 d S . .
O5 O 0.5766(3) 0.0930(3) 1.0000 0.0401(10) Uani 1 2 d S . .
O6 O 0.8068(5) 0.0445(4) 1.0000 0.0821(19) Uani 1 2 d SU . .
S1 S 0.71573(9) 0.11820(8) 0.5000 0.0259(3) Uani 1 2 d S . .
Cd1 Cd 0.72364(3) 0.15941(2) 1.0000 0.02565(18) Uani 1 2 d S . .


_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
C2 C6 1.355(8) 5_656 ?
C2 C3 1.434(8) . ?
C6 C2 1.355(8) 5_656 ?
C6 C5 1.423(8) . ?
C6 C1 1.513(7) 3_646 ?
C10 O6 1.091(9) . ?
C10 C10 1.14(2) 6_557 ?
C10 N2 1.428(10) . ?
C11 N2 1.390(11) . ?
C1 O2 1.252(8) . ?
C1 O1 1.252(7) . ?
C1 C6 1.513(7) 3_656 ?
C1 Cd1 2.677(5) . ?
C3 C4 1.421(8) . ?
C3 C3 1.435(10) 5_656 ?
C4 C5 1.365(8) . ?
C4 S1 1.794(5) . ?
C7 O5 1.244(7) . ?
C7 N1 1.301(8) . ?
C8 N1 1.431(9) . ?
C9 N1 1.457(9) . ?
N2 C11 1.390(11) 6_557 ?
N2 C10 1.428(10) 6_557 ?
O1 Cd1 2.358(4) . ?
O2 Cd1 2.326(4) . ?
O3 S1 1.459(3) . ?
O3 Cd1 2.327(3) . ?
O4 S1 1.437(5) . ?
O5 Cd1 2.242(4) . ?
O6 C10 1.091(9) 6_557 ?
O6 Cd1 2.185(5) . ?
S1 O3 1.459(3) 6_556 ?
Cd1 O3 2.327(3) 6_557 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C2 C3 121.1(5) 5_656 . ?
C2 C6 C5 120.6(5) 5_656 . ?
C2 C6 C1 120.8(5) 5_656 3_646 ?
C5 C6 C1 118.6(5) . 3_646 ?
O6 C10 C10 58.4(5) . 6_557 ?
O6 C10 N2 124.6(8) . . ?
C10 C10 N2 66.4(4) 6_557 . ?
O2 C1 O1 122.0(5) . . ?
O2 C1 C6 118.3(5) . 3_656 ?
O1 C1 C6 119.6(5) . 3_656 ?
O2 C1 Cd1 60.3(3) . . ?
O1 C1 Cd1 61.8(3) . . ?
C6 C1 Cd1 178.6(4) 3_656 . ?
C4 C3 C2 122.9(5) . . ?
C4 C3 C3 119.0(6) . 5_656 ?
C2 C3 C3 118.1(6) . 5_656 ?
C5 C4 C3 121.0(5) . . ?
C5 C4 S1 117.0(4) . . ?
C3 C4 S1 122.0(4) . . ?
C4 C5 C6 120.2(5) . . ?
O5 C7 N1 127.4(6) . . ?
C7 N1 C8 121.5(6) . . ?
C7 N1 C9 121.1(5) . . ?
C8 N1 C9 117.4(6) . . ?
C11 N2 C11 117.3(12) . 6_557 ?
C11 N2 C10 97.7(7) . 6_557 ?
C11 N2 C10 145.0(7) 6_557 6_557 ?
C11 N2 C10 145.0(7) . . ?
C11 N2 C10 97.7(7) 6_557 . ?
C10 N2 C10 47.2(8) 6_557 . ?
C1 O1 Cd1 90.3(3) . . ?
C1 O2 Cd1 91.9(3) . . ?
S1 O3 Cd1 137.1(2) . . ?
C7 O5 Cd1 145.5(4) . . ?
C10 O6 C10 63.3(10) . 6_557 ?
C10 O6 Cd1 147.7(5) . . ?
C10 O6 Cd1 147.7(5) 6_557 . ?
O4 S1 O3 113.78(18) . . ?
O4 S1 O3 113.78(18) . 6_556 ?
O3 S1 O3 109.2(3) . 6_556 ?
O4 S1 C4 105.7(3) . . ?
O3 S1 C4 106.93(17) . . ?
O3 S1 C4 106.93(17) 6_556 . ?
O6 Cd1 O5 91.4(2) . . ?
O6 Cd1 O2 147.8(2) . . ?
O5 Cd1 O2 120.81(15) . . ?
O6 Cd1 O3 97.66(8) . 6_557 ?
O5 Cd1 O3 81.65(9) . 6_557 ?
O2 Cd1 O3 87.87(7) . 6_557 ?
O6 Cd1 O3 97.66(8) . . ?
O5 Cd1 O3 81.65(9) . . ?
O2 Cd1 O3 87.87(7) . . ?
O3 Cd1 O3 157.55(19) 6_557 . ?
O6 Cd1 O1 92.0(2) . . ?
O5 Cd1 O1 176.57(15) . . ?
O2 Cd1 O1 55.76(14) . . ?
O3 Cd1 O1 97.88(9) 6_557 . ?
O3 Cd1 O1 97.88(9) . . ?
O6 Cd1 C1 119.9(2) . . ?
O5 Cd1 C1 148.67(17) . . ?
O2 Cd1 C1 27.86(17) . . ?
O3 Cd1 C1 93.24(8) 6_557 . ?
O3 Cd1 C1 93.24(8) . . ?
O1 Cd1 C1 27.90(16) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.09
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.582
_refine_diff_density_min         -1.162
_refine_diff_density_rms         0.114
_database_code_depnum_ccdc_archive 'CCDC 1005217'
#######################################################################
#
#                 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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H34 Cu N4 O14 S2'
_chemical_formula_weight         730.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cu Cu 0.3201 1.2651 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   8.6325(9)
_cell_length_b                   12.8807(14)
_cell_length_c                   14.7075(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.760(2)
_cell_angle_gamma                90.00
_cell_volume                     1631.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1731
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      24.27

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             758
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_T_max  0.828
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8885
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         24.67
_reflns_number_total             2766
_reflns_number_gt                1784
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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)+(0.0697P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2766
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C6 C 0.9691(5) 0.3561(3) 1.0123(3) 0.0323(10) Uani 1 1 d . . .
C7 C 1.0336(5) 0.3196(3) 0.9361(3) 0.0382(11) Uani 1 1 d . . .
H7 H 1.0339 0.2487 0.9242 0.046 Uiso 1 1 calc R . .
C8 C 1.0996(5) 0.3890(4) 0.8757(3) 0.0381(11) Uani 1 1 d . . .
C9 C 1.0974(5) 0.4933(3) 0.8907(3) 0.0356(11) Uani 1 1 d . . .
H9 H 1.1392 0.5380 0.8491 0.043 Uiso 1 1 calc R . .
C10 C 1.0323(5) 0.5346(3) 0.9692(3) 0.0302(10) Uani 1 1 d . . .
C11 C 1.1713(6) 0.3521(4) 0.7917(3) 0.0519(14) Uani 1 1 d . . .
O1 O 1.1991(4) 0.0699(3) 1.0010(2) 0.0468(8) Uani 1 1 d . . .
O2 O 1.0471(4) -0.0425(3) 1.1269(2) 0.0471(9) Uani 1 1 d . . .
O3 O 0.8879(3) 0.1661(2) 1.04173(18) 0.0400(8) Uani 1 1 d . . .
O4 O 0.7461(4) 0.3019(2) 1.1114(2) 0.0538(9) Uani 1 1 d . . .
O5 O 1.0076(4) 0.2655(3) 1.1675(2) 0.0601(10) Uani 1 1 d . . .
O6 O 1.1728(6) 0.2523(3) 0.7823(3) 0.0850(17) Uani 1 1 d . . .
O7 O 1.2258(6) 0.4105(3) 0.7389(3) 0.0906(15) Uani 1 1 d . . .
S1 S 0.89686(14) 0.26397(8) 1.08907(7) 0.0368(3) Uani 1 1 d . . .
Cu01 Cu 1.0000 0.0000 1.0000 0.0398(3) Uani 1 2 d S . .
N2 N 1.1123(5) -0.0065(4) 1.2736(3) 0.0643(13) Uani 1 1 d . . .
N1 N 1.4195(5) 0.1144(4) 0.9394(3) 0.0587(12) Uani 1 1 d . . .
C3 C 1.2931(6) 0.0597(4) 0.9416(3) 0.0456(12) Uani 1 1 d . . .
C4 C 1.0737(7) 0.0164(5) 1.1892(4) 0.0588(16) Uani 1 1 d . . .
C2 C 1.5291(6) 0.0999(6) 0.8677(4) 0.086(2) Uani 1 1 d . . .
H2A H 1.6149 0.1468 0.8779 0.129 Uiso 1 1 calc R . .
H2B H 1.4772 0.1137 0.8093 0.129 Uiso 1 1 calc R . .
H2C H 1.5666 0.0297 0.8693 0.129 Uiso 1 1 calc R . .
C5 C 1.1332(9) -0.1109(6) 1.3004(5) 0.109(3) Uani 1 1 d . . .
H5A H 1.1616 -0.1139 1.3646 0.163 Uiso 1 1 calc R . .
H5B H 1.2141 -0.1414 1.2674 0.163 Uiso 1 1 calc R . .
H5C H 1.0383 -0.1484 1.2875 0.163 Uiso 1 1 calc R . .
C1 C 1.4543(9) 0.1938(7) 1.0056(5) 0.115(3) Uani 1 1 d . . .
H1A H 1.5514 0.2259 0.9940 0.172 Uiso 1 1 calc R . .
H1B H 1.4613 0.1638 1.0654 0.172 Uiso 1 1 calc R . .
H1C H 1.3735 0.2452 1.0018 0.172 Uiso 1 1 calc R . .
C12 C 1.1354(11) 0.0728(7) 1.3437(5) 0.154(4) Uani 1 1 d . . .
H12A H 1.1630 0.0403 1.4013 0.231 Uiso 1 1 calc R . .
H12B H 1.0412 0.1116 1.3479 0.231 Uiso 1 1 calc R . .
H12C H 1.2172 0.1187 1.3283 0.231 Uiso 1 1 calc R . .
H3 H 1.284(5) 0.005(3) 0.897(3) 0.040(13) Uiso 1 1 d . . .
H4 H 1.065(5) 0.078(4) 1.177(3) 0.047(16) Uiso 1 1 d . . .
H13 H 1.202(8) 0.232(5) 0.737(5) 0.10(3) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6 C7 1.367(5) . ?
C6 C10 1.434(6) 3_767 ?
C6 S1 1.779(4) . ?
C7 C8 1.408(6) . ?
C8 C9 1.361(6) . ?
C8 C11 1.496(6) . ?
C9 C10 1.420(5) . ?
C10 C10 1.412(8) 3_767 ?
C10 C6 1.434(6) 3_767 ?
C11 O7 1.199(5) . ?
C11 O6 1.293(6) . ?
O1 C3 1.238(5) . ?
O1 Cu01 1.939(3) . ?
O2 C4 1.201(7) . ?
O2 Cu01 1.962(3) . ?
O3 S1 1.439(3) . ?
O4 S1 1.448(3) . ?
O5 S1 1.449(3) . ?
Cu01 O1 1.939(3) 3_757 ?
Cu01 O2 1.962(3) 3_757 ?
N2 C4 1.298(7) . ?
N2 C5 1.409(8) . ?
N2 C12 1.456(8) . ?
N1 C3 1.301(6) . ?
N1 C1 1.430(8) . ?
N1 C2 1.475(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
C7 C6 C10 120.2(4) . 3_767 ?
C7 C6 S1 118.0(3) . . ?
C10 C6 S1 121.8(3) 3_767 . ?
C6 C7 C8 120.1(4) . . ?
C9 C8 C7 120.9(4) . . ?
C9 C8 C11 117.3(4) . . ?
C7 C8 C11 121.7(4) . . ?
C8 C9 C10 120.8(4) . . ?
C10 C10 C9 118.6(5) 3_767 . ?
C10 C10 C6 119.3(5) 3_767 3_767 ?
C9 C10 C6 122.1(4) . 3_767 ?
O7 C11 O6 123.3(4) . . ?
O7 C11 C8 122.4(4) . . ?
O6 C11 C8 114.3(4) . . ?
C3 O1 Cu01 124.6(3) . . ?
C4 O2 Cu01 124.6(4) . . ?
O3 S1 O4 112.64(19) . . ?
O3 S1 O5 114.1(2) . . ?
O4 S1 O5 111.8(2) . . ?
O3 S1 C6 106.65(18) . . ?
O4 S1 C6 106.08(19) . . ?
O5 S1 C6 104.8(2) . . ?
O1 Cu01 O1 180.0 . 3_757 ?
O1 Cu01 O2 89.67(13) . . ?
O1 Cu01 O2 90.33(13) 3_757 . ?
O1 Cu01 O2 90.33(13) . 3_757 ?
O1 Cu01 O2 89.67(13) 3_757 3_757 ?
O2 Cu01 O2 180.000(1) . 3_757 ?
C4 N2 C5 120.3(6) . . ?
C4 N2 C12 122.1(6) . . ?
C5 N2 C12 117.5(6) . . ?
C3 N1 C1 120.7(5) . . ?
C3 N1 C2 121.8(5) . . ?
C1 N1 C2 117.5(5) . . ?
O1 C3 N1 123.3(5) . . ?
O2 C4 N2 127.6(6) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.67
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.077
_database_code_depnum_ccdc_archive 'CCDC 1005218'
