# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Berta Covelo'
_publ_contact_author_email       BCOVELO@UVIGO.ES

_publ_section_title              
;
From copper(II) carboxylate to copper(II)
4-pyridylsulfonate coordination polymers as a consequence of the
copper(II)-assisted oxidative cleavage of the 4,4'-dipyridyldisulfide
ligand
;
loop_
_publ_author_name
'Berta Covelo'
'Rosa Carballo'
'Nuria Fernandez-Hermida'
'Ana B Lago'
;
E.M.Vazquez-Lopez
;

# Attachment 'B816721D.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 706584'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cl2 Cu2 N2 O7 S2'
_chemical_formula_weight         584.37

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'
Cl Cl 0.1484 0.1585 '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'

_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                   8.4405(6)
_cell_length_b                   11.4677(8)
_cell_length_c                   11.7069(8)
_cell_angle_alpha                108.7040(10)
_cell_angle_beta                 95.0000(10)
_cell_angle_gamma                95.8130(10)
_cell_volume                     1059.14(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       irregular
_exptl_crystal_colour            blue
_exptl_crystal_size_max          .53
_exptl_crystal_size_mid          .32
_exptl_crystal_size_min          .20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    2.496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6803
_exptl_absorpt_correction_T_max  1.0000
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6597
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         28.02
_reflns_number_total             4601
_reflns_number_gt                3731
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0662P)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         4601
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.14452(5) 0.93803(3) 0.01230(3) 0.03418(13) Uani 1 1 d . . .
Cu2 Cu -0.11221(6) 0.79121(3) -0.21772(3) 0.04252(14) Uani 1 1 d . . .
O1 O -0.0053(3) 0.95729(19) -0.1159(2) 0.0301(5) Uani 1 1 d . . .
O11 O -0.0813(5) 0.7482(3) -0.0262(6) 0.132(2) Uani 1 1 d . . .
O12 O -0.2822(5) 0.8292(4) -0.0651(4) 0.1203(19) Uani 1 1 d . . .
O21 O 0.2957(3) 0.8667(2) -0.0947(2) 0.0462(6) Uani 1 1 d . . .
O22 O 0.1293(4) 0.7170(2) -0.2409(2) 0.0567(7) Uani 1 1 d . . .
O31 O -0.1065(3) 0.8272(2) -0.3711(2) 0.0500(6) Uani 1 1 d . . .
O32 O 0.0841(3) 0.9922(2) -0.3158(2) 0.0486(6) Uani 1 1 d . . .
C11 C -0.2062(5) 0.7828(3) -0.0029(3) 0.0464(9) Uani 1 1 d . . .
H11 H -0.2469 0.7739 0.0656 0.056 Uiso 1 1 calc R . .
C21 C 0.2617(5) 0.7736(4) -0.1897(3) 0.0506(9) Uani 1 1 d . . .
H21 H 0.3491 0.7430 -0.2266 0.061 Uiso 1 1 calc R . .
C31 C -0.0100(5) 0.9072(3) -0.3911(3) 0.0459(8) Uani 1 1 d . . .
H31 H -0.0093 0.9019 -0.4720 0.055 Uiso 1 1 calc R . .
N1 N 0.2743(3) 0.9105(2) 0.1479(2) 0.0328(6) Uani 1 1 d . . .
N2 N 0.2324(4) 0.3771(2) 0.3150(2) 0.0395(6) Uani 1 1 d . . .
S1 S 0.59778(10) 0.83705(8) 0.44128(8) 0.0400(2) Uani 1 1 d . . .
S2 S 0.45214(12) 0.77185(7) 0.54307(7) 0.0438(2) Uani 1 1 d . . .
C1 C 0.4336(4) 0.9417(3) 0.1653(3) 0.0401(7) Uani 1 1 d . . .
H1 H 0.4806 0.9790 0.1144 0.048 Uiso 1 1 calc R . .
C2 C 0.5311(4) 0.9210(3) 0.2556(3) 0.0393(7) Uani 1 1 d . . .
H2 H 0.6415 0.9443 0.2652 0.047 Uiso 1 1 calc R . .
C3 C 0.4633(4) 0.8652(3) 0.3315(3) 0.0321(6) Uani 1 1 d . . .
C4 C 0.2970(4) 0.8332(3) 0.3142(3) 0.0392(7) Uani 1 1 d . . .
H4 H 0.2468 0.7962 0.3640 0.047 Uiso 1 1 calc R . .
C5 C 0.2090(4) 0.8574(3) 0.2223(3) 0.0387(7) Uani 1 1 d . . .
H5 H 0.0981 0.8358 0.2112 0.046 Uiso 1 1 calc R . .
C6 C 0.3759(4) 0.6165(3) 0.4517(3) 0.0362(7) Uani 1 1 d . . .
C7 C 0.2557(5) 0.5565(3) 0.4930(3) 0.0442(8) Uani 1 1 d . . .
H7 H 0.2207 0.5960 0.5671 0.053 Uiso 1 1 calc R . .
C8 C 0.1876(5) 0.4374(3) 0.4237(3) 0.0467(9) Uani 1 1 d . . .
H8 H 0.1077 0.3973 0.4532 0.056 Uiso 1 1 calc R . .
C9 C 0.3510(5) 0.4348(3) 0.2771(3) 0.0452(9) Uani 1 1 d . . .
H9 H 0.3852 0.3931 0.2034 0.054 Uiso 1 1 calc R . .
C10 C 0.4265(5) 0.5545(3) 0.3421(3) 0.0438(8) Uani 1 1 d . . .
H10 H 0.5090 0.5917 0.3124 0.053 Uiso 1 1 calc R . .
H100 H 0.028(4) 0.972(3) -0.161(3) 0.033(11) Uiso 1 1 d . . .
Cl2 Cl 0.1167(3) 0.37347(17) 0.71900(18) 0.1200(7) Uani 1 1 d . . .
Cl1 Cl 0.2867(3) 0.5336(2) 0.9492(2) 0.1485(8) Uani 1 1 d . . .
C100 C 0.1035(8) 0.4770(5) 0.8615(6) 0.0946(19) Uani 1 1 d . . .
H10A H 0.0529 0.5462 0.8520 0.114 Uiso 1 1 calc R . .
H10B H 0.0352 0.4358 0.9036 0.114 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
Cu1 O21 1.923(2) . ?
Cu1 O1 1.960(2) . ?
Cu1 O1 1.973(2) 2_575 ?
Cu1 N1 1.977(3) . ?
Cu1 O11 2.637(4) . ?
Cu1 O12 2.655(4) 2_575 ?
Cu1 Cu1 2.9829(8) 2_575 ?
Cu1 Cu2 3.1808(6) . ?
Cu2 O1 1.967(2) . ?
Cu2 O31 1.971(2) . ?
Cu2 N2 2.011(3) 2_565 ?
Cu2 O22 2.292(3) . ?
Cu2 O12 2.348(5) . ?
Cu2 O11 2.443(6) . ?
O1 Cu1 1.973(2) 2_575 ?
O1 H100 0.68(3) . ?
O11 C11 1.187(5) . ?
O12 C11 1.209(5) . ?
O21 C21 1.257(4) . ?
O22 C21 1.231(5) . ?
O31 C31 1.256(4) . ?
O32 C31 1.236(4) . ?
C11 H11 0.9300 . ?
C21 H21 0.9300 . ?
C31 H31 0.9300 . ?
N1 C1 1.336(4) . ?
N1 C5 1.337(4) . ?
N2 C9 1.330(4) . ?
N2 C8 1.347(4) . ?
N2 Cu2 2.011(3) 2_565 ?
S1 C3 1.769(3) . ?
S1 S2 2.0325(13) . ?
S2 C6 1.777(3) . ?
C1 C2 1.379(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(4) . ?
C4 C5 1.371(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.376(5) . ?
C6 C10 1.381(5) . ?
C7 C8 1.379(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.391(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
Cl2 C100 1.730(6) . ?
Cl1 C100 1.721(7) . ?
C100 H10A 0.9700 . ?
C100 H10B 0.9700 . ?

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
O21 Cu1 O1 94.95(10) . . ?
O21 Cu1 O1 168.29(10) . 2_575 ?
O1 Cu1 O1 81.34(10) . 2_575 ?
O21 Cu1 N1 89.50(10) . . ?
O1 Cu1 N1 173.52(10) . . ?
O1 Cu1 N1 95.20(10) 2_575 . ?
O21 Cu1 O11 102.68(12) . . ?
O1 Cu1 O11 78.21(15) . . ?
O1 Cu1 O11 87.50(10) 2_575 . ?
N1 Cu1 O11 96.24(15) . . ?
O21 Cu1 O12 94.85(14) . 2_575 ?
O1 Cu1 O12 90.35(10) . 2_575 ?
O1 Cu1 O12 74.16(14) 2_575 2_575 ?
N1 Cu1 O12 93.98(11) . 2_575 ?
O11 Cu1 O12 159.74(13) . 2_575 ?
O21 Cu1 Cu1 134.78(8) . 2_575 ?
O1 Cu1 Cu1 40.84(6) . 2_575 ?
O1 Cu1 Cu1 40.50(7) 2_575 2_575 ?
N1 Cu1 Cu1 135.45(8) . 2_575 ?
O11 Cu1 Cu1 80.61(9) . 2_575 ?
O12 Cu1 Cu1 79.83(10) 2_575 2_575 ?
O21 Cu1 Cu2 83.41(7) . . ?
O1 Cu1 Cu2 35.99(6) . . ?
O1 Cu1 Cu2 99.48(7) 2_575 . ?
N1 Cu1 Cu2 140.58(8) . . ?
O11 Cu1 Cu2 48.56(14) . . ?
O12 Cu1 Cu2 125.19(8) 2_575 . ?
Cu1 Cu1 Cu2 65.000(16) 2_575 . ?
O1 Cu2 O31 94.16(10) . . ?
O1 Cu2 N2 176.41(10) . 2_565 ?
O31 Cu2 N2 88.01(10) . 2_565 ?
O1 Cu2 O22 91.52(9) . . ?
O31 Cu2 O22 89.76(11) . . ?
N2 Cu2 O22 91.34(11) 2_565 . ?
O1 Cu2 O12 81.89(11) . . ?
O31 Cu2 O12 134.73(13) . . ?
N2 Cu2 O12 94.55(12) 2_565 . ?
O22 Cu2 O12 135.21(12) . . ?
O1 Cu2 O11 83.09(11) . . ?
O31 Cu2 O11 172.53(12) . . ?
N2 Cu2 O11 95.09(12) 2_565 . ?
O22 Cu2 O11 83.38(12) . . ?
O12 Cu2 O11 51.89(13) . . ?
O1 Cu2 Cu1 35.82(7) . . ?
O31 Cu2 Cu1 120.62(7) . . ?
N2 Cu2 Cu1 144.16(9) 2_565 . ?
O22 Cu2 Cu1 69.54(7) . . ?
O12 Cu2 Cu1 80.43(9) . . ?
O11 Cu2 Cu1 54.02(9) . . ?
Cu1 O1 Cu2 108.19(10) . . ?
Cu1 O1 Cu1 98.66(10) . 2_575 ?
Cu2 O1 Cu1 114.61(11) . 2_575 ?
Cu1 O1 H100 117(3) . . ?
Cu2 O1 H100 97(3) . . ?
Cu1 O1 H100 122(3) 2_575 . ?
C11 O11 Cu2 90.7(4) . . ?
C11 O11 Cu1 110.9(3) . . ?
Cu2 O11 Cu1 77.42(12) . . ?
C11 O12 Cu2 94.8(3) . . ?
C21 O21 Cu1 125.0(3) . . ?
C21 O22 Cu2 126.2(2) . . ?
C31 O31 Cu2 126.9(2) . . ?
O11 C11 O12 122.2(5) . . ?
O11 C11 H11 118.9 . . ?
O12 C11 H11 118.9 . . ?
O22 C21 O21 129.3(4) . . ?
O22 C21 H21 115.3 . . ?
O21 C21 H21 115.3 . . ?
O32 C31 O31 127.6(3) . . ?
O32 C31 H31 116.2 . . ?
O31 C31 H31 116.2 . . ?
C1 N1 C5 117.8(3) . . ?
C1 N1 Cu1 119.9(2) . . ?
C5 N1 Cu1 122.3(2) . . ?
C9 N2 C8 117.5(3) . . ?
C9 N2 Cu2 124.0(2) . 2_565 ?
C8 N2 Cu2 118.4(2) . 2_565 ?
C3 S1 S2 104.07(11) . . ?
C6 S2 S1 105.32(12) . . ?
N1 C1 C2 122.7(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 S1 116.4(2) . . ?
C4 C3 S1 125.5(2) . . ?
C5 C4 C3 118.7(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 123.4(3) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C7 C6 C10 118.7(3) . . ?
C7 C6 S2 116.9(2) . . ?
C10 C6 S2 124.4(3) . . ?
C6 C7 C8 119.5(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
N2 C8 C7 122.5(3) . . ?
N2 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
N2 C9 C10 123.4(3) . . ?
N2 C9 H9 118.3 . . ?
C10 C9 H9 118.3 . . ?
C6 C10 C9 118.3(3) . . ?
C6 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
Cl1 C100 Cl2 113.4(3) . . ?
Cl1 C100 H10A 108.9 . . ?
Cl2 C100 H10A 108.9 . . ?
Cl1 C100 H10B 108.9 . . ?
Cl2 C100 H10B 108.9 . . ?
H10A C100 H10B 107.7 . . ?

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
C3 S1 S2 C6 75.28(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H100 O32 0.68(3) 1.99(4) 2.655(3) 168(4) .
C1 H1 O21 0.93 2.53 3.348(4) 146.6 2_675
C2 H2 O32 0.93 2.32 3.246(4) 172.7 2_675
C7 H7 O22 0.93 2.47 3.396(4) 175.1 1_556
C8 H8 O31 0.93 2.44 2.893(4) 109.9 2_565
C9 H9 O12 0.93 2.56 3.199(6) 126.7 2_565
C100 H10A O22 0.97 2.58 3.332(6) 134.1 1_556

_diffrn_measured_fraction_theta_max 0.898
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         0.936
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.089

# Attachment 'b816721d_3.cif'

data_bc1a
_database_code_depnum_ccdc_archive 'CCDC 706585'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H32 Cu N6 O10 S6'
_chemical_formula_weight         892.52

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'
Cu Cu 0.3201 1.2651 '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                   18.9365(13)
_cell_length_b                   10.7022(7)
_cell_length_c                   20.3222(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.9010(10)
_cell_angle_gamma                90.00
_cell_volume                     3735.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1836
_exptl_absorpt_coefficient_mu    0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8520
_exptl_absorpt_correction_T_max  1.0000
_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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11065
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         28.04
_reflns_number_total             4303
_reflns_number_gt                2781
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0247P)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         4303
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0697
_refine_ls_wR_factor_gt          0.0635
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_restrained_S_all      0.883
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.0000 0.18283(3) 0.2500 0.02771(11) Uani 1 2 d S . .
S1 S 0.08605(4) 0.62335(5) 0.49837(3) 0.03909(17) Uani 1 1 d . . .
S2 S -0.00580(4) 0.74077(5) 0.47291(4) 0.04013(18) Uani 1 1 d . . .
N1 N 0.01887(11) 0.31789(16) 0.32652(10) 0.0282(4) Uani 1 1 d . . .
N2 N 0.01003(10) 1.04825(15) 0.32486(10) 0.0266(4) Uani 1 1 d . . .
O1 O 0.13697(11) 0.1804(2) 0.28471(13) 0.0458(5) Uani 1 1 d . . .
C1 C -0.02851(13) 0.4172(2) 0.31567(13) 0.0318(6) Uani 1 1 d . . .
H1 H -0.0739 0.4211 0.2730 0.038 Uiso 1 1 calc R . .
C2 C -0.01258(13) 0.5130(2) 0.36502(13) 0.0313(6) Uani 1 1 d . . .
H2 H -0.0466 0.5803 0.3555 0.038 Uiso 1 1 calc R . .
C3 C 0.05456(13) 0.50840(19) 0.42911(12) 0.0280(5) Uani 1 1 d . . .
C4 C 0.10356(13) 0.40527(19) 0.44154(13) 0.0290(5) Uani 1 1 d . . .
H4 H 0.1488 0.3986 0.4842 0.035 Uiso 1 1 calc R . .
C5 C 0.08368(13) 0.3141(2) 0.38951(13) 0.0302(5) Uani 1 1 d . . .
H5 H 0.1167 0.2457 0.3981 0.036 Uiso 1 1 calc R . .
C6 C 0.00551(13) 0.85603(19) 0.41562(12) 0.0273(5) Uani 1 1 d . . .
C7 C -0.03607(13) 0.9664(2) 0.40873(12) 0.0304(6) Uani 1 1 d . . .
H7 H -0.0660 0.9775 0.4347 0.036 Uiso 1 1 calc R . .
C8 C -0.03245(13) 1.0582(2) 0.36335(12) 0.0290(5) Uani 1 1 d . . .
H8 H -0.0608 1.1311 0.3590 0.035 Uiso 1 1 calc R . .
C9 C 0.05120(13) 0.94232(19) 0.33313(13) 0.0293(5) Uani 1 1 d . . .
H9 H 0.0818 0.9342 0.3077 0.035 Uiso 1 1 calc R . .
C10 C 0.05035(13) 0.84528(19) 0.37740(13) 0.0306(6) Uani 1 1 d . . .
H10 H 0.0796 0.7736 0.3814 0.037 Uiso 1 1 calc R . .
H1A H 0.1680(17) 0.128(3) 0.3094(17) 0.066(12) Uiso 1 1 d . . .
H1B H 0.1535(14) 0.204(2) 0.2595(14) 0.033(9) Uiso 1 1 d . . .
S11 S 0.27351(4) 0.80720(7) 0.69609(4) 0.0498(2) Uani 1 1 d . . .
O11 O 0.19992(11) 0.75206(16) 0.68817(10) 0.0547(5) Uani 1 1 d . . .
O12 O 0.31676(12) 0.8639(2) 0.76670(12) 0.0746(6) Uani 1 1 d . . .
O13 O 0.31677(14) 0.7223(2) 0.67322(15) 0.0988(9) Uani 1 1 d . . .
N11 N 0.19685(16) 1.1236(3) 0.5305(2) 0.0841(10) Uani 1 1 d . . .
C11 C 0.21442(18) 1.1431(3) 0.5992(2) 0.0743(11) Uani 1 1 d . . .
H11 H 0.2095 1.2241 0.6134 0.089 Uiso 1 1 calc R . .
C12 C 0.23966(16) 1.0519(3) 0.65224(18) 0.0557(8) Uani 1 1 d . . .
H12 H 0.2518 1.0715 0.7004 0.067 Uiso 1 1 calc R . .
C13 C 0.24636(14) 0.9311(2) 0.63189(15) 0.0408(7) Uani 1 1 d . . .
C14 C 0.22893(17) 0.9078(3) 0.56022(18) 0.0616(9) Uani 1 1 d . . .
H14 H 0.2329 0.8276 0.5445 0.074 Uiso 1 1 calc R . .
C15 C 0.20504(19) 1.0078(4) 0.51163(19) 0.0831(12) Uani 1 1 d . . .
H15 H 0.1943 0.9922 0.4633 0.100 Uiso 1 1 calc R . .
O1W O 0.2606(2) 0.0239(3) 0.36541(17) 0.0811(9) Uani 1 1 d . . .
H1WA H 0.2854(17) 0.038(3) 0.3419(18) 0.055(12) Uiso 1 1 d . . .
H1WB H 0.249(2) -0.037(3) 0.353(2) 0.082(17) 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
Cu N1 2.0414(18) . ?
Cu N1 2.0414(18) 2 ?
Cu N2 2.0449(18) 2_545 ?
Cu N2 2.0449(18) 1_545 ?
Cu O1 2.3843(19) 2 ?
Cu O1 2.3843(19) . ?
S1 C3 1.773(2) . ?
S1 S2 2.0283(9) . ?
S2 C6 1.770(2) . ?
N1 C1 1.348(3) . ?
N1 C5 1.350(3) . ?
N2 C8 1.342(3) . ?
N2 C9 1.346(2) . ?
N2 Cu 2.0449(18) 1_565 ?
O1 H1A 0.81(3) . ?
O1 H1B 0.75(2) . ?
C1 C2 1.376(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(3) . ?
C4 C5 1.370(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C10 1.376(3) . ?
C6 C7 1.393(3) . ?
C7 C8 1.369(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.379(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
S11 O13 1.4261(19) . ?
S11 O12 1.452(2) . ?
S11 O11 1.4585(18) . ?
S11 C13 1.778(3) . ?
N11 C11 1.310(5) . ?
N11 C15 1.326(4) . ?
C11 C12 1.381(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(4) . ?
C14 C15 1.396(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
O1W H1WA 0.81(3) . ?
O1W H1WB 0.70(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu N1 89.84(10) . 2 ?
N1 Cu N2 175.62(7) . 2_545 ?
N1 Cu N2 90.02(7) 2 2_545 ?
N1 Cu N2 90.02(7) . 1_545 ?
N1 Cu N2 175.62(7) 2 1_545 ?
N2 Cu N2 90.45(10) 2_545 1_545 ?
N1 Cu O1 93.03(8) . 2 ?
N1 Cu O1 87.86(7) 2 2 ?
N2 Cu O1 91.35(8) 2_545 2 ?
N2 Cu O1 87.77(7) 1_545 2 ?
N1 Cu O1 87.86(7) . . ?
N1 Cu O1 93.03(8) 2 . ?
N2 Cu O1 87.77(7) 2_545 . ?
N2 Cu O1 91.35(8) 1_545 . ?
O1 Cu O1 178.75(12) 2 . ?
C3 S1 S2 105.17(8) . . ?
C6 S2 S1 105.74(8) . . ?
C1 N1 C5 117.09(19) . . ?
C1 N1 Cu 122.88(16) . . ?
C5 N1 Cu 119.90(15) . . ?
C8 N2 C9 116.89(19) . . ?
C8 N2 Cu 119.14(14) . 1_565 ?
C9 N2 Cu 123.62(15) . 1_565 ?
Cu O1 H1A 127(2) . . ?
Cu O1 H1B 120.6(19) . . ?
H1A O1 H1B 105(3) . . ?
N1 C1 C2 122.8(2) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 118.4(2) . . ?
C2 C3 S1 126.18(17) . . ?
C4 C3 S1 115.43(18) . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 123.7(2) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C10 C6 C7 118.1(2) . . ?
C10 C6 S2 125.97(17) . . ?
C7 C6 S2 115.91(17) . . ?
C8 C7 C6 119.3(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
N2 C8 C7 123.2(2) . . ?
N2 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
N2 C9 C10 123.4(2) . . ?
N2 C9 H9 118.3 . . ?
C10 C9 H9 118.3 . . ?
C6 C10 C9 119.0(2) . . ?
C6 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
O13 S11 O12 115.22(16) . . ?
O13 S11 O11 111.07(13) . . ?
O12 S11 O11 113.17(13) . . ?
O13 S11 C13 105.33(13) . . ?
O12 S11 C13 106.37(13) . . ?
O11 S11 C13 104.66(11) . . ?
C11 N11 C15 116.7(3) . . ?
N11 C11 C12 124.7(3) . . ?
N11 C11 H11 117.7 . . ?
C12 C11 H11 117.7 . . ?
C13 C12 C11 118.3(3) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C14 C13 C12 118.5(3) . . ?
C14 C13 S11 120.6(2) . . ?
C12 C13 S11 120.9(2) . . ?
C13 C14 C15 118.2(3) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
N11 C15 C14 123.7(3) . . ?
N11 C15 H15 118.1 . . ?
C14 C15 H15 118.1 . . ?
H1WA O1W H1WB 97(4) . . ?

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
C3 S1 S2 C6 -89.00(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WB O13 0.70(3) 2.28(3) 2.956(5) 162(4) 7_556
O1W H1WA O12 0.81(3) 2.14(3) 2.897(5) 156(3) 6_565
O1 H1B O11 0.75(2) 2.04(2) 2.786(3) 173(3) 6_565
O1 H1A O1W 0.81(3) 1.98(3) 2.783(4) 167(3) .
C2 H2 O12 0.93 2.53 3.276(3) 138.0 8_465
C9 H9 O13 0.93 2.45 3.105(3) 127.3 7_566

_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.084

# Attachment 'b816721d_4.cif'

data_126a
_database_code_depnum_ccdc_archive 'CCDC 706586'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H28 Cu N6 O8 S6'
_chemical_formula_weight         856.48

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Aba2

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

_cell_length_a                   20.144(2)
_cell_length_b                   16.6614(17)
_cell_length_c                   10.5603(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3544.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1756
_exptl_absorpt_coefficient_mu    1.028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8381
_exptl_absorpt_correction_T_max  1.0000
_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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10189
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_av_sigmaI/netI    0.1761
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         28.03
_reflns_number_total             3997
_reflns_number_gt                1907
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0162P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.47(2)
_refine_ls_number_reflns         3997
_refine_ls_number_parameters     232
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1314
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0665
_refine_ls_goodness_of_fit_ref   0.774
_refine_ls_restrained_S_all      0.773
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.5000 0.0000 0.27981(8) 0.0433(3) Uani 1 2 d S . .
S1 S 0.72774(6) 0.00663(10) -0.16210(11) 0.0469(4) Uani 1 1 d . . .
S2 S 0.71291(7) 0.10157(8) -0.27830(12) 0.0478(4) Uani 1 1 d . . .
S3 S 0.44080(7) 0.21869(9) 0.24506(14) 0.0538(4) Uani 1 1 d . . .
N1 N 0.5699(2) 0.0143(3) 0.1465(4) 0.0355(12) Uani 1 1 d . . .
N2 N 0.5679(2) 0.0267(3) -0.5854(4) 0.0404(12) Uani 1 1 d . . .
C1 C 0.5631(3) 0.0586(3) 0.0411(5) 0.0409(15) Uani 1 1 d . . .
H1 H 0.5249 0.0896 0.0331 0.049 Uiso 1 1 calc R . .
C2 C 0.6087(3) 0.0615(3) -0.0562(5) 0.0423(16) Uani 1 1 d . . .
H2 H 0.6020 0.0936 -0.1271 0.051 Uiso 1 1 calc R . .
C3 C 0.6646(3) 0.0148(3) -0.0437(5) 0.0338(15) Uani 1 1 d . . .
C4 C 0.6738(2) -0.0296(3) 0.0626(4) 0.0383(15) Uani 1 1 d . . .
H4 H 0.7123 -0.0598 0.0726 0.046 Uiso 1 1 calc R . .
C5 C 0.6258(2) -0.0296(3) 0.1554(5) 0.0397(14) Uani 1 1 d . . .
H5 H 0.6323 -0.0611 0.2270 0.048 Uiso 1 1 calc R . .
C6 C 0.6560(2) 0.0666(3) -0.3933(4) 0.0355(14) Uani 1 1 d . . .
C7 C 0.6238(3) -0.0067(3) -0.3933(5) 0.0413(16) Uani 1 1 d . . .
H7 H 0.6320 -0.0441 -0.3298 0.050 Uiso 1 1 calc R . .
C8 C 0.5800(3) -0.0233(3) -0.4878(5) 0.0411(15) Uani 1 1 d . . .
H8 H 0.5571 -0.0718 -0.4848 0.049 Uiso 1 1 calc R . .
C9 C 0.5994(3) 0.0967(3) -0.5866(5) 0.0432(15) Uani 1 1 d . . .
H9 H 0.5912 0.1319 -0.6531 0.052 Uiso 1 1 calc R . .
C10 C 0.6435(2) 0.1195(3) -0.4942(5) 0.0405(14) Uani 1 1 d . . .
H10 H 0.6647 0.1690 -0.4983 0.049 Uiso 1 1 calc R . .
O2 O 0.47677(17) 0.2932(2) 0.2597(5) 0.0801(13) Uani 1 1 d . . .
O1 O 0.47906(15) 0.14723(19) 0.2726(4) 0.0596(10) Uani 1 1 d . . .
O3 O 0.4060(2) 0.2139(3) 0.1262(4) 0.0893(16) Uani 1 1 d . . .
C11 C 0.3793(3) 0.2180(3) 0.3634(5) 0.0447(15) Uani 1 1 d . . .
C12 C 0.3127(3) 0.2062(3) 0.3349(5) 0.0526(17) Uani 1 1 d . . .
H12 H 0.2997 0.1996 0.2510 0.063 Uiso 1 1 calc R . .
C13 C 0.2658(3) 0.2042(4) 0.4291(8) 0.069(2) Uani 1 1 d . . .
H13 H 0.2216 0.1955 0.4072 0.083 Uiso 1 1 calc R . .
N14 N 0.2809(3) 0.2142(4) 0.5495(7) 0.087(2) Uani 1 1 d . . .
C15 C 0.3445(4) 0.2265(4) 0.5783(7) 0.082(2) Uani 1 1 d . . .
H15 H 0.3556 0.2335 0.6631 0.098 Uiso 1 1 calc R . .
C16 C 0.3956(3) 0.2296(4) 0.4886(6) 0.0578(19) Uani 1 1 d . . .
H16 H 0.4392 0.2391 0.5129 0.069 Uiso 1 1 calc R . .
O1W O 0.4050(2) 0.1648(3) 0.8704(5) 0.1196(19) 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
Cu N1 2.005(4) 2_655 ?
Cu N1 2.005(4) . ?
Cu N2 2.023(4) 2_656 ?
Cu N2 2.023(4) 1_556 ?
Cu O1 2.490(3) . ?
S1 C3 1.789(5) . ?
S1 S2 2.024(2) . ?
S2 C6 1.769(5) . ?
S3 O3 1.440(4) . ?
S3 O2 1.446(4) . ?
S3 O1 1.448(3) . ?
S3 C11 1.760(6) . ?
N1 C1 1.344(6) . ?
N1 C5 1.346(6) . ?
N2 C9 1.328(6) . ?
N2 C8 1.348(7) . ?
N2 Cu 2.023(4) 1_554 ?
C1 C2 1.379(6) . ?
C2 C3 1.375(7) . ?
C3 C4 1.356(6) . ?
C4 C5 1.376(6) . ?
C6 C7 1.383(7) . ?
C6 C10 1.405(7) . ?
C7 C8 1.360(7) . ?
C9 C10 1.373(7) . ?
C11 C16 1.376(7) . ?
C11 C12 1.389(7) . ?
C12 C13 1.373(8) . ?
C13 N14 1.317(7) . ?
N14 C15 1.334(8) . ?
C15 C16 1.399(8) . ?

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
N1 Cu N1 90.8(2) 2_655 . ?
N1 Cu N2 89.61(14) 2_655 2_656 ?
N1 Cu N2 174.0(2) . 2_656 ?
N1 Cu N2 174.0(2) 2_655 1_556 ?
N1 Cu N2 89.61(14) . 1_556 ?
N2 Cu N2 90.6(3) 2_656 1_556 ?
N1 Cu O1 88.64(15) 2_655 . ?
N1 Cu O1 88.89(15) . . ?
N2 Cu O1 97.10(16) 2_656 . ?
N2 Cu O1 85.39(16) 1_556 . ?
C3 S1 S2 105.04(19) . . ?
C6 S2 S1 104.8(2) . . ?
O3 S3 O2 112.6(3) . . ?
O3 S3 O1 112.9(3) . . ?
O2 S3 O1 114.7(2) . . ?
O3 S3 C11 106.0(3) . . ?
O2 S3 C11 106.4(3) . . ?
O1 S3 C11 103.1(3) . . ?
C1 N1 C5 116.2(5) . . ?
C1 N1 Cu 125.1(4) . . ?
C5 N1 Cu 118.4(4) . . ?
C9 N2 C8 117.6(5) . . ?
C9 N2 Cu 120.6(4) . 1_554 ?
C8 N2 Cu 121.6(4) . 1_554 ?
N1 C1 C2 124.7(5) . . ?
C3 C2 C1 117.0(5) . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 S1 116.1(4) . . ?
C2 C3 S1 123.9(4) . . ?
C3 C4 C5 119.5(5) . . ?
N1 C5 C4 122.6(5) . . ?
C7 C6 C10 118.0(5) . . ?
C7 C6 S2 126.5(4) . . ?
C10 C6 S2 115.5(4) . . ?
C8 C7 C6 118.9(5) . . ?
N2 C8 C7 123.5(5) . . ?
N2 C9 C10 123.1(5) . . ?
C9 C10 C6 118.8(5) . . ?
S3 O1 Cu 155.0(2) . . ?
C16 C11 C12 117.3(6) . . ?
C16 C11 S3 120.9(5) . . ?
C12 C11 S3 121.8(5) . . ?
C13 C12 C11 120.8(6) . . ?
N14 C13 C12 122.5(7) . . ?
C13 N14 C15 117.5(7) . . ?
N14 C15 C16 123.9(7) . . ?
C11 C16 C15 118.0(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12 N14 0.93 2.69 3.557(8) 155.9 8_544
C13 H13 O1W 0.93 2.63 3.557(8) 173.7 8_544
C15 H15 O1W 0.93 2.66 3.473(9) 145.8 .

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.819
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.058

# Attachment 'b816721d_5.cif'

data_121
_database_code_depnum_ccdc_archive 'CCDC 706587'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H24 Cu N2 O10 S4'
_chemical_formula_weight         572.13

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.6637(14)
_cell_length_b                   7.8319(14)
_cell_length_c                   10.2543(18)
_cell_angle_alpha                71.048(3)
_cell_angle_beta                 83.663(3)
_cell_angle_gamma                77.074(3)
_cell_volume                     566.89(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1442
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      27.55

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             295
_exptl_absorpt_coefficient_mu    1.384
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8692
_exptl_absorpt_correction_T_max  1.0000
_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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3699
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.99
_reflns_number_total             2581
_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    '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)+(0.0363P)²+0.2530P] 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         2581
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.5000 1.0000 0.5000 0.03146(15) Uani 1 2 d S . .
N1 N 0.4063(3) 0.8256(3) 0.4312(2) 0.0302(5) Uani 1 1 d . . .
O1 O 0.2921(3) 0.2506(3) 0.3504(2) 0.0571(7) Uani 1 1 d . . .
O2 O 0.0078(3) 0.4600(3) 0.2985(2) 0.0550(6) Uani 1 1 d . . .
O3 O 0.2514(3) 0.4798(3) 0.1265(2) 0.0513(6) Uani 1 1 d . . .
O4 O 0.3083(3) 0.9863(3) 0.65023(19) 0.0361(4) Uani 1 1 d . . .
S1 S 0.19912(10) 0.43089(9) 0.27194(7) 0.03586(19) Uani 1 1 d . . .
S2 S 0.30678(11) 0.82541(9) 0.78372(7) 0.0383(2) Uani 1 1 d . . .
C1 C 0.2323(4) 0.8175(4) 0.4449(3) 0.0387(7) Uani 1 1 d . . .
H1 H 0.1548 0.8938 0.4885 0.046 Uiso 1 1 calc R . .
C2 C 0.1623(4) 0.7021(4) 0.3980(3) 0.0387(7) Uani 1 1 d . . .
H2 H 0.0405 0.7008 0.4096 0.046 Uiso 1 1 calc R . .
C3 C 0.2766(4) 0.5883(3) 0.3333(3) 0.0305(6) Uani 1 1 d . . .
C4 C 0.4563(4) 0.5967(4) 0.3169(3) 0.0355(6) Uani 1 1 d . . .
H4 H 0.5359 0.5236 0.2720 0.043 Uiso 1 1 calc R . .
C5 C 0.5159(4) 0.7147(4) 0.3680(3) 0.0337(6) Uani 1 1 d . . .
H5 H 0.6374 0.7177 0.3582 0.040 Uiso 1 1 calc R . .
C6 C 0.4137(5) 0.8785(5) 0.9065(3) 0.0551(9) Uani 1 1 d . . .
H6A H 0.5356 0.8852 0.8758 0.083 Uiso 1 1 calc R . .
H6B H 0.4115 0.7841 0.9939 0.083 Uiso 1 1 calc R . .
H6C H 0.3517 0.9949 0.9162 0.083 Uiso 1 1 calc R . .
C7 C 0.0831(5) 0.8676(6) 0.8484(4) 0.0630(10) Uani 1 1 d . . .
H7A H 0.0520 0.9906 0.8545 0.094 Uiso 1 1 calc R . .
H7B H 0.0715 0.7810 0.9384 0.094 Uiso 1 1 calc R . .
H7C H 0.0043 0.8541 0.7875 0.094 Uiso 1 1 calc R . .
O1W O 0.2172(4) 0.3134(4) 0.9183(3) 0.0627(7) Uani 1 1 d . . .
H11 H 0.223(5) 0.373(6) 0.979(5) 0.084(14) Uiso 1 1 d . . .
H12 H 0.138(7) 0.394(7) 0.857(5) 0.101(17) 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
Cu O4 2.0014(19) 2_676 ?
Cu O4 2.0014(19) . ?
Cu N1 2.014(2) . ?
Cu N1 2.014(2) 2_676 ?
Cu O1 2.434(2) 1_565 ?
Cu O1 2.434(2) 2_666 ?
Cu Cu 7.8319(14) 1_565 ?
N1 C1 1.339(4) . ?
N1 C5 1.341(3) . ?
O1 S1 1.445(2) . ?
O1 Cu 2.434(2) 1_545 ?
O2 S1 1.441(2) . ?
O3 S1 1.448(2) . ?
O4 S2 1.5310(19) . ?
S1 C3 1.784(3) . ?
S2 C7 1.768(4) . ?
S2 C6 1.774(3) . ?
C1 C2 1.376(4) . ?
C2 C3 1.382(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.375(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cu O4 180.000(1) 2_676 . ?
O4 Cu N1 88.78(8) 2_676 . ?
O4 Cu N1 91.22(8) . . ?
O4 Cu N1 91.22(8) 2_676 2_676 ?
O4 Cu N1 88.78(8) . 2_676 ?
N1 Cu N1 180.000(1) . 2_676 ?
O4 Cu O1 92.03(9) 2_676 1_565 ?
O4 Cu O1 87.97(9) . 1_565 ?
N1 Cu O1 87.74(8) . 1_565 ?
N1 Cu O1 92.26(8) 2_676 1_565 ?
O4 Cu O1 87.97(9) 2_676 2_666 ?
O4 Cu O1 92.03(9) . 2_666 ?
N1 Cu O1 92.26(8) . 2_666 ?
N1 Cu O1 87.74(8) 2_676 2_666 ?
O1 Cu O1 180.0 1_565 2_666 ?
O4 Cu Cu 91.84(5) 2_676 1_565 ?
O4 Cu Cu 88.16(5) . 1_565 ?
N1 Cu Cu 150.67(6) . 1_565 ?
N1 Cu Cu 29.33(6) 2_676 1_565 ?
O1 Cu Cu 62.93(5) 1_565 1_565 ?
O1 Cu Cu 117.07(5) 2_666 1_565 ?
C1 N1 C5 117.4(2) . . ?
C1 N1 Cu 121.44(18) . . ?
C5 N1 Cu 121.13(19) . . ?
S1 O1 Cu 163.37(13) . 1_545 ?
S2 O4 Cu 125.37(12) . . ?
O2 S1 O1 113.25(15) . . ?
O2 S1 O3 113.55(14) . . ?
O1 S1 O3 113.03(14) . . ?
O2 S1 C3 106.29(13) . . ?
O1 S1 C3 104.98(12) . . ?
O3 S1 C3 104.71(12) . . ?
O4 S2 C7 103.03(16) . . ?
O4 S2 C6 106.01(14) . . ?
C7 S2 C6 98.87(18) . . ?
N1 C1 C2 123.4(3) . . ?
C1 C2 C3 118.6(3) . . ?
C2 C3 C4 118.6(2) . . ?
C2 C3 S1 121.9(2) . . ?
C4 C3 S1 119.4(2) . . ?
C5 C4 C3 119.1(2) . . ?
N1 C5 C4 122.8(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H11 O3 0.91(5) 2.00(5) 2.899(4) 174(4) 1_556
O1W H12 O2 0.91(5) 1.93(5) 2.825(4) 169(4) 2_566
O1W H12 S1 0.91(5) 2.88(5) 3.738(3) 159(4) 2_566
C1 H1 O4 0.93 2.50 2.990(3) 113.1 .
C2 H2 O2 0.93 2.57 2.927(4) 103.5 .
C5 H5 O4 0.93 2.42 2.900(3) 112.1 2_676
C6 H6C O1W 0.96 2.48 3.438(5) 172.9 1_565

_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.077


