# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013

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#                                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.
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#  fide research purposes only. It may contain copyright material
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data_[Cu(bipy)(mpba)]2



_audit_update_record             
;
2013-04-04 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H28 Cu2 N8 O12, 2(H2 O)'
_chemical_formula_sum            'C40 H32 Cu2 N8 O14'
_chemical_formula_weight         975.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_hall  '-P 2yn'

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                   11.030(2)
_cell_length_b                   13.570(3)
_cell_length_c                   13.623(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.40(3)
_cell_angle_gamma                90.00
_cell_volume                     1871.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8979
_cell_measurement_theta_min      3.2540
_cell_measurement_theta_max      66.0022

_exptl_crystal_description       Platlet
_exptl_crystal_colour            'Greenish Blue'
_exptl_crystal_size_max          0.1274
_exptl_crystal_size_mid          0.1029
_exptl_crystal_size_min          0.0314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             996
_exptl_absorpt_coefficient_mu    2.158
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_process_details   
;
'Sun Mar 04 10:16:47 2012'
;

_exptl_special_details           ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33041
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.39
_diffrn_reflns_theta_max         66.11
_reflns_number_total             3253
_reflns_number_gt                2569
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
'Sun Mar 04 10:16:47 2012'
;
_computing_cell_refinement       
;
'Sun Mar 04 10:16:47 2012'
;
_computing_data_reduction        
;
'Sun Mar 04 10:16:47 2012'
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0462P)^2^+2.4083P] where P=(Fo^2^+2Fc^2^)/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         3253
_refine_ls_number_parameters     295
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.31365(4) 0.49408(3) 0.90473(3) 0.02028(14) Uani 1 1 d . . .
O1 O 0.38671(19) 0.38225(14) 0.85602(16) 0.0228(5) Uani 1 1 d . . .
O2 O 0.3564(2) 0.21934(14) 0.83399(17) 0.0275(5) Uani 1 1 d . . .
O6 O 0.0563(2) 0.49806(16) 1.38022(17) 0.0345(5) Uani 1 1 d . . .
O3 O 0.2442(2) 0.39006(14) 0.97077(16) 0.0226(5) Uani 1 1 d . . .
O5 O -0.14297(19) 0.50620(14) 1.24755(16) 0.0251(5) Uani 1 1 d . . .
O7 O 0.2300(2) 0.52626(16) 1.58813(18) 0.0291(5) Uani 1 1 d D . .
N3 N 0.2210(2) 0.22209(17) 0.96586(18) 0.0198(5) Uani 1 1 d . . .
H3 H 0.2379 0.1699 0.9378 0.024 Uiso 1 1 calc R . .
N4 N 0.0055(2) 0.33201(17) 1.20389(19) 0.0221(5) Uani 1 1 d . . .
H4 H -0.0449 0.3109 1.2340 0.027 Uiso 1 1 calc R . .
N1 N 0.2799(2) 0.60464(17) 0.98504(19) 0.0202(5) Uani 1 1 d . . .
O4 O 0.0954(3) 0.47459(18) 1.1742(3) 0.0592(9) Uani 1 1 d . . .
N2 N 0.4116(2) 0.59759(17) 0.86379(19) 0.0221(5) Uani 1 1 d . . .
C18 C 0.1148(3) 0.2831(2) 1.0849(2) 0.0211(6) Uani 1 1 d . . .
H18 H 0.1337 0.3482 1.0750 0.025 Uiso 1 1 calc R . .
C11 C 0.3419(3) 0.2989(2) 0.8690(2) 0.0208(6) Uani 1 1 d . . .
C17 C 0.0486(3) 0.2601(2) 1.1505(2) 0.0199(6) Uani 1 1 d . . .
C6 C 0.3982(3) 0.6890(2) 0.8976(2) 0.0217(6) Uani 1 1 d . . .
C5 C 0.3253(3) 0.6928(2) 0.9681(2) 0.0219(6) Uani 1 1 d . . .
C12 C 0.2615(3) 0.3059(2) 0.9403(2) 0.0185(6) Uani 1 1 d . . .
C2 C 0.1934(3) 0.6811(2) 1.1002(3) 0.0293(7) Uani 1 1 d . . .
H2 H 0.1495 0.6753 1.1458 0.035 Uiso 1 1 calc R . .
C16 C 0.0200(3) 0.1631(2) 1.1653(3) 0.0292(7) Uani 1 1 d . . .
H16 H -0.0249 0.1482 1.2085 0.035 Uiso 1 1 calc R . .
C13 C 0.1522(3) 0.2068(2) 1.0346(2) 0.0208(6) Uani 1 1 d . . .
C19 C 0.0323(3) 0.4297(2) 1.2145(2) 0.0269(7) Uani 1 1 d . . .
C4 C 0.3043(3) 0.7777(2) 1.0149(3) 0.0279(7) Uani 1 1 d . . .
H4A H 0.3344 0.8382 1.0016 0.033 Uiso 1 1 calc R . .
C7 C 0.4516(3) 0.7706(2) 0.8678(2) 0.0261(7) Uani 1 1 d . . .
H7 H 0.4408 0.8334 0.8905 0.031 Uiso 1 1 calc R . .
C9 C 0.5352(3) 0.6637(2) 0.7706(3) 0.0310(7) Uani 1 1 d . . .
H9 H 0.5820 0.6537 0.7277 0.037 Uiso 1 1 calc R . .
C8 C 0.5208(3) 0.7569(2) 0.8040(3) 0.0303(7) Uani 1 1 d . . .
H8 H 0.5577 0.8106 0.7835 0.036 Uiso 1 1 calc R . .
C20 C -0.0221(3) 0.4823(2) 1.2881(2) 0.0240(7) Uani 1 1 d . . .
C10 C 0.4790(3) 0.5850(2) 0.8019(2) 0.0270(7) Uani 1 1 d . . .
H10 H 0.4884 0.5218 0.7793 0.032 Uiso 1 1 calc R . .
C14 C 0.1261(4) 0.1092(2) 1.0497(3) 0.0341(8) Uani 1 1 d . . .
H14 H 0.1528 0.0585 1.0169 0.041 Uiso 1 1 calc R . .
C1 C 0.2159(3) 0.5995(2) 1.0492(2) 0.0270(7) Uani 1 1 d . . .
H1 H 0.1849 0.5385 1.0603 0.032 Uiso 1 1 calc R . .
C3 C 0.2378(3) 0.7716(2) 1.0819(3) 0.0302(7) Uani 1 1 d . . .
H3A H 0.2231 0.8280 1.1144 0.036 Uiso 1 1 calc R . .
C15 C 0.0593(4) 0.0891(2) 1.1149(3) 0.0395(9) Uani 1 1 d . . .
H15 H 0.0404 0.0240 1.1248 0.047 Uiso 1 1 calc R . .
H7B H 0.205(4) 0.513(3) 1.640(2) 0.059 Uiso 1 1 d D . .
H7A H 0.160(3) 0.518(3) 1.529(2) 0.059 Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0274(2) 0.0165(2) 0.0231(2) -0.00039(17) 0.01649(18) -0.00223(17)
O1 0.0289(11) 0.0194(11) 0.0286(11) 0.0001(8) 0.0205(10) -0.0008(8)
O2 0.0394(13) 0.0201(11) 0.0357(13) -0.0033(9) 0.0286(11) 0.0007(9)
O6 0.0340(12) 0.0396(14) 0.0249(12) -0.0042(10) 0.0065(10) 0.0035(10)
O3 0.0319(11) 0.0155(10) 0.0287(11) -0.0013(8) 0.0209(10) -0.0001(8)
O5 0.0277(11) 0.0282(11) 0.0230(10) -0.0015(9) 0.0140(9) 0.0007(9)
O7 0.0351(12) 0.0312(12) 0.0261(12) -0.0017(10) 0.0176(10) -0.0046(10)
N3 0.0198(12) 0.0198(13) 0.0198(13) 0.0000(10) 0.0079(11) 0.0000(10)
N4 0.0222(13) 0.0222(13) 0.0222(13) 0.0000(10) 0.0088(11) 0.0000(10)
N1 0.0202(12) 0.0202(13) 0.0202(12) 0.0000(10) 0.0080(10) 0.0000(10)
O4 0.104(2) 0.0282(14) 0.090(2) -0.0148(13) 0.085(2) -0.0214(14)
N2 0.0221(13) 0.0221(13) 0.0221(13) 0.0000(10) 0.0088(11) 0.0000(10)
C18 0.0242(15) 0.0163(14) 0.0258(16) -0.0001(12) 0.0130(14) -0.0014(11)
C11 0.0212(15) 0.0257(17) 0.0181(15) 0.0020(12) 0.0107(13) 0.0029(12)
C17 0.0208(15) 0.0197(15) 0.0213(15) -0.0021(12) 0.0104(12) -0.0005(11)
C6 0.0237(15) 0.0220(15) 0.0186(15) 0.0016(12) 0.0077(13) 0.0012(12)
C5 0.0209(15) 0.0205(15) 0.0231(16) 0.0009(12) 0.0073(13) -0.0007(12)
C12 0.0202(14) 0.0195(15) 0.0169(14) 0.0007(11) 0.0086(12) 0.0009(11)
C2 0.0300(17) 0.0313(18) 0.0311(18) -0.0051(14) 0.0169(15) -0.0011(14)
C16 0.0422(19) 0.0215(16) 0.0378(18) 0.0011(14) 0.0305(16) -0.0054(14)
C13 0.0208(14) 0.0242(16) 0.0197(15) 0.0006(12) 0.0104(13) -0.0029(12)
C19 0.0363(18) 0.0251(16) 0.0281(17) -0.0004(13) 0.0222(15) -0.0022(14)
C4 0.0281(17) 0.0202(16) 0.0365(19) -0.0019(13) 0.0140(15) -0.0017(13)
C7 0.0278(17) 0.0217(16) 0.0276(17) 0.0038(13) 0.0098(14) -0.0041(13)
C9 0.0335(18) 0.0358(19) 0.0288(17) -0.0016(14) 0.0178(15) -0.0113(14)
C8 0.0348(18) 0.0271(17) 0.0318(18) 0.0049(14) 0.0161(15) -0.0082(14)
C20 0.0377(18) 0.0149(14) 0.0269(16) 0.0014(12) 0.0209(15) -0.0016(12)
C10 0.0327(17) 0.0269(16) 0.0268(16) -0.0038(13) 0.0176(14) -0.0033(13)
C14 0.052(2) 0.0207(16) 0.046(2) -0.0060(14) 0.0365(19) -0.0034(15)
C1 0.0332(17) 0.0248(17) 0.0271(17) -0.0003(13) 0.0165(15) -0.0043(13)
C3 0.0288(17) 0.0281(17) 0.0330(18) -0.0107(14) 0.0114(15) 0.0029(13)
C15 0.070(3) 0.0151(16) 0.053(2) -0.0006(15) 0.045(2) -0.0066(15)

_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 O1 1.9538(19) . ?
Cu1 N1 1.977(2) . ?
Cu1 N2 1.982(2) . ?
Cu1 O3 1.9840(19) . ?
Cu1 O5 2.178(2) 3_567 ?
O1 C11 1.275(3) . ?
O2 C11 1.216(3) . ?
O6 C20 1.228(4) . ?
O3 C12 1.256(3) . ?
O5 C20 1.266(4) . ?
O5 Cu1 2.178(2) 3_567 ?
O7 H7B 0.867(18) . ?
O7 H7A 0.876(19) . ?
N3 C12 1.318(4) . ?
N3 C13 1.435(4) . ?
N3 H3 0.8600 . ?
N4 C19 1.353(4) . ?
N4 C17 1.408(4) . ?
N4 H4 0.8600 . ?
N1 C1 1.326(4) . ?
N1 C5 1.353(4) . ?
O4 C19 1.209(4) . ?
N2 C10 1.339(4) . ?
N2 C6 1.351(4) . ?
C18 C13 1.391(4) . ?
C18 C17 1.395(4) . ?
C18 H18 0.9300 . ?
C11 C12 1.556(4) . ?
C17 C16 1.387(4) . ?
C6 C7 1.389(4) . ?
C6 C5 1.478(4) . ?
C5 C4 1.381(4) . ?
C2 C3 1.381(5) . ?
C2 C1 1.382(4) . ?
C2 H2 0.9300 . ?
C16 C15 1.380(4) . ?
C16 H16 0.9300 . ?
C13 C14 1.388(4) . ?
C19 C20 1.533(4) . ?
C4 C3 1.381(4) . ?
C4 H4A 0.9300 . ?
C7 C8 1.380(4) . ?
C7 H7 0.9300 . ?
C9 C8 1.374(5) . ?
C9 C10 1.385(4) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C10 H10 0.9300 . ?
C14 C15 1.388(4) . ?
C14 H14 0.9300 . ?
C1 H1 0.9300 . ?
C3 H3A 0.9300 . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 166.15(9) . . ?
O1 Cu1 N2 96.34(9) . . ?
N1 Cu1 N2 82.04(10) . . ?
O1 Cu1 O3 83.51(8) . . ?
N1 Cu1 O3 95.59(9) . . ?
N2 Cu1 O3 169.55(9) . . ?
O1 Cu1 O5 89.56(8) . 3_567 ?
N1 Cu1 O5 104.28(9) . 3_567 ?
N2 Cu1 O5 95.43(9) . 3_567 ?
O3 Cu1 O5 95.01(8) . 3_567 ?
C11 O1 Cu1 114.03(17) . . ?
C12 O3 Cu1 111.12(17) . . ?
C20 O5 Cu1 140.98(19) . 3_567 ?
H7B O7 H7A 106(3) . . ?
C12 N3 C13 128.3(2) . . ?
C12 N3 H3 115.8 . . ?
C13 N3 H3 115.8 . . ?
C19 N4 C17 129.0(3) . . ?
C19 N4 H4 115.5 . . ?
C17 N4 H4 115.5 . . ?
C1 N1 C5 119.3(2) . . ?
C1 N1 Cu1 126.3(2) . . ?
C5 N1 Cu1 114.39(19) . . ?
C10 N2 C6 119.7(3) . . ?
C10 N2 Cu1 126.0(2) . . ?
C6 N2 Cu1 114.13(19) . . ?
C13 C18 C17 118.9(3) . . ?
C13 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
O2 C11 O1 127.9(3) . . ?
O2 C11 C12 119.7(2) . . ?
O1 C11 C12 112.4(2) . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 N4 116.1(3) . . ?
C18 C17 N4 123.1(3) . . ?
N2 C6 C7 121.1(3) . . ?
N2 C6 C5 114.6(2) . . ?
C7 C6 C5 124.3(3) . . ?
N1 C5 C4 121.2(3) . . ?
N1 C5 C6 114.4(2) . . ?
C4 C5 C6 124.4(3) . . ?
O3 C12 N3 125.8(2) . . ?
O3 C12 C11 117.5(2) . . ?
N3 C12 C11 116.7(2) . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C15 C16 C17 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C14 C13 C18 121.1(3) . . ?
C14 C13 N3 115.4(3) . . ?
C18 C13 N3 123.4(3) . . ?
O4 C19 N4 125.9(3) . . ?
O4 C19 C20 120.5(3) . . ?
N4 C19 C20 113.6(2) . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
C8 C7 C6 118.8(3) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C8 C9 C10 118.9(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
O6 C20 O5 126.4(3) . . ?
O6 C20 C19 116.8(3) . . ?
O5 C20 C19 116.9(3) . . ?
N2 C10 C9 121.6(3) . . ?
N2 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C13 C14 C15 118.5(3) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
N1 C1 C2 122.6(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C16 C15 C14 121.7(3) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?

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
O7 H7A O6 0.876(19) 1.91(2) 2.744(3) 159(4) .
O7 H7B O5 0.867(18) 1.934(19) 2.799(3) 176(4) 3_568
N3 H3 O7 0.86 2.04 2.865(3) 161.5 2_547
C14 H14 O7 0.93 2.32 3.111(4) 142.8 2_547
N4 H4 O2 0.86 2.09 2.940(3) 167.5 4_566
C16 H16 O1 0.93 2.59 3.511(4) 170.0 4_566

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        66.11
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.067

_database_code_depnum_ccdc_archive 'CCDC 942307'
#######################################################################
#
#                 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(bipy)(mpba)]chain



_audit_update_record             
;
2013-04-04 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 Cu N4 O7 S'
_chemical_formula_weight         532.99

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c c a'
_symmetry_space_group_name_hall  '-P 2a 2ac'


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

_cell_length_a                   13.5402(8)
_cell_length_b                   11.3945(7)
_cell_length_c                   16.0434(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2475.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2216
_cell_measurement_theta_min      1.9641
_cell_measurement_theta_max      29.3887

_exptl_crystal_description       Platlet
_exptl_crystal_colour            'Light Blue'
_exptl_crystal_size_max          0.7155
_exptl_crystal_size_mid          0.1459
_exptl_crystal_size_min          0.0893
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    1.013
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.686
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_process_details   
;
'Wed Feb 13 10:57:06 2013'
;

_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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13505
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2536
_reflns_number_gt                1756
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
'Wed Feb 13 10:57:06 2013'
;
_computing_cell_refinement       
;
'Wed Feb 13 10:57:06 2013'
;
_computing_data_reduction        
;
'Wed Feb 13 10:57:06 2013'
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.1030P)^2^+4.2133P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0026(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2536
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1578
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   0.816
_refine_ls_restrained_S_all      0.816
_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
Cu1 Cu 0.7500 0.5000 0.19142(3) 0.0413(3) Uani 1 2 d S . .
S1 S 0.7077(4) 0.0044(6) 0.0055(2) 0.147(2) Uani 0.50 1 d P . .
O4 O 0.7500 0.0000 -0.0773(3) 0.0627(11) Uani 1 2 d S . .
O2 O 0.66040(19) 0.2598(2) 0.35924(18) 0.0575(7) Uani 1 1 d . . .
O3 O 0.83971(18) 0.3275(2) 0.21168(17) 0.0511(7) Uani 1 1 d . . .
O1 O 0.67072(18) 0.4156(2) 0.27631(15) 0.0460(6) Uani 1 1 d . . .
N2 N 0.8306(2) 0.1720(2) 0.30047(18) 0.0394(7) Uani 1 1 d . . .
H2 H 0.7962 0.1414 0.3399 0.047 Uiso 1 1 calc R . .
N1 N 0.6684(2) 0.4388(2) 0.09661(17) 0.0396(7) Uani 1 1 d . . .
C4 C 0.9175(2) 0.1114(3) 0.2751(2) 0.0390(8) Uani 1 1 d . . .
C3 C 1.0000 0.1729(4) 0.2500 0.0360(10) Uani 1 2 d S . .
H3A H 1.0000 0.2545 0.2500 0.043 Uiso 1 2 calc SR . .
C7 C 0.7027(3) 0.4668(3) 0.0209(2) 0.0380(8) Uani 1 1 d . . .
C5 C 0.9170(3) -0.0096(3) 0.2769(3) 0.0596(12) Uani 1 1 d . . .
H5 H 0.8618 -0.0504 0.2958 0.071 Uiso 1 1 calc R . .
C8 C 0.6515(3) 0.4359(3) -0.0510(2) 0.0441(9) Uani 1 1 d . . .
H8 H 0.6752 0.4575 -0.1033 0.053 Uiso 1 1 calc R . .
C6 C 1.0000 -0.0690(5) 0.2500 0.074(2) Uani 1 2 d S . .
H6 H 1.0000 -0.1506 0.2500 0.089 Uiso 1 2 calc SR . .
C11 C 0.5833(3) 0.3799(4) 0.1026(2) 0.0515(9) Uani 1 1 d . . .
H11 H 0.5587 0.3631 0.1554 0.062 Uiso 1 1 calc R . .
C2 C 0.7983(2) 0.2729(3) 0.2675(2) 0.0365(7) Uani 1 1 d . . .
C1 C 0.7001(3) 0.3188(3) 0.3051(2) 0.0383(8) Uani 1 1 d . . .
C9 C 0.5648(3) 0.3725(4) -0.0434(2) 0.0506(10) Uani 1 1 d . . .
H9 H 0.5299 0.3500 -0.0907 0.061 Uiso 1 1 calc R . .
C10 C 0.5307(3) 0.3431(4) 0.0342(3) 0.0559(10) Uani 1 1 d . . .
H10 H 0.4732 0.2993 0.0405 0.067 Uiso 1 1 calc R . .
C12 C 0.758(3) -0.097(4) 0.073(2) 0.109(14) Uani 0.25 1 d P . .
H12A H 0.7202 -0.1683 0.0711 0.163 Uiso 0.25 1 calc PR . .
H12B H 0.7567 -0.0663 0.1289 0.163 Uiso 0.25 1 calc PR . .
H12C H 0.8250 -0.1132 0.0573 0.163 Uiso 0.25 1 calc PR . .
C13 C 0.787(4) 0.118(4) 0.0510(19) 0.119(17) Uani 0.25 1 d P . .
H13A H 0.8546 0.0958 0.0450 0.178 Uiso 0.25 1 calc PR . .
H13B H 0.7711 0.1268 0.1090 0.178 Uiso 0.25 1 calc PR . .
H13C H 0.7754 0.1911 0.0227 0.178 Uiso 0.25 1 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0462(4) 0.0442(4) 0.0335(4) 0.000 0.000 0.0089(3)
S1 0.167(5) 0.201(4) 0.073(2) 0.017(3) 0.037(2) 0.043(5)
O4 0.079(3) 0.060(3) 0.049(2) 0.000 0.000 -0.001(2)
O2 0.0501(16) 0.0483(15) 0.0741(19) 0.0065(14) 0.0254(14) 0.0034(12)
O3 0.0462(15) 0.0471(14) 0.0599(16) 0.0137(12) 0.0177(12) 0.0143(12)
O1 0.0466(14) 0.0519(15) 0.0394(13) -0.0006(11) 0.0084(11) 0.0170(12)
N2 0.0326(15) 0.0341(14) 0.0514(17) 0.0028(12) 0.0108(13) -0.0023(12)
N1 0.0399(16) 0.0431(16) 0.0357(15) -0.0004(12) 0.0043(12) 0.0049(13)
C4 0.0328(17) 0.0312(16) 0.053(2) 0.0002(14) 0.0037(16) 0.0025(13)
C3 0.033(2) 0.026(2) 0.049(3) 0.000 0.001(2) 0.000
C7 0.0391(18) 0.0342(17) 0.0407(19) -0.0005(14) 0.0005(16) 0.0063(14)
C5 0.040(2) 0.0329(18) 0.105(4) 0.006(2) 0.020(2) -0.0034(16)
C8 0.045(2) 0.049(2) 0.0380(19) -0.0028(15) 0.0038(15) 0.0010(17)
C6 0.057(4) 0.027(3) 0.139(7) 0.000 0.028(4) 0.000
C11 0.048(2) 0.060(2) 0.046(2) 0.0037(18) 0.0103(18) -0.0015(18)
C2 0.0338(17) 0.0343(16) 0.0415(19) -0.0027(14) 0.0042(15) 0.0018(14)
C1 0.0351(19) 0.0360(17) 0.0440(19) -0.0094(15) 0.0034(15) 0.0039(15)
C9 0.044(2) 0.061(2) 0.047(2) -0.0111(18) -0.0011(17) -0.0034(18)
C10 0.049(2) 0.058(2) 0.060(2) -0.005(2) 0.006(2) -0.0103(19)
C12 0.15(3) 0.13(3) 0.05(2) 0.06(2) -0.033(16) -0.01(2)
C13 0.23(6) 0.097(18) 0.025(14) -0.027(12) 0.022(19) -0.05(3)

_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 O1 1.983(2) . ?
Cu1 O1 1.983(2) 2_665 ?
Cu1 N1 2.005(3) . ?
Cu1 N1 2.005(3) 2_665 ?
Cu1 O3 2.333(2) . ?
Cu1 O3 2.333(2) 2_665 ?
S1 S1 1.150(10) 2_655 ?
S1 O4 1.448(5) . ?
S1 C13 1.58(4) 2_655 ?
S1 C12 1.59(4) 2_655 ?
S1 C12 1.73(3) . ?
S1 C13 1.83(4) . ?
O4 S1 1.448(5) 2_655 ?
O2 C1 1.223(4) . ?
O3 C2 1.226(4) . ?
O1 C1 1.260(4) . ?
N2 C2 1.340(4) . ?
N2 C4 1.423(4) . ?
N2 H2 0.8600 . ?
N1 C11 1.338(5) . ?
N1 C7 1.339(4) . ?
C4 C5 1.380(4) . ?
C4 C3 1.379(4) . ?
C3 C4 1.379(4) 3_755 ?
C3 H3A 0.9300 . ?
C7 C8 1.391(5) . ?
C7 C7 1.488(7) 2_665 ?
C5 C6 1.381(5) . ?
C5 H5 0.9300 . ?
C8 C9 1.385(5) . ?
C8 H8 0.9300 . ?
C6 C5 1.381(5) 3_755 ?
C6 H6 0.9300 . ?
C11 C10 1.374(6) . ?
C11 H11 0.9300 . ?
C2 C1 1.551(5) . ?
C9 C10 1.370(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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 Cu1 O1 93.23(15) . 2_665 ?
O1 Cu1 N1 93.12(11) . . ?
O1 Cu1 N1 171.10(11) 2_665 . ?
O1 Cu1 N1 171.09(11) . 2_665 ?
O1 Cu1 N1 93.12(11) 2_665 2_665 ?
N1 Cu1 N1 81.29(16) . 2_665 ?
O1 Cu1 O3 77.16(9) . . ?
O1 Cu1 O3 91.77(10) 2_665 . ?
N1 Cu1 O3 95.72(11) . . ?
N1 Cu1 O3 96.41(10) 2_665 . ?
O1 Cu1 O3 91.77(10) . 2_665 ?
O1 Cu1 O3 77.16(9) 2_665 2_665 ?
N1 Cu1 O3 96.41(10) . 2_665 ?
N1 Cu1 O3 95.73(11) 2_665 2_665 ?
O3 Cu1 O3 163.98(13) . 2_665 ?
S1 S1 O4 66.6(2) 2_655 . ?
S1 S1 C13 83(2) 2_655 2_655 ?
O4 S1 C13 112.0(18) . 2_655 ?
S1 S1 C12 76.5(16) 2_655 2_655 ?
O4 S1 C12 122.4(13) . 2_655 ?
C13 S1 C12 104.9(18) 2_655 2_655 ?
S1 S1 C12 63.2(16) 2_655 . ?
O4 S1 C12 113.5(16) . . ?
C13 S1 C12 25.4(19) 2_655 . ?
C12 S1 C12 84(3) 2_655 . ?
S1 S1 C13 58.7(17) 2_655 . ?
O4 S1 C13 99.2(9) . . ?
C13 S1 C13 114.4(18) 2_655 . ?
C12 S1 C13 23.7(13) 2_655 . ?
C12 S1 C13 89.6(19) . . ?
S1 O4 S1 46.8(4) 2_655 . ?
C2 O3 Cu1 106.9(2) . . ?
C1 O1 Cu1 120.4(2) . . ?
C2 N2 C4 125.0(3) . . ?
C2 N2 H2 117.5 . . ?
C4 N2 H2 117.5 . . ?
C11 N1 C7 118.9(3) . . ?
C11 N1 Cu1 126.5(2) . . ?
C7 N1 Cu1 114.5(2) . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 N2 118.3(3) . . ?
C3 C4 N2 120.5(3) . . ?
C4 C3 C4 118.9(4) . 3_755 ?
C4 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 3_755 . ?
N1 C7 C8 121.3(3) . . ?
N1 C7 C7 114.8(2) . 2_665 ?
C8 C7 C7 123.9(2) . 2_665 ?
C4 C5 C6 118.6(4) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C5 C6 C5 121.3(5) 3_755 . ?
C5 C6 H6 119.3 3_755 . ?
C5 C6 H6 119.3 . . ?
N1 C11 C10 122.8(4) . . ?
N1 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
O3 C2 N2 125.1(3) . . ?
O3 C2 C1 120.3(3) . . ?
N2 C2 C1 114.6(3) . . ?
O2 C1 O1 127.1(3) . . ?
O2 C1 C2 117.9(3) . . ?
O1 C1 C2 115.0(3) . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 118.5(4) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S1 C13 H13A 109.5 . . ?
S1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.091

_database_code_depnum_ccdc_archive 'CCDC 942308'