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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1
_chemical_name_systematic        ?
_chemical_name_common            {[Cu2(Hsersal)2(H2O)].H2O}n
_chemical_formula_moiety         'C20 H24 Cu2 N2 O9, H2 O'
_chemical_formula_sum            'C20 H26 Cu2 N2 O10'
_chemical_formula_iupac          ?
_chemical_formula_weight         581.51
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.4080(10)
_cell_length_b                   14.011(2)
_cell_length_c                   21.402(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2221.4(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3115
_cell_measurement_theta_min      2.3949
_cell_measurement_theta_max      23.4410
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       regular
_exptl_crystal_colour            'clear intense green'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192

_exptl_absorpt_coefficient_mu    1.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.6239
_exptl_absorpt_correction_T_max  0.7452

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              'fine focus'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            14127
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
;

_reflns_number_total             3915
_reflns_number_gt                3314
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0954
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.969
_refine_ls_number_reflns         3915
_refine_ls_number_parameters     305
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[σ²(Fo²)+(0.0476P)²+1.3591P]
where P=(Fo²+2Fc²)/3
;

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.002
_refine_diff_density_min         -0.592
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1231 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.009(12)

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'

_computing_data_collection       'APEX2 V2011.4-1 (Bruker AXS)'
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Bruker AXS)'
_computing_publication_material  'SHELXTL (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu2 0.55814(10) 0.66920(6) 0.19783(4) 0.0140(2) Uani d . . . 1 . .
Cu Cu1 0.90013(10) 0.55605(6) 0.18410(4) 0.0137(2) Uani d . . D 1 . .
O O8 0.7100(6) 0.8118(4) 0.1715(3) 0.0260(14) Uani d . . . 1 . .
H H8A 0.8216 0.8001 0.164 0.039 Uiso d U . R 1 . .
H H8B 0.7028 0.8512 0.2021 0.039 Uiso d U . R 1 . .
O O10 0.7617(14) 0.9319(11) 0.0499(7) 0.156(6) Uani d . . G 1 . .
H H10A 0.7296 0.906 0.0841 0.234 Uiso d U . G 1 . .
H H10B 0.8722 0.9195 0.043 0.234 Uiso d U . G 1 . .
O O3 0.7449(6) 0.6103(3) 0.2511(2) 0.0152(12) Uani d . . . 1 . .
O O4 1.1067(6) 0.5049(3) 0.2296(2) 0.0154(11) Uani d . . . 1 . .
O O5 1.3591(6) 0.4216(4) 0.2190(2) 0.0251(14) Uani d . . . 1 . .
O O6 0.6922(6) 0.6004(4) 0.1357(2) 0.0150(12) Uani d . . . 1 . .
O O7 0.7303(6) 0.4137(3) 0.2020(3) 0.0181(12) Uani d . . D 1 . .
H H7 0.615(3) 0.407(3) 0.195(2) 0.027 Uiso d U . D 1 . .
O O1 0.0390(6) 0.7135(3) 0.1691(2) 0.0175(12) Uani d . . . 1 . .
O O2 0.3231(6) 0.6668(4) 0.1569(2) 0.0173(11) Uani d . . . 1 . .
N N2 1.0306(7) 0.5096(4) 0.1092(3) 0.0151(14) Uani d . . . 1 . .
H H2 1.0927 0.5644 0.0905 0.018 Uiso calc U . R 1 . .
O O9 1.2929(9) 0.4160(5) 0.0251(3) 0.0507(19) Uiso d . . . 1 . .
H H9 1.3022 0.4627 0.0023 0.076 Uiso calc U . R 1 . .
C C10 1.2190(8) 0.4565(5) 0.1967(4) 0.0160(16) Uani d . . . 1 . .
C C8 1.1713(8) 0.4394(5) 0.1284(3) 0.0160(16) Uani d . . . 1 . .
H H8 1.1186 0.3755 0.1251 0.019 Uiso calc U . R 1 . .
C C7 0.9003(10) 0.4719(5) 0.0617(3) 0.0195(17) Uani d . . . 1 . .
H H7A 0.9659 0.4393 0.0288 0.023 Uiso calc U . R 1 . .
H H7B 0.8198 0.4263 0.0813 0.023 Uiso calc U . R 1 . .
C C6 0.7928(9) 0.5514(6) 0.0342(4) 0.0159(16) Uani d . . . 1 . .
C C1 0.6934(9) 0.6144(5) 0.0727(4) 0.0142(17) Uani d . . . 1 . .
C C2 0.5982(9) 0.6888(5) 0.0456(3) 0.0165(17) Uani d . . . 1 . .
H H2A 0.5326 0.7302 0.0709 0.02 Uiso calc U . R 1 . .
C C3 0.5994(11) 0.7021(6) -0.0182(4) 0.027(2) Uani d . . . 1 . .
H H3 0.5362 0.7529 -0.0356 0.033 Uiso calc U . R 1 . .
C C4 0.6950(12) 0.6398(6) -0.0571(4) 0.031(2) Uani d . . . 1 . .
H H4 0.6942 0.6478 -0.1002 0.038 Uiso calc U . R 1 . .
C C5 0.7899(9) 0.5666(6) -0.0300(4) 0.0199(18) Uani d . . . 1 . .
H H5 0.855 0.5255 -0.0557 0.024 Uiso calc U . R 1 . .
C C9 1.3389(10) 0.4420(7) 0.0872(4) 0.029(2) Uani d . . . 1 . .
H H9A 1.3901 0.5058 0.0875 0.035 Uiso calc U . R 1 . .
H H9B 1.4288 0.3982 0.1034 0.035 Uiso calc U . R 1 . .
C C20 0.7577(9) 0.3690(5) 0.2613(4) 0.0164(18) Uani d . . D 1 . .
H H20A 0.6648 0.3892 0.2904 0.02 Uiso calc U . R 1 . .
H H20B 0.8741 0.3874 0.2782 0.02 Uiso calc U . R 1 . .
C C18 0.2498(9) 0.7602(5) 0.2474(4) 0.0142(17) Uani d . . . 1 . .
H H18 0.1628 0.7423 0.2798 0.017 Uiso calc U . R 1 . .
C C11 0.7661(9) 0.6295(5) 0.3127(4) 0.0136(16) Uani d . . . 1 . .
C C16 0.6208(9) 0.6580(5) 0.3496(4) 0.0181(17) Uani d . . . 1 . .
C C15 0.6474(10) 0.6826(6) 0.4115(4) 0.0218(19) Uani d . . . 1 . .
H H15 0.5497 0.7032 0.4352 0.026 Uiso calc U . R 1 . .
C C14 0.8181(10) 0.6773(6) 0.4392(4) 0.0250(19) Uani d . . . 1 . .
H H14 0.8354 0.6949 0.4806 0.03 Uiso calc U . R 1 . .
C C13 0.9578(10) 0.6455(5) 0.4037(4) 0.0230(19) Uani d . . . 1 . .
H H13 1.0718 0.6409 0.4217 0.028 Uiso calc U . R 1 . .
C C12 0.9363(9) 0.6200(5) 0.3420(3) 0.0168(17) Uani d . . . 1 . .
H H12 1.034 0.5965 0.3195 0.02 Uiso calc U . R 1 . .
C C17 0.4322(8) 0.6631(5) 0.3224(3) 0.0176(16) Uani d . . . 1 . .
H H17A 0.3949 0.6004 0.3082 0.021 Uiso calc U . R 1 . .
H H17B 0.3478 0.6844 0.3541 0.021 Uiso calc U . R 1 . .
N N1 0.4320(8) 0.7318(4) 0.2684(3) 0.0144(13) Uiso d . . . 1 . .
H H1 0.4993 0.7892 0.2804 0.017 Uiso calc U . R 1 . .
C C19 0.1975(8) 0.7101(5) 0.1870(4) 0.0157(17) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu2 O6 . 1.920(5) ?
Cu2 O2 . 1.950(4) ?
Cu2 O3 . 1.973(5) ?
Cu2 N1 . 1.982(6) ?
Cu2 O8 . 2.360(5) ?
Cu1 O4 . 1.950(5) ?
Cu1 O6 . 1.958(5) ?
Cu1 N2 . 1.983(6) ?
Cu1 O3 . 1.989(5) ?
Cu1 O7 . 2.389(5) ?
O8 H8A . 0.8583 ?
O8 H8B . 0.858 ?
O10 H10A . 0.85 ?
O10 H10B . 0.85 ?
O3 C11 . 1.355(9) ?
O4 C10 . 1.284(8) ?
O5 C10 . 1.243(8) ?
O6 C1 . 1.362(9) ?
O7 C20 . 1.429(9) ?
O7 H7 . 0.868(13) ?
O1 C19 . 1.236(8) ?
O2 C19 . 1.284(8) ?
N2 C8 . 1.490(8) ?
N2 C7 . 1.498(8) ?
N2 H2 . 0.98 ?
O9 C9 . 1.418(10) ?
O9 H9 . 0.82 ?
C10 C8 . 1.523(10) ?
C8 C9 . 1.524(9) ?
C8 H8 . 0.98 ?
C7 C6 . 1.489(10) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C6 C5 . 1.392(10) ?
C6 C1 . 1.414(10) ?
C1 C2 . 1.385(10) ?
C2 C3 . 1.380(10) ?
C2 H2A . 0.93 ?
C3 C4 . 1.398(11) ?
C3 H3 . 0.93 ?
C4 C5 . 1.372(11) ?
C4 H4 . 0.93 ?
C5 H5 . 0.93 ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C20 C18 3_645 1.537(10) ?
C20 H20A . 0.97 ?
C20 H20B . 0.97 ?
C18 N1 . 1.478(9) ?
C18 C19 . 1.521(10) ?
C18 C20 3_655 1.537(10) ?
C18 H18 . 0.98 ?
C11 C16 . 1.394(10) ?
C11 C12 . 1.414(10) ?
C16 C15 . 1.383(10) ?
C16 C17 . 1.516(9) ?
C15 C14 . 1.398(10) ?
C15 H15 . 0.93 ?
C14 C13 . 1.358(10) ?
C14 H14 . 0.93 ?
C13 C12 . 1.378(10) ?
C13 H13 . 0.93 ?
C12 H12 . 0.93 ?
C17 N1 . 1.503(8) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
N1 H1 . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O6 Cu2 O2 . . 98.2(2) ?
O6 Cu2 O3 . . 80.1(2) ?
O2 Cu2 O3 . . 151.5(2) ?
O6 Cu2 N1 . . 174.1(2) ?
O2 Cu2 N1 . . 86.0(2) ?
O3 Cu2 N1 . . 94.3(2) ?
O6 Cu2 O8 . . 90.8(2) ?
O2 Cu2 O8 . . 109.5(2) ?
O3 Cu2 O8 . . 99.06(19) ?
N1 Cu2 O8 . . 91.8(2) ?
O4 Cu1 O6 . . 176.7(2) ?
O4 Cu1 N2 . . 84.3(2) ?
O6 Cu1 N2 . . 93.4(2) ?
O4 Cu1 O3 . . 103.5(2) ?
O6 Cu1 O3 . . 78.8(2) ?
N2 Cu1 O3 . . 172.1(2) ?
O4 Cu1 O7 . . 91.52(18) ?
O6 Cu1 O7 . . 86.31(19) ?
N2 Cu1 O7 . . 96.4(2) ?
O3 Cu1 O7 . . 84.21(19) ?
Cu2 O8 H8A . . 110.1 ?
Cu2 O8 H8B . . 109.5 ?
H8A O8 H8B . . 109.0 ?
H10A O10 H10B . . 109.5 ?
C11 O3 Cu2 . . 124.1(4) ?
C11 O3 Cu1 . . 135.3(4) ?
Cu2 O3 Cu1 . . 98.6(2) ?
C10 O4 Cu1 . . 115.4(4) ?
C1 O6 Cu2 . . 128.1(4) ?
C1 O6 Cu1 . . 124.4(4) ?
Cu2 O6 Cu1 . . 101.5(2) ?
C20 O7 Cu1 . . 115.6(4) ?
C20 O7 H7 . . 104.(2) ?
Cu1 O7 H7 . . 125.(2) ?
C19 O2 Cu2 . . 114.4(4) ?
C8 N2 C7 . . 114.0(6) ?
C8 N2 Cu1 . . 109.5(4) ?
C7 N2 Cu1 . . 110.5(4) ?
C8 N2 H2 . . 107.5 ?
C7 N2 H2 . . 107.5 ?
Cu1 N2 H2 . . 107.5 ?
C9 O9 H9 . . 109.5 ?
O5 C10 O4 . . 122.6(7) ?
O5 C10 C8 . . 120.0(6) ?
O4 C10 C8 . . 117.3(6) ?
N2 C8 C10 . . 108.9(6) ?
N2 C8 C9 . . 113.2(6) ?
C10 C8 C9 . . 111.3(6) ?
N2 C8 H8 . . 107.7 ?
C10 C8 H8 . . 107.7 ?
C9 C8 H8 . . 107.7 ?
C6 C7 N2 . . 110.4(6) ?
C6 C7 H7A . . 109.6 ?
N2 C7 H7A . . 109.6 ?
C6 C7 H7B . . 109.6 ?
N2 C7 H7B . . 109.6 ?
H7A C7 H7B . . 108.1 ?
C5 C6 C1 . . 118.1(7) ?
C5 C6 C7 . . 120.8(7) ?
C1 C6 C7 . . 121.1(7) ?
O6 C1 C2 . . 121.2(7) ?
O6 C1 C6 . . 119.3(7) ?
C2 C1 C6 . . 119.5(7) ?
C3 C2 C1 . . 120.8(7) ?
C3 C2 H2A . . 119.6 ?
C1 C2 H2A . . 119.6 ?
C2 C3 C4 . . 120.5(7) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C5 C4 C3 . . 118.4(8) ?
C5 C4 H4 . . 120.8 ?
C3 C4 H4 . . 120.8 ?
C4 C5 C6 . . 122.6(8) ?
C4 C5 H5 . . 118.7 ?
C6 C5 H5 . . 118.7 ?
O9 C9 C8 . . 109.9(6) ?
O9 C9 H9A . . 109.7 ?
C8 C9 H9A . . 109.7 ?
O9 C9 H9B . . 109.7 ?
C8 C9 H9B . . 109.7 ?
H9A C9 H9B . . 108.2 ?
O7 C20 C18 . 3_645 108.8(6) ?
O7 C20 H20A . . 109.9 ?
C18 C20 H20A 3_645 . 109.9 ?
O7 C20 H20B . . 109.9 ?
C18 C20 H20B 3_645 . 109.9 ?
H20A C20 H20B . . 108.3 ?
N1 C18 C19 . . 111.6(6) ?
N1 C18 C20 . 3_655 109.7(6) ?
C19 C18 C20 . 3_655 110.3(6) ?
N1 C18 H18 . . 108.4 ?
C19 C18 H18 . . 108.4 ?
C20 C18 H18 3_655 . 108.4 ?
O3 C11 C16 . . 121.3(6) ?
O3 C11 C12 . . 121.1(6) ?
C16 C11 C12 . . 117.6(7) ?
C15 C16 C11 . . 120.3(7) ?
C15 C16 C17 . . 119.2(6) ?
C11 C16 C17 . . 120.5(7) ?
C16 C15 C14 . . 121.4(7) ?
C16 C15 H15 . . 119.3 ?
C14 C15 H15 . . 119.3 ?
C13 C14 C15 . . 118.1(7) ?
C13 C14 H14 . . 121.0 ?
C15 C14 H14 . . 121.0 ?
C14 C13 C12 . . 122.1(7) ?
C14 C13 H13 . . 118.9 ?
C12 C13 H13 . . 118.9 ?
C13 C12 C11 . . 120.3(7) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
N1 C17 C16 . . 109.0(5) ?
N1 C17 H17A . . 109.9 ?
C16 C17 H17A . . 109.9 ?
N1 C17 H17B . . 109.9 ?
C16 C17 H17B . . 109.9 ?
H17A C17 H17B . . 108.3 ?
C18 N1 C17 . . 114.0(5) ?
C18 N1 Cu2 . . 108.5(4) ?
C17 N1 Cu2 . . 107.6(4) ?
C18 N1 H1 . . 108.9 ?
C17 N1 H1 . . 108.9 ?
Cu2 N1 H1 . . 108.9 ?
O1 C19 O2 . . 123.5(7) ?
O1 C19 C18 . . 119.1(6) ?
O2 C19 C18 . . 117.4(6) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cu1 O4 C10 O5 . . . . 178.2(5) ?
Cu1 O4 C10 C8 . . . . -4.1(8) ?
C7 N2 C8 C10 . . . . -147.0(6) ?
Cu1 N2 C8 C10 . . . . -22.6(6) ?
C7 N2 C8 C9 . . . . 88.7(7) ?
Cu1 N2 C8 C9 . . . . -147.0(5) ?
O5 C10 C8 N2 . . . . -164.1(6) ?
O4 C10 C8 N2 . . . . 18.2(8) ?
O5 C10 C8 C9 . . . . -38.6(10) ?
O4 C10 C8 C9 . . . . 143.6(7) ?
C8 N2 C7 C6 . . . . -166.8(6) ?
Cu1 N2 C7 C6 . . . . 69.4(6) ?
N2 C7 C6 C5 . . . . 123.8(7) ?
N2 C7 C6 C1 . . . . -55.1(9) ?
Cu2 O6 C1 C2 . . . . 3.9(10) ?
Cu1 O6 C1 C2 . . . . -143.6(5) ?
Cu2 O6 C1 C6 . . . . -175.7(5) ?
Cu1 O6 C1 C6 . . . . 36.9(9) ?
C5 C6 C1 O6 . . . . 179.2(6) ?
C7 C6 C1 O6 . . . . -1.9(10) ?
C5 C6 C1 C2 . . . . -0.3(10) ?
C7 C6 C1 C2 . . . . 178.6(7) ?
O6 C1 C2 C3 . . . . -179.6(7) ?
C6 C1 C2 C3 . . . . -0.1(11) ?
C1 C2 C3 C4 . . . . 0.9(13) ?
C2 C3 C4 C5 . . . . -1.3(13) ?
C3 C4 C5 C6 . . . . 0.8(13) ?
C1 C6 C5 C4 . . . . -0.1(11) ?
C7 C6 C5 C4 . . . . -179.0(7) ?
N2 C8 C9 O9 . . . . -63.1(9) ?
C10 C8 C9 O9 . . . . 173.8(6) ?
Cu1 O7 C20 C18 . . . 3_645 -143.8(4) ?
Cu2 O3 C11 C16 . . . . 28.0(9) ?
Cu1 O3 C11 C16 . . . . -172.2(5) ?
Cu2 O3 C11 C12 . . . . -152.8(5) ?
Cu1 O3 C11 C12 . . . . 7.0(10) ?
O3 C11 C16 C15 . . . . -176.2(7) ?
C12 C11 C16 C15 . . . . 4.6(10) ?
O3 C11 C16 C17 . . . . 3.4(10) ?
C12 C11 C16 C17 . . . . -175.8(7) ?
C11 C16 C15 C14 . . . . -1.8(12) ?
C17 C16 C15 C14 . . . . 178.7(7) ?
C16 C15 C14 C13 . . . . -1.0(13) ?
C15 C14 C13 C12 . . . . 0.8(12) ?
C14 C13 C12 C11 . . . . 2.2(12) ?
O3 C11 C12 C13 . . . . 175.9(6) ?
C16 C11 C12 C13 . . . . -4.9(10) ?
C15 C16 C17 N1 . . . . 120.3(7) ?
C11 C16 C17 N1 . . . . -59.2(9) ?
C19 C18 N1 C17 . . . . -104.1(7) ?
C20 C18 N1 C17 3_655 . . . 133.4(6) ?
C19 C18 N1 Cu2 . . . . 15.7(7) ?
C20 C18 N1 Cu2 3_655 . . . -106.8(6) ?
C16 C17 N1 C18 . . . . -166.5(6) ?
C16 C17 N1 Cu2 . . . . 73.2(6) ?
Cu2 O2 C19 O1 . . . . -177.8(6) ?
Cu2 O2 C19 C18 . . . . 2.8(8) ?
N1 C18 C19 O1 . . . . 167.8(6) ?
C20 C18 C19 O1 3_655 . . . -70.1(9) ?
N1 C18 C19 O2 . . . . -12.9(9) ?
C20 C18 C19 O2 3_655 . . . 109.3(7) ?


loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O5 3_755 0.98 2.13 3.087(8) 165.0 ?
N2 H2 O2 1_655 0.98 2.64 3.254(7) 120.6 ?
O7 H7 O5 1_455 0.868(13) 1.98(3) 2.776(6) 152.(5) ?
O8 H8B O5 3_755 0.86 2.01 2.849(7) 166.2 ?
O8 H8A O1 1_655 0.86 2.02 2.800(7) 150.7 ?
O9 H9 O10 2_565 0.82 1.88 2.679(13) 166.0 ?
O10 H10A O8 . 0.85 2.29 3.123(12) 164.7 ?
C2 H2A O2 . 0.93 2.57 3.149(8) 121.1 ?
C7 H7A O9 . 0.97 2.45 3.113(10) 125.6 ?
C12 H12 O4 . 0.93 2.37 3.159(9) 141.9 ?
C20 H20B O4 . 0.97 2.6 3.281(8) 127.5 ?
_database_code_depnum_ccdc_archive 'CCDC 952777'
#######################################################################
#
#                 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_4
_chemical_name_systematic        ?
_chemical_name_common            '[Cu2(Hser-5Cl-sal)2(H2O)].CH3OH'
_chemical_formula_moiety         'C20 H22 N2 Cl2 Cu2 O9, C H4 O'
_chemical_formula_sum            'C21 H26 Cl2 Cu2 N2 O10'
_chemical_formula_iupac          ?
_chemical_formula_weight         664.44
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.4137(4)
_cell_length_b                   13.3645(7)
_cell_length_c                   13.4407(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.816(2)
_cell_angle_gamma                90
_cell_volume                     1293.18(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7561
_cell_measurement_theta_min      2.1808
_cell_measurement_theta_max      25.0768
_cell_measurement_temperature    180.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676

_exptl_absorpt_coefficient_mu    1.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.6379
_exptl_absorpt_correction_T_max  0.7452

_exptl_special_details           
;
;

_diffrn_ambient_temperature      180.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              'fine focus'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'phi and omega scan'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            9752
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             4258
_reflns_number_gt                4094
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0202
_refine_ls_wR_factor_gt          0.0408
_refine_ls_wR_factor_ref         0.0410
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_refine_ls_number_reflns         4258
_refine_ls_number_parameters     344
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    undef
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[σ²(Fo²)]
where P=(Fo²+2Fc²)/3
;

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.253
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1749 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.023(4)

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'
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'

_computing_data_collection       'APEX2 V2011.4-1 (Bruker AXS)'
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Bruker AXS)'
_computing_publication_material  'SHELXTL (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.14200(5) 0.93107(3) 0.64127(3) 0.01590(12) Uani d . . . 1 . .
Cu Cu2 0.44507(5) 1.05451(3) 0.58934(3) 0.01422(12) Uani d . . D 1 . .
Cl Cl1 -0.01720(16) 0.90211(12) 0.07710(8) 0.0560(4) Uani d . . . 1 . .
Cl Cl2 0.57895(16) 1.10862(9) 1.14306(8) 0.0359(3) Uani d . . . 1 . .
N N1 0.0987(3) 0.8818(2) 0.7716(2) 0.0127(7) Uani d . . . 1 . .
H H1 0.028 0.9343 0.7994 0.015 Uiso calc U . R 1 . .
N N2 0.5257(3) 1.0803(2) 0.4611(2) 0.0119(7) Uani d . . . 1 . .
H H11A 0.4421 1.1322 0.4206 0.014 Uiso calc U . R 1 . .
O O1 -0.0866(3) 0.8627(2) 0.58043(18) 0.0206(7) Uani d . . . 1 . .
O O2 -0.2826(3) 0.7493(2) 0.6118(2) 0.0285(7) Uani d . . . 1 . .
O O3 0.3635(3) 1.00377(19) 0.70600(18) 0.0141(6) Uani d . . . 1 . .
O O4 0.7024(3) 1.0782(2) 0.65887(18) 0.0204(7) Uani d . . . 1 . .
O O5 0.9821(3) 1.1036(2) 0.6298(2) 0.0261(7) Uani d . . . 1 . .
O O6 0.2326(3) 0.9716(2) 0.52066(18) 0.0163(6) Uani d . . . 1 . .
O O7 -0.2850(3) 0.8405(2) 0.8174(2) 0.0350(8) Uani d . . . 1 . .
H H11 -0.2435 0.893 0.8491 0.053 Uiso calc U . R 1 . .
O O8 0.6651(3) 1.2598(2) 0.36712(19) 0.0240(7) Uani d . . . 1 . .
H H14 0.5527 1.2768 0.3519 0.036 Uiso calc U . R 1 . .
O O9 0.3017(3) 1.2025(2) 0.5978(2) 0.0233(7) Uani d . . . 1 . .
O O10 0.1042(3) 0.5319(2) 0.1464(2) 0.0257(7) Uani d . . . 1 . .
H H15A 0.175 0.5495 0.2022 0.039 Uiso calc U . R 1 . .
C C1 -0.1413(5) 0.8010(3) 0.6397(3) 0.0195(9) Uani d . . . 1 . .
C C2 -0.0214(4) 0.7908(3) 0.7485(3) 0.0150(9) Uani d . . . 1 . .
H H2 0.0622 0.7319 0.7495 0.018 Uiso calc U . R 1 . .
C C3 -0.1382(5) 0.7704(3) 0.8250(3) 0.0244(10) Uani d . . . 1 . .
H H22A -0.1912 0.7022 0.8133 0.029 Uiso calc U . R 1 . .
H H22B -0.0574 0.7726 0.8952 0.029 Uiso calc U . R 1 . .
C C4 0.2788(4) 0.8648(3) 0.8486(3) 0.0146(9) Uani d . . . 1 . .
H H3A 0.2552 0.8304 0.9095 0.018 Uiso calc U . R 1 . .
H H3B 0.3605 0.8216 0.8186 0.018 Uiso calc U . R 1 . .
C C5 0.3720(4) 0.9631(3) 0.8797(3) 0.0126(9) Uani d . . . 1 . .
C C6 0.4275(4) 0.9883(3) 0.9827(3) 0.0178(9) Uani d . . . 1 . .
H H21 0.4104 0.9419 1.0332 0.021 Uiso calc U . R 1 . .
C C7 0.5076(5) 1.0805(3) 1.0123(3) 0.0183(9) Uani d . . . 1 . .
C C8 0.5315(5) 1.1490(3) 0.9407(3) 0.0227(10) Uani d . . . 1 . .
H H19 0.5825 1.213 0.9615 0.027 Uiso calc U . R 1 . .
C C9 0.4801(5) 1.1238(3) 0.8370(3) 0.0175(9) Uani d . . . 1 . .
H H18 0.4963 1.171 0.787 0.021 Uiso calc U . R 1 . .
C C10 0.4057(4) 1.0305(3) 0.8062(3) 0.0136(9) Uani d . . . 1 . .
C C11 0.8119(5) 1.0980(3) 0.6002(3) 0.0178(9) Uani d . . . 1 . .
C C12 0.7186(4) 1.1201(3) 0.4877(3) 0.0150(9) Uani d . . . 1 . .
H H7 0.7917 1.0879 0.4428 0.018 Uiso calc U . R 1 . .
C C13 0.7183(5) 1.2332(3) 0.4725(3) 0.0194(9) Uani d . . . 1 . .
H H16A 0.6313 1.2643 0.509 0.023 Uiso calc U . R 1 . .
H H16B 0.8441 1.2597 0.5028 0.023 Uiso calc U . R 1 . .
C C14 0.5042(4) 0.9860(3) 0.4007(3) 0.0199(9) Uani d . . . 1 . .
H H9B 0.5625 0.9302 0.4455 0.024 Uiso calc U . R 1 . .
H H9A 0.5689 0.9926 0.3446 0.024 Uiso calc U . R 1 . .
C C15 0.3024(5) 0.9622(3) 0.3561(3) 0.0169(9) Uani d . . . 1 . .
C C16 0.1758(5) 0.9541(3) 0.4184(3) 0.0158(9) Uani d . . . 1 . .
C C17 -0.0069(4) 0.9265(3) 0.3741(3) 0.0182(8) Uani d . . . 1 . .
H H12 -0.0927 0.9194 0.416 0.022 Uiso calc U . R 1 . .
C C18 -0.0649(5) 0.9093(3) 0.2704(3) 0.0255(10) Uani d . . . 1 . .
H H13 -0.1895 0.89 0.2411 0.031 Uiso calc U . R 1 . .
C C19 0.0579(5) 0.9203(4) 0.2098(3) 0.0299(11) Uani d . . . 1 . .
C C20 0.2409(5) 0.9464(3) 0.2517(3) 0.0263(10) Uani d . . . 1 . .
H H15 0.3248 0.9536 0.2086 0.032 Uiso calc U . R 1 . .
C C21 0.0155(6) 0.6174(4) 0.0941(3) 0.0451(14) Uani d . . . 1 . .
H H10B -0.0628 0.6486 0.1347 0.068 Uiso calc U . R 1 . .
H H10A -0.0615 0.5973 0.0273 0.068 Uiso calc U . R 1 . .
H H10C 0.1097 0.6654 0.0842 0.068 Uiso calc U . R 1 . .
H H13A 0.283(5) 1.224(3) 0.530(3) 0.068 Uiso d U . D 1 . .
H H13B 0.203(5) 1.189(3) 0.604(3) 0.068 Uiso d U . D 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 . 1.927(2) ?
Cu1 O3 . 1.927(2) ?
Cu1 N1 . 1.968(3) ?
Cu1 O6 . 1.973(2) ?
Cu1 Cu2 . 3.0010(6) ?
Cu2 O3 . 1.933(2) ?
Cu2 O4 . 1.940(2) ?
Cu2 O6 . 1.966(2) ?
Cu2 N2 . 1.984(3) ?
Cu2 O9 . 2.261(3) ?
Cl1 C19 . 1.754(4) ?
Cl2 C7 . 1.751(4) ?
N1 C2 . 1.495(4) ?
N1 C4 . 1.498(4) ?
N1 H1 . 1.0 ?
N2 C12 . 1.487(4) ?
N2 C14 . 1.488(5) ?
N2 H11A . 1.0 ?
O1 C1 . 1.279(4) ?
O2 C1 . 1.235(4) ?
O3 C10 . 1.356(4) ?
O4 C11 . 1.287(4) ?
O5 C11 . 1.231(4) ?
O6 C16 . 1.358(4) ?
O7 C3 . 1.421(5) ?
O7 H11 . 0.84 ?
O8 C13 . 1.422(4) ?
O8 H14 . 0.84 ?
O9 H13A . 0.93(4) ?
O9 H13B . 0.77(4) ?
O10 C21 . 1.418(5) ?
O10 H15A . 0.84 ?
C1 C2 . 1.526(5) ?
C2 C3 . 1.519(5) ?
C2 H2 . 1.0 ?
C3 H22A . 0.99 ?
C3 H22B . 0.99 ?
C4 C5 . 1.497(5) ?
C4 H3A . 0.99 ?
C4 H3B . 0.99 ?
C5 C6 . 1.387(5) ?
C5 C10 . 1.403(5) ?
C6 C7 . 1.384(5) ?
C6 H21 . 0.95 ?
C7 C8 . 1.371(5) ?
C8 C9 . 1.396(5) ?
C8 H19 . 0.95 ?
C9 C10 . 1.385(5) ?
C9 H18 . 0.95 ?
C11 C12 . 1.534(5) ?
C12 C13 . 1.524(5) ?
C12 H7 . 1.0 ?
C13 H16A . 0.99 ?
C13 H16B . 0.99 ?
C14 C15 . 1.506(5) ?
C14 H9B . 0.99 ?
C14 H9A . 0.99 ?
C15 C20 . 1.384(5) ?
C15 C16 . 1.403(5) ?
C16 C17 . 1.393(4) ?
C17 C18 . 1.377(5) ?
C17 H12 . 0.95 ?
C18 C19 . 1.366(5) ?
C18 H13 . 0.95 ?
C19 C20 . 1.384(5) ?
C20 H15 . 0.95 ?
C21 H10B . 0.98 ?
C21 H10A . 0.98 ?
C21 H10C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O3 . . 176.99(11) ?
O1 Cu1 N1 . . 84.57(10) ?
O3 Cu1 N1 . . 93.97(10) ?
O1 Cu1 O6 . . 102.64(10) ?
O3 Cu1 O6 . . 79.17(10) ?
N1 Cu1 O6 . . 169.43(10) ?
O1 Cu1 Cu2 . . 142.49(7) ?
O3 Cu1 Cu2 . . 39.05(7) ?
N1 Cu1 Cu2 . . 132.93(8) ?
O6 Cu1 Cu2 . . 40.30(7) ?
O3 Cu2 O4 . . 97.41(10) ?
O3 Cu2 O6 . . 79.18(10) ?
O4 Cu2 O6 . . 154.67(11) ?
O3 Cu2 N2 . . 169.36(11) ?
O4 Cu2 N2 . . 85.66(10) ?
O6 Cu2 N2 . . 93.67(10) ?
O3 Cu2 O9 . . 91.39(10) ?
O4 Cu2 O9 . . 104.65(10) ?
O6 Cu2 O9 . . 100.54(10) ?
N2 Cu2 O9 . . 97.71(11) ?
O3 Cu2 Cu1 . . 38.91(7) ?
O4 Cu2 Cu1 . . 133.06(7) ?
O6 Cu2 Cu1 . . 40.46(7) ?
N2 Cu2 Cu1 . . 134.03(8) ?
O9 Cu2 Cu1 . . 94.72(7) ?
C2 N1 C4 . . 114.1(3) ?
C2 N1 Cu1 . . 107.6(2) ?
C4 N1 Cu1 . . 111.0(2) ?
C2 N1 H1 . . 108.0 ?
C4 N1 H1 . . 108.0 ?
Cu1 N1 H1 . . 108.0 ?
C12 N2 C14 . . 114.0(3) ?
C12 N2 Cu2 . . 109.0(2) ?
C14 N2 Cu2 . . 108.1(2) ?
C12 N2 H11A . . 108.5 ?
C14 N2 H11A . . 108.5 ?
Cu2 N2 H11A . . 108.5 ?
C1 O1 Cu1 . . 114.8(2) ?
C10 O3 Cu1 . . 123.5(2) ?
C10 O3 Cu2 . . 132.1(2) ?
Cu1 O3 Cu2 . . 102.04(11) ?
C11 O4 Cu2 . . 115.5(2) ?
C16 O6 Cu2 . . 126.3(2) ?
C16 O6 Cu1 . . 134.4(2) ?
Cu2 O6 Cu1 . . 99.25(11) ?
C3 O7 H11 . . 109.5 ?
C13 O8 H14 . . 109.5 ?
Cu2 O9 H13A . . 100.(3) ?
Cu2 O9 H13B . . 105.(3) ?
H13A O9 H13B . . 105.(4) ?
C21 O10 H15A . . 109.5 ?
O2 C1 O1 . . 123.0(4) ?
O2 C1 C2 . . 119.9(3) ?
O1 C1 C2 . . 117.1(3) ?
N1 C2 C3 . . 114.4(3) ?
N1 C2 C1 . . 108.0(3) ?
C3 C2 C1 . . 111.7(3) ?
N1 C2 H2 . . 107.5 ?
C3 C2 H2 . . 107.5 ?
C1 C2 H2 . . 107.5 ?
O7 C3 C2 . . 112.5(3) ?
O7 C3 H22A . . 109.1 ?
C2 C3 H22A . . 109.1 ?
O7 C3 H22B . . 109.1 ?
C2 C3 H22B . . 109.1 ?
H22A C3 H22B . . 107.8 ?
C5 C4 N1 . . 109.6(3) ?
C5 C4 H3A . . 109.7 ?
N1 C4 H3A . . 109.7 ?
C5 C4 H3B . . 109.7 ?
N1 C4 H3B . . 109.7 ?
H3A C4 H3B . . 108.2 ?
C6 C5 C10 . . 119.1(3) ?
C6 C5 C4 . . 119.9(3) ?
C10 C5 C4 . . 121.0(3) ?
C7 C6 C5 . . 120.5(3) ?
C7 C6 H21 . . 119.7 ?
C5 C6 H21 . . 119.7 ?
C8 C7 C6 . . 120.7(3) ?
C8 C7 Cl2 . . 120.2(3) ?
C6 C7 Cl2 . . 119.1(3) ?
C7 C8 C9 . . 119.3(4) ?
C7 C8 H19 . . 120.3 ?
C9 C8 H19 . . 120.3 ?
C10 C9 C8 . . 120.6(4) ?
C10 C9 H18 . . 119.7 ?
C8 C9 H18 . . 119.7 ?
O3 C10 C9 . . 121.0(3) ?
O3 C10 C5 . . 119.5(3) ?
C9 C10 C5 . . 119.5(3) ?
O5 C11 O4 . . 124.2(3) ?
O5 C11 C12 . . 119.5(3) ?
O4 C11 C12 . . 116.2(3) ?
N2 C12 C13 . . 110.6(3) ?
N2 C12 C11 . . 110.4(3) ?
C13 C12 C11 . . 108.0(3) ?
N2 C12 H7 . . 109.2 ?
C13 C12 H7 . . 109.2 ?
C11 C12 H7 . . 109.2 ?
O8 C13 C12 . . 111.9(3) ?
O8 C13 H16A . . 109.2 ?
C12 C13 H16A . . 109.2 ?
O8 C13 H16B . . 109.2 ?
C12 C13 H16B . . 109.2 ?
H16A C13 H16B . . 107.9 ?
N2 C14 C15 . . 111.3(3) ?
N2 C14 H9B . . 109.4 ?
C15 C14 H9B . . 109.4 ?
N2 C14 H9A . . 109.4 ?
C15 C14 H9A . . 109.4 ?
H9B C14 H9A . . 108.0 ?
C20 C15 C16 . . 119.2(3) ?
C20 C15 C14 . . 119.4(3) ?
C16 C15 C14 . . 121.4(3) ?
O6 C16 C17 . . 120.9(3) ?
O6 C16 C15 . . 120.0(3) ?
C17 C16 C15 . . 119.1(3) ?
C18 C17 C16 . . 120.9(3) ?
C18 C17 H12 . . 119.5 ?
C16 C17 H12 . . 119.5 ?
C19 C18 C17 . . 119.6(3) ?
C19 C18 H13 . . 120.2 ?
C17 C18 H13 . . 120.2 ?
C18 C19 C20 . . 120.8(3) ?
C18 C19 Cl1 . . 119.7(3) ?
C20 C19 Cl1 . . 119.4(3) ?
C19 C20 C15 . . 120.3(3) ?
C19 C20 H15 . . 119.8 ?
C15 C20 H15 . . 119.8 ?
O10 C21 H10B . . 109.5 ?
O10 C21 H10A . . 109.5 ?
H10B C21 H10A . . 109.5 ?
O10 C21 H10C . . 109.5 ?
H10B C21 H10C . . 109.5 ?
H10A C21 H10C . . 109.5 ?
_database_code_depnum_ccdc_archive 'CCDC 981858'
#######################################################################
#
#                 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_2
_chemical_name_systematic        ?
_chemical_name_common            '[Cu2(4,4?-bpy)(Hsersal)2].2H2O'
_chemical_formula_moiety         'C30 H30 Cu2 N4 O8, 2(H2 O)'
_chemical_formula_sum            'C30 H34 Cu2 N4 O10'
_chemical_formula_iupac          ?
_chemical_formula_weight         737.69
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   25.187(5)
_cell_length_b                   6.6672(13)
_cell_length_c                   10.488(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.653(11)
_cell_angle_gamma                90
_cell_volume                     1730.9(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3794
_cell_measurement_theta_min      2.3260
_cell_measurement_theta_max      24.9619
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       regular
_exptl_crystal_colour            'clear dark green'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760

_exptl_absorpt_coefficient_mu    1.286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.6766
_exptl_absorpt_correction_T_max  0.7462

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              'fine focus'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'phi and Omega scans'


_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            5622
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             3007
_reflns_number_gt                2804
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1657
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_number_reflns         3007
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[σ²(Fo²)+(0.1077P)²+6.3632P]
where P=(Fo²+2Fc²)/3
;

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.311
_refine_diff_density_min         -0.479
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1201 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.045(8)

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'

_computing_data_collection       'APEX2 V2011.4-1 (Bruker AXS)'
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Bruker AXS)'
_computing_publication_material  'SHELXTL (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.29679(3) 0.75493(19) 0.63105(8) 0.0210(3) Uani d . . . 1 . .
O O7 0.5 0.950(5) 1.0 0.076(8) Uiso d . P S 0.5 . .
O O3 0.3264(2) 0.6981(9) 0.8109(6) 0.0291(16) Uani d . . . 1 . .
O O2 0.3056(3) 0.6234(12) 1.0010(6) 0.0389(17) Uani d . . . 1 . .
O O1 0.2631(2) 0.8141(8) 0.4567(5) 0.0242(15) Uani d . . . 1 . .
N N1 0.2265(3) 0.7130(10) 0.6865(6) 0.0221(19) Uani d . . . 1 . .
H H1 0.2146 0.5731 0.6614 0.026 Uiso calc U . R 1 . .
N N2 0.3704(3) 0.7619(18) 0.5857(6) 0.0258(14) Uani d . . . 1 . .
C C9 0.2341(3) 0.7256(16) 0.8308(8) 0.028(2) Uani d . . . 1 . .
H H9 0.2284 0.8688 0.8532 0.033 Uiso calc U . R 1 . .
C C8 0.2934(4) 0.6737(14) 0.8876(9) 0.029(2) Uani d . . . 1 . .
C C10 0.1936(5) 0.603(2) 0.8848(10) 0.048(3) Uani d . . . 1 . .
H H10A 0.208 0.574 0.9773 0.058 Uiso calc U . R 1 . .
H H10B 0.1601 0.6823 0.8805 0.058 Uiso calc U . R 1 . .
O O4 0.1816(6) 0.430(2) 0.8219(9) 0.099(5) Uani d . . . 1 . .
H H4 0.1857 0.3352 0.8753 0.148 Uiso calc U . R 1 . .
C C7 0.1838(4) 0.8493(14) 0.6209(9) 0.0273(19) Uani d . . . 1 . .
H H7A 0.1966 0.9899 0.6306 0.033 Uiso calc U . R 1 . .
H H7B 0.1513 0.8369 0.6606 0.033 Uiso calc U . R 1 . .
C C6 0.1701(3) 0.7944(12) 0.4782(8) 0.022(2) Uani d . . . 1 . .
C C5 0.1161(3) 0.760(2) 0.4162(7) 0.0275(17) Uani d . . . 1 . .
H H5 0.0881 0.7697 0.4655 0.033 Uiso calc U . R 1 . .
C C4 0.1033(4) 0.7154(14) 0.2896(10) 0.033(2) Uani d . . . 1 . .
H H4A 0.0666 0.6959 0.2503 0.039 Uiso calc U . R 1 . .
C C3 0.1438(4) 0.6969(13) 0.2146(9) 0.029(2) Uani d . . . 1 . .
H H3 0.1347 0.6676 0.1246 0.035 Uiso calc U . R 1 . .
C C2 0.1975(3) 0.7222(15) 0.2740(8) 0.026(2) Uani d . . . 1 . .
H H2 0.2252 0.7017 0.2249 0.031 Uiso calc U . R 1 . .
C C1 0.2119(3) 0.7779(16) 0.4065(8) 0.0209(18) Uani d . . . 1 . .
C C15 0.3770(3) 0.7979(12) 0.4626(8) 0.026(2) Uani d . . . 1 . .
H H15 0.3457 0.8238 0.3988 0.031 Uiso calc U . R 1 . .
C C14 0.4255(3) 0.7991(13) 0.4255(8) 0.027(2) Uani d . . . 1 . .
H H14 0.4279 0.8262 0.3378 0.032 Uiso calc U . R 1 . .
C C13 0.4732(3) 0.7597(19) 0.5186(7) 0.0247(15) Uani d . . . 1 . .
C C11 0.4148(3) 0.7243(15) 0.6721(8) 0.025(2) Uani d . . . 1 . .
H H11 0.411 0.6966 0.7588 0.03 Uiso calc U . R 1 . .
C C12 0.4662(3) 0.7230(15) 0.6442(9) 0.029(2) Uani d . . . 1 . .
H H12 0.4966 0.6971 0.7106 0.035 Uiso calc U . R 1 . .
O O6 0.4211(15) 0.695(6) 0.088(3) 0.147(13) Uiso d . P . 0.5 . .
O O5 0.5 0.411(5) 0 0.082(9) Uiso d . P S 0.5 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 . 1.909(6) ?
Cu1 O3 . 1.933(6) ?
Cu1 N1 . 1.984(7) ?
Cu1 N2 . 1.997(7) ?
O3 C8 . 1.269(11) ?
O2 C8 . 1.219(12) ?
O1 C1 . 1.323(10) ?
N1 C7 . 1.476(11) ?
N1 C9 . 1.493(10) ?
N1 H1 . 1.0 ?
N2 C11 . 1.328(10) ?
N2 C15 . 1.354(11) ?
C9 C10 . 1.497(16) ?
C9 C8 . 1.542(12) ?
C9 H9 . 1.0 ?
C10 O4 . 1.334(18) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
O4 H4 . 0.84 ?
C7 C6 . 1.517(12) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C6 C1 . 1.405(12) ?
C6 C5 . 1.414(11) ?
C5 C4 . 1.341(13) ?
C5 H5 . 0.95 ?
C4 C3 . 1.404(14) ?
C4 H4A . 0.95 ?
C3 C2 . 1.391(12) ?
C3 H3 . 0.95 ?
C2 C1 . 1.419(12) ?
C2 H2 . 0.95 ?
C15 C14 . 1.350(13) ?
C15 H15 . 0.95 ?
C14 C13 . 1.425(11) ?
C14 H14 . 0.95 ?
C13 C12 . 1.382(12) ?
C13 C13 2_656 1.474(15) ?
C11 C12 . 1.378(12) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O3 . . 176.2(3) ?
O1 Cu1 N1 . . 92.7(3) ?
O3 Cu1 N1 . . 83.7(3) ?
O1 Cu1 N2 . . 92.0(3) ?
O3 Cu1 N2 . . 91.7(3) ?
N1 Cu1 N2 . . 172.4(4) ?
C8 O3 Cu1 . . 117.7(6) ?
C1 O1 Cu1 . . 124.9(5) ?
C7 N1 C9 . . 112.6(7) ?
C7 N1 Cu1 . . 112.9(5) ?
C9 N1 Cu1 . . 109.6(5) ?
C7 N1 H1 . . 107.2 ?
C9 N1 H1 . . 107.2 ?
Cu1 N1 H1 . . 107.2 ?
C11 N2 C15 . . 116.6(7) ?
C11 N2 Cu1 . . 122.4(6) ?
C15 N2 Cu1 . . 120.9(6) ?
N1 C9 C10 . . 112.6(8) ?
N1 C9 C8 . . 108.2(7) ?
C10 C9 C8 . . 114.2(9) ?
N1 C9 H9 . . 107.1 ?
C10 C9 H9 . . 107.1 ?
C8 C9 H9 . . 107.1 ?
O2 C8 O3 . . 125.2(9) ?
O2 C8 C9 . . 119.4(8) ?
O3 C8 C9 . . 115.3(8) ?
O4 C10 C9 . . 113.0(10) ?
O4 C10 H10A . . 109.0 ?
C9 C10 H10A . . 109.0 ?
O4 C10 H10B . . 109.0 ?
C9 C10 H10B . . 109.0 ?
H10A C10 H10B . . 107.8 ?
C10 O4 H4 . . 109.5 ?
N1 C7 C6 . . 108.9(7) ?
N1 C7 H7A . . 109.9 ?
C6 C7 H7A . . 109.9 ?
N1 C7 H7B . . 109.9 ?
C6 C7 H7B . . 109.9 ?
H7A C7 H7B . . 108.3 ?
C1 C6 C5 . . 119.6(7) ?
C1 C6 C7 . . 119.4(7) ?
C5 C6 C7 . . 121.1(8) ?
C4 C5 C6 . . 121.7(8) ?
C4 C5 H5 . . 119.1 ?
C6 C5 H5 . . 119.1 ?
C5 C4 C3 . . 120.5(8) ?
C5 C4 H4A . . 119.7 ?
C3 C4 H4A . . 119.7 ?
C2 C3 C4 . . 119.0(8) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C3 C2 C1 . . 121.4(8) ?
C3 C2 H2 . . 119.3 ?
C1 C2 H2 . . 119.3 ?
O1 C1 C6 . . 123.0(7) ?
O1 C1 C2 . . 119.4(7) ?
C6 C1 C2 . . 117.6(7) ?
C14 C15 N2 . . 123.6(8) ?
C14 C15 H15 . . 118.2 ?
N2 C15 H15 . . 118.2 ?
C15 C14 C13 . . 119.7(8) ?
C15 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
C12 C13 C14 . . 116.5(8) ?
C12 C13 C13 . 2_656 122.4(8) ?
C14 C13 C13 . 2_656 121.1(8) ?
N2 C11 C12 . . 124.2(8) ?
N2 C11 H11 . . 117.9 ?
C12 C11 H11 . . 117.9 ?
C11 C12 C13 . . 119.4(7) ?
C11 C12 H12 . . 120.3 ?
C13 C12 H12 . . 120.3 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C9 C10 . . . . 81.7(10) ?
Cu1 N1 C9 C10 . . . . -151.8(8) ?
C7 N1 C9 C8 . . . . -151.1(8) ?
Cu1 N1 C9 C8 . . . . -24.6(9) ?
Cu1 O3 C8 O2 . . . . 174.6(8) ?
Cu1 O3 C8 C9 . . . . -9.2(11) ?
N1 C9 C8 O2 . . . . -161.0(9) ?
C10 C9 C8 O2 . . . . -34.7(13) ?
N1 C9 C8 O3 . . . . 22.6(11) ?
C10 C9 C8 O3 . . . . 148.9(9) ?
N1 C9 C10 O4 . . . . 37.3(14) ?
C8 C9 C10 O4 . . . . -86.7(13) ?
C9 N1 C7 C6 . . . . -167.5(7) ?
Cu1 N1 C7 C6 . . . . 67.8(8) ?
N1 C7 C6 C1 . . . . -51.8(11) ?
N1 C7 C6 C5 . . . . 128.4(9) ?
C1 C6 C5 C4 . . . . -1.0(16) ?
C7 C6 C5 C4 . . . . 178.8(10) ?
C6 C5 C4 C3 . . . . 1.2(17) ?
C5 C4 C3 C2 . . . . 1.2(14) ?
C4 C3 C2 C1 . . . . -3.8(14) ?
Cu1 O1 C1 C6 . . . . 35.1(13) ?
Cu1 O1 C1 C2 . . . . -145.7(7) ?
C5 C6 C1 O1 . . . . 177.7(9) ?
C7 C6 C1 O1 . . . . -2.1(14) ?
C5 C6 C1 C2 . . . . -1.5(14) ?
C7 C6 C1 C2 . . . . 178.7(8) ?
C3 C2 C1 O1 . . . . -175.3(9) ?
C3 C2 C1 C6 . . . . 4.0(14) ?
C11 N2 C15 C14 . . . . -0.7(16) ?
Cu1 N2 C15 C14 . . . . -178.2(7) ?
N2 C15 C14 C13 . . . . 0.4(14) ?
C15 C14 C13 C12 . . . . -0.4(15) ?
C15 C14 C13 C13 . . . 2_656 180.0(6) ?
C15 N2 C11 C12 . . . . 1.0(17) ?
Cu1 N2 C11 C12 . . . . 178.4(8) ?
N2 C11 C12 C13 . . . . -1.0(16) ?
C14 C13 C12 C11 . . . . 0.6(16) ?
C13 C13 C12 C11 2_656 . . . -179.7(7) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H4 O2 4_547 0.84 1.90 2.742(14) 178.6 ?
N1 H1 O1 4_546 1.00 2.26 3.089(9) 139.9 ?
C9 H9 O2 4_557 1.00 2.54 3.435(12) 149.3 ?
C15 H15 O4 4_556 0.95 2.40 3.198(13) 141.9 ?
C7 H7A O1 4_556 0.99 2.62 3.529(11) 152.0 ?


#===END

_database_code_depnum_ccdc_archive 'CCDC 952778'
#######################################################################
#
#                 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_8
_chemical_name_systematic        ?
_chemical_name_common            "[Cu2(4,4'-bpy)(Hser-5-OMe-sal)2].CH3OH"
_chemical_formula_moiety         'C32 H34 N4 Cu2 O10, C H4 O'
_chemical_formula_sum            'C33 H38 Cu2 N4 O11'
_chemical_formula_iupac          ?
_chemical_formula_weight         793.75
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   24.8013(18)
_cell_length_b                   6.8049(6)
_cell_length_c                   10.5081(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.988(4)
_cell_angle_gamma                90
_cell_volume                     1740.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3570
_cell_measurement_theta_min      2.3320
_cell_measurement_theta_max      24.9786
_cell_measurement_temperature    180.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             820

_exptl_absorpt_coefficient_mu    1.287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.6379
_exptl_absorpt_correction_T_max  0.7452

_exptl_special_details           
;
;

_diffrn_ambient_temperature      180.(2)

_diffrn_source                   'Sealed tube'
_diffrn_source_type              'Fine Focus'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'phi and omega scan'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            8112
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.16
_diffrn_reflns_theta_full        25.16
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_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.
;

_reflns_number_total             2287
_reflns_number_gt                2115
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1518
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_number_reflns         2287
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    undef
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[σ²(Fo²)+(0.1055P)²+3.3537P]
where P=(Fo²+2Fc²)/3
;

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         1.169
_refine_diff_density_min         -0.391
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 516 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.032(10)

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'

_computing_data_collection       'APEX2 V2011.4-1 (Bruker AXS)'
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Bruker AXS)'
_computing_publication_material  'SHELXTL (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.29324(3) 0.25952(19) 0.62700(6) 0.0322(3) Uani d . . . 1 . .
O O1 0.2598(2) 0.3247(9) 0.4543(4) 0.0332(13) Uani d . . . 1 . .
O O2 0.3232(2) 0.2003(9) 0.8083(5) 0.0434(16) Uani d . . . 1 . .
O O3 0.3019(3) 0.1412(12) 0.9992(5) 0.0563(18) Uani d . . . 1 . .
N N1 0.3680(2) 0.2685(17) 0.5822(5) 0.0337(13) Uani d . . . 1 . .
C C15 0.1653(3) 0.2983(12) 0.4742(6) 0.035(2) Uani d . . . 1 . .
O O5 0.0434(2) 0.1876(12) 0.2221(6) 0.060(2) Uani d . . . 1 . .
N N4 0.2222(2) 0.2231(12) 0.6834(5) 0.0331(19) Uani d . . . 1 . .
H H4 0.2107 0.0878 0.6608 0.04 Uiso calc U . R 1 . .
O O6 0.1844(5) -0.0649(16) 0.8249(7) 0.091(3) Uani d . . . 1 . .
H H6 0.1896 -0.1508 0.8806 0.137 Uiso calc U . R 1 . .
C C1 0.4132(3) 0.2354(19) 0.6724(7) 0.042(2) Uani d . . . 1 . .
H H1 0.4095 0.216 0.7579 0.05 Uiso calc U . R 1 . .
C C2 0.4651(3) 0.2290(18) 0.6429(7) 0.044(2) Uani d . . . 1 . .
H H2 0.4954 0.2007 0.7073 0.053 Uiso calc U . R 1 . .
C C3 0.4722(3) 0.2651(19) 0.5159(6) 0.0359(15) Uani d . . . 1 . .
C C4 0.4249(3) 0.2957(12) 0.4251(7) 0.035(2) Uani d . . . 1 . .
H H4A 0.4273 0.3154 0.3387 0.042 Uiso calc U . R 1 . .
C C5 0.3751(3) 0.2976(12) 0.4600(6) 0.035(2) Uani d . . . 1 . .
H H5 0.3443 0.3202 0.3961 0.042 Uiso calc U . R 1 . .
C C6 0.2076(3) 0.2834(15) 0.4040(6) 0.0319(19) Uani d . . . 1 . .
C C7 0.1104(3) 0.266(2) 0.4132(7) 0.0384(16) Uani d . . . 1 . .
H H7 0.0826 0.2781 0.4608 0.046 Uiso calc U . R 1 . .
C C8 0.0976(3) 0.2167(13) 0.2860(8) 0.045(2) Uani d . . . 1 . .
C C9 0.1386(3) 0.1969(13) 0.2138(7) 0.040(2) Uani d . . . 1 . .
H H9 0.1297 0.1624 0.1267 0.048 Uiso calc U . R 1 . .
C C10 0.1922(3) 0.2284(16) 0.2717(6) 0.036(2) Uani d . . . 1 . .
H H10 0.2194 0.2132 0.2227 0.043 Uiso calc U . R 1 . .
C C11 0.1776(4) 0.3530(16) 0.6128(7) 0.043(2) Uani d . . . 1 . .
H H11A 0.1448 0.3386 0.6498 0.051 Uiso calc U . R 1 . .
H H11B 0.1892 0.4892 0.6218 0.051 Uiso calc U . R 1 . .
C C12 0.2296(3) 0.2371(19) 0.8263(6) 0.041(2) Uani d . . . 1 . .
H H12 0.2235 0.3744 0.848 0.049 Uiso calc U . R 1 . .
C C13 0.2892(4) 0.1879(13) 0.8825(7) 0.0393(19) Uani d . . . 1 . .
C C14 0.1893(4) 0.113(2) 0.8820(8) 0.062(3) Uani d . . . 1 . .
H H14B 0.2019 0.0973 0.9747 0.075 Uiso calc U . R 1 . .
H H14A 0.1537 0.177 0.868 0.075 Uiso calc U . R 1 . .
C C100 -0.0005(5) 0.222(4) 0.2879(17) 0.144(10) Uani d . . . 1 . .
H H10B -0.0026 0.1155 0.3468 0.216 Uiso calc U . R 1 . .
H H10A -0.0343 0.2302 0.2261 0.216 Uiso calc U . R 1 . .
H H10C 0.0057 0.3427 0.3355 0.216 Uiso calc U . R 1 . .
O O7 0.4344(9) 0.098(4) 0.056(2) 0.103(6) Uiso d . P . 0.5 . .
C C16 0.4063(8) 0.040(4) 0.1195(19) 0.056(5) Uiso d . P . 0.5 . .
H H16C 0.4187 0.0854 0.2067 0.084 Uiso calc U P R 0.5 . .
H H16B 0.4065 -0.1007 0.1179 0.084 Uiso calc U P R 0.5 . .
H H16A 0.3697 0.0872 0.0878 0.084 Uiso calc U P R 0.5 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 . 1.899(4) ?
Cu1 O2 . 1.951(5) ?
Cu1 N4 . 1.978(6) ?
Cu1 N1 . 1.999(6) ?
O1 C6 . 1.331(8) ?
O2 C13 . 1.256(10) ?
O3 C13 . 1.248(9) ?
N1 C1 . 1.342(9) ?
N1 C5 . 1.344(9) ?
C15 C6 . 1.396(10) ?
C15 C7 . 1.407(10) ?
C15 C11 . 1.478(10) ?
O5 C8 . 1.397(9) ?
O5 C100 . 1.416(17) ?
N4 C12 . 1.481(8) ?
N4 C11 . 1.498(11) ?
N4 H4 . 0.98 ?
O6 C14 . 1.343(16) ?
O6 H6 . 0.82 ?
C1 C2 . 1.381(11) ?
C1 H1 . 0.93 ?
C2 C3 . 1.400(10) ?
C2 H2 . 0.93 ?
C3 C4 . 1.379(10) ?
C3 C3 2_656 1.480(13) ?
C4 C5 . 1.354(11) ?
C4 H4A . 0.93 ?
C5 H5 . 0.93 ?
C6 C10 . 1.420(10) ?
C7 C8 . 1.356(12) ?
C7 H7 . 0.93 ?
C8 C9 . 1.386(11) ?
C9 C10 . 1.370(10) ?
C9 H9 . 0.93 ?
C10 H10 . 0.93 ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
C12 C14 . 1.512(15) ?
C12 C13 . 1.521(12) ?
C12 H12 . 0.98 ?
C14 H14B . 0.97 ?
C14 H14A . 0.97 ?
C100 H10B . 0.96 ?
C100 H10A . 0.96 ?
C100 H10C . 0.96 ?
O7 C16 . 1.12(3) ?
C16 H16C . 0.96 ?
C16 H16B . 0.96 ?
C16 H16A . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O2 . . 176.1(2) ?
O1 Cu1 N4 . . 93.6(2) ?
O2 Cu1 N4 . . 82.9(2) ?
O1 Cu1 N1 . . 91.4(2) ?
O2 Cu1 N1 . . 92.2(2) ?
N4 Cu1 N1 . . 173.3(4) ?
C6 O1 Cu1 . . 123.0(5) ?
C13 O2 Cu1 . . 116.4(5) ?
C1 N1 C5 . . 117.1(6) ?
C1 N1 Cu1 . . 121.1(5) ?
C5 N1 Cu1 . . 121.7(5) ?
C6 C15 C7 . . 120.5(6) ?
C6 C15 C11 . . 120.2(7) ?
C7 C15 C11 . . 119.2(7) ?
C8 O5 C100 . . 120.0(10) ?
C12 N4 C11 . . 113.7(7) ?
C12 N4 Cu1 . . 110.5(5) ?
C11 N4 Cu1 . . 113.2(5) ?
C12 N4 H4 . . 106.3 ?
C11 N4 H4 . . 106.3 ?
Cu1 N4 H4 . . 106.3 ?
C14 O6 H6 . . 109.5 ?
N1 C1 C2 . . 122.4(7) ?
N1 C1 H1 . . 118.8 ?
C2 C1 H1 . . 118.8 ?
C1 C2 C3 . . 120.0(6) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C4 C3 C2 . . 116.2(7) ?
C4 C3 C3 . 2_656 123.4(8) ?
C2 C3 C3 . 2_656 120.4(7) ?
C5 C4 C3 . . 120.8(7) ?
C5 C4 H4A . . 119.6 ?
C3 C4 H4A . . 119.6 ?
N1 C5 C4 . . 123.4(6) ?
N1 C5 H5 . . 118.3 ?
C4 C5 H5 . . 118.3 ?
O1 C6 C15 . . 123.2(6) ?
O1 C6 C10 . . 120.3(6) ?
C15 C6 C10 . . 116.5(6) ?
C8 C7 C15 . . 120.8(7) ?
C8 C7 H7 . . 119.6 ?
C15 C7 H7 . . 119.6 ?
C7 C8 C9 . . 120.3(7) ?
C7 C8 O5 . . 122.1(8) ?
C9 C8 O5 . . 117.5(7) ?
C10 C9 C8 . . 119.6(7) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C9 C10 C6 . . 122.2(7) ?
C9 C10 H10 . . 118.9 ?
C6 C10 H10 . . 118.9 ?
C15 C11 N4 . . 109.5(7) ?
C15 C11 H11A . . 109.8 ?
N4 C11 H11A . . 109.8 ?
C15 C11 H11B . . 109.8 ?
N4 C11 H11B . . 109.8 ?
H11A C11 H11B . . 108.2 ?
N4 C12 C14 . . 113.1(8) ?
N4 C12 C13 . . 107.6(6) ?
C14 C12 C13 . . 113.1(9) ?
N4 C12 H12 . . 107.6 ?
C14 C12 H12 . . 107.6 ?
C13 C12 H12 . . 107.6 ?
O3 C13 O2 . . 123.7(8) ?
O3 C13 C12 . . 118.8(7) ?
O2 C13 C12 . . 117.5(6) ?
O6 C14 C12 . . 110.0(9) ?
O6 C14 H14B . . 109.7 ?
C12 C14 H14B . . 109.7 ?
O6 C14 H14A . . 109.7 ?
C12 C14 H14A . . 109.7 ?
H14B C14 H14A . . 108.2 ?
O5 C100 H10B . . 109.5 ?
O5 C100 H10A . . 109.5 ?
H10B C100 H10A . . 109.5 ?
O5 C100 H10C . . 109.5 ?
H10B C100 H10C . . 109.5 ?
H10A C100 H10C . . 109.5 ?
O7 C16 H16C . . 109.5 ?
O7 C16 H16B . . 109.5 ?
H16C C16 H16B . . 109.5 ?
O7 C16 H16A . . 109.5 ?
H16C C16 H16A . . 109.5 ?
H16B C16 H16A . . 109.5 ?
_database_code_depnum_ccdc_archive 'CCDC 981859'
#######################################################################
#
#                 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_9
_chemical_name_systematic        ?
_chemical_name_common            "[Cu2(4,4'-bpy)(Hser-5-NO2-sal)2].3DMSO"
_chemical_formula_moiety         'C30 H28 Cu2 N6 O12, 3(C2 H6 O S)'
_chemical_formula_sum            'C36 H46 Cu2 N6 O15 S3'
_chemical_formula_iupac          ?
_chemical_formula_weight         1026.05
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   23.4854(18)
_cell_length_b                   6.8789(5)
_cell_length_c                   13.6839(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.685(4)
_cell_angle_gamma                90
_cell_volume                     2164.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3069
_cell_measurement_theta_min      2.5569
_cell_measurement_theta_max      21.7344
_cell_measurement_temperature    180.(2)

_exptl_crystal_description       rectangular
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1060

_exptl_absorpt_coefficient_mu    1.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.6697
_exptl_absorpt_correction_T_max  0.7452

_exptl_special_details           
;
;

_diffrn_ambient_temperature      180.(2)

_diffrn_source                   'Sealed tube'
_diffrn_source_type              'fine focus'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'phi and omega scan'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            7839
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             3380
_reflns_number_gt                2773
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1451
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_refine_ls_number_reflns         3380
_refine_ls_number_parameters     281
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[σ²(Fo²)+(0.1000P)²]
where P=(Fo²+2Fc²)/3
;

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         1.099
_refine_diff_density_min         -0.405
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 882 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.020(15)

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'

_computing_data_collection       'APEX2 V2011.4-1 (Bruker AXS)'
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Bruker AXS)'
_computing_publication_material  'SHELXTL (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.25937(4) 0.23431(16) 0.89536(6) 0.0277(3) Uani d . . . 1 . .
N N1 0.3458(3) 0.2329(13) 0.9335(4) 0.0280(13) Uani d . . . 1 . .
N N2 0.1750(3) 0.2823(9) 0.8489(5) 0.0259(17) Uani d . . . 1 . .
H H2 0.1679 0.4167 0.8671 0.031 Uiso calc U . R 1 . .
N N3 0.0628(3) 0.3213(11) 1.2007(5) 0.0341(17) Uani d . . . 1 . .
O O1 0.2101(3) 0.3632(11) 0.6106(5) 0.0471(18) Uani d . . . 1 . .
O O2 0.2629(3) 0.2839(9) 0.7595(4) 0.0374(17) Uani d . . . 1 . .
O O3 0.1241(3) 0.6008(9) 0.7347(4) 0.0406(16) Uani d . . . 1 . .
H H3 0.1423 0.6598 0.6989 0.061 Uiso calc U . R 1 . .
O O4 0.2511(2) 0.1512(9) 1.0259(4) 0.0320(14) Uani d . . . 1 . .
O O5 0.0724(3) 0.3719(11) 1.2877(5) 0.053(2) Uani d . . . 1 . .
O O6 0.0135(3) 0.3081(10) 1.1495(5) 0.0471(18) Uani d . . . 1 . .
C C16 0.1623(4) 0.6513(13) 0.4351(7) 0.038(2) Uani d . . . 1 . .
H H16A 0.166 0.5274 0.4681 0.057 Uiso calc U . R 1 . .
H H16B 0.1863 0.6536 0.3861 0.057 Uiso calc U . R 1 . .
H H16C 0.1225 0.672 0.403 0.057 Uiso calc U . R 1 . .
S S1 0.18486(10) 0.8390(4) 0.52468(16) 0.0346(6) Uani d . . . 1 . .
C C1 0.3796(3) 0.2695(12) 0.8645(6) 0.030(2) Uani d . . . 1 . .
H H1 0.3613 0.2928 0.7987 0.036 Uiso calc U . R 1 . .
C C2 0.4388(4) 0.2731(12) 0.8885(6) 0.031(2) Uani d . . . 1 . .
H H2A 0.4601 0.2996 0.8397 0.037 Uiso calc U . R 1 . .
C C3 0.4677(3) 0.2368(14) 0.9870(5) 0.0263(16) Uani d . . . 1 . .
C C4 0.4333(3) 0.2035(13) 1.0557(6) 0.0280(19) Uani d . . . 1 . .
H H4 0.4505 0.183 1.1223 0.034 Uiso calc U . R 1 . .
C C5 0.3739(3) 0.2002(11) 1.0268(6) 0.0260(19) Uani d . . . 1 . .
H H5 0.352 0.1738 1.0748 0.031 Uiso calc U . R 1 . .
C C6 0.2059(4) 0.2021(12) 1.0652(6) 0.030(2) Uani d . . . 1 . .
C C7 0.2145(3) 0.2481(16) 1.1659(6) 0.0325(19) Uani d . . . 1 . .
H H7 0.2521 0.2516 1.2039 0.039 Uiso calc U . R 1 . .
C C8 0.1682(4) 0.2886(11) 1.2103(6) 0.031(2) Uani d . . . 1 . .
H H8 0.1745 0.3203 1.2777 0.037 Uiso calc U . R 1 . .
C C9 0.1126(3) 0.2816(11) 1.1539(6) 0.026(2) Uani d . . . 1 . .
C C10 0.1021(3) 0.2411(15) 1.0535(5) 0.0275(16) Uani d . . . 1 . .
H H10 0.0643 0.24 1.0163 0.033 Uiso calc U . R 1 . .
C C11 0.1484(3) 0.2022(12) 1.0089(5) 0.0248(18) Uani d . . . 1 . .
C C12 0.1383(4) 0.1566(13) 0.8996(6) 0.032(2) Uani d . . . 1 . .
H H12B 0.1475 0.0212 0.8905 0.038 Uiso calc U . R 1 . .
H H12A 0.0977 0.1769 0.8697 0.038 Uiso calc U . R 1 . .
C C13 0.1597(3) 0.2721(12) 0.7384(5) 0.028(2) Uani d . . . 1 . .
H H13 0.1467 0.1397 0.7191 0.034 Uiso calc U . R 1 . .
C C14 0.2140(4) 0.3136(13) 0.6983(6) 0.034(2) Uani d . . . 1 . .
C C15 0.1110(4) 0.4123(13) 0.6963(6) 0.036(2) Uani d . . . 1 . .
H H15A 0.1055 0.4153 0.6241 0.043 Uiso calc U . R 1 . .
H H15B 0.0751 0.368 0.7135 0.043 Uiso calc U . R 1 . .
O O7 0.1399(3) 0.8423(10) 0.5897(5) 0.0473(17) Uani d . . . 1 . .
C C17 0.1691(5) 1.0419(15) 0.4428(8) 0.047(3) Uani d . . . 1 . .
H H17A 0.1292 1.0367 0.4088 0.07 Uiso calc U . R 1 . .
H H17B 0.1938 1.0382 0.3947 0.07 Uiso calc U . R 1 . .
H H17C 0.176 1.1601 0.4806 0.07 Uiso calc U . R 1 . .
S S2 1.0084(2) 0.9330(8) 0.6353(4) 0.0493(13) Uiso d . P . 0.5 . .
O O8 0.9601(6) 0.929(2) 0.6861(11) 0.054(4) Uiso d . P . 0.5 . .
C C18 1.0020(8) 0.712(3) 0.5609(14) 0.050(5) Uiso d . P . 0.5 . .
C C19 0.9896(10) 1.100(3) 0.5331(17) 0.061(6) Uiso d . P . 0.5 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O2 . 1.909(6) ?
Cu1 O4 . 1.922(5) ?
Cu1 N2 . 1.982(7) ?
Cu1 N1 . 1.991(6) ?
N1 C5 . 1.331(10) ?
N1 C1 . 1.374(9) ?
N2 C13 . 1.483(9) ?
N2 C12 . 1.488(10) ?
N2 H2 . 0.98 ?
N3 O5 . 1.217(9) ?
N3 O6 . 1.229(9) ?
N3 C9 . 1.468(10) ?
O1 C14 . 1.232(10) ?
O2 C14 . 1.293(10) ?
O3 C15 . 1.409(11) ?
O3 H3 . 0.82 ?
O4 C6 . 1.330(9) ?
C16 S1 . 1.785(9) ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
S1 O7 . 1.513(6) ?
S1 C17 . 1.782(10) ?
C1 C2 . 1.364(11) ?
C1 H1 . 0.93 ?
C2 C3 . 1.403(11) ?
C2 H2A . 0.93 ?
C3 C4 . 1.378(10) ?
C3 C3 2_657 1.486(13) ?
C4 C5 . 1.371(11) ?
C4 H4 . 0.93 ?
C5 H5 . 0.93 ?
C6 C7 . 1.388(11) ?
C6 C11 . 1.412(11) ?
C7 C8 . 1.377(11) ?
C7 H7 . 0.93 ?
C8 C9 . 1.378(11) ?
C8 H8 . 0.93 ?
C9 C10 . 1.374(11) ?
C10 C11 . 1.377(10) ?
C10 H10 . 0.93 ?
C11 C12 . 1.499(11) ?
C12 H12B . 0.97 ?
C12 H12A . 0.97 ?
C13 C14 . 1.515(11) ?
C13 C15 . 1.518(12) ?
C13 H13 . 0.98 ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
S2 O8 . 1.447(15) ?
S2 C19 . 1.80(2) ?
S2 C18 . 1.82(2) ?
C18 C18 2_756 1.65(4) ?
C19 C19 2_756 1.11(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 Cu1 O4 . . 172.2(3) ?
O2 Cu1 N2 . . 84.0(3) ?
O4 Cu1 N2 . . 93.7(2) ?
O2 Cu1 N1 . . 90.7(2) ?
O4 Cu1 N1 . . 92.5(2) ?
N2 Cu1 N1 . . 170.0(3) ?
C5 N1 C1 . . 116.5(7) ?
C5 N1 Cu1 . . 122.2(5) ?
C1 N1 Cu1 . . 121.3(5) ?
C13 N2 C12 . . 113.8(6) ?
C13 N2 Cu1 . . 109.8(5) ?
C12 N2 Cu1 . . 112.9(5) ?
C13 N2 H2 . . 106.6 ?
C12 N2 H2 . . 106.6 ?
Cu1 N2 H2 . . 106.6 ?
O5 N3 O6 . . 123.1(7) ?
O5 N3 C9 . . 118.3(7) ?
O6 N3 C9 . . 118.6(7) ?
C14 O2 Cu1 . . 116.8(5) ?
C15 O3 H3 . . 109.5 ?
C6 O4 Cu1 . . 122.5(5) ?
S1 C16 H16A . . 109.5 ?
S1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
S1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O7 S1 C17 . . 106.1(4) ?
O7 S1 C16 . . 105.6(4) ?
C17 S1 C16 . . 98.0(5) ?
C2 C1 N1 . . 122.7(7) ?
C2 C1 H1 . . 118.6 ?
N1 C1 H1 . . 118.6 ?
C1 C2 C3 . . 120.0(7) ?
C1 C2 H2A . . 120.0 ?
C3 C2 H2A . . 120.0 ?
C4 C3 C2 . . 116.6(7) ?
C4 C3 C3 . 2_657 123.3(8) ?
C2 C3 C3 . 2_657 120.1(8) ?
C5 C4 C3 . . 120.7(7) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
N1 C5 C4 . . 123.4(7) ?
N1 C5 H5 . . 118.3 ?
C4 C5 H5 . . 118.3 ?
O4 C6 C7 . . 119.6(7) ?
O4 C6 C11 . . 122.1(7) ?
C7 C6 C11 . . 118.2(7) ?
C8 C7 C6 . . 121.0(8) ?
C8 C7 H7 . . 119.5 ?
C6 C7 H7 . . 119.5 ?
C7 C8 C9 . . 119.3(8) ?
C7 C8 H8 . . 120.3 ?
C9 C8 H8 . . 120.3 ?
C10 C9 C8 . . 121.6(7) ?
C10 C9 N3 . . 118.5(7) ?
C8 C9 N3 . . 119.9(7) ?
C9 C10 C11 . . 119.1(7) ?
C9 C10 H10 . . 120.5 ?
C11 C10 H10 . . 120.5 ?
C10 C11 C6 . . 120.7(7) ?
C10 C11 C12 . . 120.2(7) ?
C6 C11 C12 . . 119.0(7) ?
N2 C12 C11 . . 110.7(7) ?
N2 C12 H12B . . 109.5 ?
C11 C12 H12B . . 109.5 ?
N2 C12 H12A . . 109.5 ?
C11 C12 H12A . . 109.5 ?
H12B C12 H12A . . 108.1 ?
N2 C13 C14 . . 108.2(6) ?
N2 C13 C15 . . 111.4(7) ?
C14 C13 C15 . . 111.6(7) ?
N2 C13 H13 . . 108.5 ?
C14 C13 H13 . . 108.5 ?
C15 C13 H13 . . 108.5 ?
O1 C14 O2 . . 123.8(8) ?
O1 C14 C13 . . 120.1(8) ?
O2 C14 C13 . . 116.0(7) ?
O3 C15 C13 . . 110.6(7) ?
O3 C15 H15A . . 109.5 ?
C13 C15 H15A . . 109.5 ?
O3 C15 H15B . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 108.1 ?
S1 C17 H17A . . 109.5 ?
S1 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
S1 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O8 S2 C19 . . 107.0(10) ?
O8 S2 C18 . . 105.6(9) ?
C19 S2 C18 . . 97.0(10) ?
C18 C18 S2 2_756 . 123.1(7) ?
C19 C19 S2 2_756 . 124.(2) ?


#===END

_database_code_depnum_ccdc_archive 'CCDC 981860'
