#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/08/2200874.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2200874
loop_
_publ_author_name
'Naumov, Panče'
'Jovanovski, Gligor'
'Ng, Seik Weng'
_publ_section_title
;
 Aquabis(2,4'-bipyridine)di(o-sulfobenzimidato)copper(II) at 95K
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m16
_journal_page_last               m17
_journal_paper_doi               10.1107/S1600536801020657
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          '[Cu (C7 H4 N O3 S)2 (C10 H8 N2)2 (H2 O)]'
_chemical_formula_moiety         'C34 H26 Cu N6 O7 S2'
_chemical_formula_sum            'C34 H26 Cu N6 O7 S2'
_chemical_formula_weight         758.27
_chemical_name_systematic
;
Aquabis(2,4'-bipyridine)di(o-sulfobenzimidato)copper(II)
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'Manual editing of SHELXL-97 cif'
_cell_angle_alpha                90.00
_cell_angle_beta                 101.1400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.5758(3)
_cell_length_b                   12.2526(2)
_cell_length_c                   11.6563(3)
_cell_measurement_reflns_used    5360
_cell_measurement_temperature    95(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      1.78
_cell_volume                     1762.23(7)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      95(2)
_diffrn_measured_fraction_theta_full .997
_diffrn_measured_fraction_theta_max .997
_diffrn_measurement_device_type  'Siemens CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .094
_diffrn_reflns_av_sigmaI/netI    .1371
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8924
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .794
_exptl_absorpt_correction_T_max  .9689
_exptl_absorpt_correction_T_min  .8703
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             778
_exptl_crystal_size_max          .18
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .04
_refine_diff_density_max         .56
_refine_diff_density_min         -.94
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   .34(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .95
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4029
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      .95
_refine_ls_R_factor_all          .078
_refine_ls_R_factor_gt           .048
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0197P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .094
_refine_ls_wR_factor_ref         .104
_reflns_number_gt                3056
_reflns_number_total             4029
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6083.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2200874
_cod_database_fobs_code          2200874
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_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
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 .5000 .49995(5) 1.0000 .0106(2) Uani d S 1 . . Cu
S1 .43030(10) .42281(9) .72832(8) .0157(2) Uani d . 1 . . S
O1 .4144(2) .6996(2) .8457(3) .0260(10) Uani d . 1 . . O
O2 .3457(2) .3467(2) .7389(3) .0250(10) Uani d . 1 . . O
O3 .5352(2) .3781(2) .7242(3) .0240(10) Uani d . 1 . . O
O1w .5000 .3145(4) 1.0000 .0160(10) Uani d S 1 . . O
N1 .4400(2) .5167(3) .8292(3) .0110(10) Uani d . 1 . . N
N2 .3487(2) .5163(3) 1.0340(3) .0120(10) Uani d . 1 . . N
N3 -.0007(3) .6316(3) 1.1525(3) .0170(10) Uani d . 1 . . N
C1 .4119(3) .6175(4) .7843(4) .0160(10) Uani d . 1 . . C
C2 .3798(3) .6156(4) .6535(4) .0200(10) Uani d . 1 . . C
C3 .3442(4) .7023(4) .5793(4) .0360(10) Uani d . 1 . . C
C4 .3170(4) .6765(6) .4582(5) .053(2) Uani d . 1 . . C
C5 .3261(4) .5736(6) .4176(5) .047(2) Uani d . 1 . . C
C6 .3612(3) .4866(6) .4919(4) .0350(10) Uani d . 1 . . C
C7 .3866(3) .5119(4) .6102(3) .0200(10) Uani d . 1 . . C
C8 .2839(3) .4295(4) 1.0293(3) .0180(10) Uani d . 1 . . C
C9 .1850(3) .4331(4) 1.0660(4) .0180(10) Uani d . 1 . . C
C10 .1511(3) .5297(3) 1.1088(3) .0140(10) Uani d . 1 . . C
C11 .2171(3) .6209(3) 1.1094(3) .0130(10) Uani d . 1 . . C
C12 .3151(3) .6114(3) 1.0726(3) .0130(10) Uani d . 1 . . C
C13 .0498(3) .5343(3) 1.1563(4) .0150(10) Uani d . 1 . . C
C14 .0112(3) .4409(4) 1.2032(4) .0250(10) Uani d . 1 . . C
C15 -.0815(4) .4476(4) 1.2499(5) .0340(10) Uani d . 1 . . C
C16 -.1336(4) .5477(4) 1.2466(5) .0360(10) Uani d . 1 . . C
C17 -.0920(3) .6361(4) 1.1967(4) .0250(10) Uani d . 1 . . C
H1w .508(4) .276(4) 1.056(4) .020(10) Uiso d . 1 . . H
H3 .3384 .7743 .6077 .043 Uiso calc R 1 . . H
H4 .2916 .7330 .4039 .063 Uiso calc R 1 . . H
H5 .3080 .5606 .3358 .056 Uiso calc R 1 . . H
H6 .3674 .4146 .4636 .042 Uiso calc R 1 . . H
H8 .3061 .3627 .9998 .022 Uiso calc R 1 . . H
H9 .1411 .3696 1.0616 .021 Uiso calc R 1 . . H
H11 .1950 .6895 1.1350 .016 Uiso calc R 1 . . H
H12 .3600 .6741 1.0747 .016 Uiso calc R 1 . . H
H14 .0484 .3734 1.2031 .030 Uiso calc R 1 . . H
H15 -.1089 .3854 1.2834 .040 Uiso calc R 1 . . H
H16 -.1974 .5553 1.2783 .043 Uiso calc R 1 . . H
H17 -.1295 .7036 1.1934 .030 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu .3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
N1 Cu1 N1 . 2_657 168.2(2) yes
N1 Cu1 N2 . . 89.80(10) yes
N1 Cu1 N2 . 2_657 89.00(10) yes
N1 Cu1 O1w . . 95.90(10) yes
N1 Cu1 N2 2_657 . 89.00(10) no
N1 Cu1 N2 2_657 2_657 89.80(10) no
N1 Cu1 O1w 2_657 . 95.90(10) no
N2 Cu1 N2 . 2_657 168.6(2) yes
N2 Cu1 O1w . . 95.70(10) yes
N2 Cu1 O1w 2_657 . 95.70(10) no
O3 S1 O2 . . 117.0(2) no
O3 S1 N1 . . 110.6(2) no
O2 S1 N1 . . 110.4(2) no
O3 S1 C7 . . 111.1(2) no
O2 S1 C7 . . 110.2(2) no
N1 S1 C7 . . 95.4(2) no
C1 N1 S1 . . 112.7(3) no
C1 N1 Cu1 . . 119.7(3) no
S1 N1 Cu1 . . 127.3(2) no
C8 N2 C12 . . 118.3(3) no
C8 N2 Cu1 . . 120.1(3) no
C12 N2 Cu1 . . 121.2(3) no
C17 N3 C13 . . 117.1(4) no
O1 C1 N1 . . 122.9(4) no
O1 C1 C2 . . 125.1(4) no
N1 C1 C2 . . 112.0(4) no
C7 C2 C3 . . 120.9(4) no
C7 C2 C1 . . 111.4(4) no
C3 C2 C1 . . 127.7(5) no
C2 C3 C4 . . 115.8(5) no
C5 C4 C3 . . 122.0(5) no
C4 C5 C6 . . 122.2(5) no
C7 C6 C5 . . 115.6(6) no
C2 C7 C6 . . 123.5(5) no
C2 C7 S1 . . 108.5(3) no
C6 C7 S1 . . 128.0(5) no
N2 C8 C9 . . 122.5(4) no
C8 C9 C10 . . 119.6(4) no
C11 C10 C9 . . 117.7(4) no
C11 C10 C13 . . 121.4(4) no
C9 C10 C13 . . 120.9(3) no
C12 C11 C10 . . 119.7(4) no
N2 C12 C11 . . 122.1(4) no
N3 C13 C14 . . 122.8(4) no
N3 C13 C10 . . 117.0(4) no
C14 C13 C10 . . 120.2(3) no
C15 C14 C13 . . 119.3(4) no
C14 C15 C16 . . 118.1(4) no
C17 C16 C15 . . 119.3(4) no
N3 C17 C16 . . 123.4(4) no
Cu1 O1w H1w . . 127(3) no
C2 C3 H3 . . 122.1 no
C4 C3 H3 . . 122.1 no
C5 C4 H4 . . 119.0 no
C3 C4 H4 . . 119.0 no
C4 C5 H5 . . 118.9 no
C6 C5 H5 . . 118.9 no
C7 C6 H6 . . 122.2 no
C5 C6 H6 . . 122.2 no
N2 C8 H8 . . 118.8 no
C9 C8 H8 . . 118.8 no
C8 C9 H9 . . 120.2 no
C10 C9 H9 . . 120.2 no
C12 C11 H11 . . 120.1 no
C10 C11 H11 . . 120.1 no
N2 C12 H12 . . 118.9 no
C11 C12 H12 . . 118.9 no
C15 C14 H14 . . 120.3 no
C13 C14 H14 . . 120.3 no
C14 C15 H15 . . 120.9 no
C16 C15 H15 . . 120.9 no
C17 C16 H16 . . 120.3 no
C15 C16 H16 . . 120.3 no
N3 C17 H17 . . 118.3 no
C16 C17 H17 . . 118.3 no
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 N1 . 1.999(3) yes
Cu1 N1 2_657 1.999(3) no
Cu1 N2 . 2.027(3) yes
Cu1 N2 2_657 2.027(3) no
Cu1 O1w . 2.272(4) yes
S1 O3 . 1.437(3) no
S1 O2 . 1.438(3) no
S1 N1 . 1.633(3) no
S1 C7 . 1.760(4) no
O1 C1 . 1.232(5) no
N1 C1 . 1.361(5) no
N2 C8 . 1.335(5) no
N2 C12 . 1.347(5) no
N3 C17 . 1.347(5) no
N3 C13 . 1.347(5) no
C1 C2 . 1.500(6) no
C2 C7 . 1.375(7) no
C2 C3 . 1.388(6) no
C3 C4 . 1.423(8) no
C4 C5 . 1.359(8) no
C5 C6 . 1.390(8) no
C6 C7 . 1.389(6) no
C8 C9 . 1.392(5) no
C9 C10 . 1.384(6) no
C10 C11 . 1.392(5) no
C10 C13 . 1.485(5) no
C11 C12 . 1.386(5) no
C13 C14 . 1.395(6) no
C14 C15 . 1.382(6) no
C15 C16 . 1.388(6) no
C16 C17 . 1.379(6) no
O1w H1w . .79(4) no
C3 H3 . .9500 no
C4 H4 . .9500 no
C5 H5 . .9500 no
C6 H6 . .9500 no
C8 H8 . .9500 no
C9 H9 . .9500 no
C11 H11 . .9500 no
C12 H12 . .9500 no
C14 H14 . .9500 no
C15 H15 . .9500 no
C16 H16 . .9500 no
C17 H17 . .9500 no
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
O1w H1w N3 3_545 .79(4) 2.11(4) 2.862(5) 158(4) no
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
_geom_torsion_publ_flag
O3 S1 N1 C1 . 115.4(3) no
O2 S1 N1 C1 . -113.5(3) no
C7 S1 N1 C1 . .4(3) no
O3 S1 N1 Cu1 . -58.3(3) no
O2 S1 N1 Cu1 . 72.8(2) no
C7 S1 N1 Cu1 . -173.3(2) no
N1 Cu1 N1 C1 2_657 -7.5(3) no
N2 Cu1 N1 C1 . 76.8(3) no
N2 Cu1 N1 C1 2_657 -91.9(3) no
O1w Cu1 N1 C1 . 172.5(3) no
N1 Cu1 N1 S1 2_657 165.8(2) no
N2 Cu1 N1 S1 . -109.8(2) no
N2 Cu1 N1 S1 2_657 81.5(2) no
O1w Cu1 N1 S1 . -14.2(2) no
N1 Cu1 N2 C8 . 85.6(3) no
N1 Cu1 N2 C8 2_657 -106.2(3) no
N2 Cu1 N2 C8 2_657 169.6(3) no
O1w Cu1 N2 C8 . -10.4(3) no
N1 Cu1 N2 C12 . -101.0(3) no
N1 Cu1 N2 C12 2_657 67.2(3) no
N2 Cu1 N2 C12 2_657 -16.9(3) no
O1w Cu1 N2 C12 . 163.1(3) no
S1 N1 C1 O1 . -179.5(3) no
Cu1 N1 C1 O1 . -5.2(5) no
S1 N1 C1 C2 . -.3(4) no
Cu1 N1 C1 C2 . 173.9(2) no
O1 C1 C2 C7 . 179.2(4) no
N1 C1 C2 C7 . .1(5) no
O1 C1 C2 C3 . -2.6(7) no
N1 C1 C2 C3 . 178.4(4) no
C7 C2 C3 C4 . -.6(7) no
C1 C2 C3 C4 . -178.7(4) no
C2 C3 C4 C5 . -.5(8) no
C3 C4 C5 C6 . .9(9) no
C4 C5 C6 C7 . -.2(8) no
C3 C2 C7 C6 . 1.4(7) no
C1 C2 C7 C6 . 179.8(4) no
C3 C2 C7 S1 . -178.2(4) no
C1 C2 C7 S1 . .2(4) no
C5 C6 C7 C2 . -1.0(7) no
C5 C6 C7 S1 . 178.6(4) no
O3 S1 C7 C2 . -114.9(3) no
O2 S1 C7 C2 . 113.8(3) no
N1 S1 C7 C2 . -.3(3) no
O3 S1 C7 C6 . 65.6(4) no
O2 S1 C7 C6 . -65.8(4) no
N1 S1 C7 C6 . -179.9(4) no
C12 N2 C8 C9 . -2.0(6) no
Cu1 N2 C8 C9 . 171.6(3) no
N2 C8 C9 C10 . .2(6) no
C8 C9 C10 C11 . 2.1(6) no
C8 C9 C10 C13 . -175.7(4) no
C9 C10 C11 C12 . -2.8(6) no
C13 C10 C11 C12 . 175.1(3) no
C8 N2 C12 C11 . 1.3(5) no
Cu1 N2 C12 C11 . -172.2(3) no
C10 C11 C12 N2 . 1.1(6) no
C17 N3 C13 C14 . .0(6) no
C17 N3 C13 C10 . -179.3(3) no
C11 C10 C13 N3 . 28.0(5) no
C9 C10 C13 N3 . -154.2(4) no
C11 C10 C13 C14 . -151.3(4) no
C9 C10 C13 C14 . 26.5(6) no
N3 C13 C14 C15 . -1.1(7) no
C10 C13 C14 C15 . 178.2(4) no
C13 C14 C15 C16 . .9(7) no
C14 C15 C16 C17 . .4(8) no
C13 N3 C17 C16 . 1.3(7) no
C15 C16 C17 N3 . -1.5(8) no
