#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/26/2222678.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_2222678
loop_
_publ_author_name
'Mahmoud, Reda F.'
'Janiak, Christoph'
_publ_section_title
Aqua(2,2'-bipyridine-κ²N,N')bis(thiophene-2-carboxylato-κO)copper(II)
_journal_coeditor_code           FJ2230
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m909
_journal_page_last               m910
_journal_paper_doi               10.1107/S1600536809026713
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (C5 H3 O2 S)2 (C10 H8 N2) (H2 O)]'
_chemical_formula_moiety         'C20 H16 Cu N2 O5 S2'
_chemical_formula_sum            'C20 H16 Cu N2 O5 S2'
_chemical_formula_weight         492.01
_chemical_name_systematic
;
Aqua(2,2'-bipyridine-κ²N,N')bis(thiophene-2-carboxylato-
κO)copper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.5164(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8458(5)
_cell_length_b                   18.3799(15)
_cell_length_c                   16.8421(12)
_cell_measurement_reflns_used    28386
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.035
_cell_volume                     2076.5(3)
_computing_cell_refinement       'FSPROC in CrystalClear (Rigaku, 2007)'
_computing_data_collection       'D*TREK in CrystalClear (Rigaku, 2007)'
_computing_data_reduction        'FSPROC in CrystalClear (Rigaku, 2007)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact, 2009)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS Spider image-plate detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32855
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    1.288
_exptl_absorpt_correction_T_max  0.8013
_exptl_absorpt_correction_T_min  0.6613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.595
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0489P)²+2.2127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                3637
_reflns_number_total             4224
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2230.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222678
_cod_database_fobs_code          2222678
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.67488(4) 0.151034(16) 0.393556(18) 0.02638(11) Uani d . 1 . .
S S1 0.63575(13) 0.46085(4) 0.37885(5) 0.0465(2) Uani d . 1 . .
S S2 0.31914(12) 0.17767(6) 0.10820(5) 0.0497(2) Uani d . 1 . .
O O1 0.5925(3) 0.25157(10) 0.40169(12) 0.0373(4) Uani d . 1 . .
O O2 0.8271(3) 0.31699(10) 0.35780(12) 0.0355(4) Uani d . 1 . .
O O3 0.5534(3) 0.15076(10) 0.27585(11) 0.0331(4) Uani d . 1 . .
O O4 0.2930(3) 0.12147(11) 0.32959(11) 0.0351(4) Uani d . 1 . .
O O5 0.9860(3) 0.18398(12) 0.38761(14) 0.0391(5) Uani d . 1 . .
H H5A 0.964(6) 0.221(2) 0.374(2) 0.059 Uiso d . 1 . .
H H5B 1.062(6) 0.168(2) 0.368(2) 0.059 Uiso d . 1 . .
N N1 0.7125(3) 0.04250(12) 0.39954(12) 0.0266(4) Uani d . 1 . .
N N2 0.7215(3) 0.13725(11) 0.51474(12) 0.0277(4) Uani d . 1 . .
C C1 0.7038(4) -0.00185(15) 0.33635(17) 0.0340(6) Uani d . 1 . .
H H1 0.6855 0.0186 0.2836 0.041 Uiso calc R 1 . .
C C2 0.7204(4) -0.07660(16) 0.34483(19) 0.0391(6) Uani d . 1 . .
H H2 0.7140 -0.1069 0.2987 0.047 Uiso calc R 1 . .
C C3 0.7463(4) -0.10622(15) 0.4214(2) 0.0395(7) Uani d . 1 . .
H H3 0.7583 -0.1574 0.4288 0.047 Uiso calc R 1 . .
C C4 0.7545(4) -0.06063(14) 0.48737(18) 0.0324(6) Uani d . 1 . .
H H4 0.7713 -0.0802 0.5405 0.039 Uiso calc R 1 . .
C C5 0.7381(3) 0.01361(13) 0.47514(15) 0.0256(5) Uani d . 1 . .
C C6 0.7470(3) 0.06754(13) 0.54036(15) 0.0252(5) Uani d . 1 . .
C C7 0.7786(4) 0.05039(16) 0.62249(16) 0.0331(6) Uani d . 1 . .
H H7 0.7931 0.0011 0.6398 0.040 Uiso calc R 1 . .
C C8 0.7884(4) 0.10584(18) 0.67850(17) 0.0398(7) Uani d . 1 . .
H H8 0.8117 0.0951 0.7348 0.048 Uiso calc R 1 . .
C C9 0.7643(5) 0.17670(18) 0.65216(18) 0.0423(7) Uani d . 1 . .
H H9 0.7712 0.2155 0.6899 0.051 Uiso calc R 1 . .
C C10 0.7296(4) 0.19039(15) 0.56982(17) 0.0371(6) Uani d . 1 . .
H H10 0.7108 0.2393 0.5516 0.045 Uiso calc R 1 . .
C C11 0.6649(4) 0.30992(14) 0.37863(14) 0.0289(5) Uani d . 1 . .
C C12 0.5375(4) 0.37527(14) 0.38065(15) 0.0300(5) Uani d . 1 . .
C C13 0.3272(5) 0.37346(17) 0.38295(17) 0.0406(7) Uani d . 1 . .
H H13 0.2457 0.3316 0.3830 0.049 Uiso calc R 1 . .
C C14 0.2658(5) 0.45070(18) 0.3853(2) 0.0508(8) Uani d . 1 . .
H H14 0.1336 0.4647 0.3878 0.061 Uiso calc R 1 . .
C C15 0.4127(5) 0.49975(17) 0.3835(2) 0.0488(8) Uani d . 1 . .
H H15 0.3930 0.5509 0.3847 0.059 Uiso calc R 1 . .
C C16 0.3672(4) 0.13855(13) 0.27060(15) 0.0285(5) Uani d . 1 . .
C C17 0.2351(4) 0.14483(13) 0.18962(16) 0.0300(5) Uani d . 1 . .
C C18 0.0315(4) 0.12344(15) 0.16881(17) 0.0351(6) Uani d . 1 . .
H H18 -0.0438 0.1036 0.2053 0.042 Uiso calc R 1 . .
C C19 -0.0425(5) 0.13653(18) 0.0838(2) 0.0492(8) Uani d . 1 . .
H H19 -0.1754 0.1259 0.0573 0.059 Uiso calc R 1 . .
C C20 0.0926(5) 0.1648(2) 0.04594(19) 0.0513(8) Uani d . 1 . .
H H20 0.0657 0.1767 -0.0101 0.062 Uiso calc R 1 . .
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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 Cu O3 . . 90.18(8) y
O1 Cu N1 . . 167.13(8) y
O3 Cu N1 . . 94.08(8) y
O1 Cu N2 . . 92.15(8) y
O3 Cu N2 . . 163.16(8) y
N1 Cu N2 . . 80.33(8) y
O1 Cu O5 . . 92.18(8) y
O3 Cu O5 . . 99.70(8) y
N1 Cu O5 . . 99.04(8) y
N2 Cu O5 . . 96.87(8) y
C15 S1 C12 . . 91.48(15) ?
C17 S2 C20 . . 91.96(15) ?
C11 O1 Cu . . 129.96(17) ?
C16 O3 Cu . . 106.35(16) ?
Cu O5 H5A . . 97(3) ?
Cu O5 H5B . . 133(3) ?
H5A O5 H5B . . 110(4) ?
C1 N1 C5 . . 119.1(2) ?
C1 N1 Cu . . 125.59(18) ?
C5 N1 Cu . . 115.21(17) ?
C10 N2 C6 . . 119.0(2) ?
C10 N2 Cu . . 125.80(18) ?
C6 N2 Cu . . 115.21(17) ?
N1 C1 C2 . . 122.4(3) ?
N1 C1 H1 . . 118.8 ?
C2 C1 H1 . . 118.8 ?
C3 C2 C1 . . 118.8(3) ?
C3 C2 H2 . . 120.6 ?
C1 C2 H2 . . 120.6 ?
C2 C3 C4 . . 119.3(3) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C5 C4 C3 . . 119.3(3) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
N1 C5 C4 . . 121.2(2) ?
N1 C5 C6 . . 114.5(2) ?
C4 C5 C6 . . 124.3(2) ?
N2 C6 C7 . . 121.1(2) ?
N2 C6 C5 . . 114.6(2) ?
C7 C6 C5 . . 124.3(2) ?
C8 C7 C6 . . 119.2(3) ?
C8 C7 H7 . . 120.4 ?
C6 C7 H7 . . 120.4 ?
C9 C8 C7 . . 119.5(3) ?
C9 C8 H8 . . 120.3 ?
C7 C8 H8 . . 120.3 ?
C8 C9 C10 . . 118.8(3) ?
C8 C9 H9 . . 120.6 ?
C10 C9 H9 . . 120.6 ?
N2 C10 C9 . . 122.5(3) ?
N2 C10 H10 . . 118.8 ?
C9 C10 H10 . . 118.8 ?
O2 C11 O1 . . 126.9(2) ?
O2 C11 C12 . . 119.0(2) ?
O1 C11 C12 . . 114.0(2) ?
C13 C12 C11 . . 124.9(2) ?
C13 C12 S1 . . 114.7(2) ?
C11 C12 S1 . . 120.4(2) ?
C12 C13 C14 . . 105.5(3) ?
C12 C13 H13 . . 127.3 ?
C14 C13 H13 . . 127.3 ?
C15 C14 C13 . . 114.9(3) ?
C15 C14 H14 . . 122.5 ?
C13 C14 H14 . . 122.5 ?
C14 C15 S1 . . 113.4(2) ?
C14 C15 H15 . . 123.3 ?
S1 C15 H15 . . 123.3 ?
O4 C16 O3 . . 123.3(2) ?
O4 C16 C17 . . 118.9(2) ?
O3 C16 C17 . . 117.8(2) ?
C18 C17 C16 . . 126.3(2) ?
C18 C17 S2 . . 111.8(2) ?
C16 C17 S2 . . 121.8(2) ?
C17 C18 C19 . . 109.4(3) ?
C17 C18 H18 . . 125.3 ?
C19 C18 H18 . . 125.3 ?
C20 C19 C18 . . 113.7(3) ?
C20 C19 H19 . . 123.2 ?
C18 C19 H19 . . 123.2 ?
C19 C20 S2 . . 113.2(2) ?
C19 C20 H20 . . 123.4 ?
S2 C20 H20 . . 123.4 ?
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
Cu O1 . 1.9447(18) y
Cu O3 . 1.9909(19) y
Cu N1 . 2.011(2) y
Cu N2 . 2.018(2) y
Cu O5 . 2.236(2) y
S1 C15 . 1.702(3) ?
S1 C12 . 1.714(3) ?
S2 C17 . 1.700(3) ?
S2 C20 . 1.706(3) ?
O1 C11 . 1.274(3) ?
O2 C11 . 1.236(3) ?
O3 C16 . 1.280(3) ?
O4 C16 . 1.243(3) ?
O5 H5A . 0.73(4) ?
O5 H5B . 0.73(4) ?
N1 C1 . 1.332(3) ?
N1 C5 . 1.358(3) ?
N2 C10 . 1.340(3) ?
N2 C6 . 1.352(3) ?
C1 C2 . 1.384(4) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.378(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.384(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.381(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.472(4) ?
C6 C7 . 1.393(3) ?
C7 C8 . 1.381(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.375(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.383(4) ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 C12 . 1.489(4) ?
C12 C13 . 1.448(4) ?
C13 C14 . 1.483(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.355(5) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 C17 . 1.483(4) ?
C17 C18 . 1.423(4) ?
C18 C19 . 1.440(4) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.330(5) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
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
O5 H5A O2 . 0.73(4) 1.99(4) 2.682(3) 160(4)
O5 H5B O4 1_655 0.73(4) 2.02(4) 2.741(3) 171(4)
