#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/87/2018738.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_2018738
loop_
_publ_author_name
'Haghjoo, Farhad'
'Pritchard, Robin'
_publ_section_title
;
 Completing the
 bis[hydroxybis(pyridin-2-yl)methanesulfonato-κ³N,O,N']MII
 series (M = Mn to Zn) with the copper(II) and cobalt(II)
 structures
;
_journal_coeditor_code           FA3287
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              21
_journal_page_last               24
_journal_paper_doi               10.1107/S0108270112049748
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '[Cu (C11 H9 N2 O4 S1)2] , 6H2 O'
_chemical_formula_moiety         'C22 H18 Cu1 N4 O8 S2, 6(H2 O)'
_chemical_formula_sum            'C22 H30 Cu N4 O14 S2'
_chemical_formula_weight         702.16
_chemical_name_systematic
;
bis[hydroxybis(pyridin-2-yl)methanesulfonato-
κ³N,O,N']copper(II) hexahydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                108.675(2)
_cell_angle_beta                 109.920(2)
_cell_angle_gamma                101.025(4)
_cell_formula_units_Z            1
_cell_length_a                   7.5892(3)
_cell_length_b                   10.1399(4)
_cell_length_c                   10.7325(5)
_cell_measurement_reflns_used    3309
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_volume                     692.53(6)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10846
_diffrn_reflns_reduction_process
;
Scaled and merged using SORTAV
Blessing, R. H. (1987) Crystallogr. Rev. 1, 3--58.
Blessing, R. H. (1989) J. Appl. Cryst. 22, 396--397.
;
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    1.018
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.7922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             363
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.829
_refine_ls_extinction_coef       0.033(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2715
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1015P)²+1.5123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.164
_refine_ls_wR_factor_ref         0.1722
_reflns_number_gt                2315
_reflns_number_total             2715
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa3287.cif
_cod_data_source_block           I
_cod_original_cell_volume        692.53(5)
_cod_database_code               2018738
_cod_database_fobs_code          2018738
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
C C1 0.6150(6) 0.3012(5) 0.2046(4) 0.0266(9) Uani d . 1 1
C C2 0.6810(6) 0.2127(5) 0.2925(5) 0.0262(9) Uani d . 1 1
C C3 0.5819(6) 0.0621(5) 0.2357(5) 0.0281(9) Uani d . 1 1
C C4 0.6342(7) -0.0134(5) 0.3220(5) 0.0314(10) Uani d . 1 1
C C5 0.7849(7) 0.0627(5) 0.4613(5) 0.0319(10) Uani d . 1 1
C C6 0.8834(7) 0.2107(5) 0.5095(5) 0.0285(9) Uani d . 1 1
C C7 0.5903(6) 0.4428(4) 0.2915(4) 0.0254(9) Uani d . 1 1
C C8 0.4216(6) 0.4778(5) 0.2341(5) 0.0282(9) Uani d . 1 1
C C9 0.4013(7) 0.6061(5) 0.3169(5) 0.0326(10) Uani d . 1 1
C C10 0.5499(7) 0.6934(5) 0.4568(5) 0.0309(10) Uani d . 1 1
C C11 0.7135(7) 0.6543(5) 0.5065(5) 0.0291(9) Uani d . 1 1
N N1 0.8352(5) 0.2863(4) 0.4270(4) 0.0258(7) Uani d . 1 1
N N2 0.7388(5) 0.5336(4) 0.4257(4) 0.0259(7) Uani d . 1 1
O O1 0.4390(5) 0.2109(3) 0.0764(3) 0.0299(7) Uani d . 1 1
O O2 0.9784(4) 0.4490(3) 0.2649(3) 0.0314(7) Uani d . 1 1
O O3 0.7117(5) 0.4123(4) 0.0373(4) 0.0373(8) Uani d . 1 1
O O4 0.8184(5) 0.2070(3) 0.0609(4) 0.0347(7) Uani d . 1 1
O O5 0.7610(5) 0.7115(4) 0.1590(4) 0.0393(8) Uani d D 1 1
O O6 0.1634(5) 0.1313(4) 0.1628(4) 0.0409(8) Uani d D 1 1
O O7 0.8760(6) 0.1270(4) -0.1964(4) 0.0483(9) Uani d D 1 1
S S1 0.79797(16) 0.34699(12) 0.13544(11) 0.0296(3) Uani d . 1 1
Cu Cu1 1 0.5 0.5 0.0257(3) Uani d S 1 2
H H5A 0.739(8) 0.6078(17) 0.119(6) 0.050(16) Uiso d D 1 1
H H5B 0.641(6) 0.721(6) 0.100(7) 0.09(3) Uiso d D 1 1
H H6A 0.047(5) 0.158(5) 0.127(6) 0.053(17) Uiso d D 1 1
H H6B 0.110(7) 0.037(4) 0.163(7) 0.061(19) Uiso d D 1 1
H H7A 0.855(7) 0.177(5) -0.113(4) 0.047(16) Uiso d D 1 1
H H7B 1.011(4) 0.182(6) -0.171(6) 0.07(2) Uiso d D 1 1
H H1 0.342(9) 0.191(6) 0.095(6) 0.038(15) Uiso d . 1 1
H H3 0.501(9) 0.014(6) 0.143(7) 0.042(15) Uiso d . 1 1
H H4 0.564(8) -0.114(6) 0.279(6) 0.039(14) Uiso d . 1 1
H H5 0.812(7) 0.017(5) 0.525(5) 0.026(12) Uiso d . 1 1
H H6 0.994(8) 0.269(6) 0.604(6) 0.036(13) Uiso d . 1 1
H H8 0.323(12) 0.406(9) 0.144(8) 0.08(2) Uiso d . 1 1
H H9 0.274(8) 0.634(6) 0.279(6) 0.035(13) Uiso d . 1 1
H H10 0.537(8) 0.772(6) 0.512(6) 0.033(13) Uiso d . 1 1
H H11 0.809(7) 0.708(5) 0.593(6) 0.025(12) Uiso d . 1 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 0 '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 0.006 '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'
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 C1 C2 . . 110.1(3) ?
O1 C1 C7 . . 111.0(3) ?
C2 C1 C7 . . 113.6(3) ?
O1 C1 S1 . . 103.3(3) ?
C2 C1 S1 . . 108.7(3) ?
C7 C1 S1 . . 109.5(3) ?
N1 C2 C3 . . 121.7(4) ?
N1 C2 C1 . . 118.0(4) ?
C3 C2 C1 . . 120.2(4) ?
C4 C3 C2 . . 119.1(4) ?
C4 C3 H3 . . 121(4) ?
C2 C3 H3 . . 120(4) ?
C5 C4 C3 . . 119.3(4) ?
C5 C4 H4 . . 125(3) ?
C3 C4 H4 . . 116(3) ?
C4 C5 C6 . . 119.0(4) ?
C4 C5 H5 . . 121(3) ?
C6 C5 H5 . . 120(3) ?
N1 C6 C5 . . 122.7(4) ?
N1 C6 H6 . . 114(3) ?
C5 C6 H6 . . 123(3) ?
N2 C7 C8 . . 121.1(4) ?
N2 C7 C1 . . 118.1(4) ?
C8 C7 C1 . . 120.8(4) ?
C7 C8 C9 . . 119.6(4) ?
C7 C8 H8 . . 115(5) ?
C9 C8 H8 . . 125(5) ?
C10 C9 C8 . . 118.4(4) ?
C10 C9 H9 . . 120(3) ?
C8 C9 H9 . . 122(3) ?
C11 C10 C9 . . 119.3(4) ?
C11 C10 H10 . . 121(4) ?
C9 C10 H10 . . 120(4) ?
N2 C11 C10 . . 123.0(4) ?
N2 C11 H11 . . 116(3) ?
C10 C11 H11 . . 121(3) ?
C6 N1 C2 . . 118.1(4) ?
C6 N1 Cu1 . . 120.2(3) ?
C2 N1 Cu1 . . 121.6(3) ?
C11 N2 C7 . . 118.5(4) ?
C11 N2 Cu1 . . 119.6(3) ?
C7 N2 Cu1 . . 121.8(3) ?
C1 O1 H1 . . 111(4) ?
S1 O2 Cu1 . . 121.35(17) ?
H5A O5 H5B . . 104.4(15) ?
H6A O6 H6B . . 103.4(14) ?
H7A O7 H7B . . 103.4(14) ?
O2 S1 O3 . . 114.08(19) ?
O2 S1 O4 . . 113.06(19) ?
O3 S1 O4 . . 113.0(2) ?
O2 S1 C1 . . 104.81(18) ?
O3 S1 C1 . . 105.4(2) ?
O4 S1 C1 . . 105.45(19) ?
N2 Cu1 N2 2_766 . 180.0000(10) ?
N2 Cu1 N1 2_766 . 94.09(14) ?
N2 Cu1 N1 . . 85.91(14) y
N2 Cu1 N1 2_766 2_766 85.91(14) ?
N2 Cu1 N1 . 2_766 94.09(14) ?
N1 Cu1 N1 . 2_766 180.0(2) ?
N2 Cu1 O2 2_766 2_766 85.52(13) ?
N2 Cu1 O2 . 2_766 94.48(13) ?
N1 Cu1 O2 . 2_766 91.37(12) ?
N1 Cu1 O2 2_766 2_766 88.63(12) ?
N2 Cu1 O2 2_766 . 94.48(13) ?
N2 Cu1 O2 . . 85.52(13) y
N1 Cu1 O2 . . 88.63(12) y
N1 Cu1 O2 2_766 . 91.37(12) ?
O2 Cu1 O2 2_766 . 180 ?
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
C1 O1 . 1.410(5) ?
C1 C2 . 1.530(6) ?
C1 C7 . 1.527(6) ?
C1 S1 . 1.836(5) ?
C2 N1 . 1.354(5) ?
C2 C3 . 1.386(6) ?
C3 C4 . 1.385(6) ?
C3 H3 . 0.87(6) ?
C4 C5 . 1.378(7) ?
C4 H4 . 0.93(6) ?
C5 C6 . 1.375(6) ?
C5 H5 . 0.93(5) ?
C6 N1 . 1.352(6) ?
C6 H6 . 0.96(5) ?
C7 N2 . 1.357(5) ?
C7 C8 . 1.386(6) ?
C8 C9 . 1.392(7) ?
C8 H8 . 0.93(8) ?
C9 C10 . 1.387(7) ?
C9 H9 . 1.04(5) ?
C10 C11 . 1.362(7) ?
C10 H10 . 0.87(6) ?
C11 N2 . 1.345(6) ?
C11 H11 . 0.87(5) ?
N1 Cu1 . 2.020(3) y
N2 Cu1 . 2.009(4) y
O1 H1 . 0.83(6) ?
O2 S1 . 1.455(3) y
O2 Cu1 . 2.347(3) y
O3 S1 . 1.455(3) y
O4 S1 . 1.456(3) y
O5 H5A . 0.956(10) ?
O5 H5B . 0.957(10) ?
O6 H6A . 0.963(10) ?
O6 H6B . 0.966(10) ?
O7 H7A . 0.963(10) ?
O7 H7B . 0.962(10) ?
Cu1 N2 2_766 2.009(4) ?
Cu1 N1 2_766 2.020(4) ?
Cu1 O2 2_766 2.347(3) ?
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
O1 H1 O6 . 0.83(6) 1.84(6) 2.653(5) 167(6)
O5 H5A O3 . 0.956(10) 1.828(12) 2.783(5) 176(6)
O5 H5B O1 2_665 0.957(10) 2.15(6) 2.902(5) 134(7)
O5 H5B O3 2_665 0.957(10) 2.41(4) 3.212(5) 141(5)
O6 H6A O4 1_455 0.963(10) 1.865(12) 2.828(5) 178(5)
O6 H6B O7 2_655 0.966(10) 1.82(2) 2.731(6) 155(4)
O7 H7A O4 . 0.963(10) 1.91(2) 2.828(5) 157(5)
O7 H7B O5 2_765 0.962(10) 1.798(17) 2.745(5) 168(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_4
_geom_torsion
O1 C1 C2 N1 . -172.8(4)
C7 C1 C2 N1 . -47.6(5)
S1 C1 C2 N1 . 74.6(4)
O1 C1 C2 C3 . 6.1(6)
C7 C1 C2 C3 . 131.3(4)
S1 C1 C2 C3 . -106.5(4)
N1 C2 C3 C4 . 4.0(7)
C1 C2 C3 C4 . -174.9(4)
C2 C3 C4 C5 . -0.8(7)
C3 C4 C5 C6 . -1.9(7)
C4 C5 C6 N1 . 1.7(7)
O1 C1 C7 N2 . 172.8(3)
C2 C1 C7 N2 . 48.0(5)
S1 C1 C7 N2 . -73.8(4)
O1 C1 C7 C8 . -7.8(5)
C2 C1 C7 C8 . -132.5(4)
S1 C1 C7 C8 . 105.7(4)
N2 C7 C8 C9 . -1.9(6)
C1 C7 C8 C9 . 178.7(4)
C7 C8 C9 C10 . -1.6(6)
C8 C9 C10 C11 . 2.5(6)
C9 C10 C11 N2 . -0.1(7)
C5 C6 N1 C2 . 1.3(7)
C5 C6 N1 Cu1 . -175.5(3)
C3 C2 N1 C6 . -4.1(6)
C1 C2 N1 C6 . 174.7(4)
C3 C2 N1 Cu1 . 172.6(3)
C1 C2 N1 Cu1 . -8.5(5)
C10 C11 N2 C7 . -3.3(6)
C10 C11 N2 Cu1 . 172.4(3)
C8 C7 N2 C11 . 4.3(6)
C1 C7 N2 C11 . -176.3(4)
C8 C7 N2 Cu1 . -171.4(3)
C1 C7 N2 Cu1 . 8.0(5)
Cu1 O2 S1 O3 . 121.5(2)
Cu1 O2 S1 O4 . -107.6(2)
Cu1 O2 S1 C1 . 6.7(3)
O1 C1 S1 O2 . 176.1(3)
C2 C1 S1 O2 . -67.0(3)
C7 C1 S1 O2 . 57.7(3)
O1 C1 S1 O3 . 55.4(3)
C2 C1 S1 O3 . 172.3(3)
C7 C1 S1 O3 . -63.0(3)
O1 C1 S1 O4 . -64.4(3)
C2 C1 S1 O4 . 52.6(3)
C7 C1 S1 O4 . 177.3(3)
C11 N2 Cu1 N1 . 137.9(3)
C7 N2 Cu1 N1 . -46.5(3)
C11 N2 Cu1 N1 2_766 -42.1(3)
C7 N2 Cu1 N1 2_766 133.5(3)
C11 N2 Cu1 O2 2_766 46.8(3)
C7 N2 Cu1 O2 2_766 -137.6(3)
C11 N2 Cu1 O2 . -133.2(3)
C7 N2 Cu1 O2 . 42.4(3)
C6 N1 Cu1 N2 2_766 43.5(3)
C2 N1 Cu1 N2 2_766 -133.2(3)
C6 N1 Cu1 N2 . -136.5(3)
C2 N1 Cu1 N2 . 46.8(3)
C6 N1 Cu1 O2 2_766 -42.1(3)
C2 N1 Cu1 O2 2_766 141.2(3)
C6 N1 Cu1 O2 . 137.9(3)
C2 N1 Cu1 O2 . -38.8(3)
S1 O2 Cu1 N2 2_766 130.8(2)
S1 O2 Cu1 N2 . -49.2(2)
S1 O2 Cu1 N1 . 36.8(2)
S1 O2 Cu1 N1 2_766 -143.2(2)
