#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/69/2236915.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_2236915
loop_
_publ_author_name
'Zhang, Lai-Ping'
'Wen, Shu-Tang'
'Fu, Xiao-Ning'
_publ_section_title
;
 catena-Poly[[[diaquacopper(II)]-bis[μ-1,5-bis(1H-imidazol-1-yl)pentane-κ²N³:N^3'^]]
 naphthalene-1,5-disulfonate]
;
_journal_coeditor_code           HY2599
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1505
_journal_paper_doi               10.1107/S1600536812045679
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Cu (C11 H16 N4)2 (H2 O)2] (C10 H6 O6 S2)'
_chemical_formula_moiety         'C22 H32 Cu N8 O2 +, C10 H6 O6 S2 -'
_chemical_formula_sum            'C32 H38 Cu N8 O8 S2'
_chemical_formula_weight         790.37
_chemical_melting_point          ?
_chemical_name_systematic
;
catena-Poly[[[diaquacopper(II)]-bis[μ-1,5-bis(1H-imidazol-1-
yl)pentane-κ²N³:N^3'^]] naphthalene-1,5-disulfonate]
;
_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_creation_method           SHELXL-97
_cell_angle_alpha                95.490(5)
_cell_angle_beta                 102.930(5)
_cell_angle_gamma                114.000(5)
_cell_formula_units_Z            1
_cell_length_a                   9.300(5)
_cell_length_b                   9.880(5)
_cell_length_c                   11.020(5)
_cell_measurement_reflns_used    3995
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     881.5(8)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_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  0.0757
_diffrn_reflns_av_sigmaI/netI    0.1119
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8706
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             411
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.624
_refine_ls_extinction_coef       0.015(3)
_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   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3995
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1426
_refine_ls_R_factor_gt           0.0739
_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)+(0.0505P)²+1.4149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1672
_reflns_number_gt                2218
_reflns_number_total             3995
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2599.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               2236915
_cod_database_fobs_code          2236915
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.5000 0.5000 0.5000 0.0421(3) Uani d S 1 2 . .
C C1 0.2899(6) 0.3794(7) 0.2360(5) 0.0641(17) Uani d . 1 1 A .
H H1 0.1991 0.3656 0.2646 0.077 Uiso calc R 1 1 . .
C C2 0.5349(6) 0.4438(6) 0.2291(5) 0.0485(13) Uani d . 1 1 A .
H H2 0.6490 0.4841 0.2538 0.058 Uiso calc R 1 1 . .
C C3 0.4368(7) 0.3741(8) 0.1108(5) 0.0675(18) Uani d . 1 1 A .
H H3 0.4693 0.3573 0.0391 0.081 Uiso calc R 1 1 . .
C C4 0.1318(13) 0.1980(15) 0.0189(10) 0.053(4) Uani d P 0.554(18) 1 A 1
H H4A 0.1603 0.1171 -0.0048 0.063 Uiso calc PR 0.554(18) 1 A 1
H H4B 0.0399 0.1584 0.0543 0.063 Uiso calc PR 0.554(18) 1 A 1
C C5 0.0905(13) 0.2632(15) -0.0932(11) 0.058(4) Uani d P 0.554(18) 1 A 1
H H5A 0.1793 0.2974 -0.1322 0.069 Uiso calc PR 0.554(18) 1 A 1
H H5B 0.0664 0.3470 -0.0694 0.069 Uiso calc PR 0.554(18) 1 A 1
C C4' 0.1284(16) 0.305(2) 0.0057(13) 0.056(5) Uani d P 0.446(18) 1 A 2
H H4'1 0.0332 0.2855 0.0362 0.068 Uiso calc PR 0.446(18) 1 A 2
H H4'2 0.1494 0.3908 -0.0355 0.068 Uiso calc PR 0.446(18) 1 A 2
C C5' 0.1049(18) 0.1697(19) -0.0814(16) 0.065(5) Uani d P 0.446(18) 1 A 2
H H5'1 0.1007 0.0890 -0.0365 0.078 Uiso calc PR 0.446(18) 1 A 2
H H5'2 0.1929 0.1935 -0.1212 0.078 Uiso calc PR 0.446(18) 1 A 2
C C6 -0.0690(7) 0.1223(9) -0.1858(6) 0.082(2) Uani d . 1 1 . .
C C7 -0.1086(8) 0.2045(7) -0.2907(6) 0.078(2) Uani d D 1 1 A .
H H7A -0.1019 0.3000 -0.2517 0.094 Uiso calc R 1 1 . .
H H7B -0.0273 0.2267 -0.3370 0.094 Uiso calc R 1 1 . .
C C8 -0.2770(7) 0.1114(6) -0.3822(5) 0.0565(15) Uani d D 1 1 . .
H H8A -0.3585 0.0944 -0.3364 0.068 Uiso calc R 1 1 A .
H H8B -0.2967 0.1679 -0.4461 0.068 Uiso calc R 1 1 . .
C C9 -0.2189(6) -0.0582(6) -0.5301(5) 0.0482(13) Uani d . 1 1 . .
H H9 -0.1436 0.0150 -0.5605 0.058 Uiso calc R 1 1 A .
C C11 -0.3937(6) -0.1703(6) -0.4280(5) 0.0445(12) Uani d . 1 1 . .
H H11 -0.4599 -0.1853 -0.3738 0.053 Uiso calc R 1 1 A .
C C10 -0.2722(6) -0.2088(6) -0.5604(5) 0.0511(13) Uani d . 1 1 . .
H H10 -0.2386 -0.2577 -0.6164 0.061 Uiso calc R 1 1 . .
C C12 0.4074(6) 0.7806(6) 1.1100(5) 0.0474(13) Uani d . 1 1 . .
H H12 0.3943 0.7151 1.1664 0.057 Uiso calc R 1 1 . .
C C13 0.2935(6) 0.7343(5) 0.9885(5) 0.0432(12) Uani d . 1 1 . .
H H13 0.2051 0.6385 0.9657 0.052 Uiso calc R 1 1 . .
C C14 0.3102(5) 0.8269(5) 0.9041(4) 0.0349(11) Uani d . 1 1 . .
C C15 0.4423(5) 0.9768(5) 0.9385(4) 0.0366(11) Uani d . 1 1 . .
C C16 0.4633(6) 1.0791(6) 0.8548(4) 0.0422(12) Uani d . 1 1 . .
H H16 0.3876 1.0500 0.7748 0.051 Uiso calc R 1 1 . .
N N2 0.2814(6) 0.3331(7) 0.1160(4) 0.0786(18) Uani d . 1 1 . .
N N1 0.4413(5) 0.4466(4) 0.3081(4) 0.0413(10) Uani d . 1 1 . .
N N3 -0.2978(5) -0.0341(4) -0.4455(4) 0.0411(10) Uani d . 1 1 A .
N N4 -0.3829(5) -0.2802(5) -0.4970(4) 0.0426(10) Uani d . 1 1 . .
O O1 0.0560(4) 0.6024(4) 0.7469(4) 0.0597(10) Uani d . 1 1 . .
O O2 0.2596(4) 0.7717(4) 0.6604(3) 0.0529(10) Uani d . 1 1 . .
O O3 0.0816(4) 0.8556(4) 0.7419(3) 0.0544(10) Uani d . 1 1 . .
S S1 0.16398(15) 0.75847(15) 0.75061(12) 0.0442(4) Uani d . 1 1 . .
O O1W 0.2295(5) 0.5212(5) 0.4900(4) 0.0657(12) Uani d D 1 1 . .
H H1A 0.217(7) 0.588(6) 0.542(5) 0.099 Uiso d D 1 1 . .
H H1B 0.144(5) 0.486(7) 0.420(3) 0.099 Uiso d 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'
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'
H H 0.0000 0.0000 '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
N4 Cu N4 2 1_666 180.0000(10)
N4 Cu N1 2 2_666 91.92(16)
N4 Cu N1 1_666 2_666 88.08(16)
N4 Cu N1 2 . 88.08(16)
N4 Cu N1 1_666 . 91.92(16)
N1 Cu N1 2_666 . 180.0000(10)
O1W Cu N1 . . 91.80(17)
O1W Cu N4 . 1_666 91.02(18)
O1W Cu N4 . 2_555 88.98(18)
O1W Cu O1W . 2_666 180.00
O1W Cu N1 . 2_666 88.20(17)
N1 C1 N2 . . 111.5(5)
N1 C1 H1 . . 124.3
N2 C1 H1 . . 124.3
C3 C2 N1 . . 109.5(5)
C3 C2 H2 . . 125.3
N1 C2 H2 . . 125.3
C2 C3 N2 . . 106.4(5)
C2 C3 H3 . . 126.8
N2 C3 H3 . . 126.8
C5 C4 N2 . . 104.6(10)
C5 C4 H4A . . 110.8
N2 C4 H4A . . 110.8
C5 C4 H4B . . 110.8
N2 C4 H4B . . 110.8
H4A C4 H4B . . 108.9
C4 C5 C6 . . 102.3(10)
C4 C5 H5A . . 111.3
C6 C5 H5A . . 111.3
C4 C5 H5B . . 111.3
C6 C5 H5B . . 111.3
H5A C5 H5B . . 109.2
C5' C4' N2 . . 102.7(13)
C5' C4' H4'1 . . 111.2
N2 C4' H4'1 . . 111.2
C5' C4' H4'2 . . 111.2
N2 C4' H4'2 . . 111.2
H4'1 C4' H4'2 . . 109.1
C4' C5' C6 . . 103.8(12)
C4' C5' H5'1 . . 111.0
C6 C5' H5'1 . . 111.0
C4' C5' H5'2 . . 111.0
C6 C5' H5'2 . . 111.0
H5'1 C5' H5'2 . . 109.0
C7 C6 C5 . . 97.8(7)
C7 C6 C5' . . 128.2(9)
C8 C7 C6 . . 112.0(5)
C8 C7 H7A . . 109.2
C6 C7 H7A . . 109.2
C8 C7 H7B . . 109.2
C6 C7 H7B . . 109.2
H7A C7 H7B . . 107.9
N3 C8 C7 . . 112.9(5)
N3 C8 H8A . . 109.0
C7 C8 H8A . . 109.0
N3 C8 H8B . . 109.0
C7 C8 H8B . . 109.0
H8A C8 H8B . . 107.8
C10 C9 N3 . . 106.1(5)
C10 C9 H9 . . 127.0
N3 C9 H9 . . 127.0
N4 C11 N3 . . 111.7(5)
N4 C11 H11 . . 124.2
N3 C11 H11 . . 124.2
C9 C10 N4 . . 110.3(5)
C9 C10 H10 . . 124.8
N4 C10 H10 . . 124.8
C16 C12 C13 2_677 . 120.1(5)
C16 C12 H12 2_677 . 120.0
C13 C12 H12 . . 120.0
C14 C13 C12 . . 121.2(4)
C14 C13 H13 . . 119.4
C12 C13 H13 . . 119.4
C13 C14 C15 . . 120.5(4)
C13 C14 S1 . . 118.6(4)
C15 C14 S1 . . 120.9(4)
C16 C15 C15 . 2_677 119.2(5)
C16 C15 C14 . . 122.7(4)
C15 C15 C14 2_677 . 118.1(5)
C12 C16 C15 2_677 . 120.9(5)
C12 C16 H16 2_677 . 119.5
C15 C16 H16 . . 119.5
C1 N2 C3 . . 107.3(4)
C1 N2 C4 . . 125.1(6)
C3 N2 C4 . . 122.1(6)
C1 N2 C4' . . 120.2(7)
C3 N2 C4' . . 127.6(7)
C1 N1 C2 . . 105.4(4)
C1 N1 Cu . . 122.5(4)
C2 N1 Cu . . 131.1(3)
C11 N3 C9 . . 106.9(4)
C11 N3 C8 . . 126.2(5)
C9 N3 C8 . . 126.8(5)
C11 N4 C10 . . 105.0(4)
C11 N4 Cu . 1_444 126.0(4)
C10 N4 Cu . 1_444 129.0(4)
O1 S1 O3 . . 113.4(2)
O1 S1 O2 . . 112.4(2)
O3 S1 O2 . . 113.0(2)
O1 S1 C14 . . 105.8(2)
O3 S1 C14 . . 105.9(2)
O2 S1 C14 . . 105.5(2)
H1A O1W H1B . . 107(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu N4 2 1.988(4)
Cu N1 . 2.021(4)
Cu O1W . 2.587(5)
C1 N1 . 1.302(6)
C1 N2 . 1.331(7)
C1 H1 . 0.9300
C2 C3 . 1.339(7)
C2 N1 . 1.368(6)
C2 H2 . 0.9300
C3 N2 . 1.350(7)
C3 H3 . 0.9300
C4 C5 . 1.49(2)
C4 N2 . 1.553(11)
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 C6 . 1.597(12)
C5 H5A . 0.9700
C5 H5B . 0.9700
C4' C5' . 1.48(3)
C4' N2 . 1.555(14)
C4' H4'1 . 0.9700
C4' H4'2 . 0.9700
C5' C6 . 1.615(15)
C5' H5'1 . 0.9700
C5' H5'2 . 0.9700
C6 C7 . 1.537(10)
C7 C8 . 1.504(7)
C7 H7A . 0.9700
C7 H7B . 0.9700
C8 N3 . 1.453(6)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 C10 . 1.343(7)
C9 N3 . 1.367(6)
C9 H9 . 0.9300
C11 N4 . 1.316(6)
C11 N3 . 1.339(6)
C11 H11 . 0.9300
C10 N4 . 1.368(6)
C10 H10 . 0.9300
C12 C16 2_677 1.360(7)
C12 C13 . 1.406(7)
C12 H12 . 0.9300
C13 C14 . 1.355(6)
C13 H13 . 0.9300
C14 C15 . 1.432(6)
C14 S1 . 1.781(4)
C15 C16 . 1.417(6)
C15 C15 2_677 1.425(9)
C16 C12 2_677 1.360(7)
C16 H16 . 0.9300
N4 Cu 1_444 1.988(4)
O1 S1 . 1.448(4)
O2 S1 . 1.457(4)
O3 S1 . 1.449(4)
O1W H1A . 0.89(6)
O1W H1B . 0.89(4)
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
O1W H1A O2 . 0.89(6) 1.97(6) 2.836(6) 163(6)
O1W H1B O1 2_566 0.89(4) 2.11(4) 3.001(6) 178(7)
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_4
_geom_torsion
N1 C2 C3 N2 . . -0.1(7)
N2 C4 C5 C6 . . -177.0(7)
N2 C4' C5' C6 . . 171.5(9)
C4 C5 C6 C7 . . 175.4(10)
C4 C5 C6 C5' . . -34.7(13)
C4' C5' C6 C7 . . 70.9(16)
C4' C5' C6 C5 . . 31.7(12)
C5 C6 C7 C8 . . -167.3(7)
C5' C6 C7 C8 . . 170.4(9)
C6 C7 C8 N3 . . -59.1(7)
N3 C9 C10 N4 . . 0.1(6)
C16 C12 C13 C14 2_677 . 0.5(8)
C12 C13 C14 C15 . . -2.0(7)
C12 C13 C14 S1 . . 178.4(4)
C13 C14 C15 C16 . . -178.6(5)
S1 C14 C15 C16 . . 0.9(6)
C13 C14 C15 C15 . 2_677 2.1(8)
S1 C14 C15 C15 . 2_677 -178.3(4)
C15 C15 C16 C12 2_677 2_677 0.8(8)
C14 C15 C16 C12 . 2_677 -178.5(5)
N1 C1 N2 C3 . . -0.5(8)
N1 C1 N2 C4 . . 153.4(8)
N1 C1 N2 C4' . . -157.5(9)
C2 C3 N2 C1 . . 0.3(8)
C2 C3 N2 C4 . . -154.5(8)
C2 C3 N2 C4' . . 155.1(10)
C5 C4 N2 C1 . . 125.9(9)
C5 C4 N2 C3 . . -83.8(12)
C5 C4 N2 C4' . . 28.3(11)
C5' C4' N2 C1 . . -142.0(11)
C5' C4' N2 C3 . . 66.1(17)
C5' C4' N2 C4 . . -31.9(11)
N2 C1 N1 C2 . . 0.5(7)
N2 C1 N1 Cu . . -169.3(4)
C3 C2 N1 C1 . . -0.2(7)
C3 C2 N1 Cu . . 168.3(4)
N4 Cu N1 C1 2 . 61.3(5)
N4 Cu N1 C1 1_666 . -118.7(5)
N4 Cu N1 C2 2 . -105.5(5)
N4 Cu N1 C2 1_666 . 74.5(5)
N4 C11 N3 C9 . . -0.7(5)
N4 C11 N3 C8 . . -178.5(4)
C10 C9 N3 C11 . . 0.3(5)
C10 C9 N3 C8 . . 178.1(5)
C7 C8 N3 C11 . . 111.1(6)
C7 C8 N3 C9 . . -66.2(7)
N3 C11 N4 C10 . . 0.7(5)
N3 C11 N4 Cu . 1_444 179.0(3)
C9 C10 N4 C11 . . -0.5(6)
C9 C10 N4 Cu . 1_444 -178.7(3)
C13 C14 S1 O1 . . -3.7(5)
C15 C14 S1 O1 . . 176.8(4)
C13 C14 S1 O3 . . 117.0(4)
C15 C14 S1 O3 . . -62.6(4)
C13 C14 S1 O2 . . -123.0(4)
C15 C14 S1 O2 . . 57.4(4)
