#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/49/2224981.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_2224981
loop_
_publ_author_name
'Li, Yu-Feng'
'Wang, Lin-Tong'
'Jian, Fang-Fang'
_publ_section_title
;
 Bis(2,2'-bipyridyl)(dichloroacetato)copper(II) dichloroacetate
 dihydrate
;
_journal_coeditor_code           HB5295
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m141
_journal_paper_doi               10.1107/S1600536809055640
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac
'[Cu (C2 H Cl2 O2) (C10 H8 N2)2] (C2 H Cl2 O2), 2H2 O'
_chemical_formula_moiety
'C22 H17 Cl2 Cu N4 O2 +, C2 H Cl2 O2 -, 2(H2 O)'
_chemical_formula_sum            'C24 H22 Cl4 Cu N4 O6'
_chemical_formula_weight         667.80
_chemical_name_systematic
;
Bis(2,2'-bipyridyl)(dichloroacetato)copper(II) dichloroacetate dihydrate
;
_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                105.4070(10)
_cell_angle_beta                 101.4990(10)
_cell_angle_gamma                95.5130(10)
_cell_formula_units_Z            2
_cell_length_a                   9.9710(7)
_cell_length_b                   11.7307(9)
_cell_length_c                   12.4736(9)
_cell_measurement_reflns_used    2240
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.21
_cell_volume                     1361.07(17)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    '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_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'phi and omega 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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7789
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    1.242
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             678
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.639
_refine_ls_extinction_coef       0.0256(15)
_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   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5280
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0343
_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)+(0.0542P)²+0.3598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0965
_reflns_number_gt                4592
_reflns_number_total             5280
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5295.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_database_code               2224981
_cod_database_fobs_code          2224981
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_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.02070(3) 0.28505(2) 0.24318(2) 0.03074(11) Uani d U 1 . .
Cl Cl1 0.45242(8) 0.39464(9) 0.06435(8) 0.0741(3) Uani d D 1 . .
Cl Cl2 0.50350(6) 0.30032(6) 0.25678(6) 0.04867(17) Uani d . 1 . .
O O1 0.21727(16) 0.36582(14) 0.27220(14) 0.0396(4) Uani d . 1 . .
O O2 0.17501(17) 0.31459(16) 0.08196(15) 0.0459(4) Uani d . 1 . .
N N1 -0.06224(19) 0.43199(16) 0.24029(15) 0.0318(4) Uani d . 1 . .
N N2 -0.05985(19) 0.31277(16) 0.39146(15) 0.0326(4) Uani d . 1 . .
N N3 -0.13923(19) 0.17107(16) 0.11654(15) 0.0328(4) Uani d . 1 . .
N N4 0.08416(19) 0.12907(17) 0.24147(16) 0.0347(4) Uani d U 1 . .
C C1 -0.0573(3) 0.4885(2) 0.1606(2) 0.0406(5) Uani d . 1 . .
H H1 -0.0007 0.4659 0.1103 0.049 Uiso calc R 1 . .
C C2 -0.1329(3) 0.5790(2) 0.1503(2) 0.0465(6) Uani d . 1 . .
H H2 -0.1280 0.6162 0.0936 0.056 Uiso calc R 1 . .
C C3 -0.2157(3) 0.6134(2) 0.2255(2) 0.0467(6) Uani d . 1 . .
H H3 -0.2691 0.6732 0.2193 0.056 Uiso calc R 1 . .
C C4 -0.2185(2) 0.5581(2) 0.3104(2) 0.0415(5) Uani d . 1 . .
H H4 -0.2722 0.5816 0.3629 0.050 Uiso calc R 1 . .
C C5 -0.1403(2) 0.46721(18) 0.31641(18) 0.0303(4) Uani d . 1 . .
C C6 -0.1365(2) 0.40123(18) 0.40308(17) 0.0299(4) Uani d . 1 . .
C C7 -0.2055(2) 0.4282(2) 0.4908(2) 0.0404(5) Uani d . 1 . .
H H6 -0.2572 0.4905 0.4982 0.049 Uiso calc R 1 . .
C C8 -0.1960(3) 0.3608(2) 0.5670(2) 0.0460(6) Uani d . 1 . .
H H8 -0.2415 0.3771 0.6263 0.055 Uiso calc R 1 . .
C C9 -0.1187(3) 0.2699(2) 0.5541(2) 0.0472(6) Uani d . 1 . .
H H9 -0.1114 0.2233 0.6041 0.057 Uiso calc R 1 . .
C C10 -0.0515(3) 0.2483(2) 0.4653(2) 0.0411(5) Uani d . 1 . .
H H10 0.0013 0.1868 0.4569 0.049 Uiso calc R 1 . .
C C11 -0.2514(2) 0.1998(2) 0.0568(2) 0.0405(5) Uani d . 1 . .
H H11 -0.2605 0.2802 0.0702 0.049 Uiso calc R 1 . .
C C12 -0.3538(3) 0.1155(3) -0.0237(2) 0.0495(6) Uani d . 1 . .
H H12 -0.4300 0.1383 -0.0644 0.059 Uiso calc R 1 . .
C C13 -0.3404(3) -0.0027(3) -0.0422(2) 0.0525(7) Uani d . 1 . .
H H13 -0.4082 -0.0614 -0.0960 0.063 Uiso calc R 1 . .
C C14 -0.2268(3) -0.0348(2) 0.0188(2) 0.0457(6) Uani d . 1 . .
H H14 -0.2175 -0.1150 0.0072 0.055 Uiso calc R 1 . .
C C15 -0.1260(2) 0.05451(19) 0.09785(18) 0.0334(5) Uani d . 1 . .
C C16 0.0007(2) 0.0309(2) 0.16703(19) 0.0351(5) Uani d . 1 . .
C C17 0.0356(3) -0.0829(2) 0.1571(2) 0.0478(6) Uani d . 1 . .
H H17 -0.0222 -0.1500 0.1051 0.057 Uiso calc R 1 . .
C C18 0.1576(3) -0.0946(3) 0.2256(3) 0.0571(8) Uani d . 1 . .
H H18 0.1831 -0.1698 0.2199 0.069 Uiso calc R 1 . .
C C19 0.2412(3) 0.0060(3) 0.3024(2) 0.0528(7) Uani d . 1 . .
H H19 0.3232 -0.0005 0.3495 0.063 Uiso calc R 1 . .
C C20 0.2015(3) 0.1165(2) 0.3086(2) 0.0450(6) Uani d . 1 . .
H H20 0.2577 0.1843 0.3607 0.054 Uiso calc R 1 . .
C C21 0.2517(2) 0.35388(19) 0.1777(2) 0.0341(5) Uani d . 1 . .
C C22 0.4076(2) 0.3961(2) 0.1938(2) 0.0402(5) Uani d . 1 . .
H H22 0.4324 0.4778 0.2456 0.048 Uiso calc R 1 . .
Cl Cl3 0.17481(9) 0.06640(8) 0.59492(10) 0.0833(3) Uani d . 1 . .
Cl Cl4 0.36379(9) -0.04850(8) 0.72163(7) 0.0722(2) Uani d . 1 . .
O O3 0.4801(3) 0.2075(2) 0.7501(2) 0.0807(7) Uani d . 1 . .
O O4 0.4943(3) 0.1598(2) 0.5687(3) 0.0971(9) Uani d . 1 . .
C C23 0.3436(3) 0.0293(2) 0.6185(2) 0.0466(6) Uani d . 1 . .
H H23A 0.3545 -0.0240 0.5466 0.056 Uiso calc R 1 . .
C C24 0.4501(3) 0.1442(3) 0.6506(3) 0.0550(7) Uani d . 1 . .
O O1W 0.4574(3) 0.3842(2) 0.5424(2) 0.0744(7) Uani d D 1 . .
H H1A 0.455(4) 0.384(4) 0.4747(19) 0.089 Uiso d D 1 . .
H H1B 0.467(4) 0.312(2) 0.543(3) 0.089 Uiso d D 1 . .
O O2W 0.2759(3) 0.6333(2) 0.1579(3) 0.0885(8) Uani d D 1 . .
H H2A 0.299(3) 0.579(2) 0.104(2) 0.106 Uiso d D 1 . .
H H2B 0.349(3) 0.686(3) 0.192(3) 0.106 Uiso d D 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'
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'
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 N4 . . 174.19(8) ?
N1 Cu1 O1 . . 94.77(7) ?
N4 Cu1 O1 . . 91.01(7) ?
N1 Cu1 N3 . . 94.63(7) ?
N4 Cu1 N3 . . 80.37(7) ?
O1 Cu1 N3 . . 142.56(7) ?
N1 Cu1 N2 . . 79.44(7) ?
N4 Cu1 N2 . . 98.73(7) ?
O1 Cu1 N2 . . 114.17(7) ?
N3 Cu1 N2 . . 103.17(7) ?
C21 O1 Cu1 . . 109.56(14) ?
C1 N1 C5 . . 119.18(19) ?
C1 N1 Cu1 . . 123.79(15) ?
C5 N1 Cu1 . . 116.62(15) ?
C10 N2 C6 . . 118.93(19) ?
C10 N2 Cu1 . . 127.95(16) ?
C6 N2 Cu1 . . 112.90(14) ?
C11 N3 C15 . . 118.69(19) ?
C11 N3 Cu1 . . 127.97(16) ?
C15 N3 Cu1 . . 113.30(14) ?
C20 N4 C16 . . 119.4(2) ?
C20 N4 Cu1 . . 124.53(17) ?
C16 N4 Cu1 . . 116.08(15) ?
N1 C1 C2 . . 122.5(2) ?
N1 C1 H1 . . 118.7 ?
C2 C1 H1 . . 118.7 ?
C3 C2 C1 . . 118.8(2) ?
C3 C2 H2 . . 120.6 ?
C1 C2 H2 . . 120.6 ?
C2 C3 C4 . . 119.2(2) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C3 C4 C5 . . 119.4(2) ?
C3 C4 H4 . . 120.3 ?
C5 C4 H4 . . 120.3 ?
N1 C5 C4 . . 120.8(2) ?
N1 C5 C6 . . 115.24(18) ?
C4 C5 C6 . . 123.9(2) ?
N2 C6 C7 . . 121.7(2) ?
N2 C6 C5 . . 114.97(18) ?
C7 C6 C5 . . 123.4(2) ?
C8 C7 C6 . . 118.9(2) ?
C8 C7 H6 . . 120.6 ?
C6 C7 H6 . . 120.6 ?
C9 C8 C7 . . 119.2(2) ?
C9 C8 H8 . . 120.4 ?
C7 C8 H8 . . 120.4 ?
C8 C9 C10 . . 119.0(2) ?
C8 C9 H9 . . 120.5 ?
C10 C9 H9 . . 120.5 ?
N2 C10 C9 . . 122.3(2) ?
N2 C10 H10 . . 118.8 ?
C9 C10 H10 . . 118.8 ?
N3 C11 C12 . . 122.9(2) ?
N3 C11 H11 . . 118.5 ?
C12 C11 H11 . . 118.5 ?
C13 C12 C11 . . 118.3(3) ?
C13 C12 H12 . . 120.9 ?
C11 C12 H12 . . 120.9 ?
C12 C13 C14 . . 120.0(2) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C13 C14 C15 . . 119.0(2) ?
C13 C14 H14 . . 120.5 ?
C15 C14 H14 . . 120.5 ?
N3 C15 C14 . . 121.1(2) ?
N3 C15 C16 . . 115.17(19) ?
C14 C15 C16 . . 123.8(2) ?
N4 C16 C17 . . 121.1(2) ?
N4 C16 C15 . . 115.04(19) ?
C17 C16 C15 . . 123.8(2) ?
C18 C17 C16 . . 119.0(3) ?
C18 C17 H17 . . 120.5 ?
C16 C17 H17 . . 120.5 ?
C19 C18 C17 . . 119.5(2) ?
C19 C18 H18 . . 120.3 ?
C17 C18 H18 . . 120.3 ?
C18 C19 C20 . . 119.1(3) ?
C18 C19 H19 . . 120.5 ?
C20 C19 H19 . . 120.5 ?
N4 C20 C19 . . 121.9(3) ?
N4 C20 H20 . . 119.0 ?
C19 C20 H20 . . 119.0 ?
O2 C21 O1 . . 126.7(2) ?
O2 C21 C22 . . 120.8(2) ?
O1 C21 C22 . . 112.5(2) ?
C21 C22 Cl1 . . 112.61(17) ?
C21 C22 Cl2 . . 108.80(16) ?
Cl1 C22 Cl2 . . 108.94(13) ?
C21 C22 H22 . . 108.8 ?
Cl1 C22 H22 . . 108.8 ?
Cl2 C22 H22 . . 108.8 ?
C24 C23 Cl4 . . 113.67(19) ?
C24 C23 Cl3 . . 109.08(18) ?
Cl4 C23 Cl3 . . 109.69(15) ?
C24 C23 H23A . . 108.1 ?
Cl4 C23 H23A . . 108.1 ?
Cl3 C23 H23A . . 108.1 ?
O3 C24 O4 . . 128.5(3) ?
O3 C24 C23 . . 118.1(3) ?
O4 C24 C23 . . 113.4(3) ?
H1A O1W H1B . . 104(4) ?
H2A O2W H2B . . 107(2) ?
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 . 1.9879(18) y
Cu1 N4 . 1.9889(18) y
Cu1 O1 . 2.0121(16) y
Cu1 N3 . 2.0711(18) y
Cu1 N2 . 2.1201(18) y
Cl1 C22 . 1.755(3) ?
Cl2 C22 . 1.780(2) ?
O1 C21 . 1.268(3) ?
O2 C21 . 1.225(3) ?
N1 C1 . 1.340(3) ?
N1 C5 . 1.352(3) ?
N2 C10 . 1.333(3) ?
N2 C6 . 1.341(3) ?
N3 C11 . 1.339(3) ?
N3 C15 . 1.349(3) ?
N4 C20 . 1.341(3) ?
N4 C16 . 1.350(3) ?
C1 C2 . 1.378(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.377(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.385(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.388(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.484(3) ?
C6 C7 . 1.388(3) ?
C7 C8 . 1.384(4) ?
C7 H6 . 0.9300 ?
C8 C9 . 1.369(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.385(3) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.378(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.368(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.377(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.390(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.476(3) ?
C16 C17 . 1.391(3) ?
C17 C18 . 1.382(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.377(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.379(4) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C21 C22 . 1.542(3) ?
C22 H22 . 0.9800 ?
Cl3 C23 . 1.766(3) ?
Cl4 C23 . 1.757(3) ?
O3 C24 . 1.225(4) ?
O4 C24 . 1.239(4) ?
C23 C24 . 1.540(4) ?
C23 H23A . 0.9800 ?
O1W H1A . 0.839(18) ?
O1W H1B . 0.861(19) ?
O2W H2A . 0.884(16) ?
O2W H2B . 0.867(18) ?
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 Cl2 . 0.839(18) 2.79(2) 3.571(3) 155(4)
O1W H1B O4 . 0.861(19) 1.93(2) 2.787(4) 171(4)
O2W H2A Cl1 . 0.884(16) 2.756(17) 3.511(3) 144(3)
O2W H2B O3 2_666 0.867(18) 1.89(2) 2.757(3) 172(4)
