#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/26/2232616.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_2232616
loop_
_publ_author_name
'Qiu, Xiumin'
'Li, Leilei'
'Li, Dacheng'
_publ_section_title
;
 Chlorido[1-(pyridin-2-yl)ethanone
 oximato-κ²N,N'][1-(2-pyridyl)ethanone
 oxime-κ²N,N']copper(II) trihydrate
;
_journal_coeditor_code           BX2382
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1810
_journal_page_last               m1811
_journal_paper_doi               10.1107/S1600536811049129
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu (C7 H7 N2 O1) Cl (C7 H8 N2 O1)], 3H2 O'
_chemical_formula_moiety         'C14 H15 Cl Cu N4 O2, 3(H2 O)'
_chemical_formula_sum            'C14 H21 Cl Cu N4 O5'
_chemical_formula_weight         424.34
_chemical_name_systematic
;
Chlorido[1-(pyridin-2-yl)ethanone
oximato-κ²N,N'][1-(2-pyridyl)ethanone
oxime-κ²N,N']copper(II) trihydrate
;
_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                114.199(2)
_cell_angle_beta                 93.4620(10)
_cell_angle_gamma                103.9720(10)
_cell_formula_units_Z            2
_cell_length_a                   8.3980(9)
_cell_length_b                   10.2559(11)
_cell_length_c                   12.1121(13)
_cell_measurement_reflns_used    2075
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.7955
_cell_measurement_theta_min      2.541
_cell_volume                     908.29(17)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Siemens SMART 1000 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  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4646
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    1.381
_exptl_absorpt_correction_T_max  0.7328
_exptl_absorpt_correction_T_min  0.5753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            dark-green
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0446P)²+0.7087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                2493
_reflns_number_total             3156
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bx2382.cif
_cod_data_source_block           I
_cod_database_code               2232616
_cod_database_fobs_code          2232616
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
Cu Cu1 0.08870(5) 0.44895(4) 0.68063(3) 0.03697(15) Uani d . 1 1
Cl Cl1 0.35260(11) 0.46847(10) 0.79450(8) 0.0481(2) Uani d . 1 1
N N1 0.0912(4) 0.2780(3) 0.5265(2) 0.0418(7) Uani d . 1 1
N N2 0.1968(3) 0.5577(3) 0.5806(2) 0.0364(6) Uani d . 1 1
N N3 -0.0916(3) 0.3230(3) 0.7265(3) 0.0403(7) Uani d . 1 1
N N4 0.0355(3) 0.6084(3) 0.8295(2) 0.0355(6) Uani d . 1 1
O O1 0.0222(3) 0.1363(2) 0.5044(2) 0.0568(7) Uani d . 1 1
H H1 -0.0247 0.1338 0.5613 0.085 Uiso calc R 1 1
O O2 -0.1472(3) 0.1713(3) 0.6666(2) 0.0555(7) Uani d . 1 1
O O3 0.4005(4) 0.0145(3) 0.8601(3) 0.0820(10) Uani d . 1 1
H H3C 0.3588 0.0494 0.8165 0.098 Uiso d R 1 1
H H3D 0.4073 0.0722 0.9355 0.098 Uiso d R 1 1
O O4 0.7339(4) 0.8940(3) 0.3036(3) 0.0840(10) Uani d . 1 1
H H4C 0.8180 0.9495 0.3605 0.101 Uiso d R 1 1
H H4D 0.7251 0.8032 0.2868 0.101 Uiso d R 1 1
O O5 0.5675(4) 0.8149(3) 0.8877(3) 0.0795(9) Uani d . 1 1
H H5C 0.5105 0.8684 0.8772 0.095 Uiso d R 1 1
H H5D 0.5043 0.7260 0.8616 0.095 Uiso d R 1 1
C C1 0.1862(6) 0.1812(4) 0.3309(3) 0.0639(11) Uani d . 1 1
H H1A 0.2069 0.1028 0.3481 0.096 Uiso calc R 1 1
H H1B 0.2772 0.2196 0.2977 0.096 Uiso calc R 1 1
H H1C 0.0847 0.1424 0.2722 0.096 Uiso calc R 1 1
C C2 0.1705(4) 0.3039(4) 0.4468(3) 0.0421(8) Uani d . 1 1
C C3 0.2392(4) 0.4625(4) 0.4784(3) 0.0373(7) Uani d . 1 1
C C4 0.3404(4) 0.5153(4) 0.4109(3) 0.0474(9) Uani d . 1 1
H H4 0.3695 0.4487 0.3416 0.057 Uiso calc R 1 1
C C5 0.3981(5) 0.6664(5) 0.4465(3) 0.0534(10) Uani d . 1 1
H H5 0.4678 0.7030 0.4024 0.064 Uiso calc R 1 1
C C6 0.3516(5) 0.7628(4) 0.5479(3) 0.0506(9) Uani d . 1 1
H H6 0.3880 0.8655 0.5732 0.061 Uiso calc R 1 1
C C7 0.2498(4) 0.7036(4) 0.6111(3) 0.0439(8) Uani d . 1 1
H H7 0.2163 0.7687 0.6786 0.053 Uiso calc R 1 1
C C8 -0.3054(5) 0.3094(4) 0.8534(4) 0.0558(10) Uani d . 1 1
H H8A -0.3315 0.2037 0.8035 0.084 Uiso calc R 1 1
H H8B -0.4012 0.3419 0.8436 0.084 Uiso calc R 1 1
H H8C -0.2750 0.3313 0.9382 0.084 Uiso calc R 1 1
C C9 -0.1636(4) 0.3891(4) 0.8147(3) 0.0397(8) Uani d . 1 1
C C10 -0.0901(4) 0.5520(4) 0.8775(3) 0.0375(7) Uani d . 1 1
C C11 -0.1392(5) 0.6427(4) 0.9816(3) 0.0502(9) Uani d . 1 1
H H11 -0.2280 0.6026 1.0116 0.060 Uiso calc R 1 1
C C12 -0.0552(5) 0.7932(4) 1.0402(4) 0.0577(10) Uani d . 1 1
H H12 -0.0871 0.8559 1.1100 0.069 Uiso calc R 1 1
C C13 0.0756(5) 0.8495(4) 0.9948(3) 0.0505(9) Uani d . 1 1
H H13 0.1353 0.9503 1.0339 0.061 Uiso calc R 1 1
C C14 0.1169(4) 0.7534(4) 0.8898(3) 0.0436(8) Uani d . 1 1
H H14 0.2063 0.7920 0.8595 0.052 Uiso calc R 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 0.0000 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
_geom_angle_publ_flag
N1 Cu1 N3 92.87(11) y
N1 Cu1 N4 168.50(11) y
N3 Cu1 N4 78.92(10) y
N1 Cu1 N2 78.86(11) y
N3 Cu1 N2 157.52(11) y
N4 Cu1 N2 105.76(10) y
N1 Cu1 Cl1 96.51(9) ?
N3 Cu1 Cl1 105.86(8) ?
N4 Cu1 Cl1 93.50(8) ?
N2 Cu1 Cl1 95.89(8) ?
C2 N1 O1 118.3(3) ?
C2 N1 Cu1 118.7(2) ?
O1 N1 Cu1 122.9(2) ?
C7 N2 C3 118.0(3) ?
C7 N2 Cu1 129.7(2) ?
C3 N2 Cu1 111.4(2) ?
C9 N3 O2 117.7(3) ?
C9 N3 Cu1 118.3(2) ?
O2 N3 Cu1 123.9(2) ?
C14 N4 C10 117.7(3) ?
C14 N4 Cu1 128.6(2) ?
C10 N4 Cu1 113.4(2) ?
N1 O1 H1 109.5 ?
H3C O3 H3D 108.6 ?
H4C O4 H4D 108.7 ?
H5C O5 H5D 108.6 ?
C2 C1 H1A 109.5 ?
C2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
N1 C2 C3 114.2(3) ?
N1 C2 C1 122.3(3) ?
C3 C2 C1 123.5(3) ?
N2 C3 C4 121.1(3) ?
N2 C3 C2 115.3(3) ?
C4 C3 C2 123.6(3) ?
C5 C4 C3 119.8(3) ?
C5 C4 H4 120.1 ?
C3 C4 H4 120.1 ?
C4 C5 C6 119.3(3) ?
C4 C5 H5 120.4 ?
C6 C5 H5 120.4 ?
C5 C6 C7 118.3(3) ?
C5 C6 H6 120.8 ?
C7 C6 H6 120.8 ?
N2 C7 C6 123.4(3) ?
N2 C7 H7 118.3 ?
C6 C7 H7 118.3 ?
C9 C8 H8A 109.5 ?
C9 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C9 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
N3 C9 C10 113.8(3) ?
N3 C9 C8 123.8(3) ?
C10 C9 C8 122.3(3) ?
N4 C10 C11 121.6(3) ?
N4 C10 C9 115.3(3) ?
C11 C10 C9 123.0(3) ?
C12 C11 C10 119.3(3) ?
C12 C11 H11 120.4 ?
C10 C11 H11 120.4 ?
C13 C12 C11 119.3(3) ?
C13 C12 H12 120.3 ?
C11 C12 H12 120.3 ?
C12 C13 C14 118.5(3) ?
C12 C13 H13 120.7 ?
C14 C13 H13 120.7 ?
N4 C14 C13 123.5(3) ?
N4 C14 H14 118.2 ?
C13 C14 H14 118.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N1 1.975(3) y
Cu1 N3 2.004(3) y
Cu1 N4 2.038(2) y
Cu1 N2 2.071(3) y
Cu1 Cl1 2.4584(10) y
N1 C2 1.284(4) ?
N1 O1 1.333(3) ?
N2 C7 1.333(4) ?
N2 C3 1.357(4) ?
N3 C9 1.284(4) ?
N3 O2 1.359(3) ?
N4 C14 1.331(4) ?
N4 C10 1.357(4) ?
O1 H1 0.8200 ?
O3 H3C 0.8500 ?
O3 H3D 0.8499 ?
O4 H4C 0.8500 ?
O4 H4D 0.8499 ?
O5 H5C 0.8501 ?
O5 H5D 0.8500 ?
C1 C2 1.492(4) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 C3 1.462(5) ?
C3 C4 1.382(5) ?
C4 C5 1.374(5) ?
C4 H4 0.9300 ?
C5 C6 1.374(5) ?
C5 H5 0.9300 ?
C6 C7 1.377(5) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.490(5) ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
C9 C10 1.467(5) ?
C10 C11 1.382(5) ?
C11 C12 1.379(5) ?
C11 H11 0.9300 ?
C12 C13 1.367(5) ?
C12 H12 0.9300 ?
C13 C14 1.379(5) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
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 H5D Cl1 . 0.85 2.40 3.244(3) 173.6
O5 H5C O3 1_565 0.85 2.01 2.857(5) 173.3
O4 H4D Cl1 2_666 0.85 2.44 3.275(3) 167.5
O4 H4C O1 2_666 0.85 2.60 3.165(4) 125.5
O4 H4C O1 1_665 0.85 2.23 3.063(4) 167.1
O3 H3D O5 2_667 0.85 1.94 2.785(4) 172.6
O3 H3C O4 2_666 0.85 1.96 2.802(4) 172.0
O1 H1 O2 . 0.82 1.67 2.452(4) 159.7
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
N3 Cu1 N1 C2 167.8(3)
N4 Cu1 N1 C2 123.8(5)
N2 Cu1 N1 C2 8.9(3)
Cl1 Cu1 N1 C2 -85.9(3)
N3 Cu1 N1 O1 -16.2(3)
N4 Cu1 N1 O1 -60.2(7)
N2 Cu1 N1 O1 -175.1(3)
Cl1 Cu1 N1 O1 90.2(3)
N1 Cu1 N2 C7 179.7(3)
N3 Cu1 N2 C7 109.7(4)
N4 Cu1 N2 C7 10.5(3)
Cl1 Cu1 N2 C7 -84.8(3)
N1 Cu1 N2 C3 -11.2(2)
N3 Cu1 N2 C3 -81.2(3)
N4 Cu1 N2 C3 179.6(2)
Cl1 Cu1 N2 C3 84.3(2)
N1 Cu1 N3 C9 -167.7(3)
N4 Cu1 N3 C9 4.2(2)
N2 Cu1 N3 C9 -100.3(3)
Cl1 Cu1 N3 C9 94.7(2)
N1 Cu1 N3 O2 9.6(3)
N4 Cu1 N3 O2 -178.5(3)
N2 Cu1 N3 O2 76.9(4)
Cl1 Cu1 N3 O2 -88.0(2)
N1 Cu1 N4 C14 -144.0(5)
N3 Cu1 N4 C14 171.0(3)
N2 Cu1 N4 C14 -31.6(3)
Cl1 Cu1 N4 C14 65.5(3)
N1 Cu1 N4 C10 43.0(6)
N3 Cu1 N4 C10 -2.0(2)
N2 Cu1 N4 C10 155.4(2)
Cl1 Cu1 N4 C10 -107.5(2)
O1 N1 C2 C3 179.1(3)
Cu1 N1 C2 C3 -4.7(4)
O1 N1 C2 C1 0.6(5)
Cu1 N1 C2 C1 176.8(3)
C7 N2 C3 C4 2.8(5)
Cu1 N2 C3 C4 -167.7(3)
C7 N2 C3 C2 -177.2(3)
Cu1 N2 C3 C2 12.3(3)
N1 C2 C3 N2 -5.6(4)
C1 C2 C3 N2 172.9(3)
N1 C2 C3 C4 174.4(3)
C1 C2 C3 C4 -7.2(5)
N2 C3 C4 C5 -0.8(5)
C2 C3 C4 C5 179.3(3)
C3 C4 C5 C6 -1.1(6)
C4 C5 C6 C7 0.8(6)
C3 N2 C7 C6 -3.2(5)
Cu1 N2 C7 C6 165.3(3)
C5 C6 C7 N2 1.5(6)
O2 N3 C9 C10 177.3(3)
Cu1 N3 C9 C10 -5.3(4)
O2 N3 C9 C8 -0.9(5)
Cu1 N3 C9 C8 176.5(3)
C14 N4 C10 C11 3.7(5)
Cu1 N4 C10 C11 177.5(3)
C14 N4 C10 C9 -173.8(3)
Cu1 N4 C10 C9 0.0(3)
N3 C9 C10 N4 3.4(4)
C8 C9 C10 N4 -178.4(3)
N3 C9 C10 C11 -174.1(3)
C8 C9 C10 C11 4.1(5)
N4 C10 C11 C12 -2.2(5)
C9 C10 C11 C12 175.2(3)
C10 C11 C12 C13 -0.4(6)
C11 C12 C13 C14 1.3(6)
C10 N4 C14 C13 -2.8(5)
Cu1 N4 C14 C13 -175.6(3)
C12 C13 C14 N4 0.4(6)
