#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/67/2236702.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_2236702
loop_
_publ_author_name
'Ourari, Ali'
'Derafa, Wassila'
'Bouacida, Sofiane'
'Aggoun, Djouhra'
'Daran, Jean-Claude'
_publ_section_title
;
 Bis[μ-(3-acetyl-2-hydroxy-6-methyl-4H-pyran-4-one-κ³O:O',O'')]diaquatetrakis(pyridine-κN)dicopper(II)
 diperchlorate
;
_journal_coeditor_code           WM2685
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1356
_journal_page_last               m1357
_journal_paper_doi               10.1107/S1600536812041608
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Cu (C8 H7 O4) (H2 O) (C5 H5 N)2]2 (Cl O4)2'
_chemical_formula_moiety         'C36 H38 Cu2 N4 O10, 2(Cl O4)'
_chemical_formula_sum            'C36 H38 Cl2 Cu2 N4 O18'
_chemical_formula_weight         1012.70
_chemical_name_systematic
;
Bis[μ-(3-acetyl-2-hydroxy-6-methyl-4H-pyran-4-one-κ³O:
O',O'')]diaquatetrakis(pyridine-κN)dicopper(II)
diperchlorate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_cell_angle_alpha                99.624(4)
_cell_angle_beta                 90.540(3)
_cell_angle_gamma                97.895(4)
_cell_formula_units_Z            1
_cell_length_a                   9.9371(4)
_cell_length_b                   10.3072(4)
_cell_length_c                   10.4440(5)
_cell_measurement_reflns_used    12265
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.57
_cell_volume                     1044.09(8)
_computing_cell_refinement       'CrysAlisPro (Agilent, 2011)'
_computing_data_collection       'CrysAlisPro (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro (Agilent, 2011)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2005)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 8.2632
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Agilent Xcalibur'
_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  0.0368
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20280
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    1.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Agilent, 2011)
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.137
_refine_diff_density_min         -0.647
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0537
_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)+(0.0426P)²+3.6572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                3889
_reflns_number_total             4692
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wm2685.cif
_cod_data_source_block           I
_cod_database_code               2236702
_cod_database_fobs_code          2236702
loop_
_space_group_symop_operation_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 0.13889(5) 0.33620(4) 0.22133(5) 0.02379(14) Uani d . 1 1
Cl Cl1 0.54880(11) 0.73089(10) 0.34098(11) 0.0366(3) Uani d . 1 1
O O3 0.2147(3) 0.7115(3) -0.0994(3) 0.0314(6) Uani d . 1 1
O O4 0.0272(3) 0.7603(3) -0.0061(3) 0.0397(7) Uani d . 1 1
O O2 0.0424(3) 0.4919(3) 0.2469(3) 0.0287(6) Uani d . 1 1
O O1 0.2610(3) 0.4210(3) 0.1090(3) 0.0294(6) Uani d . 1 1
O O1W 0.2668(4) 0.4378(4) 0.4076(4) 0.0436(8) Uani d . 1 1
H H1W 0.322(6) 0.498(6) 0.387(6) 0.052 Uiso d . 1 1
H H2W 0.304(6) 0.415(6) 0.459(6) 0.052 Uiso d . 1 1
O O14 0.5337(5) 0.8399(4) 0.4391(4) 0.0721(13) Uani d . 1 1
N N1 0.2368(3) 0.1771(3) 0.1824(3) 0.0240(6) Uani d . 1 1
N N2 -0.0062(3) 0.2363(3) 0.3136(3) 0.0248(7) Uani d . 1 1
O O13 0.5953(5) 0.7736(5) 0.2227(4) 0.0706(12) Uani d . 1 1
C C12 0.3329(4) 0.5426(4) -0.0505(4) 0.0270(8) Uani d . 1 1
H H12 0.404 0.4928 -0.0678 0.032 Uiso calc R 1 1
C C1 0.2806(4) 0.1181(4) 0.2765(4) 0.0293(8) Uani d . 1 1
H H1 0.2662 0.1531 0.3625 0.035 Uiso calc R 1 1
C C16 0.1369(4) 0.5980(3) 0.0778(4) 0.0223(7) Uani d . 1 1
C C15 0.1196(4) 0.6938(4) -0.0055(4) 0.0267(8) Uani d . 1 1
C C2 0.3464(5) 0.0069(4) 0.2508(4) 0.0347(10) Uani d . 1 1
H H2 0.3773 -0.0312 0.3182 0.042 Uiso calc R 1 1
C C18 -0.0449(5) 0.6868(4) 0.2296(4) 0.0332(9) Uani d . 1 1
H H18A -0.1173 0.6794 0.1662 0.05 Uiso calc R 1 1
H H18B 0.0055 0.7746 0.2409 0.05 Uiso calc R 1 1
H H18C -0.0821 0.6706 0.3109 0.05 Uiso calc R 1 1
C C5 0.2587(4) 0.1269(4) 0.0587(4) 0.0302(9) Uani d . 1 1
H H5 0.2309 0.1692 -0.0069 0.036 Uiso calc R 1 1
C C11 0.2416(4) 0.5159(3) 0.0508(4) 0.0230(7) Uani d . 1 1
C C4 0.3208(5) 0.0149(4) 0.0251(4) 0.0372(10) Uani d . 1 1
H H4 0.3326 -0.019 -0.0616 0.045 Uiso calc R 1 1
C C3 0.3650(5) -0.0458(4) 0.1227(4) 0.0371(10) Uani d . 1 1
H H3 0.407 -0.1216 0.1024 0.044 Uiso calc R 1 1
C C10 -0.0591(4) 0.1101(4) 0.2648(4) 0.0293(8) Uani d . 1 1
H H10 -0.021 0.0671 0.1914 0.035 Uiso calc R 1 1
C C13 0.3180(4) 0.6368(4) -0.1201(4) 0.0277(8) Uani d . 1 1
C C14 0.4058(5) 0.6759(5) -0.2262(5) 0.0427(11) Uani d . 1 1
H H14A 0.4826 0.6283 -0.2323 0.064 Uiso calc R 1 1
H H14B 0.4368 0.7697 -0.2076 0.064 Uiso calc R 1 1
H H14C 0.3545 0.6549 -0.3071 0.064 Uiso calc R 1 1
C C17 0.0485(4) 0.5860(4) 0.1837(4) 0.0230(7) Uani d . 1 1
C C9 -0.1668(5) 0.0422(4) 0.3184(4) 0.0363(10) Uani d . 1 1
H H9 -0.1997 -0.0455 0.2829 0.044 Uiso calc R 1 1
C C8 -0.2253(5) 0.1065(5) 0.4261(5) 0.0395(10) Uani d . 1 1
H H8 -0.3 0.0637 0.4629 0.047 Uiso calc R 1 1
C C7 -0.1711(5) 0.2350(5) 0.4780(4) 0.0410(11) Uani d . 1 1
H H7 -0.2075 0.2797 0.5515 0.049 Uiso calc R 1 1
O O11 0.6447(9) 0.6599(10) 0.3795(6) 0.179(5) Uani d . 1 1
O O12 0.4201(7) 0.6613(8) 0.3069(6) 0.140(3) Uani d . 1 1
C C6 -0.0622(5) 0.2967(4) 0.4196(4) 0.0318(9) Uani d . 1 1
H H6 -0.0261 0.3835 0.455 0.038 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 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'
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_3
_geom_angle
O1 Cu1 O2 . 89.43(12)
O1 Cu1 N2 . 171.16(14)
O2 Cu1 N2 . 90.52(13)
O1 Cu1 N1 . 88.01(13)
O2 Cu1 N1 . 176.25(14)
N2 Cu1 N1 . 91.58(14)
O1 Cu1 O1W . 92.98(14)
O2 Cu1 O1W . 86.49(13)
N2 Cu1 O1W . 95.84(14)
N1 Cu1 O1W . 96.38(14)
O1 Cu1 O4 2_565 87.05(12)
O2 Cu1 O4 2_565 87.41(12)
N2 Cu1 O4 2_565 84.12(13)
N1 Cu1 O4 2_565 89.71(12)
O1W Cu1 O4 2_565 173.90(11)
O11 Cl1 O12 . 116.7(6)
O11 Cl1 O14 . 110.3(4)
O12 Cl1 O14 . 107.6(4)
O11 Cl1 O13 . 106.5(4)
O12 Cl1 O13 . 103.9(4)
O14 Cl1 O13 . 111.7(3)
C13 O3 C15 . 122.2(3)
C17 O2 Cu1 . 129.4(2)
C11 O1 Cu1 . 127.4(2)
Cu1 O1W H1W . 107(4)
Cu1 O1W H2W . 135(5)
H1W O1W H2W . 103(6)
C1 N1 C5 . 118.5(3)
C1 N1 Cu1 . 122.0(3)
C5 N1 Cu1 . 119.5(3)
C6 N2 C10 . 117.7(4)
C6 N2 Cu1 . 120.9(3)
C10 N2 Cu1 . 121.1(3)
C13 C12 C11 . 121.4(4)
C13 C12 H12 . 119.3
C11 C12 H12 . 119.3
N1 C1 C2 . 122.5(4)
N1 C1 H1 . 118.7
C2 C1 H1 . 118.7
C17 C16 C11 . 121.5(3)
C17 C16 C15 . 119.6(3)
C11 C16 C15 . 118.9(3)
O4 C15 O3 . 114.4(3)
O4 C15 C16 . 127.6(4)
O3 C15 C16 . 118.0(3)
C3 C2 C1 . 118.4(4)
C3 C2 H2 . 120.8
C1 C2 H2 . 120.8
C17 C18 H18A . 109.5
C17 C18 H18B . 109.5
H18A C18 H18B . 109.5
C17 C18 H18C . 109.5
H18A C18 H18C . 109.5
H18B C18 H18C . 109.5
N1 C5 C4 . 122.4(4)
N1 C5 H5 . 118.8
C4 C5 H5 . 118.8
O1 C11 C16 . 125.5(4)
O1 C11 C12 . 117.0(3)
C16 C11 C12 . 117.6(3)
C5 C4 C3 . 118.7(4)
C5 C4 H4 . 120.6
C3 C4 H4 . 120.6
C4 C3 C2 . 119.4(4)
C4 C3 H3 . 120.3
C2 C3 H3 . 120.3
N2 C10 C9 . 122.9(4)
N2 C10 H10 . 118.5
C9 C10 H10 . 118.5
C12 C13 O3 . 121.5(4)
C12 C13 C14 . 127.0(4)
O3 C13 C14 . 111.5(3)
C13 C14 H14A . 109.5
C13 C14 H14B . 109.5
H14A C14 H14B . 109.5
C13 C14 H14C . 109.5
H14A C14 H14C . 109.5
H14B C14 H14C . 109.5
O2 C17 C16 . 123.2(3)
O2 C17 C18 . 114.3(3)
C16 C17 C18 . 122.4(3)
C10 C9 C8 . 118.8(4)
C10 C9 H9 . 120.6
C8 C9 H9 . 120.6
C7 C8 C9 . 118.8(4)
C7 C8 H8 . 120.6
C9 C8 H8 . 120.6
C8 C7 C6 . 119.2(4)
C8 C7 H7 . 120.4
C6 C7 H7 . 120.4
N2 C6 C7 . 122.5(4)
N2 C6 H6 . 118.7
C7 C6 H6 . 118.7
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 O1 . 1.922(3) y
Cu1 O2 . 1.962(3) y
Cu1 N2 . 2.005(3) y
Cu1 N1 . 2.006(3) y
Cu1 O1W . 2.325(3) y
Cu1 O4 2_565 2.737(3) y
Cl1 O11 . 1.374(5) ?
Cl1 O12 . 1.390(6) ?
Cl1 O14 . 1.414(4) ?
Cl1 O13 . 1.439(4) ?
O3 C13 . 1.363(5) ?
O3 C15 . 1.386(5) ?
O4 C15 . 1.219(5) ?
O2 C17 . 1.256(4) ?
O1 C11 . 1.269(4) ?
O1W H1W . 0.82(6) ?
O1W H2W . 0.74(6) ?
N1 C1 . 1.337(5) ?
N1 C5 . 1.340(5) ?
N2 C6 . 1.341(5) ?
N2 C10 . 1.346(5) ?
C12 C13 . 1.329(5) ?
C12 C11 . 1.437(5) ?
C12 H12 . 0.93 ?
C1 C2 . 1.385(5) ?
C1 H1 . 0.93 ?
C16 C17 . 1.430(5) ?
C16 C11 . 1.431(5) ?
C16 C15 . 1.447(5) ?
C2 C3 . 1.382(6) ?
C2 H2 . 0.93 ?
C18 C17 . 1.509(5) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C5 C4 . 1.379(5) ?
C5 H5 . 0.93 ?
C4 C3 . 1.380(6) ?
C4 H4 . 0.93 ?
C3 H3 . 0.93 ?
C10 C9 . 1.373(6) ?
C10 H10 . 0.93 ?
C13 C14 . 1.491(6) ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C9 C8 . 1.383(6) ?
C9 H9 . 0.93 ?
C8 C7 . 1.377(7) ?
C8 H8 . 0.93 ?
C7 C6 . 1.378(6) ?
C7 H7 . 0.93 ?
C6 H6 . 0.93 ?
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
_geom_hbond_publ_flag
O1W H1W O12 . 0.83(6) 2.13(6) 2.934(9) 165(6) yes
O1W H2W O11 2_666 0.74(6) 2.06(6) 2.772(9) 164(6) yes
C9 H9 O13 1_445 0.9300 2.5600 3.389(7) 148.00 yes
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
O1 Cu1 O2 C17 14.4(3)
N2 Cu1 O2 C17 -156.7(3)
O1W Cu1 O2 C17 107.5(3)
O2 Cu1 O1 C11 -19.7(3)
N1 Cu1 O1 C11 157.4(3)
O1W Cu1 O1 C11 -106.1(3)
O1 Cu1 N1 C1 130.8(3)
N2 Cu1 N1 C1 -58.0(3)
O1W Cu1 N1 C1 38.0(3)
O1 Cu1 N1 C5 -49.7(3)
N2 Cu1 N1 C5 121.5(3)
O1W Cu1 N1 C5 -142.6(3)
O2 Cu1 N2 C6 -39.9(3)
N1 Cu1 N2 C6 143.3(3)
O1W Cu1 N2 C6 46.5(3)
O2 Cu1 N2 C10 134.0(3)
N1 Cu1 N2 C10 -42.8(3)
O1W Cu1 N2 C10 -139.6(3)
C5 N1 C1 C2 -0.5(6)
Cu1 N1 C1 C2 179.0(3)
C13 O3 C15 O4 -174.1(4)
C13 O3 C15 C16 3.8(5)
C17 C16 C15 O4 -8.3(6)
C11 C16 C15 O4 170.9(4)
C17 C16 C15 O3 174.0(3)
C11 C16 C15 O3 -6.7(5)
N1 C1 C2 C3 -1.2(7)
C1 N1 C5 C4 2.0(6)
Cu1 N1 C5 C4 -177.5(3)
Cu1 O1 C11 C16 13.9(6)
Cu1 O1 C11 C12 -166.1(3)
C17 C16 C11 O1 5.2(6)
C15 C16 C11 O1 -174.0(4)
C17 C16 C11 C12 -174.8(3)
C15 C16 C11 C12 6.0(5)
C13 C12 C11 O1 177.6(4)
C13 C12 C11 C16 -2.4(6)
N1 C5 C4 C3 -1.6(7)
C5 C4 C3 C2 -0.1(7)
C1 C2 C3 C4 1.5(7)
C6 N2 C10 C9 0.2(6)
Cu1 N2 C10 C9 -174.0(3)
C11 C12 C13 O3 -0.7(6)
C11 C12 C13 C14 179.1(4)
C15 O3 C13 C12 -0.1(6)
C15 O3 C13 C14 -179.9(4)
Cu1 O2 C17 C16 -2.4(5)
Cu1 O2 C17 C18 178.1(3)
C11 C16 C17 O2 -11.1(6)
C15 C16 C17 O2 168.1(4)
C11 C16 C17 C18 168.4(4)
C15 C16 C17 C18 -12.4(5)
N2 C10 C9 C8 1.1(7)
C10 C9 C8 C7 -1.9(7)
C9 C8 C7 C6 1.4(7)
C10 N2 C6 C7 -0.7(6)
Cu1 N2 C6 C7 173.5(3)
C8 C7 C6 N2 -0.1(7)
