#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/15/2211530.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_2211530
loop_
_publ_author_name
'Xu-Yan Ma'
'Xin-Dian Dong'
'Yan-Ping Li'
'Zhi-Gang Zhang'
_publ_section_title
;
 (2,2'-Bipyridyl)methanolbis(trichloroacetato)copper(II)
;
_journal_coeditor_code           NC2025
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m3467
_journal_page_last               m3469
_journal_paper_doi               10.1107/S1600536806049105
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Cu (C2 Cl3 O2)2 (C10 H8 N2) (C H4 O)]'
_chemical_formula_moiety         'C15 H12 Cl6 Cu N2 O5'
_chemical_formula_sum            'C15 H12 Cl6 Cu N2 O5'
_chemical_formula_weight         576.51
_chemical_name_systematic
;
(2,2'-Bipyridyl)methanolbis(trichloroacetato)copper(II)
;
_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                76.540(3)
_cell_angle_beta                 76.941(3)
_cell_angle_gamma                87.618(4)
_cell_formula_units_Z            2
_cell_length_a                   9.278(3)
_cell_length_b                   9.863(3)
_cell_length_c                   12.356(3)
_cell_measurement_reflns_used    2841
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.52
_cell_volume                     1071.1(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4439
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.798
_exptl_absorpt_correction_T_max  0.615
_exptl_absorpt_correction_T_min  0.533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             574
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.561
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0584P)²+1.0108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1234
_reflns_number_gt                3233
_reflns_number_total             3695
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2025.cif
_cod_data_source_block           I
_cod_database_code               2211530
_cod_database_fobs_code          2211530
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
Cu Cu1 0.58166(5) 0.75028(5) 0.68362(4) 0.04209(17) Uani d . 1
N N1 0.5505(3) 0.7244(3) 0.5346(2) 0.0377(7) Uani d . 1
N N2 0.4115(3) 0.8773(3) 0.6691(3) 0.0412(7) Uani d . 1
O O1 0.7632(3) 0.6427(3) 0.6710(2) 0.0520(7) Uani d . 1
O O2 0.7005(3) 0.4648(4) 0.8222(3) 0.0674(9) Uani d . 1
O O3 0.6191(3) 0.8061(4) 0.8158(3) 0.0592(8) Uani d . 1
O O4 0.7894(4) 0.9637(4) 0.7132(3) 0.0714(9) Uani d . 1
O O5 0.4325(3) 0.5722(3) 0.8034(2) 0.0539(7) Uani d . 1
H H11 0.4981 0.5211 0.8239 0.065 Uiso calc R 1
Cl Cl1 0.96254(16) 0.37020(14) 0.63365(13) 0.0776(4) Uani d . 1
Cl Cl2 0.99905(16) 0.40411(17) 0.85058(12) 0.0841(4) Uani d . 1
Cl Cl3 1.07541(13) 0.62839(13) 0.65420(11) 0.0673(3) Uani d . 1
Cl Cl4 0.6296(2) 0.8344(2) 1.03595(11) 0.1021(6) Uani d . 1
Cl Cl5 0.9271(2) 0.8037(2) 0.91668(15) 0.1181(7) Uani d . 1
Cl Cl6 0.8017(3) 1.0762(2) 0.90936(16) 0.1226(8) Uani d . 1
C C1 0.6312(4) 0.6440(4) 0.4706(3) 0.0446(9) Uani d . 1
H H1 0.7127 0.5983 0.4935 0.053 Uiso calc R 1
C C2 0.5968(5) 0.6271(4) 0.3716(3) 0.0512(10) Uani d . 1
H H2 0.6551 0.5716 0.3279 0.061 Uiso calc R 1
C C3 0.4760(5) 0.6929(5) 0.3387(3) 0.0532(11) Uani d . 1
H H3 0.4497 0.6812 0.2731 0.064 Uiso calc R 1
C C4 0.3934(5) 0.7769(4) 0.4039(3) 0.0473(9) Uani d . 1
H H4 0.3115 0.8232 0.3822 0.057 Uiso calc R 1
C C5 0.4334(4) 0.7918(4) 0.5014(3) 0.0365(8) Uani d . 1
C C6 0.3542(4) 0.8786(4) 0.5779(3) 0.0380(8) Uani d . 1
C C7 0.2310(5) 0.9560(4) 0.5604(4) 0.0508(10) Uani d . 1
H H7 0.1940 0.9586 0.4960 0.061 Uiso calc R 1
C C8 0.1636(5) 1.0291(5) 0.6398(4) 0.0609(12) Uani d . 1
H H8 0.0781 1.0788 0.6309 0.073 Uiso calc R 1
C C9 0.2223(5) 1.0287(5) 0.7317(4) 0.0592(12) Uani d . 1
H H9 0.1785 1.0796 0.7849 0.071 Uiso calc R 1
C C10 0.3470(5) 0.9520(5) 0.7445(4) 0.0533(11) Uani d . 1
H H10 0.3877 0.9519 0.8068 0.064 Uiso calc R 1
C C11 0.9500(5) 0.4899(4) 0.7231(4) 0.0483(10) Uani d . 1
C C12 0.7869(4) 0.5377(5) 0.7436(3) 0.0461(10) Uani d . 1
C C13 0.7652(5) 0.9033(5) 0.9129(4) 0.0581(12) Uani d . 1
C C14 0.7201(5) 0.8933(4) 0.8010(3) 0.0462(10) Uani d . 1
C C15 0.3273(6) 0.5939(6) 0.9011(4) 0.0739(15) Uani d . 1
H H15A 0.3687 0.6560 0.9357 0.111 Uiso calc R 1
H H15B 0.3028 0.5063 0.9549 0.111 Uiso calc R 1
H H15C 0.2396 0.6340 0.8784 0.111 Uiso calc R 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'
Cu Cu 0.3201 1.2651 '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'
O O 0.0106 0.0060 '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
O3 Cu1 O1 90.68(13)
O3 Cu1 N2 94.66(13)
O1 Cu1 N2 170.13(12)
O3 Cu1 N1 170.90(13)
O1 Cu1 N1 92.35(12)
N2 Cu1 N1 81.16(12)
O3 Cu1 O5 89.46(12)
O1 Cu1 O5 95.77(12)
N2 Cu1 O5 92.58(12)
N1 Cu1 O5 98.76(11)
C1 N1 C5 119.3(3)
C1 N1 Cu1 125.9(3)
C5 N1 Cu1 114.7(2)
C10 N2 C6 119.5(4)
C10 N2 Cu1 125.6(3)
C6 N2 Cu1 114.8(2)
C12 O1 Cu1 125.0(3)
C14 O3 Cu1 118.6(3)
C15 O5 Cu1 121.3(3)
C15 O5 H11 109.5
Cu1 O5 H11 97.7
N1 C1 C2 121.9(4)
N1 C1 H1 119.1
C2 C1 H1 119.1
C3 C2 C1 119.1(4)
C3 C2 H2 120.5
C1 C2 H2 120.5
C2 C3 C4 119.2(4)
C2 C3 H3 120.4
C4 C3 H3 120.4
C5 C4 C3 119.5(4)
C5 C4 H4 120.3
C3 C4 H4 120.3
N1 C5 C4 121.0(3)
N1 C5 C6 114.5(3)
C4 C5 C6 124.5(4)
N2 C6 C7 121.1(4)
N2 C6 C5 114.7(3)
C7 C6 C5 124.2(3)
C8 C7 C6 118.9(4)
C8 C7 H7 120.6
C6 C7 H7 120.6
C9 C8 C7 120.0(4)
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 C10 119.0(4)
C8 C9 H9 120.5
C10 C9 H9 120.5
N2 C10 C9 121.4(4)
N2 C10 H10 119.3
C9 C10 H10 119.3
C12 C11 Cl2 111.9(3)
C12 C11 Cl3 112.7(3)
Cl2 C11 Cl3 108.7(2)
C12 C11 Cl1 105.6(3)
Cl2 C11 Cl1 108.7(2)
Cl3 C11 Cl1 109.0(2)
O2 C12 O1 129.7(4)
O2 C12 C11 116.4(4)
O1 C12 C11 113.8(4)
C14 C13 Cl6 110.1(3)
C14 C13 Cl4 112.8(3)
Cl6 C13 Cl4 109.3(3)
C14 C13 Cl5 105.7(3)
Cl6 C13 Cl5 110.2(3)
Cl4 C13 Cl5 108.7(3)
O4 C14 O3 129.0(4)
O4 C14 C13 117.0(4)
O3 C14 C13 113.9(4)
O5 C15 H15A 109.5
O5 C15 H15B 109.5
H15A C15 H15B 109.5
O5 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O3 1.945(3) y
Cu1 O1 1.949(3) y
Cu1 N2 1.988(3) y
Cu1 N1 2.000(3) y
Cu1 O5 2.293(3) y
N1 C1 1.338(5) ?
N1 C5 1.344(5) ?
N2 C10 1.342(5) ?
N2 C6 1.347(5) ?
O1 C12 1.251(5) ?
O2 C12 1.214(5) ?
O3 C14 1.252(5) ?
O4 C14 1.201(5) ?
O5 C15 1.423(5) ?
O5 H11 0.8200 ?
Cl1 C11 1.779(4) ?
Cl2 C11 1.754(4) ?
Cl3 C11 1.757(4) ?
Cl4 C13 1.755(5) ?
Cl5 C13 1.764(5) ?
Cl6 C13 1.742(5) ?
C1 C2 1.379(6) ?
C1 H1 0.9300 ?
C2 C3 1.366(6) ?
C2 H2 0.9300 ?
C3 C4 1.379(6) ?
C3 H3 0.9300 ?
C4 C5 1.378(5) ?
C4 H4 0.9300 ?
C5 C6 1.475(5) ?
C6 C7 1.378(6) ?
C7 C8 1.373(6) ?
C7 H7 0.9300 ?
C8 C9 1.366(7) ?
C8 H8 0.9300 ?
C9 C10 1.375(6) ?
C9 H9 0.9300 ?
C10 H10 0.9300 ?
C11 C12 1.549(6) ?
C13 C14 1.558(5) ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
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
O5 H11 O2 . 0.82 1.93 2.699(5) 155.0 y
C4 H4 O4 2_676 0.93 2.42 3.247(6) 148.0 y
C7 H7 O4 2_676 0.93 2.49 3.336(7) 151.0 y
