#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/28/2222884.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_2222884
loop_
_publ_author_name
'Xie, Qing-Fan'
'Chen, Yan-Min'
'Huang, Miao-Ling'
_publ_section_title
{4,4'-Dibromo-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}copper(II)
_journal_coeditor_code           TK2481
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m903
_journal_paper_doi               10.1107/S1600536809024015
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (C16 H12 Br2 N2 O2)]'
_chemical_formula_moiety         'C16 H12 Br2 Cu1 N2 O2'
_chemical_formula_sum            'C16 H12 Br2 Cu N2 O2'
_chemical_formula_weight         487.68
_chemical_name_systematic
;
{4,4'-Dibromo-2,2'-[ethane-1,2-\
diylbis(nitrilomethylidyne)]diphenolato}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                115.601(6)
_cell_angle_beta                 92.866(4)
_cell_angle_gamma                101.527(5)
_cell_formula_units_Z            2
_cell_length_a                   8.2848(4)
_cell_length_b                   9.6302(5)
_cell_length_c                   10.9984(6)
_cell_measurement_reflns_used    3643
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.6
_cell_measurement_theta_min      2.4
_cell_volume                     766.10(8)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ
;
_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  0.030
_diffrn_reflns_av_sigmaI/netI    0.039
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6303
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.4
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    6.651
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    2.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             474
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.027
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0298P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.059
_refine_ls_wR_factor_ref         0.060
_reflns_number_gt                2128
_reflns_number_total             2641
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2481.cif
_cod_data_source_block           I
_cod_original_cell_volume        766.10(7)
_cod_original_formula_sum        'C16 H12 Br2 Cu1 N2 O2'
_cod_database_code               2222884
_cod_database_fobs_code          2222884
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 0.98239(6) 1.20034(5) 0.06363(4) 0.02426(13) Uani d . 1 . .
Br Br1 0.55269(5) 0.80260(4) 0.44272(4) 0.03477(13) Uani d . 1 . .
Br Br2 1.24837(5) 1.57593(5) -0.37940(4) 0.03793(13) Uani d . 1 . .
O O2 0.9055(3) 1.2075(3) -0.1004(2) 0.0258(6) Uani d . 1 . .
O O1 0.7760(3) 1.0630(3) 0.0529(2) 0.0332(6) Uani d . 1 . .
N N2 1.1879(4) 1.3606(3) 0.1009(3) 0.0241(7) Uani d . 1 . .
N N1 1.0890(4) 1.1769(3) 0.2128(3) 0.0241(7) Uani d . 1 . .
C C16 0.9859(5) 1.2886(4) -0.1568(4) 0.0250(8) Uani d . 1 . .
C C15 0.9173(5) 1.2616(4) -0.2887(4) 0.0273(8) Uani d . 1 . .
H H15A 0.8176 1.1854 -0.3323 0.033 Uiso calc R 1 . .
C C14 0.9942(5) 1.3449(4) -0.3533(4) 0.0272(9) Uani d . 1 . .
H H14A 0.9469 1.3238 -0.4399 0.033 Uiso calc R 1 . .
C C13 1.1434(5) 1.4613(4) -0.2894(4) 0.0280(9) Uani d . 1 . .
C C12 1.2146(5) 1.4889(4) -0.1645(4) 0.0278(9) Uani d . 1 . .
H H12A 1.3138 1.5666 -0.1229 0.033 Uiso calc R 1 . .
C C11 1.1425(5) 1.4034(4) -0.0966(4) 0.0246(8) Uani d . 1 . .
C C10 1.2328(5) 1.4321(4) 0.0297(4) 0.0257(8) Uani d . 1 . .
H H10A 1.3328 1.5096 0.0626 0.031 Uiso calc R 1 . .
C C5 0.7334(5) 1.0083(4) 0.1394(4) 0.0266(8) Uani d . 1 . .
C C4 0.5657(5) 0.9251(4) 0.1244(4) 0.0295(9) Uani d . 1 . .
H H4A 0.4890 0.9111 0.0529 0.035 Uiso calc R 1 . .
C C3 0.5139(5) 0.8652(4) 0.2115(4) 0.0281(9) Uani d . 1 . .
H H3A 0.4029 0.8122 0.1992 0.034 Uiso calc R 1 . .
C C2 0.6253(5) 0.8827(4) 0.3184(4) 0.0257(8) Uani d . 1 . .
C C1 0.7877(5) 0.9614(4) 0.3382(4) 0.0248(8) Uani d . 1 . .
H H1A 0.8613 0.9728 0.4105 0.030 Uiso calc R 1 . .
C C6 0.8457(5) 1.0256(4) 0.2511(4) 0.0246(8) Uani d . 1 . .
C C7 1.0206(5) 1.1058(4) 0.2782(4) 0.0254(8) Uani d . 1 . .
H H7A 1.0876 1.1053 0.3483 0.030 Uiso calc R 1 . .
C C8 1.2681(5) 1.2481(4) 0.2451(4) 0.0290(9) Uani d . 1 . .
H H8A 1.3272 1.1760 0.1838 0.035 Uiso calc R 1 . .
H H8B 1.3095 1.2730 0.3381 0.035 Uiso calc R 1 . .
C C9 1.2922(5) 1.3988(4) 0.2276(4) 0.0279(8) Uani d . 1 . .
H H9A 1.2599 1.4812 0.3043 0.033 Uiso calc R 1 . .
H H9B 1.4083 1.4368 0.2233 0.033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
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
O1 Cu1 O2 . . 91.88(10) ?
O1 Cu1 N1 . . 92.75(11) ?
O2 Cu1 N1 . . 170.19(12) ?
O1 Cu1 N2 . . 171.68(11) ?
O2 Cu1 N2 . . 92.89(11) ?
N1 Cu1 N2 . . 83.60(12) ?
C16 O2 Cu1 . . 127.2(2) ?
C5 O1 Cu1 . . 127.5(2) ?
C10 N2 C9 . . 120.6(3) ?
C10 N2 Cu1 . . 126.9(3) ?
C9 N2 Cu1 . . 112.5(2) ?
C7 N1 C8 . . 119.9(3) ?
C7 N1 Cu1 . . 127.3(3) ?
C8 N1 Cu1 . . 112.8(2) ?
O2 C16 C15 . . 118.8(3) ?
O2 C16 C11 . . 124.6(3) ?
C15 C16 C11 . . 116.6(3) ?
C14 C15 C16 . . 121.9(3) ?
C14 C15 H15A . . 119.1 ?
C16 C15 H15A . . 119.1 ?
C15 C14 C13 . . 120.2(3) ?
C15 C14 H14A . . 119.9 ?
C13 C14 H14A . . 119.9 ?
C12 C13 C14 . . 119.8(3) ?
C12 C13 Br2 . . 120.3(3) ?
C14 C13 Br2 . . 119.9(3) ?
C13 C12 C11 . . 121.8(3) ?
C13 C12 H12A . . 119.1 ?
C11 C12 H12A . . 119.1 ?
C12 C11 C16 . . 119.6(3) ?
C12 C11 C10 . . 117.8(3) ?
C16 C11 C10 . . 122.5(3) ?
N2 C10 C11 . . 125.6(3) ?
N2 C10 H10A . . 117.2 ?
C11 C10 H10A . . 117.2 ?
O1 C5 C4 . . 119.4(3) ?
O1 C5 C6 . . 124.3(3) ?
C4 C5 C6 . . 116.3(3) ?
C3 C4 C5 . . 122.0(4) ?
C3 C4 H4A . . 119.0 ?
C5 C4 H4A . . 119.0 ?
C4 C3 C2 . . 120.5(4) ?
C4 C3 H3A . . 119.8 ?
C2 C3 H3A . . 119.8 ?
C1 C2 C3 . . 120.3(3) ?
C1 C2 Br1 . . 119.0(3) ?
C3 C2 Br1 . . 120.7(3) ?
C2 C1 C6 . . 120.9(3) ?
C2 C1 H1A . . 119.5 ?
C6 C1 H1A . . 119.5 ?
C1 C6 C5 . . 119.9(3) ?
C1 C6 C7 . . 117.5(3) ?
C5 C6 C7 . . 122.6(3) ?
N1 C7 C6 . . 124.6(3) ?
N1 C7 H7A . . 117.7 ?
C6 C7 H7A . . 117.7 ?
N1 C8 C9 . . 105.9(3) ?
N1 C8 H8A . . 110.6 ?
C9 C8 H8A . . 110.6 ?
N1 C8 H8B . . 110.6 ?
C9 C8 H8B . . 110.6 ?
H8A C8 H8B . . 108.7 ?
N2 C9 C8 . . 107.7(3) ?
N2 C9 H9A . . 110.2 ?
C8 C9 H9A . . 110.2 ?
N2 C9 H9B . . 110.2 ?
C8 C9 H9B . . 110.2 ?
H9A C9 H9B . . 108.5 ?
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 . 1.905(2) ?
Cu1 O2 . 1.917(2) ?
Cu1 N1 . 1.943(3) ?
Cu1 N2 . 1.945(3) ?
Br1 C2 . 1.907(3) ?
Br2 C13 . 1.898(3) ?
O2 C16 . 1.301(4) ?
O1 C5 . 1.302(4) ?
N2 C10 . 1.272(4) ?
N2 C9 . 1.461(4) ?
N1 C7 . 1.273(4) ?
N1 C8 . 1.459(4) ?
C16 C15 . 1.423(5) ?
C16 C11 . 1.432(5) ?
C15 C14 . 1.374(5) ?
C15 H15A . 0.9300 ?
C14 C13 . 1.399(5) ?
C14 H14A . 0.9300 ?
C13 C12 . 1.358(5) ?
C12 C11 . 1.404(5) ?
C12 H12A . 0.9300 ?
C11 C10 . 1.431(5) ?
C10 H10A . 0.9300 ?
C5 C4 . 1.420(5) ?
C5 C6 . 1.432(5) ?
C4 C3 . 1.362(5) ?
C4 H4A . 0.9300 ?
C3 C2 . 1.385(5) ?
C3 H3A . 0.9300 ?
C2 C1 . 1.361(5) ?
C1 C6 . 1.404(5) ?
C1 H1A . 0.9300 ?
C6 C7 . 1.447(5) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.521(5) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
