#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/93/2219319.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_2219319
loop_
_publ_author_name
'Westcott, Barry L.'
'Kopp-Vaughn, Kristin M.'
'Daniels, Lee M.'
'Zeller, Matthias'
_publ_section_title
;Di-μ-bromido-bis[bromido(di-2-pyridylmethanediol-κ²N,N')copper(II)]
 dihydrate
;
_journal_coeditor_code           FJ2132
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1122
_journal_page_last               m1123
_journal_paper_doi               10.1107/S1600536808024203
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Cu2 Br4 (C11 H10 N2 O2)2], 2H2 O'
_chemical_formula_moiety         'C22 H20 Br4 Cu2 N4 O4, 2(H2 O)'
_chemical_formula_sum            'C22 H24 Br4 Cu2 N4 O6'
_chemical_formula_weight         887.18
_chemical_name_systematic
;
Di-μ-bromido-bis[bromido(di-2-pyridylmethanediol-κ²N,N')copper(II)]
dihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.749(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.2685(7)
_cell_length_b                   9.1275(3)
_cell_length_c                   14.4731(4)
_cell_measurement_reflns_used    13358
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.83
_cell_measurement_theta_min      2.72
_cell_volume                     2760.34(15)
_computing_cell_refinement       'TwinSolve (Rigaku/MSC, 2002)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2004)'
_computing_data_reduction        'TwinSolve (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'CrystalStructure (Rigaku, 2006)'
_computing_publication_material  'publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       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  0.058
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            46376
_diffrn_reflns_theta_full        30.07
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         2.73
_diffrn_standards_decay_%        <0.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.376
_exptl_absorpt_correction_T_max  0.38
_exptl_absorpt_correction_T_min  0.08
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(TwinSolve; Rigaku/MSC, 2002)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    2.135
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_refine_diff_density_max         1.542
_refine_diff_density_min         -1.582
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         7508
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0647
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0753P)²+82.8356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1907
_refine_ls_wR_factor_ref         0.1983
_reflns_number_gt                6192
_reflns_number_total             7508
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2132.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2219319
_cod_database_fobs_code          2219319
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Br Br1 0.15441(3) 0.62635(7) 0.55691(4) 0.01359(14) Uani d . 1
Br Br2 0.02135(3) 0.54295(7) 0.38142(4) 0.01492(15) Uani d . 1
Cu Cu1 0.08934(3) 0.41245(8) 0.50766(5) 0.00990(16) Uani d . 1
O O1 0.1794(2) 0.2937(5) 0.4473(3) 0.0137(8) Uani d D 1
H H12 0.165(4) 0.306(9) 0.394(3) 0.014 Uiso d D 1
O O2 0.2056(2) 0.0447(5) 0.4596(4) 0.0163(9) Uani d D 1
H H9 0.241(2) 0.052(10) 0.484(6) 0.016 Uiso d D 1
O O3 0.1174(2) 0.3109(6) 0.2691(4) 0.0216(10) Uani d . 1
H H10 0.091(5) 0.391(10) 0.270(6) 0.022 Uiso d . 1
H H11 0.126(4) 0.334(10) 0.215(7) 0.022 Uiso d . 1
N N1 0.1400(2) 0.2914(6) 0.6142(4) 0.0121(9) Uani d . 1
N N2 0.0544(2) 0.2175(6) 0.4509(4) 0.0107(9) Uani d . 1
C C1 0.1432(3) 0.3159(8) 0.7059(5) 0.0199(14) Uani d . 1
H H1 0.1210 0.3957 0.7238 0.024 Uiso calc R 1
C C2 0.1773(3) 0.2300(8) 0.7748(5) 0.0208(14) Uani d . 1
H H2 0.1792 0.2528 0.8379 0.025 Uiso calc R 1
C C3 0.2088(3) 0.1091(9) 0.7493(5) 0.0231(15) Uani d . 1
H H3 0.2320 0.0486 0.7951 0.028 Uiso calc R 1
C C4 0.2058(3) 0.0783(8) 0.6545(5) 0.0168(12) Uani d . 1
H H4 0.2256 -0.0045 0.6356 0.020 Uiso calc R 1
C C5 0.1724(3) 0.1751(7) 0.5888(4) 0.0134(11) Uani d . 1
C C6 0.1666(3) 0.1538(7) 0.4830(4) 0.0103(10) Uani d . 1
C C7 0.0974(3) 0.1111(6) 0.4443(4) 0.0106(10) Uani d . 1
C C8 0.0795(3) -0.0259(7) 0.4077(4) 0.0139(11) Uani d . 1
H H5 0.1098 -0.0990 0.4065 0.017 Uiso calc R 1
C C9 0.0145(3) -0.0511(7) 0.3725(4) 0.0146(11) Uani d . 1
H H6 0.0010 -0.1415 0.3465 0.017 Uiso calc R 1
C C10 -0.0295(3) 0.0584(7) 0.3766(4) 0.0149(12) Uani d . 1
H H7 -0.0727 0.0438 0.3522 0.018 Uiso calc R 1
C C11 -0.0078(3) 0.1923(7) 0.4184(5) 0.0137(11) Uani d . 1
H H8 -0.0374 0.2654 0.4237 0.016 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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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
N1 Cu1 N2 . 86.2(2)
N1 Cu1 Br2 . 175.12(15)
N2 Cu1 Br2 . 90.21(14)
N1 Cu1 Br1 . 91.25(15)
N2 Cu1 Br1 . 165.08(15)
Br2 Cu1 Br1 . 93.07(3)
N1 Cu1 Br2 5_566 91.44(15)
N2 Cu1 Br2 5_566 93.91(15)
Br2 Cu1 Br2 5_566 85.54(3)
Br1 Cu1 Br2 5_566 100.85(3)
C6 O1 H12 . 114(6)
C6 O2 H9 . 114(7)
H10 O3 H11 . 93(8)
C1 N1 C5 . 117.9(6)
C1 N1 Cu1 . 125.7(5)
C5 N1 Cu1 . 116.5(4)
C11 N2 C7 . 119.3(5)
C11 N2 Cu1 . 123.6(4)
C7 N2 Cu1 . 117.1(4)
N1 C1 C2 . 123.4(7)
N1 C1 H1 . 118.3
C2 C1 H1 . 118.3
C1 C2 C3 . 119.0(6)
C1 C2 H2 . 120.5
C3 C2 H2 . 120.5
C2 C3 C4 . 119.4(6)
C2 C3 H3 . 120.3
C4 C3 H3 . 120.3
C3 C4 C5 . 118.0(7)
C3 C4 H4 . 121.0
C5 C4 H4 . 121.0
N1 C5 C4 . 122.3(6)
N1 C5 C6 . 115.0(5)
C4 C5 C6 . 122.7(6)
O2 C6 O1 . 113.3(5)
O2 C6 C7 . 108.0(5)
O1 C6 C7 . 109.5(4)
O2 C6 C5 . 113.5(5)
O1 C6 C5 . 105.3(5)
C7 C6 C5 . 107.1(5)
N2 C7 C8 . 122.5(6)
N2 C7 C6 . 114.2(5)
C8 C7 C6 . 123.3(5)
C7 C8 C9 . 118.0(6)
C7 C8 H5 . 121.0
C9 C8 H5 . 121.0
C10 C9 C8 . 119.9(6)
C10 C9 H6 . 120.1
C8 C9 H6 . 120.1
C9 C10 C11 . 118.6(6)
C9 C10 H7 . 120.7
C11 C10 H7 . 120.7
N2 C11 C10 . 121.7(6)
N2 C11 H8 . 119.2
C10 C11 H8 . 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 Cu1 . 2.4222(10)
Br2 Cu1 . 2.4212(9)
Cu1 N1 . 2.034(5)
Cu1 N2 . 2.041(5)
Cu1 Br2 5_566 3.1138(10)
O1 C6 . 1.423(7)
O1 H12 . 0.78(4)
O2 C6 . 1.378(7)
O2 H9 . 0.77(4)
O3 H10 . 0.92(10)
O3 H11 . 0.86(10)
N1 C1 . 1.335(8)
N1 C5 . 1.353(8)
N2 C11 . 1.339(8)
N2 C7 . 1.349(7)
C1 C2 . 1.367(10)
C1 H1 . 0.9300
C2 C3 . 1.377(11)
C2 H2 . 0.9300
C3 C4 . 1.390(10)
C3 H3 . 0.9300
C4 C5 . 1.392(9)
C4 H4 . 0.9300
C5 C6 . 1.527(8)
C6 C7 . 1.525(8)
C7 C8 . 1.382(9)
C8 C9 . 1.402(9)
C8 H5 . 0.9300
C9 C10 . 1.377(9)
C9 H6 . 0.9300
C10 C11 . 1.403(9)
C10 H7 . 0.9300
C11 H8 . 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
O3 H11 Br1 6_565 0.85(6) 2.53(6) 3.361(5) 166(9)
O2 H9 O1 7_556 0.77(6) 2.21(7) 2.961(7) 147(9)
O2 H9 Br1 7_556 0.77(6) 2.87(9) 3.411(5) 123(8)
O3 H10 Br2 . 0.85(6) 2.80(8) 3.542(6) 147(9)
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
N2 Cu1 N1 C1 -131.0(6)
Br1 Cu1 N1 C1 63.9(5)
N2 Cu1 N1 C5 47.9(5)
Br1 Cu1 N1 C5 -117.3(4)
N1 Cu1 N2 C11 131.8(6)
Br1 Cu1 N2 C11 -147.0(5)
Br2 Cu1 N2 C11 -44.9(5)
N1 Cu1 N2 C7 -49.1(5)
Br2 Cu1 N2 C7 134.2(4)
C5 N1 C1 C2 0.3(10)
Cu1 N1 C1 C2 179.1(5)
N1 C1 C2 C3 -2.1(11)
C1 C2 C3 C4 0.8(11)
C2 C3 C4 C5 2.2(10)
C1 N1 C5 C4 2.9(9)
Cu1 N1 C5 C4 -176.0(5)
C1 N1 C5 C6 179.6(6)
Cu1 N1 C5 C6 0.6(7)
C3 C4 C5 N1 -4.2(10)
C3 C4 C5 C6 179.4(6)
N1 C5 C6 O2 173.1(5)
C4 C5 C6 O2 -10.3(9)
N1 C5 C6 O1 49.0(7)
C4 C5 C6 O1 -134.4(6)
N1 C5 C6 C7 -67.6(7)
C4 C5 C6 C7 109.0(7)
C11 N2 C7 C8 -1.5(9)
Cu1 N2 C7 C8 179.3(5)
C11 N2 C7 C6 179.7(6)
Cu1 N2 C7 C6 0.6(7)
O2 C6 C7 N2 -171.3(5)
O1 C6 C7 N2 -47.5(7)
C5 C6 C7 N2 66.6(7)
O2 C6 C7 C8 10.0(8)
O1 C6 C7 C8 133.8(6)
C5 C6 C7 C8 -112.1(7)
N2 C7 C8 C9 3.0(9)
C6 C7 C8 C9 -178.4(6)
C7 C8 C9 C10 -2.0(10)
C7 N2 C11 C10 -1.0(10)
C9 C10 C11 N2 1.9(10)
