#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:14:06 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179563 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/32/4503222.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4503222
loop_
_publ_author_name
'Stephenson, Maria D.'
'Prior, Timothy J.'
'Hardie, Michaele J.'
_publ_section_title
;
 New Network Structures from Cu(II) Complexes of Chelating Ligands with
 Appended Hydrogen Bonding Sites
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              643
_journal_paper_doi               10.1021/cg700820d
_journal_volume                  8
_journal_year                    2008
_chemical_formula_sum            'C16 H16 Br2 Cu N6 O5'
_chemical_formula_weight         595.71
_chemical_name_systematic
; 
  [aquodibromo(pyrazino[2,3-f][1,10]phenanthroline-2,3-diamide)
  copper(II)] hydrate  
;
_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                103.24(3)
_cell_angle_beta                 97.97(3)
_cell_angle_gamma                107.36(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4572(19)
_cell_length_b                   10.011(2)
_cell_length_c                   11.879(2)
_cell_measurement_temperature    150(2)
_cell_volume                     1018.6(4)
_computing_cell_refinement       'APEXII (Bruker, 2004)'
_computing_data_collection       'APEXII (Bruker, 2004)'
_computing_data_reduction        'APEXII (Bruker, 2004)'
_computing_molecular_graphics    'XSeed (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18455
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    5.037
_exptl_absorpt_correction_T_max  0.9060
_exptl_absorpt_correction_T_min  0.1718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.942
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'needle '
_exptl_crystal_F_000             586
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.050
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0242
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0387P)²+1.0661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0679
_reflns_number_gt                4568
_reflns_number_total             5020
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg700820d-file001.cif
_cod_data_source_block           complex2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_cell_volume        1018.7(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4503222
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br -0.61373(2) 0.49992(2) 1.156723(19) 0.02038(6) Uani 1 1 d .
Cu1 Cu -0.59423(3) 0.24759(3) 1.18581(2) 0.01572(7) Uani 1 1 d .
O1 O -0.5308(2) 0.3277(2) 1.35994(15) 0.0239(3) Uani 1 1 d .
N1 N -0.3699(2) 0.28322(19) 1.18361(15) 0.0155(3) Uani 1 1 d .
C1 C -0.2486(2) 0.3388(2) 1.27465(18) 0.0191(4) Uani 1 1 d .
H1 H -0.2646 0.3557 1.3531 0.023 Uiso 1 1 calc R
Br2 Br -0.85170(2) 0.12344(2) 1.194788(19) 0.02034(6) Uani 1 1 d .
O2 O 0.13204(19) 0.25139(18) 0.65713(14) 0.0239(3) Uani 1 1 d .
N2 N -0.6170(2) 0.15061(18) 1.01094(15) 0.0155(3) Uani 1 1 d .
C2 C -0.0991(2) 0.3731(2) 1.25895(18) 0.0199(4) Uani 1 1 d .
H2 H -0.0160 0.4122 1.3258 0.024 Uiso 1 1 calc R
O3 O -0.1874(2) 0.1755(2) 0.49415(14) 0.0297(4) Uani 1 1 d .
N3 N -0.0482(2) 0.28819(18) 0.90018(15) 0.0152(3) Uani 1 1 d .
C3 C -0.0733(2) 0.3495(2) 1.14455(18) 0.0172(4) Uani 1 1 d .
H3 H 0.0271 0.3755 1.1319 0.021 Uiso 1 1 calc R
O4 O -0.2369(2) 0.4357(2) 0.59532(18) 0.0337(4) Uani 1 1 d .
N4 N -0.3099(2) 0.13017(19) 0.71764(15) 0.0165(3) Uani 1 1 d .
C4 C -0.2002(2) 0.2861(2) 1.04794(17) 0.0139(4) Uani 1 1 d .
O5 O -0.3193(2) 0.6032(2) 1.46864(16) 0.0278(4) Uani 1 1 d .
N5 N 0.2327(2) 0.3675(2) 0.85352(16) 0.0195(3) Uani 1 1 d .
H5B H 0.3263 0.3948 0.8432 0.023 Uiso 1 1 calc R
H5A H 0.2154 0.3914 0.9250 0.023 Uiso 1 1 calc R
C5 C -0.3459(2) 0.2533(2) 1.07175(17) 0.0139(4) Uani 1 1 d .
N6 N -0.1627(2) -0.0275(2) 0.53752(17) 0.0253(4) Uani 1 1 d .
H6B H -0.1690 -0.0730 0.4632 0.030 Uiso 1 1 calc R
H6A H -0.1508 -0.0704 0.5933 0.030 Uiso 1 1 calc R
C6 C -0.4809(2) 0.1786(2) 0.97738(17) 0.0141(4) Uani 1 1 d .
C7 C -0.4700(2) 0.1336(2) 0.85869(17) 0.0147(4) Uani 1 1 d .
C8 C -0.6053(2) 0.0523(2) 0.77206(18) 0.0176(4) Uani 1 1 d .
H8 H -0.6024 0.0186 0.6912 0.021 Uiso 1 1 calc R
C9 C -0.7427(2) 0.0222(2) 0.80695(19) 0.0189(4) Uani 1 1 d .
H9 H -0.8351 -0.0331 0.7501 0.023 Uiso 1 1 calc R
C10 C -0.7443(2) 0.0744(2) 0.92744(19) 0.0183(4) Uani 1 1 d .
H10 H -0.8391 0.0547 0.9501 0.022 Uiso 1 1 calc R
C11 C -0.3197(2) 0.1717(2) 0.83231(17) 0.0148(4) Uani 1 1 d .
C12 C -0.1875(2) 0.2486(2) 0.92401(17) 0.0147(4) Uani 1 1 d .
C13 C -0.0391(2) 0.2471(2) 0.78713(17) 0.0153(4) Uani 1 1 d .
C14 C 0.1177(2) 0.2900(2) 0.76129(18) 0.0168(4) Uani 1 1 d .
C15 C -0.1716(2) 0.1647(2) 0.69535(17) 0.0166(4) Uani 1 1 d .
C16 C -0.1709(2) 0.1062(2) 0.56553(18) 0.0201(4) Uani 1 1 d .
H1A H -0.472(5) 0.422(5) 1.386(4) 0.057(11) Uiso 1 1 d .
H7A H -0.282(6) 0.435(6) 0.660(5) 0.096(17) Uiso 1 1 d .
H1B H -0.586(5) 0.317(4) 1.390(3) 0.041(11) Uiso 1 1 d .
H4B H -0.248(5) 0.345(5) 0.554(4) 0.077(14) Uiso 1 1 d .
H5C H -0.267(5) 0.560(4) 1.513(4) 0.058(11) Uiso 1 1 d .
H5D H -0.266(5) 0.649(5) 1.425(4) 0.065(12) Uiso 1 1 d .
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
O1 Cu1 N2 166.79(7)
O1 Cu1 N1 87.69(8)
N2 Cu1 N1 80.84(8)
O1 Cu1 Br2 92.09(7)
N2 Cu1 Br2 96.34(6)
N1 Cu1 Br2 159.38(5)
O1 Cu1 Br1 92.82(6)
N2 Cu1 Br1 95.52(6)
N1 Cu1 Br1 99.59(6)
Br2 Cu1 Br1 101.01(3)
C1 N1 C5 118.07(18)
C1 N1 Cu1 129.11(14)
C5 N1 Cu1 112.67(14)
N1 C1 C2 122.75(19)
C10 N2 C6 118.37(17)
C10 N2 Cu1 128.78(14)
C6 N2 Cu1 112.70(14)
C3 C2 C1 119.48(19)
C13 N3 C12 117.34(18)
C2 C3 C4 118.30(19)
C15 N4 C11 117.21(18)
C5 C4 C3 118.41(17)
C5 C4 C12 118.29(18)
C3 C4 C12 123.28(18)
N1 C5 C4 122.86(18)
N1 C5 C6 115.77(18)
C4 C5 C6 121.31(17)
N2 C6 C7 122.70(18)
N2 C6 C5 116.34(17)
C7 C6 C5 120.93(18)
C6 C7 C8 118.10(18)
C6 C7 C11 118.25(18)
C8 C7 C11 123.65(18)
C9 C8 C7 118.90(19)
C8 C9 C10 119.50(19)
N2 C10 C9 122.40(19)
N4 C11 C12 121.00(19)
N4 C11 C7 118.05(18)
C12 C11 C7 120.95(17)
N3 C12 C11 121.40(18)
N3 C12 C4 118.52(18)
C11 C12 C4 120.07(18)
N3 C13 C15 121.23(18)
N3 C13 C14 117.05(18)
C15 C13 C14 121.71(17)
O2 C14 N5 124.2(2)
O2 C14 C13 119.32(19)
N5 C14 C13 116.51(18)
N4 C15 C13 121.72(18)
N4 C15 C16 113.57(18)
C13 C15 C16 124.70(18)
O3 C16 N6 125.0(2)
O3 C16 C15 121.12(19)
N6 C16 C15 113.70(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 Cu1 2.6824(6)
Cu1 O1 1.9724(18)
Cu1 N2 2.0326(18)
Cu1 N1 2.0482(18)
Cu1 Br2 2.4109(8)
N1 C1 1.340(3)
N1 C5 1.360(2)
C1 C2 1.401(3)
O2 C14 1.248(3)
N2 C10 1.338(3)
N2 C6 1.368(3)
C2 C3 1.393(3)
O3 C16 1.234(3)
N3 C13 1.334(3)
N3 C12 1.348(3)
C3 C4 1.410(3)
N4 C15 1.330(3)
N4 C11 1.355(3)
C4 C5 1.403(3)
C4 C12 1.465(3)
N5 C14 1.328(3)
C5 C6 1.448(3)
N6 C16 1.332(3)
C6 C7 1.407(3)
C7 C8 1.410(3)
C7 C11 1.456(3)
C8 C9 1.387(3)
C9 C10 1.410(3)
C11 C12 1.416(3)
C13 C15 1.426(3)
C13 C14 1.511(3)
C15 C16 1.521(3)
