#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:25:23 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180038 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/32/7033229.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_7033229
loop_
_publ_author_name
'Hurley, Nicholas J.'
'Rawson, Jeremy M.'
'Pilkington, Melanie'
_publ_section_title
;
 3,3'-di(pyrazinamoyl)-2,2'-bipyridine: rational ligand design for the
 self-assembly of a 1-D coordination polymer.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1866
_journal_page_last               1874
_journal_paper_doi               10.1039/c4dt03220a
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety
'2(C26 H21 Cl Cu3 N8 O8), 2(C H4 O), 2(H O0.50)'
_chemical_formula_sum            'C54 H52 Cl2 Cu6 N16 O19'
_chemical_formula_weight         1681.25
_chemical_name_systematic
;
 ?
;
_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   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-08-20 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                94.368(6)
_cell_angle_beta                 101.891(4)
_cell_angle_gamma                112.023(4)
_cell_formula_units_Z            1
_cell_length_a                   10.1126(16)
_cell_length_b                   12.3344(19)
_cell_length_c                   14.390(2)
_cell_measurement_reflns_used    6259
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.35
_cell_volume                     1604.8(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.815
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_unetI/netI     0.0870
_diffrn_reflns_Laue_measured_fraction_full 0.815
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6425
_diffrn_reflns_point_group_measured_fraction_full 0.815
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.537
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.120
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.777
_refine_diff_density_rms         0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         4726
_refine_ls_number_restraints     138
_refine_ls_restrained_S_all      1.202
_refine_ls_R_factor_all          0.1607
_refine_ls_R_factor_gt           0.1096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0001P)²+53.7921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2180
_refine_ls_wR_factor_ref         0.2575
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3348
_reflns_number_total             4726
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4dt03220a2.cif
_cod_data_source_block           nhjan
_cod_depositor_comments
'Adding full bibliography for 7033228--7033229.cif.'
_cod_database_code               7033229
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.4292(2) 0.54954(17) 0.44479(12) 0.0218(5) Uani 1 1 d . U .
Cu2 Cu 0.0474(2) 0.82190(19) 0.14164(13) 0.0277(5) Uani 1 1 d . U .
Cu3 Cu -0.1654(2) 0.97716(19) 0.22572(13) 0.0331(6) Uani 1 1 d . U .
Cl1 Cl 0.0865(6) 0.9952(5) 0.2497(4) 0.0611(14) Uani 1 1 d . U .
O1 O 0.6246(11) 0.6640(10) 0.4406(7) 0.032(2) Uani 1 1 d . U .
O2 O 0.4386(11) 0.4429(9) 0.3412(7) 0.028(2) Uani 1 1 d . U .
O3 O 0.4422(14) 0.6432(11) 0.5644(7) 0.041(3) Uani 1 1 d . U .
O4 O 0.2547(12) 0.4205(11) 0.4632(8) 0.037(3) Uani 1 1 d . U .
O5 O 0.4817(12) 0.8862(12) 0.1967(8) 0.042(3) Uani 1 1 d . U .
O6 O -0.1480(12) 0.7206(10) 0.1509(8) 0.034(2) Uani 1 1 d . U .
O7 O -0.2497(14) 0.8124(11) 0.2386(8) 0.040(3) Uani 1 1 d . U .
O8 O -0.1373(14) 1.3100(11) 0.2922(8) 0.043(3) Uani 1 1 d . U .
O10 O 0.777(2) 0.403(2) 0.1351(13) 0.094(6) Uani 1 1 d . U .
H10S H 0.8364 0.4088 0.1854 0.141 Uiso 1 1 calc R U .
O1S O 0.879(6) 0.501(4) 0.410(4) 0.134(16) Uiso 0.5 1 d D . P
H1S H 0.94(4) 0.48(4) 0.46(4) 0.201 Uiso 0.5 1 d D U P
H2S H 0.78(3) 0.44(3) 0.39(4) 0.201 Uiso 0.5 1 d D U P
N1 N 0.2964(14) 0.6238(12) 0.3513(9) 0.027(3) Uani 1 1 d . U .
N2 N 0.1336(15) 0.7239(13) 0.2363(9) 0.033(3) Uani 1 1 d . U .
N3 N 0.2456(14) 0.8777(13) 0.1269(8) 0.030(3) Uani 1 1 d . U .
N4 N -0.0206(13) 0.7957(13) -0.0077(9) 0.029(3) Uani 1 1 d . U .
N5 N -0.2471(14) 0.9573(12) 0.0756(8) 0.026(3) Uani 1 1 d . U .
N6 N -0.1174(14) 1.1429(12) 0.2244(8) 0.030(2) Uani 1 1 d . U .
N7 N -0.2321(13) 1.0189(13) 0.3456(9) 0.031(3) Uani 1 1 d . U .
N8 N -0.3287(18) 1.1040(15) 0.4897(12) 0.050(4) Uani 1 1 d . U .
C1 C 0.069(2) 0.6410(17) 0.2861(13) 0.044(5) Uani 1 1 d . U .
H1 H -0.0307 0.6169 0.2822 0.053 Uiso 1 1 calc R U .
C2 C 0.1510(19) 0.5901(16) 0.3439(11) 0.035(4) Uani 1 1 d . U .
H2 H 0.1043 0.5321 0.3777 0.042 Uiso 1 1 calc R U .
C3 C 0.3563(19) 0.7056(15) 0.3010(10) 0.033(4) Uani 1 1 d . U .
H3 H 0.4562 0.7297 0.3040 0.040 Uiso 1 1 calc R U .
C4 C 0.2762(17) 0.7575(15) 0.2436(10) 0.028(3) Uani 1 1 d . U .
C5 C 0.3481(17) 0.8486(16) 0.1865(10) 0.030(4) Uani 1 1 d . U .
C6 C 0.2964(16) 0.9663(15) 0.0721(10) 0.024(3) Uani 1 1 d . U .
C7 C 0.4282(17) 1.0635(15) 0.1041(11) 0.031(3) Uani 1 1 d . U .
H7 H 0.4905 1.0703 0.1636 0.037 Uiso 1 1 calc R U .
C8 C 0.469(2) 1.1510(15) 0.0490(11) 0.033(4) Uani 1 1 d . U .
H8 H 0.5570 1.2177 0.0710 0.039 Uiso 1 1 calc R U .
C9 C 0.0676(15) 0.8493(14) -0.0658(10) 0.020(3) Uani 1 1 d . U .
C10 C -0.1450(18) 0.6983(17) -0.0468(12) 0.038(4) Uani 1 1 d . U .
H10 H -0.2055 0.6636 -0.0073 0.045 Uiso 1 1 calc R U .
C11 C -0.1870(18) 0.6476(18) -0.1425(11) 0.040(4) Uani 1 1 d . U .
H11 H -0.2742 0.5807 -0.1671 0.048 Uiso 1 1 calc R U .
C12 C -0.2423(17) 0.7215(15) 0.1972(10) 0.028(3) Uani 1 1 d . U .
C13 C -0.358(2) 0.6032(16) 0.1966(14) 0.049(5) Uani 1 1 d . U .
H13A H -0.3182 0.5440 0.1933 0.074 Uiso 1 1 calc R U .
H13B H -0.4398 0.5846 0.1416 0.074 Uiso 1 1 calc R U .
H13C H -0.3912 0.6046 0.2544 0.074 Uiso 1 1 calc R U .
C14 C -0.3752(19) 0.8629(16) 0.0397(11) 0.032(4) Uani 1 1 d . U .
H14 H -0.4024 0.8036 0.0768 0.039 Uiso 1 1 calc R U .
C15 C -0.2049(15) 1.0452(14) 0.0212(9) 0.019(3) Uani 1 1 d . U .
C16 C 0.096(2) 1.3017(16) 0.2010(13) 0.042(4) Uani 1 1 d . U .
H16 H 0.1204 1.3351 0.2655 0.051 Uiso 1 1 calc R U .
C17 C -0.0299(19) 1.2008(15) 0.1625(11) 0.032(3) Uani 1 1 d . U .
C18 C -0.1531(19) 1.2063(16) 0.2861(11) 0.034(3) Uani 1 1 d . U .
C19 C -0.2226(18) 1.1326(16) 0.3553(11) 0.033(3) Uani 1 1 d . U .
C20 C -0.2715(19) 1.1749(17) 0.4276(13) 0.040(4) Uani 1 1 d . U .
H20 H -0.2652 1.2524 0.4337 0.048 Uiso 1 1 calc R U .
C21 C -0.332(2) 0.9979(19) 0.4800(16) 0.056(5) Uani 1 1 d . U .
H21 H -0.3669 0.9492 0.5235 0.067 Uiso 1 1 calc R U .
C22 C -0.286(2) 0.9541(17) 0.4073(14) 0.043(4) Uani 1 1 d . U .
H22 H -0.2931 0.8763 0.4023 0.051 Uiso 1 1 calc R U .
C23 C 0.7396(18) 0.6558(16) 0.4869(12) 0.035(4) Uani 1 1 d . U .
C24 C 0.8875(19) 0.7491(18) 0.4807(14) 0.051(5) Uani 1 1 d . U .
H24A H 0.8811 0.7635 0.4156 0.076 Uiso 1 1 calc R U .
H24B H 0.9636 0.7206 0.4998 0.076 Uiso 1 1 calc R U .
H24C H 0.9105 0.8215 0.5227 0.076 Uiso 1 1 calc R U .
C25 C 0.4942(18) 0.3701(15) 0.3554(11) 0.030(4) Uani 1 1 d . U .
C26 C 0.489(2) 0.291(2) 0.2698(13) 0.058(6) Uani 1 1 d . U .
H26A H 0.4552 0.3177 0.2122 0.086 Uiso 1 1 calc R U .
H26B H 0.4224 0.2113 0.2692 0.086 Uiso 1 1 calc R U .
H26C H 0.5857 0.2935 0.2729 0.086 Uiso 1 1 calc R U .
C27 C 0.849(3) 0.423(2) 0.0591(17) 0.077(7) Uani 1 1 d . U .
H27A H 0.9518 0.4725 0.0853 0.115 Uiso 1 1 calc R U .
H27B H 0.8054 0.4615 0.0144 0.115 Uiso 1 1 calc R U .
H27C H 0.8388 0.3484 0.0265 0.115 Uiso 1 1 calc R U .
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O3 Cu1 O2 169.0(4) . .
O3 Cu1 O4 89.5(5) . .
O2 Cu1 O4 89.7(5) . .
O3 Cu1 O1 90.3(5) . .
O2 Cu1 O1 88.4(5) . .
O4 Cu1 O1 169.3(4) . .
O3 Cu1 N1 95.2(4) . .
O2 Cu1 N1 95.9(4) . .
O4 Cu1 N1 93.1(5) . .
O1 Cu1 N1 97.5(5) . .
O3 Cu1 Cu1 85.2(3) . 2_666
O2 Cu1 Cu1 83.7(3) . 2_666
O4 Cu1 Cu1 83.2(3) . 2_666
O1 Cu1 Cu1 86.1(3) . 2_666
N1 Cu1 Cu1 176.3(4) . 2_666
N3 Cu2 O6 163.0(5) . .
N3 Cu2 N4 86.6(5) . .
O6 Cu2 N4 92.0(5) . .
N3 Cu2 N2 80.3(5) . .
O6 Cu2 N2 87.9(5) . .
N4 Cu2 N2 131.0(5) . .
N3 Cu2 Cl1 95.5(4) . .
O6 Cu2 Cl1 99.0(4) . .
N4 Cu2 Cl1 125.9(4) . .
N2 Cu2 Cl1 102.4(4) . .
N6 Cu3 O7 167.0(5) . .
N6 Cu3 N7 80.3(6) . .
O7 Cu3 N7 88.8(5) . .
N6 Cu3 N5 84.8(5) . .
O7 Cu3 N5 98.3(5) . .
N7 Cu3 N5 135.0(5) . .
N6 Cu3 Cl1 94.7(4) . .
O7 Cu3 Cl1 96.6(4) . .
N7 Cu3 Cl1 117.8(4) . .
N5 Cu3 Cl1 105.5(4) . .
Cu2 Cl1 Cu3 99.7(2) . .
C23 O1 Cu1 120.2(11) . .
C25 O2 Cu1 123.4(10) . .
C25 O3 Cu1 121.3(10) 2_666 .
C23 O4 Cu1 124.0(10) 2_666 .
C12 O6 Cu2 139.5(12) . .
C12 O7 Cu3 131.7(11) . .
C3 N1 C2 116.9(13) . .
C3 N1 Cu1 121.3(10) . .
C2 N1 Cu1 121.8(10) . .
C4 N2 C1 118.6(13) . .
C4 N2 Cu2 109.7(10) . .
C1 N2 Cu2 131.7(11) . .
C5 N3 C6 118.0(13) . .
C5 N3 Cu2 119.2(10) . .
C6 N3 Cu2 121.5(9) . .
C10 N4 C9 119.0(13) . .
C10 N4 Cu2 114.4(10) . .
C9 N4 Cu2 124.4(10) . .
C14 N5 C15 118.8(12) . .
C14 N5 Cu3 113.5(10) . .
C15 N5 Cu3 125.1(10) . .
C18 N6 C17 119.6(14) . .
C18 N6 Cu3 120.9(12) . .
C17 N6 Cu3 119.2(10) . .
C22 N7 C19 117.5(15) . .
C22 N7 Cu3 131.0(13) . .
C19 N7 Cu3 111.3(10) . .
C21 N8 C20 117.6(16) . .
N2 C1 C2 120.8(16) . .
N1 C2 C1 120.9(16) . .
N1 C3 C4 122.7(16) . .
N2 C4 C3 120.2(15) . .
N2 C4 C5 118.8(12) . .
C3 C4 C5 121.0(14) . .
O5 C5 N3 129.2(15) . .
O5 C5 C4 119.7(13) . .
N3 C5 C4 111.1(13) . .
C7 C6 N3 123.4(13) . .
C7 C6 C15 118.9(14) . 2_575
N3 C6 C15 117.7(14) . 2_575
C6 C7 C8 120.8(14) . .
C7 C8 C14 118.1(17) . 2_575
N4 C9 C17 119.4(15) . 2_575
N4 C9 C15 118.2(12) . 2_575
C17 C9 C15 122.3(14) 2_575 2_575
N4 C10 C11 123.2(16) . .
C10 C11 C16 118.4(17) . 2_575
O7 C12 O6 126.3(16) . .
O7 C12 C13 118.3(14) . .
O6 C12 C13 115.3(15) . .
N5 C14 C8 123.8(15) . 2_575
N5 C15 C6 119.7(14) . 2_575
N5 C15 C9 117.0(11) . 2_575
C6 C15 C9 123.2(13) 2_575 2_575
C17 C16 C11 119.1(17) . 2_575
C16 C17 C9 120.9(16) . 2_575
C16 C17 N6 119.2(14) . .
C9 C17 N6 119.8(15) 2_575 .
O8 C18 N6 129.5(17) . .
O8 C18 C19 119.6(15) . .
N6 C18 C19 111.0(15) . .
N7 C19 C20 120.0(16) . .
N7 C19 C18 116.0(14) . .
C20 C19 C18 123.9(16) . .
N8 C20 C19 120.6(17) . .
N8 C21 C22 122.4(18) . .
N7 C22 C21 121.8(18) . .
O4 C23 O1 126.4(16) 2_666 .
O4 C23 C24 116.6(14) 2_666 .
O1 C23 C24 117.0(15) . .
O2 C25 O3 126.3(14) . 2_666
O2 C25 C26 117.7(14) . .
O3 C25 C26 116.0(14) 2_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O3 1.950(11) .
Cu1 O2 1.952(10) .
Cu1 O4 1.967(11) .
Cu1 O1 1.967(11) .
Cu1 N1 2.195(11) .
Cu1 Cu1 2.595(3) 2_666
Cu2 N3 1.923(13) .
Cu2 O6 1.940(12) .
Cu2 N4 2.077(12) .
Cu2 N2 2.151(12) .
Cu2 Cl1 2.399(6) .
Cu3 N6 1.918(14) .
Cu3 O7 1.927(12) .
Cu3 N7 2.074(13) .
Cu3 N5 2.107(12) .
Cu3 Cl1 2.421(6) .
O1 C23 1.260(18) .
O2 C25 1.236(18) .
O3 C25 1.254(18) 2_666
O4 C23 1.238(19) 2_666
O5 C5 1.226(18) .
O6 C12 1.274(18) .
O7 C12 1.263(19) .
O8 C18 1.222(19) .
O10 C27 1.42(3) .
N1 C3 1.32(2) .
N1 C2 1.35(2) .
N2 C4 1.321(19) .
N2 C1 1.34(2) .
N3 C5 1.378(18) .
N3 C6 1.398(19) .
N4 C10 1.35(2) .
N4 C9 1.371(18) .
N5 C14 1.34(2) .
N5 C15 1.374(18) .
N6 C18 1.33(2) .
N6 C17 1.43(2) .
N7 C22 1.31(2) .
N7 C19 1.36(2) .
N8 C21 1.29(2) .
N8 C20 1.36(2) .
C1 C2 1.40(2) .
C3 C4 1.394(19) .
C4 C5 1.50(2) .
C6 C7 1.38(2) .
C6 C15 1.430(18) 2_575
C7 C8 1.38(2) .
C8 C14 1.38(2) 2_575
C9 C17 1.39(2) 2_575
C9 C15 1.48(2) 2_575
C10 C11 1.38(2) .
C11 C16 1.38(2) 2_575
C12 C13 1.49(2) .
C14 C8 1.38(2) 2_575
C15 C6 1.430(18) 2_575
C15 C9 1.48(2) 2_575
C16 C17 1.38(2) .
C16 C11 1.38(2) 2_575
C17 C9 1.39(2) 2_575
C18 C19 1.50(2) .
C19 C20 1.39(2) .
C21 C22 1.38(3) .
C23 O4 1.238(19) 2_666
C23 C24 1.53(2) .
C25 O3 1.254(18) 2_666
C25 C26 1.49(2) .
