#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:00:20 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179608 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/72/4507271.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_4507271
loop_
_publ_author_name
'Mastropietro, Teresa F.'
'Marino, Nadia'
'Armentano, Donatella'
'De Munno, Giovanni'
'Yuste, Consuelo'
'Lloret, Francesc'
'Julve, Miguel'
_publ_section_title
;
 Anion-Directed Self-Assembly of Unusual Discrete and One-Dimensional
 Copper(II) Complexes of 3,6-Bis(2′-pyridyl)pyridazine
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              270
_journal_paper_doi               10.1021/cg301415p
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C14 H12 Cu2 N16 O'
_chemical_formula_weight         547.48
_chemical_name_systematic
; 
 ? 
;
_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                90.149(7)
_cell_angle_beta                 96.531(8)
_cell_angle_gamma                100.772(7)
_cell_formula_units_Z            2
_cell_length_a                   8.1979(8)
_cell_length_b                   10.6608(9)
_cell_length_c                   11.2985(11)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      15
_cell_volume                     963.46(16)
_computing_cell_refinement       'Bruker P3'
_computing_data_collection       'Bruker P3'
_computing_data_reduction        'Bruker XDISK'
_computing_molecular_graphics    'SHELXTL NT Bruker XP'
_computing_publication_material  'SHELXTL NT Package Bruker'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'R3m/V automatic four-circle diffractometer'
_diffrn_measurement_method       omega/2-theta-scans
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6719
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.81
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.257
_exptl_absorpt_correction_T_max  0.9778
_exptl_absorpt_correction_T_min  0.5706
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   psi-scan
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PARALLELEPIPED
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         5614
_refine_ls_number_restraints     367
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0352P)²+0.4775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0955
_reflns_number_gt                3874
_reflns_number_total             5614
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301415p_si_005.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4507271
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
_atom_site_disorder_group
Cu1 Cu -0.63705(5) 0.42031(3) 0.36422(3) 0.03285(11) Uani 1 1 d DU .
Cu2 Cu -0.38369(5) 0.46027(3) 0.13601(3) 0.03052(10) Uani 1 1 d DU .
N1 N -0.7258(3) 0.2760(2) 0.4692(2) 0.0321(5) Uani 1 1 d U .
N2 N -0.5501(3) 0.27283(19) 0.29546(19) 0.0250(4) Uani 1 1 d U .
N3 N -0.4600(3) 0.28722(19) 0.20483(19) 0.0257(5) Uani 1 1 d U .
N4 N -0.2799(3) 0.34807(19) 0.03379(19) 0.0274(5) Uani 1 1 d U .
C1 C -0.8207(4) 0.2854(3) 0.5568(3) 0.0426(7) Uani 1 1 d U .
H1 H -0.8471 0.3643 0.5735 0.051 Uiso 1 1 calc R .
C2 C -0.8801(4) 0.1826(3) 0.6222(3) 0.0469(8) Uani 1 1 d U .
H2 H -0.9455 0.1921 0.6825 0.056 Uiso 1 1 calc R .
C3 C -0.8425(4) 0.0646(3) 0.5985(3) 0.0445(7) Uani 1 1 d U .
H3 H -0.8801 -0.0057 0.6433 0.053 Uiso 1 1 calc R .
C4 C -0.7479(4) 0.0538(3) 0.5067(3) 0.0368(7) Uani 1 1 d U .
H4 H -0.7225 -0.0247 0.4875 0.044 Uiso 1 1 calc R .
C5 C -0.6919(3) 0.1607(2) 0.4441(2) 0.0282(5) Uani 1 1 d U .
C6 C -0.5927(3) 0.1596(2) 0.3425(2) 0.0266(5) Uani 1 1 d U .
C7 C -0.5457(4) 0.0515(2) 0.2968(2) 0.0320(6) Uani 1 1 d U .
H7 H -0.5772 -0.0284 0.3291 0.038 Uiso 1 1 calc R .
C8 C -0.4520(4) 0.0664(2) 0.2031(2) 0.0319(6) Uani 1 1 d U .
H8 H -0.4177 -0.0030 0.1704 0.038 Uiso 1 1 calc R .
C9 C -0.4092(3) 0.1887(2) 0.1580(2) 0.0273(5) Uani 1 1 d U .
C10 C -0.3059(3) 0.2224(2) 0.0594(2) 0.0276(5) Uani 1 1 d U .
C11 C -0.2392(4) 0.1357(3) -0.0006(3) 0.0362(6) Uani 1 1 d U .
H11 H -0.2601 0.0496 0.0181 0.043 Uiso 1 1 calc R .
C12 C -0.1411(4) 0.1778(3) -0.0885(3) 0.0432(7) Uani 1 1 d U .
H12 H -0.0951 0.1205 -0.1305 0.052 Uiso 1 1 calc R .
C13 C -0.1113(4) 0.3065(3) -0.1141(3) 0.0411(7) Uani 1 1 d U .
H13 H -0.0436 0.3372 -0.1724 0.049 Uiso 1 1 calc R .
C14 C -0.1841(4) 0.3883(3) -0.0515(3) 0.0342(6) Uani 1 1 d U .
H14 H -0.1656 0.4746 -0.0694 0.041 Uiso 1 1 calc R .
N5 N -0.5114(3) 0.52982(19) 0.2509(2) 0.0323(5) Uani 1 1 d DU .
N6 N -0.5100(3) 0.6454(2) 0.2527(2) 0.0329(5) Uani 1 1 d DU .
N7 N -0.5091(4) 0.7514(2) 0.2541(3) 0.0503(7) Uani 1 1 d DU .
N8 N -0.6756(5) 0.5514(3) 0.4723(3) 0.0664(9) Uani 1 1 d DU .
N9 N -0.7111(4) 0.6525(2) 0.4570(3) 0.0452(7) Uani 1 1 d DU .
N10 N -0.7381(5) 0.7529(3) 0.4515(4) 0.0869(12) Uani 1 1 d DU .
N11 N -0.3377(4) 0.6059(2) 0.0337(2) 0.0427(6) Uani 1 1 d DU .
N12 N -0.3037(3) 0.7183(2) 0.0506(2) 0.0384(6) Uani 1 1 d DU .
N13 N -0.2731(5) 0.8277(3) 0.0595(3) 0.0676(10) Uani 1 1 d DU .
N14A N -0.9023(5) 0.3762(7) 0.2492(5) 0.0496(11) Uani 0.639(6) 1 d PDU 1
N15A N -1.0167(5) 0.4255(4) 0.2612(4) 0.0392(11) Uani 0.639(6) 1 d PDU 1
N16A N -1.121(2) 0.4814(17) 0.271(2) 0.042(3) Uani 0.639(6) 1 d PDU 1
O1WA O -0.9212(19) 0.1101(6) 0.1858(12) 0.069(3) Uani 0.639(6) 1 d PDU 1
H1WA H -0.862(9) 0.124(7) 0.117(4) 0.104 Uiso 0.639(6) 1 d PD 1
H2WA H -0.904(13) 0.198(3) 0.211(8) 0.104 Uiso 0.639(6) 1 d PD 1
N14B N -0.8794(10) 0.3485(10) 0.2287(10) 0.0496(11) Uani 0.361(6) 1 d PDU 2
N15B N -0.9166(12) 0.2344(8) 0.2199(8) 0.048(2) Uani 0.361(6) 1 d PDU 2
N16B N -0.955(4) 0.1259(11) 0.215(3) 0.066(5) Uani 0.361(6) 1 d PDU 2
O1WB O -1.152(3) 0.466(3) 0.282(3) 0.050(5) Uani 0.361(6) 1 d PDU 2
H1WB H -1.090(15) 0.400(9) 0.276(9) 0.075 Uiso 0.361(6) 1 d PD 2
H2WB H -1.140(14) 0.471(10) 0.368(4) 0.075 Uiso 0.361(6) 1 d PD 2
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'
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
N8 Cu1 N5 99.66(11) . .
N8 Cu1 N1 93.31(11) . .
N5 Cu1 N1 164.68(9) . .
N8 Cu1 N2 162.54(12) . .
N5 Cu1 N2 86.68(8) . .
N1 Cu1 N2 78.60(9) . .
N8 Cu1 N14A 99.43(18) . .
N5 Cu1 N14A 98.9(2) . .
N1 Cu1 N14A 86.9(2) . .
N2 Cu1 N14A 95.59(15) . .
N8 Cu1 N14B 110.4(3) . .
N5 Cu1 N14B 96.2(4) . .
N1 Cu1 N14B 86.8(4) . .
N2 Cu1 N14B 84.8(3) . .
N14A Cu1 N14B 11.0(3) . .
N8 Cu1 N8 80.81(14) . 2_466
N5 Cu1 N8 88.40(10) . 2_466
N1 Cu1 N8 85.64(9) . 2_466
N2 Cu1 N8 83.14(8) . 2_466
N14A Cu1 N8 172.57(19) . 2_466
N14B Cu1 N8 166.8(3) . 2_466
N8 Cu1 Cu2 127.40(10) . .
N5 Cu1 Cu2 28.86(6) . .
N1 Cu1 Cu2 136.32(6) . .
N2 Cu1 Cu2 57.84(6) . .
N14A Cu1 Cu2 99.40(16) . .
N14B Cu1 Cu2 91.9(4) . .
N8 Cu1 Cu2 86.16(6) 2_466 .
N8 Cu1 Cu1 50.30(12) . 2_466
N5 Cu1 Cu1 93.70(7) . 2_466
N1 Cu1 Cu1 88.31(7) . 2_466
N2 Cu1 Cu1 113.42(6) . 2_466
N14A Cu1 Cu1 149.00(14) . 2_466
N14B Cu1 Cu1 159.8(3) . 2_466
N8 Cu1 Cu1 30.51(5) 2_466 2_466
Cu2 Cu1 Cu1 105.079(17) . 2_466
N11 Cu2 N5 100.31(10) . .
N11 Cu2 N4 92.94(10) . .
N5 Cu2 N4 166.01(9) . .
N11 Cu2 N3 165.94(10) . .
N5 Cu2 N3 86.96(8) . .
N4 Cu2 N3 79.15(9) . .
N11 Cu2 O1WB 108.8(7) . 1_655
N5 Cu2 O1WB 91.6(6) . 1_655
N4 Cu2 O1WB 88.4(6) . 1_655
N3 Cu2 O1WB 82.8(7) . 1_655
N11 Cu2 N16A 102.4(5) . 1_655
N5 Cu2 N16A 95.9(4) . 1_655
N4 Cu2 N16A 85.5(4) . 1_655
N3 Cu2 N16A 88.7(5) . 1_655
O1WB Cu2 N16A 7.1(12) 1_655 1_655
N11 Cu2 N11 81.94(10) . 2_465
N5 Cu2 N11 93.39(9) . 2_465
N4 Cu2 N11 83.96(8) . 2_465
N3 Cu2 N11 85.65(8) . 2_465
O1WB Cu2 N11 167.2(7) 1_655 2_465
N16A Cu2 N11 168.8(4) 1_655 2_465
N11 Cu2 Cu1 128.39(8) . .
N5 Cu2 Cu1 28.86(6) . .
N4 Cu2 Cu1 137.23(6) . .
N3 Cu2 Cu1 58.11(6) . .
O1WB Cu2 Cu1 87.9(7) 1_655 .
N16A Cu2 Cu1 94.4(5) 1_655 .
N11 Cu2 Cu1 90.80(5) 2_465 .
N11 Cu2 Cu2 49.80(8) . 2_465
N5 Cu2 Cu2 98.15(7) . 2_465
N4 Cu2 Cu2 86.92(6) . 2_465
N3 Cu2 Cu2 117.57(6) . 2_465
O1WB Cu2 Cu2 157.7(7) 1_655 2_465
N16A Cu2 Cu2 150.7(5) 1_655 2_465
N11 Cu2 Cu2 32.15(5) 2_465 2_465
Cu1 Cu2 Cu2 110.152(17) . 2_465
N11 Cu2 Cu1 101.02(9) . 1_655
N5 Cu2 Cu1 112.57(7) . 1_655
N4 Cu2 Cu1 68.72(6) . 1_655
N3 Cu2 Cu1 87.03(6) . 1_655
O1WB Cu2 Cu1 21.2(6) 1_655 1_655
N16A Cu2 Cu1 16.9(4) 1_655 1_655
N11 Cu2 Cu1 152.58(5) 2_465 1_655
Cu1 Cu2 Cu1 107.515(13) . 1_655
Cu2 Cu2 Cu1 141.943(14) 2_465 1_655
C1 N1 C5 118.4(2) . .
C1 N1 Cu1 125.2(2) . .
C5 N1 Cu1 116.28(18) . .
N3 N2 C6 120.9(2) . .
N3 N2 Cu1 121.98(15) . .
C6 N2 Cu1 117.04(18) . .
N2 N3 C9 121.2(2) . .
N2 N3 Cu2 121.90(15) . .
C9 N3 Cu2 116.79(17) . .
C14 N4 C10 118.5(2) . .
C14 N4 Cu2 125.63(18) . .
C10 N4 Cu2 115.84(18) . .
N1 C1 C2 122.0(3) . .
N1 C1 H1 119.0 . .
C2 C1 H1 119.0 . .
C1 C2 C3 119.8(3) . .
C1 C2 H2 120.1 . .
C3 C2 H2 120.1 . .
C4 C3 C2 118.4(3) . .
C4 C3 H3 120.8 . .
C2 C3 H3 120.8 . .
C5 C4 C3 119.0(3) . .
C5 C4 H4 120.5 . .
C3 C4 H4 120.5 . .
N1 C5 C4 122.3(3) . .
N1 C5 C6 114.1(2) . .
C4 C5 C6 123.6(2) . .
N2 C6 C7 121.0(2) . .
N2 C6 C5 113.9(2) . .
C7 C6 C5 125.1(2) . .
C8 C7 C6 118.1(2) . .
C8 C7 H7 121.0 . .
C6 C7 H7 121.0 . .
C7 C8 C9 118.4(2) . .
C7 C8 H8 120.8 . .
C9 C8 H8 120.8 . .
N3 C9 C8 120.4(2) . .
N3 C9 C10 114.1(2) . .
C8 C9 C10 125.5(2) . .
N4 C10 C11 122.2(3) . .
N4 C10 C9 114.1(2) . .
C11 C10 C9 123.8(2) . .
C10 C11 C12 119.0(3) . .
C10 C11 H11 120.5 . .
C12 C11 H11 120.5 . .
C11 C12 C13 119.3(3) . .
C11 C12 H12 120.3 . .
C13 C12 H12 120.3 . .
C14 C13 C12 118.7(3) . .
C14 C13 H13 120.6 . .
C12 C13 H13 120.6 . .
N4 C14 C13 122.3(3) . .
N4 C14 H14 118.8 . .
C13 C14 H14 118.8 . .
N6 N5 Cu1 119.15(19) . .
N6 N5 Cu2 118.56(19) . .
Cu1 N5 Cu2 122.28(10) . .
N7 N6 N5 179.8(4) . .
N9 N8 Cu1 132.9(3) . .
N10 N9 N8 174.2(4) . .
N12 N11 Cu2 134.2(2) . .
N13 N12 N11 175.7(3) . .
N15A N14A Cu1 126.1(4) . .
N16A N15A N14A 175.1(12) . .
N16A N15A H1WB 56(4) . .
N14A N15A H1WB 128(4) . .
N15A N16A Cu2 125.0(17) . 1_455
N15A N16A H1WB 35(8) . .
Cu2 N16A H1WB 108(7) 1_455 .
N15A N16A H2WB 104(6) . .
Cu2 N16A H2WB 113(6) 1_455 .
H1WB N16A H2WB 87(5) . .
H1WA O1WA H2WA 96.3(13) . .
N15B N14B Cu1 113.1(7) . .
N16B N15B N14B 177.9(15) . .
N16B N15B H2WA 32(10) . .
N14B N15B H2WA 149(10) . .
N15B N16B H1WA 89(3) . .
N15B N16B H2WA 17(6) . .
H1WA N16B H2WA 75(3) . .
Cu2 O1WB H1WB 115(7) 1_455 .
Cu2 O1WB H2WB 133(7) 1_455 .
H1WB O1WB H2WB 96.4(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N8 1.946(3) .
Cu1 N5 1.981(2) .
Cu1 N1 2.023(2) .
Cu1 N2 2.030(2) .
Cu1 N14A 2.369(3) .
Cu1 N14B 2.369(3) .
Cu1 N8 2.950(4) 2_466
Cu1 Cu2 3.4694(6) .
Cu1 Cu1 3.7851(8) 2_466
Cu2 N11 1.944(2) .
Cu2 N5 1.981(2) .
Cu2 N4 2.021(2) .
Cu2 N3 2.022(2) .
Cu2 O1WB 2.36(3) 1_655
Cu2 N16A 2.47(2) 1_655
Cu2 N11 2.790(3) 2_465
Cu2 Cu2 3.6173(8) 2_465
Cu2 Cu1 6.4564(8) 1_655
N1 C1 1.341(4) .
N1 C5 1.346(3) .
N2 N3 1.322(3) .
N2 C6 1.323(3) .
N3 C9 1.329(3) .
N4 C14 1.333(4) .
N4 C10 1.354(3) .
C1 C2 1.368(5) .
C1 H1 0.9300 .
C2 C3 1.382(5) .
C2 H2 0.9300 .
C3 C4 1.381(4) .
C3 H3 0.9300 .
C4 C5 1.376(4) .
C4 H4 0.9300 .
C5 C6 1.481(4) .
C6 C7 1.397(4) .
C7 C8 1.370(4) .
C7 H7 0.9300 .
C8 C9 1.399(4) .
C8 H8 0.9300 .
C9 C10 1.480(4) .
C10 C11 1.373(4) .
C11 C12 1.373(4) .
C11 H11 0.9300 .
C12 C13 1.385(4) .
C12 H12 0.9300 .
C13 C14 1.380(4) .
C13 H13 0.9300 .
C14 H14 0.9300 .
N5 N6 1.231(3) .
N6 N7 1.129(3) .
N8 N9 1.176(3) .
N9 N10 1.133(4) .
N11 N12 1.189(3) .
N12 N13 1.148(3) .
N14A N15A 1.178(5) .
N15A N16A 1.142(8) .
N15A H1WB 0.65(13) .
N16A Cu2 2.47(2) 1_455
N16A H1WB 0.95(5) .
N16A H2WB 1.12(7) .
O1WA H1WA 0.957(10) .
O1WA H2WA 0.962(10) .
N14B N15B 1.199(8) .
N15B N16B 1.139(8) .
N15B H2WA 0.43(4) .
N16B H1WA 1.41(4) .
N16B H2WA 0.81(5) .
O1WB Cu2 2.36(3) 1_455
O1WB H1WB 0.959(10) .
O1WB H2WB 0.959(10) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1WA H2WA N14A 0.962(10) 1.94(2) 2.895(10) 172(10)
O1WB H1WB N14B 0.959(10) 2.03(8) 2.88(2) 147(12)
