#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:29:59 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179973 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/67/7026703.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_7026703
loop_
_publ_author_name
'Allen, John J.'
'Hamilton, Christopher E.'
'Barron, Andrew R.'
_publ_section_title
;
 Synthesis and characterization of aryl substituted bis(2-pyridyl)amines
 and their copper olefin complexes: investigation of remote steric control
 over olefin binding.
;
_journal_issue                   47
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11451
_journal_page_last               11468
_journal_paper_doi               10.1039/c0dt00608d
_journal_volume                  39
_journal_year                    2010
_chemical_formula_moiety         'C32 H26 Cl4 Cu2 N6'
_chemical_formula_sum            'C32 H26 Cl4 Cu2 N6'
_chemical_formula_weight         763.47
_chemical_melting_point          538
_chemical_name_systematic
(dichloro)-di-(mu-chloro)-bis(N-Phenyl-N,N-(2,2-dipyridyl)amine)-dicopper(II)
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.28(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.282(3)
_cell_length_b                   7.3669(15)
_cell_length_c                   27.085(5)
_cell_measurement_reflns_used    5781
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.7103
_cell_measurement_theta_min      2.5512
_cell_volume                     3186.0(11)
_computing_cell_refinement       'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_collection       'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction        'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_molecular_graphics    'SHELXTL v5.1'
_computing_publication_material  'SHELXTL v5.1'
_computing_structure_refinement  'SHELXTL v5.1'
_computing_structure_solution    'SHELXTL v5.1 (Bruker-AXS, 1998)'
_diffrn_ambient_pressure         101.33
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19085
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.53
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker SMART CCD'
_exptl_absorpt_coefficient_mu    1.704
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.6786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS, 2003)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1544
_exptl_crystal_recrystallization_method
'sat. soln in MeOH cooled to -12 deg C for several days'
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.00453(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0286
_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)+(0.0339P)²+2.3737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0747
_reflns_number_gt                3139
_reflns_number_total             3900
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt00608d.txt
_cod_data_source_block           cuphdpa
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7026703
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_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
Cu1 Cu 0.025997(14) 0.01426(3) 0.437126(8) 0.02869(9) Uani 1 1 d .
N1 N 0.15900(10) 0.0803(2) 0.37712(6) 0.0348(4) Uani 1 1 d .
N2 N 0.04580(10) 0.2379(2) 0.39755(6) 0.0324(3) Uani 1 1 d .
N3 N 0.15226(10) 0.00303(19) 0.46024(6) 0.0286(3) Uani 1 1 d .
C1 C 0.10541(12) 0.2342(3) 0.37002(7) 0.0331(4) Uani 1 1 d .
C2 C 0.11634(15) 0.3736(3) 0.33789(9) 0.0468(5) Uani 1 1 d .
H2A H 0.1585 0.3682 0.3192 0.056 Uiso 1 1 calc R
C3 C 0.06334(18) 0.5211(3) 0.33407(10) 0.0535(6) Uani 1 1 d .
H3A H 0.0683 0.6152 0.3119 0.064 Uiso 1 1 calc R
C4 C 0.00275(17) 0.5283(3) 0.36340(9) 0.0507(6) Uani 1 1 d .
H4A H -0.0326 0.6280 0.3619 0.061 Uiso 1 1 calc R
C5 C -0.00393(14) 0.3857(3) 0.39452(8) 0.0437(5) Uani 1 1 d .
H5A H -0.0444 0.3906 0.4144 0.052 Uiso 1 1 calc R
C6 C 0.20114(12) 0.0477(2) 0.42742(7) 0.0300(4) Uani 1 1 d .
C7 C 0.28672(12) 0.0680(3) 0.44213(9) 0.0400(5) Uani 1 1 d .
H7A H 0.3189 0.1052 0.4191 0.048 Uiso 1 1 calc R
C8 C 0.32387(13) 0.0323(3) 0.49150(9) 0.0416(5) Uani 1 1 d .
H8A H 0.3816 0.0408 0.5020 0.050 Uiso 1 1 calc R
C9 C 0.27401(14) -0.0161(3) 0.52498(9) 0.0401(5) Uani 1 1 d .
H9A H 0.2977 -0.0417 0.5583 0.048 Uiso 1 1 calc R
C10 C 0.18858(13) -0.0262(3) 0.50845(8) 0.0349(4) Uani 1 1 d .
H10A H 0.1550 -0.0542 0.5315 0.042 Uiso 1 1 calc R
C11 C 0.17232(13) -0.0253(3) 0.33572(8) 0.0337(4) Uani 1 1 d .
C12 C 0.11724(15) -0.0123(3) 0.28987(8) 0.0412(5) Uani 1 1 d .
H12A H 0.0723 0.0676 0.2864 0.049 Uiso 1 1 calc R
C13 C 0.12816(16) -0.1166(3) 0.24908(8) 0.0494(6) Uani 1 1 d .
H13A H 0.0910 -0.1050 0.2185 0.059 Uiso 1 1 calc R
C14 C 0.19362(17) -0.2373(3) 0.25363(9) 0.0555(6) Uani 1 1 d .
H14A H 0.2013 -0.3067 0.2262 0.067 Uiso 1 1 calc R
C15 C 0.24747(16) -0.2541(3) 0.29924(10) 0.0560(6) Uani 1 1 d .
H15A H 0.2915 -0.3365 0.3026 0.067 Uiso 1 1 calc R
C16 C 0.23754(14) -0.1505(3) 0.34031(8) 0.0449(5) Uani 1 1 d .
H16A H 0.2744 -0.1645 0.3710 0.054 Uiso 1 1 calc R
Cl1 Cl 0.00678(3) -0.22625(6) 0.486347(19) 0.03434(12) Uani 1 1 d .
Cl2 Cl -0.09756(3) -0.02755(8) 0.38393(2) 0.04405(14) Uani 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'
Cl Cl 0.1484 0.1585 '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_3
N2 Cu1 N3 86.55(6) .
N2 Cu1 Cl2 89.28(5) .
N3 Cu1 Cl2 156.14(5) .
N2 Cu1 Cl1 176.19(5) .
N3 Cu1 Cl1 91.98(5) .
Cl2 Cu1 Cl1 93.46(3) .
N2 Cu1 Cl1 90.66(5) 5_556
N3 Cu1 Cl1 97.23(5) 5_556
Cl2 Cu1 Cl1 106.31(3) 5_556
Cl1 Cu1 Cl1 86.04(2) 5_556
C11 N1 C1 121.10(16) .
C11 N1 C6 123.13(16) .
C1 N1 C6 115.67(15) .
C1 N2 C5 118.39(17) .
C1 N2 Cu1 119.17(12) .
C5 N2 Cu1 122.19(14) .
C10 N3 C6 118.53(17) .
C10 N3 Cu1 122.26(13) .
C6 N3 Cu1 118.74(13) .
N2 C1 C2 122.32(18) .
N2 C1 N1 115.79(16) .
C2 C1 N1 121.85(18) .
C3 C2 C1 118.5(2) .
C3 C2 H2A 120.7 .
C1 C2 H2A 120.7 .
C2 C3 C4 119.6(2) .
C2 C3 H3A 120.2 .
C4 C3 H3A 120.2 .
C5 C4 C3 118.5(2) .
C5 C4 H4A 120.7 .
C3 C4 H4A 120.7 .
N2 C5 C4 122.6(2) .
N2 C5 H5A 118.7 .
C4 C5 H5A 118.7 .
N3 C6 C7 122.02(19) .
N3 C6 N1 115.97(16) .
C7 C6 N1 121.96(18) .
C6 C7 C8 119.0(2) .
C6 C7 H7A 120.5 .
C8 C7 H7A 120.5 .
C9 C8 C7 118.9(2) .
C9 C8 H8A 120.5 .
C7 C8 H8A 120.5 .
C8 C9 C10 119.2(2) .
C8 C9 H9A 120.4 .
C10 C9 H9A 120.4 .
N3 C10 C9 122.2(2) .
N3 C10 H10A 118.9 .
C9 C10 H10A 118.9 .
C12 C11 C16 118.29(19) .
C12 C11 N1 119.95(18) .
C16 C11 N1 121.68(19) .
C13 C12 C11 121.0(2) .
C13 C12 H12A 119.5 .
C11 C12 H12A 119.5 .
C14 C13 C12 120.4(2) .
C14 C13 H13A 119.8 .
C12 C13 H13A 119.8 .
C15 C14 C13 119.1(2) .
C15 C14 H14A 120.5 .
C13 C14 H14A 120.5 .
C14 C15 C16 121.3(2) .
C14 C15 H15A 119.4 .
C16 C15 H15A 119.4 .
C15 C16 C11 120.0(2) .
C15 C16 H16A 120.0 .
C11 C16 H16A 120.0 .
Cu1 Cl1 Cu1 93.96(2) 5_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 2.0254(16) .
Cu1 N3 2.0301(17) .
Cu1 Cl2 2.2546(9) .
Cu1 Cl1 2.2754(6) .
Cu1 Cl1 2.7300(7) 5_556
Cu1 Cu1 3.6728(9) 5_556
N1 C11 1.416(3) .
N1 C1 1.421(2) .
N1 C6 1.421(3) .
N2 C1 1.335(2) .
N2 C5 1.350(2) .
N3 C10 1.341(3) .
N3 C6 1.345(2) .
C1 C2 1.380(3) .
C2 C3 1.379(3) .
C2 H2A 0.9300 .
C3 C4 1.383(4) .
C3 H3A 0.9300 .
C4 C5 1.364(3) .
C4 H4A 0.9300 .
C5 H5A 0.9300 .
C6 C7 1.380(3) .
C7 C8 1.381(3) .
C7 H7A 0.9300 .
C8 C9 1.377(3) .
C8 H8A 0.9300 .
C9 C10 1.377(3) .
C9 H9A 0.9300 .
C10 H10A 0.9300 .
C11 C12 1.385(3) .
C11 C16 1.394(3) .
C12 C13 1.385(3) .
C12 H12A 0.9300 .
C13 C14 1.375(3) .
C13 H13A 0.9300 .
C14 C15 1.373(4) .
C14 H14A 0.9300 .
C15 C16 1.384(3) .
C15 H15A 0.9300 .
C16 H16A 0.9300 .
Cl1 Cu1 2.7300(7) 5_556
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N3 Cu1 N2 C1 46.29(15) . . .
Cl2 Cu1 N2 C1 -110.21(15) . . .
Cl1 Cu1 N2 C1 113.8(6) . . .
N3 Cu1 N2 C5 -139.55(17) . . .
Cl2 Cu1 N2 C5 63.95(16) . . .
Cl1 Cu1 N2 C5 -72.0(7) . . .
N2 Cu1 N3 C10 134.57(15) . . .
Cl2 Cu1 N3 C10 -145.06(13) . . .
Cl1 Cu1 N3 C10 -41.91(14) . . .
Cl1 Cu1 N3 C10 44.35(14) 5_556 . .
N2 Cu1 N3 C6 -37.34(14) . . .
Cl2 Cu1 N3 C6 43.0(2) . . .
Cl1 Cu1 N3 C6 146.18(13) . . .
Cl1 Cu1 N3 C6 -127.57(13) 5_556 . .
C5 N2 C1 C2 -1.6(3) . . .
Cu1 N2 C1 C2 172.76(17) . . .
C5 N2 C1 N1 176.28(18) . . .
Cu1 N2 C1 N1 -9.3(2) . . .
C11 N1 C1 N2 127.5(2) . . .
C6 N1 C1 N2 -56.0(2) . . .
C11 N1 C1 C2 -54.6(3) . . .
C6 N1 C1 C2 121.9(2) . . .
N2 C1 C2 C3 -0.3(3) . . .
N1 C1 C2 C3 -178.1(2) . . .
C1 C2 C3 C4 2.0(4) . . .
C2 C3 C4 C5 -1.6(4) . . .
C1 N2 C5 C4 2.0(3) . . .
Cu1 N2 C5 C4 -172.17(18) . . .
C3 C4 C5 N2 -0.4(4) . . .
C10 N3 C6 C7 -1.5(3) . . .
Cu1 N3 C6 C7 170.75(15) . . .
C10 N3 C6 N1 -178.88(16) . . .
Cu1 N3 C6 N1 -6.7(2) . . .
C11 N1 C6 N3 -117.87(19) . . .
C1 N1 C6 N3 65.8(2) . . .
C11 N1 C6 C7 64.7(3) . . .
C1 N1 C6 C7 -111.6(2) . . .
N3 C6 C7 C8 3.4(3) . . .
N1 C6 C7 C8 -179.34(18) . . .
C6 C7 C8 C9 -2.3(3) . . .
C7 C8 C9 C10 -0.5(3) . . .
C6 N3 C10 C9 -1.5(3) . . .
Cu1 N3 C10 C9 -173.47(14) . . .
C8 C9 C10 N3 2.5(3) . . .
C1 N1 C11 C12 -17.6(3) . . .
C6 N1 C11 C12 166.20(18) . . .
C1 N1 C11 C16 165.70(19) . . .
C6 N1 C11 C16 -10.4(3) . . .
C16 C11 C12 C13 -2.1(3) . . .
N1 C11 C12 C13 -178.86(19) . . .
C11 C12 C13 C14 0.9(3) . . .
C12 C13 C14 C15 0.6(4) . . .
C13 C14 C15 C16 -0.7(4) . . .
C14 C15 C16 C11 -0.5(4) . . .
C12 C11 C16 C15 1.9(3) . . .
N1 C11 C16 C15 178.6(2) . . .
N3 Cu1 Cl1 Cu1 97.11(5) . . 5_556
Cl2 Cu1 Cl1 Cu1 -106.13(3) . . 5_556
N3 Cu1 Cu1 N2 -89.12(7) . 5_556 5_556
N3 Cu1 Cu1 Cl2 11.69(5) . 5_556 5_556
N1 Cu1 Cu1 Cl2 -3.14(6) . 5_556 5_556
Cl1 Cl1 N3 N2 -56.49(5) 5_556 . .
