#------------------------------------------------------------------------------
#$Date: 2016-03-23 04:03:07 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179275 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/95/4319581.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_4319581
loop_
_publ_author_name
'Salim Haddad'
'Roger D. Willett'
_publ_section_title
;
 Polymorphism in Bis(4-dimethylamino- pyridinium)tetrachlorocuprate(II)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2457
_journal_page_last               2460
_journal_paper_doi               10.1021/ic000613c
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C14 H22 Cl4 Cu N4'
_chemical_formula_weight         451.70
_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                84.7480(10)
_cell_angle_beta                 84.7100(10)
_cell_angle_gamma                66.3510(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7013(4)
_cell_length_b                   8.7917(4)
_cell_length_c                   15.9492(7)
_cell_measurement_temperature    293(2)
_cell_volume                     983.22(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4988
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    1.657
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             462
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         3255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0415P)²+0.4486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0898
_reflns_number_gt                2868
_reflns_number_total             3255
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic000613c_1.cif
_cod_data_source_block           200sht-green
_cod_database_code               4319581
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_assembly
_atom_site_disorder_group
Cu Cu 0.32284(5) 0.97944(4) 0.25459(2) 0.03980(13) Uani 1 1 d . . .
Cl1 Cl 0.35128(15) 1.22501(11) 0.25893(5) 0.0604(3) Uani 1 1 d . . .
Cl2 Cl 0.17389(15) 0.99704(11) 0.38350(6) 0.0685(3) Uani 1 1 d . . .
Cl3 Cl 0.45222(13) 0.69886(10) 0.26389(5) 0.0569(2) Uani 1 1 d . . .
Cl4 Cl 0.30872(16) 1.00158(11) 0.11370(5) 0.0640(3) Uani 1 1 d . . .
C1 C -0.2335(4) 1.3671(4) 0.05822(19) 0.0411(7) Uani 1 1 d . . .
C2 C -0.2513(5) 1.3460(4) -0.0277(2) 0.0458(7) Uani 1 1 d . . .
H2 H -0.248(5) 1.253(4) -0.043(2) 0.050(9) Uiso 1 1 d . . .
C3 C -0.2756(5) 1.4725(5) -0.0867(2) 0.0524(8) Uani 1 1 d . . .
H3 H -0.286(5) 1.462(4) -0.138(2) 0.051(10) Uiso 1 1 d . . .
N2 N -0.2806(4) 1.6187(4) -0.0670(2) 0.0539(7) Uani 1 1 d . . .
H2' H -0.295(6) 1.688(5) -0.100(3) 0.063(13) Uiso 1 1 d . . .
C4 C -0.2644(5) 1.6454(4) 0.0127(2) 0.0529(8) Uani 1 1 d . . .
H4 H -0.279(5) 1.755(5) 0.019(2) 0.062(10) Uiso 1 1 d . . .
C5 C -0.2400(5) 1.5252(4) 0.0746(2) 0.0489(8) Uani 1 1 d . . .
H5 H -0.240(6) 1.555(5) 0.124(3) 0.066(11) Uiso 1 1 d . . .
C6 C -0.1872(8) 1.2710(6) 0.2057(3) 0.0652(10) Uani 1 1 d . . .
H6A H -0.282(8) 1.348(7) 0.227(3) 0.101(18) Uiso 1 1 d . . .
H6B H -0.094(8) 1.300(7) 0.207(3) 0.11(2) Uiso 1 1 d . . .
H6C H -0.158(8) 1.155(8) 0.237(4) 0.13(2) Uiso 1 1 d . . .
C7 C -0.2089(8) 1.0860(5) 0.1023(3) 0.0679(11) Uani 1 1 d . . .
H7A H -0.087(10) 1.014(8) 0.078(4) 0.15(2) Uiso 1 1 d . . .
H7B H -0.293(10) 1.082(7) 0.064(4) 0.14(2) Uiso 1 1 d . . .
H7C H -0.272(9) 1.057(7) 0.143(4) 0.13(2) Uiso 1 1 d . . .
N1 N -0.2140(4) 1.2484(3) 0.11894(17) 0.0490(6) Uani 1 1 d . . .
C8 C -0.2102(4) 1.6160(4) 0.43469(19) 0.0435(7) Uani 1 1 d . . .
C9 C -0.3146(5) 1.6637(4) 0.5130(2) 0.0485(8) Uani 1 1 d . . .
H9 H -0.354(5) 1.764(5) 0.528(2) 0.065(12) Uiso 1 1 d . . .
C10 C -0.3454(5) 1.5504(4) 0.5681(2) 0.0487(8) Uani 1 1 d . . .
H10 H -0.417(5) 1.578(4) 0.620(2) 0.054(9) Uiso 1 1 d . . .
N4 N -0.2806(4) 1.3905(4) 0.55108(18) 0.0482(7) Uani 1 1 d . . .
H4' H -0.303(6) 1.328(5) 0.585(3) 0.069(13) Uiso 1 1 d . . .
C11 C -0.1799(5) 1.3388(4) 0.4784(2) 0.0508(8) Uani 1 1 d . . .
H11 H -0.140(5) 1.230(4) 0.471(2) 0.056(10) Uiso 1 1 d . . .
C12 C -0.1439(5) 1.4452(4) 0.4200(2) 0.0487(8) Uani 1 1 d . . .
H12 H -0.078(5) 1.408(4) 0.370(2) 0.059(10) Uiso 1 1 d . . .
N3 N -0.1749(4) 1.7269(4) 0.37968(18) 0.0542(7) Uani 1 1 d . . .
C13 C -0.0684(8) 1.6800(8) 0.2995(3) 0.0738(12) Uani 1 1 d . . .
H13A H -0.136(10) 1.660(8) 0.256(4) 0.15(2) Uiso 1 1 d . . .
H13B H 0.024(8) 1.577(7) 0.297(3) 0.11(2) Uiso 1 1 d . . .
H13C H -0.015(9) 1.750(7) 0.282(4) 0.13(2) Uiso 1 1 d . . .
C14 C -0.2600(9) 1.9036(6) 0.3935(4) 0.0786(13) Uani 1 1 d . . .
H14A H -0.392(12) 1.944(9) 0.393(5) 0.17(3) Uiso 1 1 d . . .
H14B H -0.226(7) 1.933(6) 0.440(3) 0.090(16) Uiso 1 1 d . . .
H14C H -0.226(10) 1.961(8) 0.344(4) 0.16(3) 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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Cu Cl4 149.29(5) . . ?
Cl2 Cu Cl3 93.53(3) . . ?
Cl4 Cu Cl3 94.92(3) . . ?
Cl2 Cu Cl1 93.53(3) . . ?
Cl4 Cu Cl1 93.67(3) . . ?
Cl3 Cu Cl1 150.14(4) . . ?
N1 C1 C5 122.2(3) . . ?
N1 C1 C2 122.7(3) . . ?
C5 C1 C2 115.1(3) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 118(2) . . ?
C1 C2 H2 121(2) . . ?
N2 C3 C2 121.6(3) . . ?
N2 C3 H3 117(2) . . ?
C2 C3 H3 122(2) . . ?
C3 N2 C4 120.6(3) . . ?
C3 N2 H2' 120(3) . . ?
C4 N2 H2' 119(3) . . ?
N2 C4 C5 121.0(3) . . ?
N2 C4 H4 112(2) . . ?
C5 C4 H4 127(2) . . ?
C4 C5 C1 121.4(3) . . ?
C4 C5 H5 115(3) . . ?
C1 C5 H5 123(3) . . ?
N1 C6 H6A 112(3) . . ?
N1 C6 H6B 110(4) . . ?
H6A C6 H6B 106(5) . . ?
N1 C6 H6C 105(3) . . ?
H6A C6 H6C 113(5) . . ?
H6B C6 H6C 111(5) . . ?
N1 C7 H7A 112(4) . . ?
N1 C7 H7B 118(4) . . ?
H7A C7 H7B 102(5) . . ?
N1 C7 H7C 108(4) . . ?
H7A C7 H7C 125(5) . . ?
H7B C7 H7C 90(5) . . ?
C1 N1 C6 121.4(3) . . ?
C1 N1 C7 122.3(3) . . ?
C6 N1 C7 116.3(3) . . ?
N3 C8 C12 122.9(3) . . ?
N3 C8 C9 121.6(3) . . ?
C12 C8 C9 115.5(3) . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 118(3) . . ?
C8 C9 H9 121(3) . . ?
N4 C10 C9 121.4(3) . . ?
N4 C10 H10 116(2) . . ?
C9 C10 H10 123(2) . . ?
C10 N4 C11 120.2(3) . . ?
C10 N4 H4' 118(3) . . ?
C11 N4 H4' 122(3) . . ?
N4 C11 C12 121.8(3) . . ?
N4 C11 H11 116(2) . . ?
C12 C11 H11 123(2) . . ?
C11 C12 C8 120.3(3) . . ?
C11 C12 H12 121(2) . . ?
C8 C12 H12 119(2) . . ?
C8 N3 C14 121.1(3) . . ?
C8 N3 C13 122.1(3) . . ?
C14 N3 C13 116.4(4) . . ?
N3 C13 H13A 116(4) . . ?
N3 C13 H13B 118(3) . . ?
H13A C13 H13B 92(5) . . ?
N3 C13 H13C 110(4) . . ?
H13A C13 H13C 113(5) . . ?
H13B C13 H13C 107(5) . . ?
N3 C14 H14A 110(4) . . ?
N3 C14 H14B 115(3) . . ?
H14A C14 H14B 111(5) . . ?
N3 C14 H14C 107(4) . . ?
H14A C14 H14C 103(5) . . ?
H14B C14 H14C 109(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu Cl2 2.2467(9) . ?
Cu Cl4 2.2466(9) . ?
Cu Cl3 2.2556(9) . ?
Cu Cl1 2.2636(8) . ?
C1 N1 1.329(4) . ?
C1 C5 1.418(4) . ?
C1 C2 1.425(4) . ?
C2 C3 1.353(5) . ?
C2 H2 0.86(3) . ?
C3 N2 1.336(5) . ?
C3 H3 0.85(4) . ?
N2 C4 1.341(5) . ?
N2 H2' 0.75(4) . ?
C4 C5 1.345(5) . ?
C4 H4 0.94(4) . ?
C5 H5 0.85(4) . ?
C6 N1 1.460(5) . ?
C6 H6A 0.84(6) . ?
C6 H6B 0.86(6) . ?
C6 H6C 1.04(6) . ?
C7 N1 1.460(5) . ?
C7 H7A 0.97(7) . ?
C7 H7B 0.94(7) . ?
C7 H7C 0.86(6) . ?
C8 N3 1.344(4) . ?
C8 C12 1.413(5) . ?
C8 C9 1.422(5) . ?
C9 C10 1.346(5) . ?
C9 H9 0.86(4) . ?
C10 N4 1.334(4) . ?
C10 H10 0.95(4) . ?
N4 C11 1.342(5) . ?
N4 H4' 0.80(4) . ?
C11 C12 1.349(5) . ?
C11 H11 0.90(3) . ?
C12 H12 0.91(4) . ?
N3 C14 1.452(6) . ?
N3 C13 1.453(5) . ?
C13 H13A 0.98(7) . ?
C13 H13B 0.90(5) . ?
C13 H13C 0.88(6) . ?
C14 H14A 0.93(8) . ?
C14 H14B 0.90(5) . ?
C14 H14C 0.97(7) . ?
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
_geom_hbond_site_symmetry_A
N2 H2' Cl1 0.75(4) 2.60(4) 3.238(3) 145(4) 2_585
N2 H2' Cl4 0.75(4) 2.68(4) 3.277(3) 138(4) 2_585
N4 H4' Cl2 0.80(4) 2.63(4) 3.261(3) 137(4) 2_576
N4 H4' Cl3 0.80(4) 2.60(4) 3.281(3) 144(4) 2_576
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 178.3(3) . . . . ?
C5 C1 C2 C3 -1.1(5) . . . . ?
C1 C2 C3 N2 1.1(5) . . . . ?
C2 C3 N2 C4 -1.1(5) . . . . ?
C3 N2 C4 C5 1.0(6) . . . . ?
N2 C4 C5 C1 -1.0(5) . . . . ?
N1 C1 C5 C4 -178.3(3) . . . . ?
C2 C1 C5 C4 1.0(5) . . . . ?
C5 C1 N1 C6 -3.6(5) . . . . ?
C2 C1 N1 C6 177.1(4) . . . . ?
C5 C1 N1 C7 179.5(4) . . . . ?
C2 C1 N1 C7 0.1(5) . . . . ?
N3 C8 C9 C10 -178.6(3) . . . . ?
C12 C8 C9 C10 0.1(5) . . . . ?
C8 C9 C10 N4 -0.4(5) . . . . ?
C9 C10 N4 C11 1.0(5) . . . . ?
C10 N4 C11 C12 -1.2(5) . . . . ?
N4 C11 C12 C8 0.8(5) . . . . ?
N3 C8 C12 C11 178.4(3) . . . . ?
C9 C8 C12 C11 -0.3(5) . . . . ?
C12 C8 N3 C14 174.3(4) . . . . ?
C9 C8 N3 C14 -7.1(5) . . . . ?
C12 C8 N3 C13 1.3(5) . . . . ?
C9 C8 N3 C13 180.0(4) . . . . ?
