#------------------------------------------------------------------------------
#$Date: 2016-03-23 04:03:07 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179275 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/95/4319582.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_4319582
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           15
_symmetry_cell_setting           monoclinic
_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                 113.861(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.973(3)
_cell_length_b                   12.522(3)
_cell_length_c                   14.523(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1991.3(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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4923
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    1.636
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             924
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0012(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0334
_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)+(0.0565P)²+2.1873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                1599
_reflns_number_total             1698
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic000613c_2.cif
_cod_data_source_block           201sht-yellow
_cod_database_code               4319582
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.0000 -0.54895(3) 0.2500 0.0448(2) Uani 1 2 d S . .
Cl1 Cl 0.07959(8) -0.43059(6) 0.17751(7) 0.0639(3) Uani 1 1 d . . .
Cl2 Cl 0.15631(6) -0.66564(5) 0.29206(5) 0.0527(2) Uani 1 1 d . . .
C1 C 0.3817(2) -0.3689(2) 0.50118(19) 0.0456(6) Uani 1 1 d . . .
C2 C 0.2919(3) -0.4504(2) 0.4778(2) 0.0553(7) Uani 1 1 d . . .
H2 H 0.273(3) -0.492(3) 0.426(3) 0.063(9) Uiso 1 1 d . . .
C3 C 0.2311(3) -0.4656(3) 0.5368(3) 0.0652(9) Uani 1 1 d . . .
H3 H 0.174(4) -0.513(4) 0.519(3) 0.090(13) Uiso 1 1 d . . .
N2 N 0.2508(3) -0.4048(3) 0.6174(2) 0.0644(7) Uani 1 1 d . . .
H2' H 0.216(4) -0.417(3) 0.648(3) 0.073(12) Uiso 1 1 d . . .
C4 C 0.3327(3) -0.3260(3) 0.6418(2) 0.0595(8) Uani 1 1 d . . .
H4 H 0.346(3) -0.291(3) 0.699(3) 0.077(11) Uiso 1 1 d . . .
C5 C 0.3982(3) -0.3066(2) 0.5870(2) 0.0530(7) Uani 1 1 d . . .
H5 H 0.448(3) -0.259(3) 0.603(2) 0.054(9) Uiso 1 1 d . . .
N1 N 0.4457(2) -0.3524(2) 0.44578(18) 0.0557(6) Uani 1 1 d . . .
C6 C 0.5403(3) -0.2708(3) 0.4734(3) 0.0743(10) Uani 1 1 d . . .
H6A H 0.5463 -0.2359 0.5341 0.111 Uiso 1 1 calc R . .
H6B H 0.5198 -0.2192 0.4201 0.111 Uiso 1 1 calc R . .
H6C H 0.6171 -0.3034 0.4842 0.111 Uiso 1 1 calc R . .
C7 C 0.4223(4) -0.4128(3) 0.3537(2) 0.0737(9) Uani 1 1 d . . .
H7A H 0.3586 -0.4639 0.3434 0.111 Uiso 1 1 calc R . .
H7B H 0.4954 -0.4493 0.3597 0.111 Uiso 1 1 calc R . .
H7C H 0.3975 -0.3647 0.2975 0.111 Uiso 1 1 calc R . .
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
Cu Cu Cl1 0(6) 2 2 ?
Cu Cu Cl1 0(10) 2 . ?
Cl1 Cu Cl1 97.22(5) 2 . ?
Cu Cu Cl2 0(10) 2 2 ?
Cl1 Cu Cl2 95.26(3) 2 2 ?
Cl1 Cu Cl2 139.91(3) . 2 ?
Cu Cu Cl2 0(10) 2 . ?
Cl1 Cu Cl2 139.91(3) 2 . ?
Cl1 Cu Cl2 95.26(3) . . ?
Cl2 Cu Cl2 99.23(5) 2 . ?
Cu Cl1 Cu 0.000(16) 2 . ?
Cu Cl2 Cu 0.0 2 . ?
N1 C1 C5 122.5(3) . . ?
N1 C1 C2 122.1(3) . . ?
C5 C1 C2 115.4(3) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 117(2) . . ?
C1 C2 H2 123(2) . . ?
N2 C3 C2 122.0(3) . . ?
N2 C3 H3 120(3) . . ?
C2 C3 H3 118(3) . . ?
C4 N2 C3 120.3(3) . . ?
C4 N2 H2' 122(3) . . ?
C3 N2 H2' 118(3) . . ?
N2 C4 C5 121.2(3) . . ?
N2 C4 H4 116(2) . . ?
C5 C4 H4 122(2) . . ?
C4 C5 C1 121.0(3) . . ?
C4 C5 H5 120(2) . . ?
C1 C5 H5 119(2) . . ?
C1 N1 C6 121.0(3) . . ?
C1 N1 C7 121.9(3) . . ?
C6 N1 C7 117.0(3) . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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 Cu 0.0000(9) 2 ?
Cu Cl1 2.2416(8) 2 ?
Cu Cl1 2.2416(8) . ?
Cu Cl2 2.2552(8) 2 ?
Cu Cl2 2.2552(8) . ?
Cl1 Cu 2.2416(8) 2 ?
Cl2 Cu 2.2552(8) 2 ?
C1 N1 1.332(4) . ?
C1 C5 1.416(4) . ?
C1 C2 1.420(4) . ?
C2 C3 1.342(5) . ?
C2 H2 0.87(4) . ?
C3 N2 1.335(5) . ?
C3 H3 0.86(5) . ?
N2 C4 1.334(5) . ?
N2 H2' 0.73(4) . ?
C4 C5 1.346(5) . ?
C4 H4 0.90(4) . ?
C5 H5 0.81(3) . ?
N1 C6 1.457(4) . ?
N1 C7 1.461(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
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 0.73(4) 2.66(4) 3.265(3) 141(4) 6_546
N2 H2' Cl2 0.73(4) 2.68(4) 3.289(3) 142(4) 6_546
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
Cl1 Cu Cl1 Cu 0.0(14) 2 . . 2 ?
Cl2 Cu Cl1 Cu 0(41) 2 . . 2 ?
Cl2 Cu Cl1 Cu 0(75) . . . 2 ?
Cl1 Cu Cl2 Cu 0(8) 2 . . 2 ?
Cl1 Cu Cl2 Cu 0(29) . . . 2 ?
Cl2 Cu Cl2 Cu 0(47) 2 . . 2 ?
N1 C1 C2 C3 178.7(3) . . . . ?
C5 C1 C2 C3 -1.4(4) . . . . ?
C1 C2 C3 N2 1.0(5) . . . . ?
C2 C3 N2 C4 0.1(5) . . . . ?
C3 N2 C4 C5 -0.8(5) . . . . ?
N2 C4 C5 C1 0.3(5) . . . . ?
N1 C1 C5 C4 -179.4(3) . . . . ?
C2 C1 C5 C4 0.7(4) . . . . ?
C5 C1 N1 C6 2.3(4) . . . . ?
C2 C1 N1 C6 -177.8(3) . . . . ?
C5 C1 N1 C7 -176.0(3) . . . . ?
C2 C1 N1 C7 3.9(4) . . . . ?
