#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/36/2013618.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2013618
loop_
_publ_author_name
'Goreshnik, Evgeny'
'Schollmeier, Dieter'
'Mys'kiv, Marian'
_publ_section_title
;
 Influence of Cl/Br substitution on the stereochemical peculiarities of
 copper(I) π-complexes with the 1-allyl-2-aminopyridinium cation
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m478
_journal_page_last               m481
_journal_paper_doi               10.1107/S0108270103021978
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          '(C8 H11 N2)2 [Cu2 Br2.2 Cl1.8]'
_chemical_formula_moiety         'C16 H22 Br2.2 Cl1.8 Cu2 N4'
_chemical_formula_sum            'C16 H22 Br2.2 Cl1.8 Cu2 N4'
_chemical_formula_weight         637.07
_chemical_name_systematic
;
1-allyl-2-aminopyridinium di-μ-(chloro/bromo)-bis[(chloro/bromo)copper(II)]
;
_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                78.096(12)
_cell_angle_beta                 74.172(9)
_cell_angle_gamma                73.642(9)
_cell_formula_units_Z            1
_cell_length_a                   6.8847(5)
_cell_length_b                   8.6835(12)
_cell_length_c                   9.6042(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      74
_cell_measurement_theta_min      65
_cell_volume                     524.80(12)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'Corinc (Dräger, 1971)'
_computing_molecular_graphics    'Diamond (Bergerhoff, 1996)'
_computing_publication_material  'enCIFer (CCDC, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       θ/2ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2262
_diffrn_reflns_theta_full        73.77
_diffrn_reflns_theta_max         73.77
_diffrn_reflns_theta_min         4.83
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    9.58
_exptl_absorpt_correction_T_max  0.414
_exptl_absorpt_correction_T_min  0.180
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(de Meulenaer & Tompa, 1965)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.016
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             311.6
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.72
_refine_diff_density_min         -0.61
_refine_ls_extinction_coef       0.0060(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0359
_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)+(0.0454P)²+0.8022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0971
_refine_ls_wR_factor_ref         0.0973
_reflns_number_gt                2096
_reflns_number_total             2129
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1181.cif
_cod_data_source_block           II
_cod_original_cell_volume        524.80(11)
_cod_database_code               2013618
_cod_database_fobs_code          2013618
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 0.53515(9) 0.50138(7) 0.32042(6) 0.0416(2) Uani d . 1 . . Cu
Br1 0.3842(5) 0.3189(4) 0.2539(3) 0.0433(3) Uani d P 0.793(5) A 1 Br
Cl2 0.2819(8) 0.6755(6) 0.4812(5) 0.055(3) Uani d P 0.692(5) . 1 Cl
Cl1 0.369(5) 0.331(4) 0.271(3) 0.0433(3) Uani d P 0.207(5) A 2 Cl
Br2 0.2834(5) 0.6751(4) 0.4811(4) 0.0307(14) Uani d P 0.308(5) . 2 Br
N1 0.9747(5) 0.7954(3) 0.2562(3) 0.0356(6) Uani d . 1 A . N
C2 0.9176(6) 0.9339(4) 0.3164(4) 0.0369(7) Uani d . 1 . . C
C3 1.0231(7) 1.0576(5) 0.2470(4) 0.0453(9) Uani d . 1 . . C
H3 0.9852 1.1549 0.2848 0.061(14) Uiso calc R 1 . . H
C4 1.1784(7) 1.0351(5) 0.1265(4) 0.0478(9) Uani d . 1 . . C
H4 1.2467 1.1172 0.0821 0.050(12) Uiso calc R 1 . . H
C5 1.2379(6) 0.8895(5) 0.0674(4) 0.0473(9) Uani d . 1 . . C
H5 1.3453 0.8727 -0.0153 0.043(11) Uiso calc R 1 . . H
C6 1.1323(6) 0.7739(5) 0.1357(4) 0.0425(8) Uani d . 1 . . C
H6 1.1694 0.6763 0.0985 0.032(9) Uiso calc R 1 . . H
C7 0.8683(6) 0.6607(4) 0.3182(4) 0.0406(8) Uani d . 1 . . C
H7A 0.7897 0.6734 0.4174 0.052(12) Uiso calc R 1 A . H
H7B 0.9701 0.5575 0.3204 0.060(14) Uiso calc R 1 . . H
C8 0.7242(6) 0.6649(5) 0.2233(4) 0.0415(8) Uani d . 1 A . C
H8 0.6048 0.7487 0.2265 0.10(2) Uiso calc R 1 . . H
C9 0.7587(7) 0.5547(6) 0.1344(4) 0.0528(11) Uani d . 1 A . C
H9A 0.8768 0.4696 0.1290 0.088(14) Uiso calc R 1 . . H
H9B 0.6644 0.5634 0.0783 0.088(14) Uiso calc R 1 . . H
N10 0.7661(6) 0.9546(4) 0.4360(4) 0.0533(9) Uani d . 1 . . N
H10A 0.7576(7) 1.045(4) 0.4617(13) 0.088(14) Uiso d R 1 . . H
H10B 0.705(2) 0.874(4) 0.498(3) 0.088(14) Uiso d R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 Cu1 C9 . 37.40(16) yes
C9 Cu1 Cl1 . 108.7(6) yes
C8 Cu1 Cl1 . 143.6(7) yes
C9 Cu1 Br2 . 130.33(16) yes
C8 Cu1 Br2 . 96.23(14) yes
Cl1 Cu1 Br2 . 107.3(6) yes
C9 Cu1 Br1 . 104.60(13) yes
C8 Cu1 Br1 . 140.07(12) yes
Br2 Cu1 Br1 . 111.43(10) no
C9 Cu1 Cl2 . 130.38(18) no
C8 Cu1 Cl2 . 96.32(17) no
Cl1 Cu1 Cl2 . 107.1(6) no
Br1 Cu1 Cl2 . 111.26(14) no
C9 Cu1 Br2 2_666 109.22(16) ?
C8 Cu1 Br2 2_666 102.66(13) ?
Cl1 Cu1 Br2 2_666 102.6(8) no
Br2 Cu1 Br2 2_666 94.94(11) no
Br1 Cu1 Br2 2_666 102.99(11) no
Cl2 Cu1 Br2 2_666 95.08(13) no
C9 Cu1 Cl2 2_666 109.05(18) ?
C8 Cu1 Cl2 2_666 102.52(16) ?
Cl1 Cu1 Cl2 2_666 102.7(8) no
Br2 Cu1 Cl2 2_666 95.06(15) no
Br1 Cu1 Cl2 2_666 103.05(15) no
Cl2 Cu1 Cl2 2_666 95.20(14) no
Cu1 Cl2 Cu1 2_666 84.80(14) no
Cu1 Br2 Cu1 2_666 85.06(11) no
C2 N1 C6 . 121.0(3) no
C2 N1 C7 . 121.9(3) no
C6 N1 C7 . 117.1(3) no
N10 C2 N1 . 121.3(3) no
N10 C2 C3 . 120.8(3) no
N1 C2 C3 . 117.9(3) no
C4 C3 C2 . 120.5(4) no
C4 C3 H3 . 119.8 no
C2 C3 H3 . 119.8 no
C3 C4 C5 . 120.8(4) no
C3 C4 H4 . 119.6 no
C5 C4 H4 . 119.6 no
C6 C5 C4 . 117.3(4) no
C6 C5 H5 . 121.3 no
C4 C5 H5 . 121.3 no
N1 C6 C5 . 122.5(4) no
N1 C6 H6 . 118.7 no
C5 C6 H6 . 118.7 no
N1 C7 C8 . 108.3(3) no
N1 C7 H7A . 110.0 no
C8 C7 H7A . 110.0 no
N1 C7 H7B . 110.0 no
C8 C7 H7B . 110.0 no
H7A C7 H7B . 108.4 no
C9 C8 C7 . 123.7(4) no
C9 C8 Cu1 . 70.5(2) no
C7 C8 Cu1 . 110.6(2) no
C9 C8 H8 . 118.2 no
C7 C8 H8 . 118.2 no
Cu1 C8 H8 . 88.9 no
C8 C9 Cu1 . 72.1(2) no
C8 C9 H9A . 120.0 no
Cu1 C9 H9A . 109.2 no
C8 C9 H9B . 120.0 no
Cu1 C9 H9B . 88.8 no
H9A C9 H9B . 120.0 no
C2 N10 H10A . 108.5 no
C2 N10 H10B . 126.2 no
H10A N10 H10B . 123.1 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 Br1 . 2.388(3) yes
Cu1 Br2 . 2.385(3) yes
Cu1 Br2 2_666 2.561(4) yes
Cu1 Cl1 . 2.30(3) yes
Cu1 Cl2 . 2.391(5) yes
Cu1 Cl2 2_666 2.567(4) yes
Cu1 C8 . 2.101(3) yes
Cu1 C9 . 2.082(4) yes
N1 C2 . 1.353(5) yes
N1 C6 . 1.357(5) yes
N1 C7 . 1.490(4) yes
C2 N10 . 1.329(5) yes
C2 C3 . 1.416(5) yes
C3 C4 . 1.350(6) yes
C3 H3 . 0.9300 no
C4 C5 . 1.402(6) yes
C4 H4 . 0.9300 no
C5 C6 . 1.359(5) yes
C5 H5 . 0.9300 no
C6 H6 . 0.9300 no
C7 C8 . 1.509(5) yes
C7 H7A . 0.9700 no
C7 H7B . 0.9700 no
C8 C9 . 1.341(6) yes
C8 H8 . 0.9300 no
C9 H9A . 0.9300 no
C9 H9B . 0.9300 no
N10 H10A . 0.8562 no
N10 H10B . 0.9374 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N10 H10A Cl2 2_676 0.86 2.52 3.373(6) 175
N10 H10A Br2 2_676 0.86 2.52 3.374(5) 175
N10 H10B Cl1 2_666 0.94 2.57 3.45(3) 157
N10 H10B Br1 2_666 0.94 2.64 3.516(5) 155
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C9 Cu1 Cl2 Cu1 . 2_666 -120.50(19)
C8 Cu1 Cl2 Cu1 . 2_666 -103.24(15)
Cl1 Cu1 Cl2 Cu1 . 2_666 105.0(8)
Br2 Cu1 Cl2 Cu1 . 2_666 -4E1(7)
Br1 Cu1 Cl2 Cu1 . 2_666 106.19(14)
Br2 Cu1 Cl2 Cu1 2_666 2_666 0.12(19)
Cl2 Cu1 Cl2 Cu1 2_666 2_666 0.0
C9 Cu1 Br2 Cu1 . 2_666 -120.45(18)
C8 Cu1 Br2 Cu1 . 2_666 -103.34(12)
Cl1 Cu1 Br2 Cu1 . 2_666 104.8(8)
Br1 Cu1 Br2 Cu1 . 2_666 106.04(11)
Cl2 Cu1 Br2 Cu1 . 2_666 14E1(7)
Br2 Cu1 Br2 Cu1 2_666 2_666 0.0
Cl2 Cu1 Br2 Cu1 2_666 2_666 -0.13(19)
C6 N1 C2 N10 . . -178.7(3)
C7 N1 C2 N10 . . 1.5(5)
C6 N1 C2 C3 . . 1.9(5)
C7 N1 C2 C3 . . -177.9(3)
N10 C2 C3 C4 . . 179.3(4)
N1 C2 C3 C4 . . -1.3(6)
C2 C3 C4 C5 . . 0.1(6)
C3 C4 C5 C6 . . 0.4(6)
C2 N1 C6 C5 . . -1.4(6)
C7 N1 C6 C5 . . 178.5(3)
C4 C5 C6 N1 . . 0.2(6)
C2 N1 C7 C8 . . 103.2(4)
C6 N1 C7 C8 . . -76.7(4)
N1 C7 C8 C9 . . 108.7(4)
N1 C7 C8 Cu1 . . -171.5(2)
Cl1 Cu1 C8 C9 . . -27.7(14)
Br2 Cu1 C8 C9 . . -158.3(3)
Br1 Cu1 C8 C9 . . -23.7(4)
Cl2 Cu1 C8 C9 . . -158.2(3)
Br2 Cu1 C8 C9 2_666 . 105.2(3)
Cl2 Cu1 C8 C9 2_666 . 105.1(3)
C9 Cu1 C8 C7 . . -119.7(4)
Cl1 Cu1 C8 C7 . . -147.4(13)
Br2 Cu1 C8 C7 . . 82.0(3)
Br1 Cu1 C8 C7 . . -143.4(2)
Cl2 Cu1 C8 C7 . . 82.1(3)
Br2 Cu1 C8 C7 2_666 . -14.5(3)
Cl2 Cu1 C8 C7 2_666 . -14.6(3)
C7 C8 C9 Cu1 . . 102.3(3)
Cl1 Cu1 C9 C8 . . 163.0(9)
Br2 Cu1 C9 C8 . . 28.8(3)
Br1 Cu1 C9 C8 . . 164.6(2)
Cl2 Cu1 C9 C8 . . 29.0(4)
Br2 Cu1 C9 C8 2_666 . -85.8(3)
Cl2 Cu1 C9 C8 2_666 . -85.8(3)
