#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/84/2228467.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_2228467
loop_
_publ_author_name
'Wei, Bin'
_publ_section_title
;
 1-Cyanomethyl-1,4-diazoniabicyclo[2.2.2]octane
 tetrachloridocuprate(II)
;
_journal_coeditor_code           NC2197
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1625
_journal_paper_doi               10.1107/S1600536810047501
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '(C8 H15 N3) [Cu Cl4]'
_chemical_formula_moiety         'C8 H15 N3 2+, Cl4 Cu 2-'
_chemical_formula_sum            'C8 H15 Cl4 Cu N3'
_chemical_formula_weight         358.57
_chemical_name_systematic
;
1-Cyanomethyl-1,4-diazoniabicyclo[2.2.2]octane tetrachloridocuprate(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 96.501(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2714(6)
_cell_length_b                   13.6585(8)
_cell_length_c                   12.1636(10)
_cell_measurement_reflns_used    3825
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4894
_cell_measurement_theta_min      2.4784
_cell_volume                     1365.35(17)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_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  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14635
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    2.359
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.001
_refine_diff_density_min         -0.998
_refine_ls_extinction_coef       0.0055(11)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0416
_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)+(0.0585P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                2307
_reflns_number_total             3123
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            nc2197.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228467
_cod_database_fobs_code          2228467
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
Cu Cu1 0.72905(6) 0.23247(4) -0.01548(4) 0.02929(17) Uani d . 1 . .
Cl Cl2 0.51578(11) 0.14877(7) 0.04825(7) 0.0260(2) Uani d . 1 . .
Cl Cl3 0.74393(12) 0.25165(8) -0.19747(8) 0.0354(3) Uani d . 1 . .
Cl Cl4 0.95764(12) 0.14720(8) 0.03958(8) 0.0352(3) Uani d . 1 . .
Cl Cl1 0.67871(13) 0.38977(7) 0.02896(9) 0.0358(3) Uani d . 1 . .
N N1 0.3987(4) 0.3497(2) 0.1903(3) 0.0289(7) Uani d . 1 . .
H H1C 0.4947 0.3162 0.1788 0.035 Uiso d R 1 . .
C C8 -0.0796(5) 0.5439(3) 0.2033(3) 0.0309(9) Uani d . 1 . .
C C3 0.3247(5) 0.2807(3) 0.2658(3) 0.0314(9) Uani d . 1 . .
H H3A 0.3944 0.2750 0.3352 0.038 Uiso calc R 1 . .
H H3B 0.3131 0.2163 0.2322 0.038 Uiso calc R 1 . .
N N2 0.1337(3) 0.4183(2) 0.2368(2) 0.0230(7) Uani d . 1 . .
C C1 0.2879(5) 0.3613(3) 0.0877(3) 0.0338(9) Uani d . 1 . .
H H1A 0.2638 0.2978 0.0543 0.041 Uiso calc R 1 . .
H H1B 0.3394 0.4012 0.0356 0.041 Uiso calc R 1 . .
C C7 -0.0253(5) 0.4565(3) 0.2655(3) 0.0321(9) Uani d . 1 . .
H H7A -0.1071 0.4058 0.2514 0.039 Uiso calc R 1 . .
H H7B -0.0153 0.4715 0.3440 0.039 Uiso calc R 1 . .
C C5 0.4289(5) 0.4464(3) 0.2451(4) 0.0372(10) Uani d . 1 . .
H H5A 0.4701 0.4923 0.1940 0.045 Uiso calc R 1 . .
H H5B 0.5097 0.4397 0.3089 0.045 Uiso calc R 1 . .
N N3 -0.1269(5) 0.6094(3) 0.1516(3) 0.0440(10) Uani d . 1 . .
C C2 0.1332(5) 0.4093(4) 0.1134(3) 0.0405(11) Uani d . 1 . .
H H2A 0.0405 0.3705 0.0830 0.049 Uiso calc R 1 . .
H H2B 0.1237 0.4737 0.0798 0.049 Uiso calc R 1 . .
C C6 0.2706(5) 0.4844(3) 0.2810(4) 0.0479(12) Uani d . 1 . .
H H6A 0.2783 0.4865 0.3611 0.057 Uiso calc R 1 . .
H H6B 0.2501 0.5503 0.2531 0.057 Uiso calc R 1 . .
C C4 0.1615(5) 0.3192(3) 0.2863(4) 0.0451(12) Uani d . 1 . .
H H4A 0.0774 0.2749 0.2544 0.054 Uiso calc R 1 . .
H H4B 0.1552 0.3226 0.3654 0.054 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl3 Cu1 Cl4 . . 102.42(4) ?
Cl3 Cu1 Cl1 . . 99.01(4) ?
Cl4 Cu1 Cl1 . . 126.09(5) ?
Cl3 Cu1 Cl2 . . 121.19(4) ?
Cl4 Cu1 Cl2 . . 106.93(4) ?
Cl1 Cu1 Cl2 . . 102.79(4) ?
C1 N1 C5 . . 110.0(3) ?
C1 N1 C3 . . 109.3(3) ?
C5 N1 C3 . . 110.2(3) ?
C1 N1 H1C . . 112.4 ?
C5 N1 H1C . . 113.4 ?
C3 N1 H1C . . 101.2 ?
N3 C8 C7 . . 176.8(4) ?
N1 C3 C4 . . 108.7(3) ?
N1 C3 H3A . . 110.0 ?
C4 C3 H3A . . 110.0 ?
N1 C3 H3B . . 110.0 ?
C4 C3 H3B . . 110.0 ?
H3A C3 H3B . . 108.3 ?
C4 N2 C7 . . 108.9(3) ?
C4 N2 C6 . . 109.1(3) ?
C7 N2 C6 . . 110.8(3) ?
C4 N2 C2 . . 108.2(3) ?
C7 N2 C2 . . 111.0(3) ?
C6 N2 C2 . . 108.8(3) ?
N1 C1 C2 . . 109.5(3) ?
N1 C1 H1A . . 109.8 ?
C2 C1 H1A . . 109.8 ?
N1 C1 H1B . . 109.8 ?
C2 C1 H1B . . 109.8 ?
H1A C1 H1B . . 108.2 ?
C8 C7 N2 . . 113.1(3) ?
C8 C7 H7A . . 109.0 ?
N2 C7 H7A . . 109.0 ?
C8 C7 H7B . . 109.0 ?
N2 C7 H7B . . 109.0 ?
H7A C7 H7B . . 107.8 ?
N1 C5 C6 . . 109.0(3) ?
N1 C5 H5A . . 109.9 ?
C6 C5 H5A . . 109.9 ?
N1 C5 H5B . . 109.9 ?
C6 C5 H5B . . 109.9 ?
H5A C5 H5B . . 108.3 ?
C1 C2 N2 . . 109.7(3) ?
C1 C2 H2A . . 109.7 ?
N2 C2 H2A . . 109.7 ?
C1 C2 H2B . . 109.7 ?
N2 C2 H2B . . 109.7 ?
H2A C2 H2B . . 108.2 ?
N2 C6 C5 . . 109.4(3) ?
N2 C6 H6A . . 109.8 ?
C5 C6 H6A . . 109.8 ?
N2 C6 H6B . . 109.8 ?
C5 C6 H6B . . 109.8 ?
H6A C6 H6B . . 108.2 ?
N2 C4 C3 . . 110.7(3) ?
N2 C4 H4A . . 109.5 ?
C3 C4 H4A . . 109.5 ?
N2 C4 H4B . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 108.1 ?
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 Cl3 . 2.2463(11) ?
Cu1 Cl4 . 2.2568(10) ?
Cu1 Cl1 . 2.2655(11) ?
Cu1 Cl2 . 2.3085(10) ?
N1 C1 . 1.471(5) ?
N1 C5 . 1.488(5) ?
N1 C3 . 1.495(5) ?
N1 H1C . 0.9405 ?
C8 N3 . 1.137(5) ?
C8 C7 . 1.458(6) ?
C3 C4 . 1.496(5) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
N2 C4 . 1.488(5) ?
N2 C7 . 1.492(4) ?
N2 C6 . 1.499(5) ?
N2 C2 . 1.506(5) ?
C1 C2 . 1.502(5) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C5 C6 . 1.518(6) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
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
N1 H1C Cl3 4_566 0.94 2.58 3.325(3) 136.0
N1 H1C Cl1 . 0.94 2.70 3.247(3) 118.0
N1 H1C Cl2 . 0.94 2.80 3.441(3) 126.1
