#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/05/2230517.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_2230517
loop_
_publ_author_name
'Reynolds, Bryan J.'
'Bond, Marcus R.'
_publ_section_title
;
 Bis(1-methylpiperidinium) tetrachloridocuprate(II)
;
_journal_coeditor_code           WM2484
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m725
_journal_page_last               m726
_journal_paper_doi               10.1107/S1600536811016382
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '(C6 H14 N)2 [Cu Cl4]'
_chemical_formula_moiety         '2(C6 H14 N1 +), Cl4 Cu1 2-'
_chemical_formula_sum            'C12 H28 Cl4 Cu N2'
_chemical_formula_weight         405.7
_chemical_name_systematic
;
Bis(1-methylpiperidinium) tetrachloridocuprate(II)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 96.8650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2264(2)
_cell_length_b                   11.3442(2)
_cell_length_c                   13.3455(2)
_cell_measurement_reflns_used    8818
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.631
_cell_measurement_theta_min      0.998
_cell_volume                     1837.73(5)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and ORTEPIII (Burnett & Johnson,
1996)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16568
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        35.63
_diffrn_reflns_theta_max         35.63
_diffrn_reflns_theta_min         3.97
_exptl_absorpt_coefficient_mu    1.76
_exptl_absorpt_correction_T_max  0.694
_exptl_absorpt_correction_T_min  0.628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.579
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         8453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0249P)²+0.6467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.061
_refine_ls_wR_factor_ref         0.0668
_reflns_number_gt                6647
_reflns_number_total             8453
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wm2484.cif
_cod_data_source_block           I
_cod_database_code               2230517
_cod_database_fobs_code          2230517
loop_
_space_group_symop_operation_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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.251677(12) 0.415201(12) 0.299141(10) 0.01376(4) Uani d . 1 1 . .
Cl Cl1 0.06546(2) 0.42579(2) 0.25734(2) 0.01674(5) Uani d . 1 1 . .
Cl Cl2 0.27180(2) 0.52180(2) 0.44100(2) 0.01610(5) Uani d . 1 1 . .
Cl Cl3 0.30403(3) 0.43621(3) 0.14382(2) 0.02020(6) Uani d . 1 1 . .
Cl Cl4 0.35629(3) 0.25748(3) 0.34713(2) 0.01954(6) Uani d . 1 1 . .
N N11 0.07370(8) 0.22960(9) 0.08737(7) 0.01501(17) Uani d . 1 1 . .
H H11 0.0798(13) 0.2956(15) 0.1244(12) 0.020(4) Uiso d . 1 1 . .
C C11 0.14106(11) 0.13720(12) 0.14522(10) 0.0219(2) Uani d . 1 1 . .
H H11A 0.1456(15) 0.0723(16) 0.1014(13) 0.028(5) Uiso d . 1 1 . .
H H11B 0.2116(14) 0.1704(15) 0.1677(12) 0.024(4) Uiso d . 1 1 . .
H H11C 0.1045(16) 0.1151(17) 0.2025(15) 0.037(5) Uiso d . 1 1 . .
C C12 -0.04575(10) 0.19611(12) 0.07114(10) 0.0206(2) Uani d . 1 1 . .
H H12A -0.0483(14) 0.1249(16) 0.0391(12) 0.023(4) Uiso d . 1 1 . .
H H12B -0.0671(14) 0.1811(15) 0.1347(13) 0.024(4) Uiso d . 1 1 . .
C C13 -0.11317(11) 0.29197(12) 0.01392(10) 0.0211(2) Uani d . 1 1 . .
H H13A -0.1880(15) 0.2688(15) 0.0042(13) 0.026(4) Uiso d . 1 1 . .
H H13B -0.1108(14) 0.3600(16) 0.0564(13) 0.026(4) Uiso d . 1 1 . .
C C14 -0.07016(12) 0.32027(14) -0.08588(10) 0.0264(3) Uani d . 1 1 . .
H H14A -0.0764(15) 0.2522(17) -0.1302(14) 0.033(5) Uiso d . 1 1 . .
H H14B -0.1129(15) 0.3849(17) -0.1173(14) 0.033(5) Uiso d . 1 1 . .
C C15 0.05150(12) 0.35232(14) -0.06641(11) 0.0275(3) Uani d . 1 1 . .
H H15A 0.0813(15) 0.3663(17) -0.1260(14) 0.031(5) Uiso d . 1 1 . .
H H15B 0.0616(17) 0.4262(18) -0.0268(15) 0.040(5) Uiso d . 1 1 . .
C C16 0.11738(11) 0.25462(11) -0.01073(9) 0.0190(2) Uani d . 1 1 . .
H H16A 0.1110(13) 0.1833(14) -0.0472(11) 0.017(4) Uiso d . 1 1 . .
H H16B 0.1918(14) 0.2742(14) 0.0066(12) 0.019(4) Uiso d . 1 1 . .
N N21 0.51192(8) 0.25190(9) 0.15565(8) 0.01564(18) Uani d . 1 1 . .
H H21 0.4620(13) 0.2945(14) 0.1731(12) 0.017(4) Uiso d . 1 1 . .
C C21 0.45664(12) 0.14160(12) 0.11569(11) 0.0232(2) Uani d . 1 1 . .
H H21A 0.5108(15) 0.0891(16) 0.0926(14) 0.030(5) Uiso d . 1 1 . .
H H21B 0.4240(16) 0.1038(17) 0.1704(15) 0.036(5) Uiso d . 1 1 . .
H H21C 0.4060(14) 0.1605(16) 0.0588(13) 0.028(4) Uiso d . 1 1 . .
C C22 0.55885(11) 0.31840(12) 0.07359(9) 0.0203(2) Uani d . 1 1 . .
H H22A 0.6091(13) 0.2664(14) 0.0498(12) 0.020(4) Uiso d . 1 1 . .
H H22B 0.4995(15) 0.3324(16) 0.0233(13) 0.027(4) Uiso d . 1 1 . .
C C23 0.61029(13) 0.43323(12) 0.11370(11) 0.0259(3) Uani d . 1 1 . .
H H23A 0.6408(16) 0.4715(17) 0.0596(14) 0.034(5) Uiso d . 1 1 . .
H H23B 0.5515(15) 0.4840(16) 0.1296(13) 0.030(5) Uiso d . 1 1 . .
C C24 0.69579(12) 0.41383(14) 0.20480(11) 0.0276(3) Uani d . 1 1 . .
H H24A 0.7614(16) 0.3662(18) 0.1844(14) 0.039(5) Uiso d . 1 1 . .
H H24B 0.7199(17) 0.491(2) 0.2345(15) 0.045(6) Uiso d . 1 1 . .
C C25 0.64709(12) 0.34239(14) 0.28531(10) 0.0256(3) Uani d . 1 1 . .
H H25A 0.7000(15) 0.3232(16) 0.3397(13) 0.030(5) Uiso d . 1 1 . .
H H25B 0.5928(15) 0.3843(16) 0.3125(13) 0.025(4) Uiso d . 1 1 . .
C C26 0.59873(11) 0.22741(12) 0.24265(9) 0.0206(2) Uani d . 1 1 . .
H H26A 0.6515(13) 0.1796(14) 0.2156(11) 0.019(4) Uiso d . 1 1 . .
H H26B 0.5624(13) 0.1821(14) 0.2901(12) 0.018(4) Uiso d . 1 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 0 '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
Cl1 Cu1 Cl2 . . 100.615(11) yes
Cl1 Cu1 Cl3 . . 98.880(12) yes
Cl1 Cu1 Cl4 . . 128.967(13) yes
Cl2 Cu1 Cl3 . . 135.003(13) yes
Cl2 Cu1 Cl4 . . 100.840(12) yes
Cl3 Cu1 Cl4 . . 97.568(12) yes
C11 N11 C16 . . 110.68(10) ?
C11 N11 C12 . . 111.41(10) ?
C16 N11 C12 . . 111.37(10) ?
C11 N11 H11 . . 107.3(10) ?
C16 N11 H11 . . 108.0(10) ?
C12 N11 H11 . . 107.9(10) ?
N11 C11 H11A . . 107.3(11) ?
N11 C11 H11B . . 107.9(10) ?
H11A C11 H11B . . 112.6(15) ?
N11 C11 H11C . . 108.3(12) ?
H11A C11 H11C . . 110.8(16) ?
H11B C11 H11C . . 109.9(15) ?
N11 C12 C13 . . 110.66(10) ?
N11 C12 H12A . . 105.7(11) ?
C13 C12 H12A . . 114.4(11) ?
N11 C12 H12B . . 106.7(10) ?
C13 C12 H12B . . 113.3(10) ?
H12A C12 H12B . . 105.4(15) ?
C12 C13 C14 . . 111.60(11) ?
C12 C13 H13A . . 109.2(10) ?
C14 C13 H13A . . 111.6(10) ?
C12 C13 H13B . . 107.7(10) ?
C14 C13 H13B . . 111.1(10) ?
H13A C13 H13B . . 105.4(14) ?
C15 C14 C13 . . 109.47(11) ?
C15 C14 H14A . . 107.4(11) ?
C13 C14 H14A . . 110.8(11) ?
C15 C14 H14B . . 111.1(11) ?
C13 C14 H14B . . 108.3(11) ?
H14A C14 H14B . . 109.9(15) ?
C16 C15 C14 . . 111.15(12) ?
C16 C15 H15A . . 107.8(12) ?
C14 C15 H15A . . 111.8(11) ?
C16 C15 H15B . . 109.5(12) ?
C14 C15 H15B . . 110.5(12) ?
H15A C15 H15B . . 106.0(16) ?
N11 C16 C15 . . 110.09(10) ?
N11 C16 H16A . . 105.8(9) ?
C15 C16 H16A . . 111.7(9) ?
N11 C16 H16B . . 105.4(10) ?
C15 C16 H16B . . 113.0(10) ?
H16A C16 H16B . . 110.4(13) ?
C21 N21 C22 . . 110.98(10) ?
C21 N21 C26 . . 111.69(10) ?
C22 N21 C26 . . 111.15(10) ?
C21 N21 H21 . . 105.7(11) ?
C22 N21 H21 . . 105.7(11) ?
C26 N21 H21 . . 111.4(11) ?
N21 C21 H21A . . 109.4(11) ?
N21 C21 H21B . . 108.1(11) ?
H21A C21 H21B . . 109.0(15) ?
N21 C21 H21C . . 108.8(11) ?
H21A C21 H21C . . 106.9(15) ?
H21B C21 H21C . . 114.5(16) ?
N21 C22 C23 . . 110.69(10) ?
N21 C22 H22A . . 104.8(10) ?
C23 C22 H22A . . 113.6(10) ?
N21 C22 H22B . . 106.0(11) ?
C23 C22 H22B . . 111.0(11) ?
H22A C22 H22B . . 110.3(14) ?
C22 C23 C24 . . 111.97(12) ?
C22 C23 H23A . . 107.8(11) ?
C24 C23 H23A . . 112.2(11) ?
C22 C23 H23B . . 107.6(11) ?
C24 C23 H23B . . 111.7(10) ?
H23A C23 H23B . . 105.3(15) ?
C23 C24 C25 . . 110.59(12) ?
C23 C24 H24A . . 110.3(11) ?
C25 C24 H24A . . 106.9(11) ?
C23 C24 H24B . . 109.7(12) ?
C25 C24 H24B . . 108.0(12) ?
H24A C24 H24B . . 111.3(16) ?
C26 C25 C24 . . 111.17(11) ?
C26 C25 H25A . . 107.1(11) ?
C24 C25 H25A . . 112.2(11) ?
C26 C25 H25B . . 108.9(11) ?
C24 C25 H25B . . 111.3(11) ?
H25A C25 H25B . . 106.1(15) ?
N21 C26 C25 . . 109.82(11) ?
N21 C26 H26A . . 105.2(9) ?
C25 C26 H26A . . 112.5(10) ?
N21 C26 H26B . . 105.5(9) ?
C25 C26 H26B . . 113.7(9) ?
H26A C26 H26B . . 109.5(13) ?
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 Cl1 . 2.2816(3) yes
Cu1 Cl2 . 2.2351(3) yes
Cu1 Cl3 . 2.2539(3) yes
Cu1 Cl4 . 2.2475(3) yes
N11 C11 . 1.4904(16) ?
N11 C16 . 1.4990(15) ?
N11 C12 . 1.4995(16) ?
N11 H11 . 0.895(17) ?
C11 H11A . 0.946(18) ?
C11 H11B . 0.957(17) ?
C11 H11C . 0.96(2) ?
C12 C13 . 1.5148(18) ?
C12 H12A . 0.913(18) ?
C12 H12B . 0.932(17) ?
C13 C14 . 1.5233(19) ?
C13 H13A . 0.946(18) ?
C13 H13B . 0.956(18) ?
C14 C15 . 1.523(2) ?
C14 H14A . 0.970(19) ?
C14 H14B . 0.966(19) ?
C15 C16 . 1.5121(19) ?
C15 H15A . 0.927(18) ?
C15 H15B . 0.99(2) ?
C16 H16A . 0.943(16) ?
C16 H16B . 0.938(16) ?
N21 C21 . 1.4903(16) ?
N21 C22 . 1.4992(16) ?
N21 C26 . 1.5024(16) ?
N21 H21 . 0.833(16) ?
C21 H21A . 0.968(19) ?
C21 H21B . 0.97(2) ?
C21 H21C . 0.945(18) ?
C22 C23 . 1.5160(19) ?
C22 H22A . 0.934(17) ?
C22 H22B . 0.941(18) ?
C23 C24 . 1.522(2) ?
C23 H23A . 0.955(19) ?
C23 H23B . 0.964(19) ?
C24 C25 . 1.523(2) ?
C24 H24A . 1.03(2) ?
C24 H24B . 0.99(2) ?
C25 C26 . 1.515(2) ?
C25 H25A . 0.938(18) ?
C25 H25B . 0.925(18) ?
C26 H26A . 0.948(16) ?
C26 H26B . 0.964(16) ?
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
_geom_hbond_publ_flag
N11 H11 Cl1 . 0.895(16) 2.331(16) 3.1880(10) 160.0(10) yes
N21 H21 Cl3 . 0.833(17) 2.508(16) 3.2800(10) 155.0(10) yes
N21 H21 Cl4 . 0.833(17) 2.821(17) 3.3640(10) 125.0(10) yes
