##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4
_journal_date_recd_electronic     2011-04-19
_journal_date_accepted     2011-04-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      6
_journal_page_first     m725
_journal_page_last     m726
_journal_paper_category     QM
_journal_coeditor_code     WM2484
_publ_contact_author_name     'Bond, Marcus R.'
_publ_contact_author_address
;
Department of Chemistry
Southeast Missouri State University
Cape Girardeau, MO 63701
;
_publ_contact_author_email     'bond@mbond2.st.semo.edu'
_publ_contact_author_fax     '(573)-986-6433'
_publ_contact_author_phone     '(573-651-2580'
_publ_section_title
;
Bis(1-methylpiperidinium) tetrachloridocuprate(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'Reynolds, Bryan J.'
;
Department of Chemistry
Southeast Missouri State University
Cape Girardeau, MO 63701
USA
;
    'Bond, Marcus R.'
;
Department of Chemistry
Southeast Missouri State University
Cape Girardeau, MO 63701
USA
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4
_chemical_name_systematic
;
Bis(1-methylpiperidinium) tetrachloridocuprate(II)
;
_chemical_formula_moiety     '2(C6 H14 N1 +), Cl4 Cu1 2-'
_chemical_formula_sum     'C12 H28 Cl4 Cu N2'
_chemical_formula_iupac     '(C6 H14 N)2 [Cu Cl4]'
_chemical_formula_weight     405.7
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     12.2264(2)
_cell_length_b     11.3442(2)
_cell_length_c     13.3455(2)
_cell_angle_alpha     90
_cell_angle_beta     96.8650(10)
_cell_angle_gamma     90
_cell_volume     1837.73(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8818
_cell_measurement_theta_min     0.998
_cell_measurement_theta_max     35.631
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.23
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.466
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     844
_exptl_absorpt_coefficient_mu     1.76
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min     0.628
_exptl_absorpt_correction_T_max     0.694
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_device     '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     16568
_diffrn_reflns_av_R_equivalents     0.026
_diffrn_reflns_theta_min     3.97
_diffrn_reflns_theta_max     35.63
_diffrn_reflns_theta_full     35.63
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_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
;
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     8453
_reflns_number_gt     6647
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0482
_refine_ls_R_factor_gt     0.0299
_refine_ls_wR_factor_gt     0.061
_refine_ls_wR_factor_ref     0.0668
_refine_ls_goodness_of_fit_ref     1.05
_refine_ls_restrained_S_all     1.05
_refine_ls_number_reflns     8453
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0249P)²+0.6467P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.006
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.573
_refine_diff_density_min     -0.579
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0017(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'COLLECT (Hooft, 1998)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and ORTEPIII (Burnett & Johnson,
1996)
;
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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_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_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
