#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/04/2220480.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_2220480
loop_
_publ_author_name
'Fan, Le-Qing'
_publ_section_title
(2,2'-Bipyridine-κ²N,N')iodido(piperidine-1-carbodithioato-κ²S,S')copper(II)
_journal_coeditor_code           EZ2153
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m6
_journal_paper_doi               10.1107/S1600536808039901
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (C6 H10 N S2) I (C10 H8 N2)]'
_chemical_formula_moiety         'C16 H18 Cu I N3 S2'
_chemical_formula_sum            'C16 H18 Cu I N3 S2'
_chemical_formula_weight         506.89
_chemical_name_systematic
;
(2,2'-Bipyridine-κ²N,N')iodido(piperidine-1-
carbodithioato-κ²S,S')copper(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                 108.047(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.532(3)
_cell_length_b                   16.859(7)
_cell_length_c                   17.578(7)
_cell_measurement_reflns_used    3988
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4719
_cell_measurement_theta_min      3.2801
_cell_volume                     1840.5(14)
_computing_cell_refinement       'CrystalClear (Rigaku, 2000)'
_computing_data_collection       'CrystalClear (Rigaku, 2000)'
_computing_data_reduction        'CrystalClear (Rigaku, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13746
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.092
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku,2000)'
_exptl_crystal_colour            Black
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.633
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.043P)²+2.8277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                3389
_reflns_number_total             3946
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2153.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220480
_cod_database_fobs_code          2220480
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 0.43714(10) 0.66212(3) 0.42086(3) 0.04099(17) Uani d . 1 . .
I I1 0.19321(6) 0.80141(2) 0.36188(2) 0.05420(14) Uani d . 1 . .
S S1 0.6396(2) 0.64039(8) 0.33518(8) 0.0502(3) Uani d . 1 . .
S S2 0.2619(3) 0.55763(9) 0.34096(8) 0.0586(4) Uani d . 1 . .
N N1 0.4731(7) 0.5184(2) 0.2378(2) 0.0423(9) Uani d . 1 . .
N N2 0.6611(7) 0.7232(2) 0.5076(2) 0.0401(9) Uani d . 1 . .
N N3 0.3271(7) 0.6421(2) 0.5154(2) 0.0420(9) Uani d . 1 . .
C C1 0.4607(8) 0.5651(3) 0.2965(3) 0.0386(10) Uani d . 1 . .
C C2 0.6306(8) 0.5319(3) 0.1943(3) 0.0496(12) Uani d . 1 . .
H H2A 0.7044 0.4828 0.1907 0.059 Uiso calc R 1 . .
H H2B 0.7370 0.5706 0.2225 0.059 Uiso calc R 1 . .
C C3 0.5104(9) 0.5620(3) 0.1113(3) 0.0556(14) Uani d . 1 . .
H H3A 0.6106 0.5693 0.0811 0.067 Uiso calc R 1 . .
H H3B 0.4459 0.6130 0.1154 0.067 Uiso calc R 1 . .
C C4 0.3347(10) 0.5035(4) 0.0674(3) 0.0620(15) Uani d . 1 . .
H H4A 0.2530 0.5255 0.0160 0.074 Uiso calc R 1 . .
H H4B 0.4004 0.4544 0.0578 0.074 Uiso calc R 1 . .
C C5 0.1852(9) 0.4865(3) 0.1159(3) 0.0533(13) Uani d . 1 . .
H H5A 0.1057 0.5342 0.1194 0.064 Uiso calc R 1 . .
H H5B 0.0822 0.4461 0.0891 0.064 Uiso calc R 1 . .
C C6 0.3075(9) 0.4585(3) 0.1993(3) 0.0499(13) Uani d . 1 . .
H H6A 0.2094 0.4515 0.2304 0.060 Uiso calc R 1 . .
H H6B 0.3757 0.4079 0.1966 0.060 Uiso calc R 1 . .
C C7 0.8254(8) 0.7641(3) 0.4972(3) 0.0464(12) Uani d . 1 . .
H H7A 0.8406 0.7663 0.4464 0.056 Uiso calc R 1 . .
C C8 0.9733(9) 0.8031(3) 0.5591(3) 0.0537(13) Uani d . 1 . .
H H8A 1.0845 0.8323 0.5503 0.064 Uiso calc R 1 . .
C C9 0.9520(10) 0.7979(3) 0.6347(4) 0.0615(16) Uani d . 1 . .
H H9A 1.0515 0.8226 0.6777 0.074 Uiso calc R 1 . .
C C10 0.7829(9) 0.7558(3) 0.6462(3) 0.0553(14) Uani d . 1 . .
H H10A 0.7675 0.7519 0.6969 0.066 Uiso calc R 1 . .
C C11 0.6367(8) 0.7197(3) 0.5814(3) 0.0430(11) Uani d . 1 . .
C C12 0.4453(9) 0.6746(3) 0.5851(3) 0.0417(11) Uani d . 1 . .
C C13 0.3853(10) 0.6676(3) 0.6542(3) 0.0528(13) Uani d . 1 . .
H H13A 0.4662 0.6917 0.7016 0.063 Uiso calc R 1 . .
C C14 0.2037(10) 0.6243(3) 0.6510(3) 0.0587(15) Uani d . 1 . .
H H14A 0.1636 0.6173 0.6970 0.070 Uiso calc R 1 . .
C C15 0.0828(10) 0.5918(3) 0.5800(4) 0.0614(16) Uani d . 1 . .
H H15A -0.0417 0.5634 0.5769 0.074 Uiso calc R 1 . .
C C16 0.1483(9) 0.6016(3) 0.5129(3) 0.0515(13) Uani d . 1 . .
H H16A 0.0661 0.5794 0.4646 0.062 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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 '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
N3 Cu1 N2 . . 79.95(16) ?
N3 Cu1 S1 . . 157.11(12) ?
N2 Cu1 S1 . . 98.30(12) ?
N3 Cu1 S2 . . 97.80(12) ?
N2 Cu1 S2 . . 160.43(12) ?
S1 Cu1 S2 . . 76.17(5) ?
N3 Cu1 I1 . . 97.76(11) ?
N2 Cu1 I1 . . 92.69(11) ?
S1 Cu1 I1 . . 105.13(5) ?
S2 Cu1 I1 . . 106.86(6) ?
C1 S1 Cu1 . . 85.37(16) ?
C1 S2 Cu1 . . 85.37(16) ?
C1 N1 C2 . . 122.3(4) ?
C1 N1 C6 . . 123.4(4) ?
C2 N1 C6 . . 113.3(4) ?
C7 N2 C11 . . 119.4(4) ?
C7 N2 Cu1 . . 125.5(3) ?
C11 N2 Cu1 . . 115.1(3) ?
C16 N3 C12 . . 119.0(4) ?
C16 N3 Cu1 . . 125.6(3) ?
C12 N3 Cu1 . . 115.4(3) ?
N1 C1 S2 . . 123.5(4) ?
N1 C1 S1 . . 123.5(4) ?
S2 C1 S1 . . 113.1(2) ?
N1 C2 C3 . . 108.3(4) ?
N1 C2 H2A . . 110.0 ?
C3 C2 H2A . . 110.0 ?
N1 C2 H2B . . 110.0 ?
C3 C2 H2B . . 110.0 ?
H2A C2 H2B . . 108.4 ?
C2 C3 C4 . . 110.8(4) ?
C2 C3 H3A . . 109.5 ?
C4 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
C5 C4 C3 . . 110.6(4) ?
C5 C4 H4A . . 109.5 ?
C3 C4 H4A . . 109.5 ?
C5 C4 H4B . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 108.1 ?
C6 C5 C4 . . 111.5(5) ?
C6 C5 H5A . . 109.3 ?
C4 C5 H5A . . 109.3 ?
C6 C5 H5B . . 109.3 ?
C4 C5 H5B . . 109.3 ?
H5A C5 H5B . . 108.0 ?
N1 C6 C5 . . 108.8(4) ?
N1 C6 H6A . . 109.9 ?
C5 C6 H6A . . 109.9 ?
N1 C6 H6B . . 109.9 ?
C5 C6 H6B . . 109.9 ?
H6A C6 H6B . . 108.3 ?
N2 C7 C8 . . 122.3(5) ?
N2 C7 H7A . . 118.8 ?
C8 C7 H7A . . 118.8 ?
C7 C8 C9 . . 118.3(6) ?
C7 C8 H8A . . 120.8 ?
C9 C8 H8A . . 120.8 ?
C10 C9 C8 . . 119.9(5) ?
C10 C9 H9A . . 120.1 ?
C8 C9 H9A . . 120.1 ?
C9 C10 C11 . . 119.2(5) ?
C9 C10 H10A . . 120.4 ?
C11 C10 H10A . . 120.4 ?
N2 C11 C10 . . 120.9(5) ?
N2 C11 C12 . . 114.5(4) ?
C10 C11 C12 . . 124.7(5) ?
N3 C12 C13 . . 121.5(5) ?
N3 C12 C11 . . 115.1(4) ?
C13 C12 C11 . . 123.4(5) ?
C14 C13 C12 . . 118.7(5) ?
C14 C13 H13A . . 120.6 ?
C12 C13 H13A . . 120.6 ?
C15 C14 C13 . . 119.6(5) ?
C15 C14 H14A . . 120.2 ?
C13 C14 H14A . . 120.2 ?
C14 C15 C16 . . 119.1(6) ?
C14 C15 H15A . . 120.4 ?
C16 C15 H15A . . 120.4 ?
N3 C16 C15 . . 121.9(5) ?
N3 C16 H16A . . 119.1 ?
C15 C16 H16A . . 119.1 ?
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 N3 . 2.033(4) ?
Cu1 N2 . 2.035(4) ?
Cu1 S1 . 2.3205(15) ?
Cu1 S2 . 2.3218(15) ?
Cu1 I1 . 2.8470(11) ?
S1 C1 . 1.717(5) ?
S2 C1 . 1.716(5) ?
N1 C1 . 1.320(6) ?
N1 C2 . 1.476(6) ?
N1 C6 . 1.482(6) ?
N2 C7 . 1.335(6) ?
N2 C11 . 1.357(6) ?
N3 C16 . 1.342(6) ?
N3 C12 . 1.345(6) ?
C2 C3 . 1.514(7) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.529(7) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.511(8) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.510(7) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.379(7) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.380(8) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.379(9) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.380(7) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.481(7) ?
C12 C13 . 1.392(6) ?
C13 C14 . 1.380(8) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.369(8) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.384(7) ?
C15 H15A . 0.9300 ?
C16 H16A . 0.9300 ?
