#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/60/2236094.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_2236094
loop_
_publ_author_name
'Sathiyaraj, E.'
'Thirumaran, S.'
'Selvanayagam, S.'
_publ_section_title
;
 Bis[N-benzyl-N-(2-phenylethyl)dithiocarbamato-κ²S,S']lead(II)
;
_journal_coeditor_code           BT5972
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1217
_journal_paper_doi               10.1107/S1600536812036161
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Pb (C16 H16 N S2)2]'
_chemical_formula_moiety         'C32 H32 N2 Pb S4'
_chemical_formula_sum            'C32 H32 N2 Pb S4'
_chemical_formula_weight         780.03
_chemical_name_systematic
;
Bis[N-benzyl-N-(2-phenylethyl)dithiocarbamato-
κ²S,S']lead(II)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 101.600(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.5467(12)
_cell_length_b                   5.5321(2)
_cell_length_c                   19.4158(8)
_cell_measurement_reflns_used    5527
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      1.5
_cell_volume                     3003.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEXII area-detector'
_diffrn_measurement_method       'ω and φ scans'
_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  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13027
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.920
_exptl_absorpt_correction_T_max  0.3839
_exptl_absorpt_correction_T_min  0.3839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.432
_refine_diff_density_min         -1.251
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0278
_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)+(0.0254P)²+1.6570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0622
_reflns_number_gt                3006
_reflns_number_total             3711
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5972.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2236094
_cod_database_fobs_code          2236094
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Pb Pb1 1.0000 1.14280(3) 0.7500 0.05084(8) Uani d S 1 2
S S1 0.99115(3) 0.94809(17) 0.61154(4) 0.04494(19) Uani d . 1 1
S S2 0.93213(3) 0.80487(16) 0.71424(4) 0.0473(2) Uani d . 1 1
N N1 0.92789(9) 0.5899(4) 0.59107(12) 0.0373(6) Uani d . 1 1
C C1 0.94871(10) 0.7651(6) 0.63419(14) 0.0339(6) Uani d . 1 1
C C2 0.94211(11) 0.5417(6) 0.52408(15) 0.0440(7) Uani d . 1 1
H H2A 0.9397 0.3691 0.5153 0.053 Uiso calc R 1 1
H H2B 0.9755 0.5862 0.5287 0.053 Uiso calc R 1 1
C C3 0.91358(11) 0.6706(5) 0.46061(15) 0.0343(6) Uani d . 1 1
C C4 0.88722(12) 0.8758(5) 0.46490(17) 0.0427(7) Uani d . 1 1
H H4 0.8853 0.9369 0.5089 0.051 Uiso calc R 1 1
C C5 0.86360(12) 0.9926(6) 0.40547(17) 0.0498(8) Uani d . 1 1
H H5 0.8460 1.1317 0.4095 0.060 Uiso calc R 1 1
C C6 0.86593(13) 0.9041(7) 0.34018(18) 0.0571(10) Uani d . 1 1
H H6 0.8501 0.9832 0.2999 0.069 Uiso calc R 1 1
C C7 0.89154(14) 0.6993(8) 0.33484(17) 0.0569(10) Uani d . 1 1
H H7 0.8931 0.6391 0.2906 0.068 Uiso calc R 1 1
C C8 0.91528(12) 0.5799(6) 0.39433(16) 0.0453(8) Uani d . 1 1
H H8 0.9323 0.4393 0.3900 0.054 Uiso calc R 1 1
C C9 0.89245(11) 0.4222(6) 0.61033(17) 0.0419(7) Uani d . 1 1
H H9A 0.8957 0.4225 0.6610 0.050 Uiso calc R 1 1
H H9B 0.8992 0.2598 0.5962 0.050 Uiso calc R 1 1
C C10 0.84215(12) 0.4865(8) 0.5771(2) 0.0612(10) Uani d . 1 1
H H10A 0.8382 0.4756 0.5264 0.073 Uiso calc R 1 1
H H10B 0.8360 0.6523 0.5888 0.073 Uiso calc R 1 1
C C11 0.80629(12) 0.3225(6) 0.60110(19) 0.0492(8) Uani d . 1 1
C C12 0.78865(14) 0.1181(7) 0.5636(2) 0.0564(9) Uani d . 1 1
H H12 0.8000 0.0762 0.5236 0.068 Uiso calc R 1 1
C C13 0.75473(12) -0.0232(7) 0.58444(19) 0.0542(9) Uani d . 1 1
H H13 0.7434 -0.1599 0.5585 0.065 Uiso calc R 1 1
C C14 0.73735(13) 0.0338(7) 0.6428(2) 0.0579(9) Uani d . 1 1
H H14 0.7137 -0.0608 0.6561 0.070 Uiso calc R 1 1
C C15 0.75511(14) 0.2325(8) 0.68166(19) 0.0629(10) Uani d . 1 1
H H15 0.7439 0.2719 0.7220 0.075 Uiso calc R 1 1
C C16 0.78937(14) 0.3730(6) 0.6612(2) 0.0584(10) Uani d . 1 1
H H16 0.8015 0.5057 0.6885 0.070 Uiso calc R 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 0.0000 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 '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
S2 Pb1 S2 2_756 . 91.59(4)
S2 Pb1 S1 2_756 2_756 64.61(2)
S2 Pb1 S1 . 2_756 84.46(2)
S2 Pb1 S1 2_756 . 84.46(2)
S2 Pb1 S1 . . 64.61(2)
S1 Pb1 S1 2_756 . 135.74(4)
C1 S1 Pb1 . . 85.08(10)
C1 S2 Pb1 . . 90.43(11)
C1 N1 C2 . . 121.3(3)
C1 N1 C9 . . 122.5(2)
C2 N1 C9 . . 116.0(2)
N1 C1 S1 . . 121.2(2)
N1 C1 S2 . . 119.2(2)
S1 C1 S2 . . 119.63(17)
N1 C2 C3 . . 116.0(2)
N1 C2 H2A . . 108.3
C3 C2 H2A . . 108.3
N1 C2 H2B . . 108.3
C3 C2 H2B . . 108.3
H2A C2 H2B . . 107.4
C4 C3 C8 . . 118.4(3)
C4 C3 C2 . . 123.5(3)
C8 C3 C2 . . 118.1(3)
C3 C4 C5 . . 121.3(3)
C3 C4 H4 . . 119.3
C5 C4 H4 . . 119.3
C6 C5 C4 . . 120.0(3)
C6 C5 H5 . . 120.0
C4 C5 H5 . . 120.0
C7 C6 C5 . . 119.5(3)
C7 C6 H6 . . 120.2
C5 C6 H6 . . 120.2
C6 C7 C8 . . 120.9(3)
C6 C7 H7 . . 119.6
C8 C7 H7 . . 119.6
C7 C8 C3 . . 119.8(3)
C7 C8 H8 . . 120.1
C3 C8 H8 . . 120.1
N1 C9 C10 . . 112.9(3)
N1 C9 H9A . . 109.0
C10 C9 H9A . . 109.0
N1 C9 H9B . . 109.0
C10 C9 H9B . . 109.0
H9A C9 H9B . . 107.8
C9 C10 C11 . . 112.1(3)
C9 C10 H10A . . 109.2
C11 C10 H10A . . 109.2
C9 C10 H10B . . 109.2
C11 C10 H10B . . 109.2
H10A C10 H10B . . 107.9
C16 C11 C12 . . 117.3(3)
C16 C11 C10 . . 121.0(3)
C12 C11 C10 . . 121.7(3)
C13 C12 C11 . . 121.1(3)
C13 C12 H12 . . 119.5
C11 C12 H12 . . 119.5
C14 C13 C12 . . 120.8(3)
C14 C13 H13 . . 119.6
C12 C13 H13 . . 119.6
C13 C14 C15 . . 119.2(3)
C13 C14 H14 . . 120.4
C15 C14 H14 . . 120.4
C16 C15 C14 . . 120.1(3)
C16 C15 H15 . . 119.9
C14 C15 H15 . . 119.9
C15 C16 C11 . . 121.5(3)
C15 C16 H16 . . 119.2
C11 C16 H16 . . 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Pb1 S2 2_756 2.6813(8)
Pb1 S2 . 2.6813(8)
Pb1 S1 2_756 2.8597(9)
Pb1 S1 . 2.8597(9)
S1 C1 . 1.703(3)
S2 C1 . 1.727(3)
N1 C1 . 1.339(4)
N1 C2 . 1.463(4)
N1 C9 . 1.475(4)
C2 C3 . 1.512(4)
C2 H2A . 0.9700
C2 H2B . 0.9700
C3 C4 . 1.373(4)
C3 C8 . 1.391(4)
C4 C5 . 1.375(4)
C4 H4 . 0.9300
C5 C6 . 1.373(5)
C5 H5 . 0.9300
C6 C7 . 1.363(5)
C6 H6 . 0.9300
C7 C8 . 1.384(5)
C7 H7 . 0.9300
C8 H8 . 0.9300
C9 C10 . 1.494(4)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 C11 . 1.510(5)
C10 H10A . 0.9700
C10 H10B . 0.9700
C11 C16 . 1.378(5)
C11 C12 . 1.384(5)
C12 C13 . 1.368(5)
C12 H12 . 0.9300
C13 C14 . 1.362(5)
C13 H13 . 0.9300
C14 C15 . 1.372(6)
C14 H14 . 0.9300
C15 C16 . 1.369(5)
C15 H15 . 0.9300
C16 H16 . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C9 H9A S2 0.97 2.49 2.986(3) 112
C2 H2B S1 0.97 2.55 2.990(4) 107
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
S2 Pb1 S1 C1 2_756 91.43(10)
S2 Pb1 S1 C1 . -2.98(10)
S1 Pb1 S1 C1 2_756 47.21(10)
S2 Pb1 S2 C1 2_756 -80.18(10)
S1 Pb1 S2 C1 2_756 -144.48(10)
S1 Pb1 S2 C1 . 2.93(10)
C2 N1 C1 S1 . 2.6(4)
C9 N1 C1 S1 . 177.5(2)
C2 N1 C1 S2 . -177.3(2)
C9 N1 C1 S2 . -2.4(4)
Pb1 S1 C1 N1 . -175.1(2)
Pb1 S1 C1 S2 . 4.81(16)
Pb1 S2 C1 N1 . 174.8(2)
Pb1 S2 C1 S1 . -5.11(17)
C1 N1 C2 C3 . -92.9(3)
C9 N1 C2 C3 . 91.9(3)
N1 C2 C3 C4 . 20.9(5)
N1 C2 C3 C8 . -160.9(3)
C8 C3 C4 C5 . -1.1(5)
C2 C3 C4 C5 . 177.0(3)
C3 C4 C5 C6 . 0.3(5)
C4 C5 C6 C7 . 0.4(5)
C5 C6 C7 C8 . -0.1(6)
C6 C7 C8 C3 . -0.8(5)
C4 C3 C8 C7 . 1.4(5)
C2 C3 C8 C7 . -176.9(3)
C1 N1 C9 C10 . 101.6(3)
C2 N1 C9 C10 . -83.3(3)
N1 C9 C10 C11 . -176.3(3)
C9 C10 C11 C16 . 87.0(4)
C9 C10 C11 C12 . -93.8(4)
C16 C11 C12 C13 . 1.9(5)
C10 C11 C12 C13 . -177.3(3)
C11 C12 C13 C14 . 0.1(5)
C12 C13 C14 C15 . -1.5(6)
C13 C14 C15 C16 . 1.0(6)
C14 C15 C16 C11 . 1.1(6)
C12 C11 C16 C15 . -2.5(5)
C10 C11 C16 C15 . 176.7(4)
