##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2004-10-06
_journal_date_accepted     2004-10-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue     11
_journal_page_first     m1662
_journal_page_last     m1663
_journal_paper_category     EM
_publ_contact_author_name     'Prof. Bohari M. Yamin'
_publ_contact_author_address
;
      X-ray Crystallography Laboratory
      School of Chemical Sciences and Food Technology
      Universiti Kebangsaan Malaysia
      43600 Bangi, Selangor
      MALAYSIA
;
_publ_contact_author_email     bohari@pkrisc.cc.ukm.my
_publ_contact_author_fax     '6 03 89292410 '
_publ_contact_author_phone     '6 03 89293880'
_publ_section_title
;
(N-Ethyl-N-propyldithiocarbamato)triphenyltin(IV)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Sanuddin, M.' ?
;
School of Chemical Sciences and Food Technology
Universiti Kebangsaan Malaysia
43600 Bangi
Selangor
Malaysia
;
    'Farina, Yang' ?
;
School of Chemical Sciences and Food Technology
Universiti Kebangsaan Malaysia
43600 Bangi
Selangor
Malaysia
;
    'Yamin, Bohari M.' ?
;
School of Chemical Sciences and Food Technology
Universiti Kebangsaan Malaysia
43600 Bangi
Selangor
Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(N-Ethyl-N-propyldithiocarbamato)triphenyltin(IV)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H27 N S2 Sn'
_chemical_formula_sum     'C24 H27 N S2 Sn'
_chemical_formula_iupac     '[Sn (C6 H5)3 (C6 H12 N S2)]'
_chemical_formula_weight     512.28
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     9.4395(18)
_cell_length_b     26.225(5)
_cell_length_c     9.8059(19)
_cell_angle_alpha     90.00
_cell_angle_beta     98.954(3)
_cell_angle_gamma     90.00
_cell_volume     2397.9(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     983
_cell_measurement_theta_min     2.2
_cell_measurement_theta_max     26.5
_cell_measurement_temperature     273(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.29
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.419
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1040
_exptl_absorpt_coefficient_mu     1.249
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.648
_exptl_absorpt_correction_T_max     0.825
_exptl_special_details
;
;
_diffrn_ambient_temperature     273(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     83.66
_diffrn_reflns_number     13102
_diffrn_reflns_av_R_equivalents     0.0166
_diffrn_reflns_av_sigmaI/netI     0.0200
_diffrn_reflns_theta_min     2.2
_diffrn_reflns_theta_max     26.5
_diffrn_reflns_theta_full     26.5
_diffrn_measured_fraction_theta_max     0.99
_diffrn_measured_fraction_theta_full     0.99
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -22
_diffrn_reflns_limit_k_max     32
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
;
_reflns_number_total     4928
_reflns_number_gt     4481
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.032
_refine_ls_R_factor_gt     0.028
_refine_ls_wR_factor_gt     0.061
_refine_ls_wR_factor_ref     0.063
_refine_ls_goodness_of_fit_ref     1.14
_refine_ls_restrained_S_all     1.14
_refine_ls_number_reflns     4928
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0247P)²+0.9515P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.45
_refine_diff_density_min     -0.23
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Sn' 'Sn' -0.6537 1.4246
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1997)'
_computing_cell_refinement     'SAINT (Siemens, 1997)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement     SHELXTL
_computing_molecular_graphics     SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
loop_
    _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
    _atom_site_type_symbol
    Sn1 0.634073(16) 0.081382(6) 0.208680(16) 0.04317(6) Uani d . 1 . . Sn
    S1 0.81744(7) 0.12090(2) 0.38232(7) 0.05446(16) Uani d . 1 . . S
    S2 0.57525(8) 0.19172(3) 0.29688(8) 0.06112(18) Uani d . 1 . . S
    N1 0.8206(2) 0.21815(8) 0.4522(2) 0.0531(5) Uani d . 1 . . N
    C1 0.7417(3) 0.18211(9) 0.3820(2) 0.0469(5) Uani d . 1 . . C
    C2 0.7685(4) 0.27123(10) 0.4540(3) 0.0695(8) Uani d . 1 . . C
    H2A 0.7098 0.2788 0.3661 0.083 Uiso calc R 1 . . H
    H2B 0.8500 0.2942 0.4650 0.083 Uiso calc R 1 . . H
    C3 0.6823(4) 0.28072(13) 0.5680(4) 0.0886(11) Uani d . 1 . . C
    H3A 0.5997 0.2588 0.5560 0.133 Uiso calc R 1 . . H
    H3B 0.6518 0.3157 0.5654 0.133 Uiso calc R 1 . . H
    H3C 0.7402 0.2737 0.6554 0.133 Uiso calc R 1 . . H
    C4 0.9661(3) 0.20913(11) 0.5261(3) 0.0578(6) Uani d . 1 . . C
    H4A 0.9747 0.1737 0.5547 0.069 Uiso calc R 1 . . H
    H4B 0.9813 0.2301 0.6086 0.069 Uiso calc R 1 . . H
    C5 1.0805(3) 0.22104(13) 0.4395(3) 0.0726(8) Uani d . 1 . . C
    H5A 1.0722 0.2565 0.4110 0.087 Uiso calc R 1 . . H
    H5B 1.0656 0.2001 0.3570 0.087 Uiso calc R 1 . . H
    C6 1.2293(4) 0.21159(15) 0.5169(4) 0.0921(11) Uani d . 1 . . C
    H6A 1.2458 0.2332 0.5968 0.138 Uiso calc R 1 . . H
    H6B 1.2988 0.2190 0.4579 0.138 Uiso calc R 1 . . H
    H6C 1.2380 0.1765 0.5452 0.138 Uiso calc R 1 . . H
    C7 0.5182(3) 0.10838(11) -0.0919(3) 0.0645(7) Uani d . 1 . . C
    H7 0.4365 0.0921 -0.0719 0.077 Uiso calc R 1 . . H
    C8 0.5217(5) 0.12657(13) -0.2244(3) 0.0880(11) Uani d . 1 . . C
    H8 0.4426 0.1220 -0.2927 0.106 Uiso calc R 1 . . H
    C9 0.6399(6) 0.15095(14) -0.2548(4) 0.0959(14) Uani d . 1 . . C
    H9 0.6417 0.1629 -0.3438 0.115 Uiso calc R 1 . . H
    C10 0.7564(5) 0.15796(14) -0.1543(4) 0.0921(12) Uani d . 1 . . C
    H10 0.8367 0.1751 -0.1749 0.110 Uiso calc R 1 . . H
    C11 0.7551(3) 0.13957(12) -0.0224(3) 0.0707(8) Uani d . 1 . . C
    H11 0.8350 0.1441 0.0450 0.085 Uiso calc R 1 . . H
    C12 0.6354(3) 0.11436(9) 0.0102(3) 0.0491(6) Uani d . 1 . . C
    C13 0.8031(3) -0.00604(10) 0.0932(3) 0.0552(6) Uani d . 1 . . C
    H13 0.7854 0.0130 0.0123 0.066 Uiso calc R 1 . . H
    C14 0.8820(3) -0.05091(12) 0.0954(3) 0.0697(8) Uani d . 1 . . C
    H14 0.9175 -0.0615 0.0167 0.084 Uiso calc R 1 . . H
    C15 0.9073(4) -0.07926(11) 0.2130(4) 0.0745(9) Uani d . 1 . . C
    H15 0.9591 -0.1095 0.2143 0.089 Uiso calc R 1 . . H
    C16 0.8566(3) -0.06344(12) 0.3296(3) 0.0693(8) Uani d . 1 . . C
    H16 0.8745 -0.0828 0.4100 0.083 Uiso calc R 1 . . H
    C17 0.7789(3) -0.01881(10) 0.3274(3) 0.0545(6) Uani d . 1 . . C
    H17 0.7448 -0.0084 0.4070 0.065 Uiso calc R 1 . . H
    C18 0.7506(2) 0.01074(9) 0.2093(2) 0.0431(5) Uani d . 1 . . C
    C19 0.4292(2) 0.06185(10) 0.2598(2) 0.0459(5) Uani d . 1 . . C
    C20 0.4001(3) 0.01084(10) 0.2769(3) 0.0564(6) Uani d . 1 . . C
    H20 0.4717 -0.0133 0.2739 0.068 Uiso calc R 1 . . H
    C21 0.2649(3) -0.00480(12) 0.2986(3) 0.0665(7) Uani d . 1 . . C
    H21 0.2470 -0.0392 0.3107 0.080 Uiso calc R 1 . . H
    C22 0.1585(3) 0.02988(13) 0.3022(3) 0.0666(8) Uani d . 1 . . C
    H22 0.0679 0.0192 0.3162 0.080 Uiso calc R 1 . . H
    C23 0.1853(3) 0.08044(13) 0.2853(4) 0.0736(9) Uani d . 1 . . C
    H23 0.1127 0.1042 0.2875 0.088 Uiso calc R 1 . . H
    C25 0.3201(3) 0.09647(12) 0.2647(3) 0.0652(7) Uani d . 1 . . C
    H25 0.3374 0.1310 0.2541 0.078 Uiso calc R 1 . . H
_geom_special_details
;
?
;
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
    Sn1 S1 . 2.4600(7) yes
    Sn1 S2 . 3.0950(10) yes
    Sn1 C12 . 2.132(2) yes
    Sn1 C19 . 2.134(2) yes
    Sn1 C18 . 2.154(2) yes
    S1 C1 . 1.757(2) yes
    S2 C1 . 1.679(3) yes
    N1 C1 . 1.328(3) yes
    N1 C4 . 1.469(3) yes
    N1 C2 . 1.478(3) yes
    C2 C3 . 1.502(5) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 H3A . 0.9600 ?
    C3 H3B . 0.9600 ?
    C3 H3C . 0.9600 ?
    C4 C5 . 1.506(4) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 C6 . 1.510(5) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C7 C12 . 1.380(4) ?
    C7 C8 . 1.389(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.359(6) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.370(6) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.382(5) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.389(4) ?
    C11 H11 . 0.9300 ?
    C13 C18 . 1.383(3) ?
    C13 C14 . 1.391(4) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.362(5) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.370(5) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.380(4) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.384(3) ?
    C17 H17 . 0.9300 ?
    C19 C25 . 1.379(4) ?
    C19 C20 . 1.381(4) ?
    C20 C21 . 1.387(4) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.360(4) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.365(4) ?
    C22 H22 . 0.9300 ?
    C23 C25 . 1.384(4) ?
    C23 H23 . 0.9300 ?
    C25 H25 . 0.9300 ?
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
    C12 Sn1 C19 . . 116.49(9) yes
    C12 Sn1 C18 . . 106.03(9) yes
    C19 Sn1 C18 . . 105.89(9) yes
    C12 Sn1 S1 . . 110.95(7) yes
    C19 Sn1 S1 . . 120.29(7) yes
    C18 Sn1 S1 . . 93.23(6) yes
    C18 Sn1 S2 . . 156.50(6) yes
    C1 S1 Sn1 . . 98.11(8) ?
    C1 N1 C4 . . 123.2(2) ?
    C1 N1 C2 . . 121.0(2) ?
    C4 N1 C2 . . 115.7(2) ?
    N1 C1 S2 . . 123.86(19) ?
    N1 C1 S1 . . 116.98(19) ?
    S2 C1 S1 . . 119.15(14) ?
    N1 C2 C3 . . 112.7(3) ?
    N1 C2 H2A . . 109.1 ?
    C3 C2 H2A . . 109.1 ?
    N1 C2 H2B . . 109.1 ?
    C3 C2 H2B . . 109.1 ?
    H2A C2 H2B . . 107.8 ?
    C2 C3 H3A . . 109.5 ?
    C2 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 109.5 ?
    C2 C3 H3C . . 109.5 ?
    H3A C3 H3C . . 109.5 ?
    H3B C3 H3C . . 109.5 ?
    N1 C4 C5 . . 112.7(2) ?
    N1 C4 H4A . . 109.1 ?
    C5 C4 H4A . . 109.1 ?
    N1 C4 H4B . . 109.1 ?
    C5 C4 H4B . . 109.1 ?
    H4A C4 H4B . . 107.8 ?
    C4 C5 C6 . . 112.0(3) ?
    C4 C5 H5A . . 109.2 ?
    C6 C5 H5A . . 109.2 ?
    C4 C5 H5B . . 109.2 ?
    C6 C5 H5B . . 109.2 ?
    H5A C5 H5B . . 107.9 ?
    C5 C6 H6A . . 109.5 ?
    C5 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C5 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    C12 C7 C8 . . 120.5(3) ?
    C12 C7 H7 . . 119.8 ?
    C8 C7 H7 . . 119.8 ?
    C9 C8 C7 . . 120.4(4) ?
    C9 C8 H8 . . 119.8 ?
    C7 C8 H8 . . 119.8 ?
    C8 C9 C10 . . 120.0(3) ?
    C8 C9 H9 . . 120.0 ?
    C10 C9 H9 . . 120.0 ?
    C9 C10 C11 . . 120.2(4) ?
    C9 C10 H10 . . 119.9 ?
    C11 C10 H10 . . 119.9 ?
    C10 C11 C12 . . 120.5(3) ?
    C10 C11 H11 . . 119.7 ?
    C12 C11 H11 . . 119.7 ?
    C7 C12 C11 . . 118.4(3) ?
    C7 C12 Sn1 . . 119.9(2) ?
    C11 C12 Sn1 . . 121.6(2) ?
    C18 C13 C14 . . 121.1(3) ?
    C18 C13 H13 . . 119.5 ?
    C14 C13 H13 . . 119.5 ?
    C15 C14 C13 . . 119.8(3) ?
    C15 C14 H14 . . 120.1 ?
    C13 C14 H14 . . 120.1 ?
    C14 C15 C16 . . 120.2(3) ?
    C14 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C15 C16 C17 . . 119.9(3) ?
    C15 C16 H16 . . 120.1 ?
    C17 C16 H16 . . 120.1 ?
    C16 C17 C18 . . 121.4(3) ?
    C16 C17 H17 . . 119.3 ?
    C18 C17 H17 . . 119.3 ?
    C13 C18 C17 . . 117.6(2) ?
    C13 C18 Sn1 . . 121.30(18) ?
    C17 C18 Sn1 . . 121.06(17) ?
    C25 C19 C20 . . 118.0(2) ?
    C25 C19 Sn1 . . 124.0(2) ?
    C20 C19 Sn1 . . 117.78(18) ?
    C19 C20 C21 . . 120.7(3) ?
    C19 C20 H20 . . 119.7 ?
    C21 C20 H20 . . 119.7 ?
    C22 C21 C20 . . 120.5(3) ?
    C22 C21 H21 . . 119.8 ?
    C20 C21 H21 . . 119.8 ?
    C21 C22 C23 . . 119.6(3) ?
    C21 C22 H22 . . 120.2 ?
    C23 C22 H22 . . 120.2 ?
    C22 C23 C25 . . 120.3(3) ?
    C22 C23 H23 . . 119.8 ?
    C25 C23 H23 . . 119.8 ?
    C19 C25 C23 . . 120.9(3) ?
    C19 C25 H25 . . 119.6 ?
    C23 C25 H25 . . 119.6 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    C2 H2A S2 . . 1_555 0.97 2.65 3.029(3) 104 no
    C4 H4A S1 . . 1_555 0.97 2.49 2.949(3) 109 no
    C25 H25 S2 . . 1_555 0.93 2.73 3.450(3) 135 no
    C4 H4B S2 . . 4_666 0.97 2.81 3.745(3) 162 no
