#------------------------------------------------------------------------------
#$Date: 2017-03-05 08:30:02 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193926 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/20/2242051.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_2242051
loop_
_publ_author_name
'Mohamad, Rapidah'
'Awang, Normah'
'Kamaludin, Nurul F.'
'Jotani, Mukesh M.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Di-n-butylbis[N-(2-methoxyethyl)-N-methyldithiocarbamato-κ²S,S']tin(IV):
 crystal structure and Hirshfeld surface analysis
;
_journal_coeditor_code           HB7654
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              260
_journal_page_last               265
_journal_paper_doi               10.1107/S2056989017001098
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          '[Sn (C4 H9)2 (C5 H10 N O S2)2]'
_chemical_formula_moiety         'C18 H38 N2 O2 S4 Sn'
_chemical_formula_sum            'C18 H38 N2 O2 S4 Sn'
_chemical_formula_weight         561.43
_chemical_name_systematic
Di-n-butylbis[N-(2-methoxyethyl)-N-methyldithiocarbamato-κ²S,S']tin(IV)
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 108.877(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1021(4)
_cell_length_b                   18.0761(8)
_cell_length_c                   10.8809(7)
_cell_measurement_reflns_used    6472
_cell_measurement_temperature    148(2)
_cell_measurement_theta_max      31.3890
_cell_measurement_theta_min      4.4790
_cell_volume                     1321.74(14)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXL97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      148(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device_type
'Agilent Technologies SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10631
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.695
_diffrn_reflns_theta_min         3.778
_exptl_absorpt_coefficient_mu    1.297
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.557
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         4063
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0272
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0308P)²+0.5383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0717
_reflns_number_gt                3712
_reflns_number_total             4063
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7654sup1.cif
_cod_data_source_block           I
_cod_database_code               2242051
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.563
_shelx_estimated_absorpt_t_max   0.625
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn Sn 0.63209(3) 0.2500 0.65708(2) 0.02489(6) Uani d 1 . .
S S1 0.36767(7) 0.15500(2) 0.65625(5) 0.02861(11) Uani d 1 . .
S S2 0.76229(7) 0.09574(3) 0.66305(5) 0.02966(11) Uani d 1 . .
O O1 0.3352(2) -0.06447(9) 0.86623(16) 0.0396(3) Uani d 1 . .
N N1 0.4586(2) 0.01192(8) 0.66892(16) 0.0266(3) Uani d 1 . .
C C1 0.5266(3) 0.08039(10) 0.66318(17) 0.0234(3) Uani d 1 . .
C C2 0.5918(3) -0.05193(11) 0.6850(2) 0.0341(4) Uani d 1 . .
H H2A 0.6388 -0.0555 0.6099 0.051 Uiso calc 1 . .
H H2B 0.5197 -0.0972 0.6916 0.051 Uiso calc 1 . .
H H2C 0.7059 -0.0458 0.7642 0.051 Uiso calc 1 . .
C C3 0.2511(3) -0.00359(11) 0.6614(2) 0.0298(4) Uani d 1 . .
H H3A 0.2103 -0.0516 0.6170 0.036 Uiso calc 1 . .
H H3B 0.1637 0.0351 0.6080 0.036 Uiso calc 1 . .
C C4 0.2207(3) -0.00634(11) 0.7922(2) 0.0325(4) Uani d 1 . .
H H4A 0.2615 0.0413 0.8380 0.039 Uiso calc 1 . .
H H4B 0.0781 -0.0144 0.7807 0.039 Uiso calc 1 . .
C C5 0.2984(4) -0.07280(17) 0.9863(3) 0.0531(7) Uani d 1 . .
H H5A 0.3355 -0.0272 1.0371 0.080 Uiso calc 1 . .
H H5B 0.3776 -0.1141 1.0350 0.080 Uiso calc 1 . .
H H5C 0.1568 -0.0829 0.9697 0.080 Uiso calc 1 . .
C C6 0.8488(4) 0.2500 0.8477(3) 0.0309(6) Uani d 1 A .
H H6A 0.8300 0.2943 0.8959 0.037 Uiso calc 0.5 . .
H H6B 0.8300 0.2057 0.8959 0.037 Uiso calc 0.5 . .
C C7 1.0587(5) 0.2500 0.8393(3) 0.0453(8) Uani d 1 . .
H H7A 1.0830 0.2982 0.8039 0.054 Uiso calc 0.5 A .
H H7B 1.0677 0.2111 0.7773 0.054 Uiso calc 0.5 . .
C C8 1.2246(7) 0.2366(3) 0.9707(5) 0.0471(18) Uani d 0.5 A -1
H H8A 1.1858 0.1960 1.0186 0.056 Uiso calc 0.5 A -1
H H8B 1.3502 0.2226 0.9557 0.056 Uiso calc 0.5 A -1
C C9 1.2526(10) 0.3068(4) 1.0476(7) 0.0674(16) Uiso d 0.5 A -1
H H9A 1.2572 0.3488 0.9916 0.101 Uiso calc 0.5 A -1
H H9B 1.3776 0.3043 1.1202 0.101 Uiso calc 0.5 A -1
H H9C 1.1413 0.3133 1.0813 0.101 Uiso calc 0.5 A -1
C C10 0.6376(4) 0.2500 0.4618(3) 0.0278(5) Uani d 1 B .
H H10A 0.5652 0.2058 0.4167 0.033 Uiso calc 0.5 . .
H H10B 0.5652 0.2942 0.4167 0.033 Uiso calc 0.5 . .
C C11 0.8436(5) 0.2500 0.4497(3) 0.0442(8) Uani d 1 . .
H H11A 0.9132 0.2039 0.4883 0.053 Uiso calc 0.5 B .
H H11B 0.9200 0.2923 0.4994 0.053 Uiso calc 0.5 . .
C C12 0.8384(7) 0.2556(15) 0.3070(4) 0.059(3) Uani d 0.5 B -2
H H12A 0.7967 0.2074 0.2637 0.071 Uiso calc 0.5 B -2
H H12B 0.7378 0.2929 0.2615 0.071 Uiso calc 0.5 B -2
C C13 1.0384(9) 0.2771(5) 0.2943(6) 0.086(3) Uani d 0.5 B -2
H H13A 1.0801 0.3251 0.3361 0.129 Uiso calc 0.5 B -2
H H13B 1.0263 0.2805 0.2021 0.129 Uiso calc 0.5 B -2
H H13C 1.1378 0.2395 0.3364 0.129 Uiso calc 0.5 B -2
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'
O O 0.0106 0.0060 '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'
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
C10 Sn C6 . . 136.27(11)
C10 Sn S1 . . 104.32(6)
C6 Sn S1 . . 107.55(5)
C10 Sn S1 . 4_565 104.32(6)
C6 Sn S1 . 4_565 107.55(5)
S1 Sn S1 . 4_565 84.97(2)
C10 Sn S2 . . 85.12(2)
C6 Sn S2 . . 81.73(2)
S1 Sn S2 . . 65.482(14)
S1 Sn S2 4_565 . 150.431(15)
C1 S1 Sn . . 93.17(6)
C1 S2 Sn . . 81.45(6)
C4 O1 C5 . . 111.11(19)
C1 N1 C2 . . 120.35(16)
C1 N1 C3 . . 122.84(15)
C2 N1 C3 . . 116.80(15)
N1 C1 S2 . . 121.49(14)
N1 C1 S1 . . 118.64(14)
S2 C1 S1 . . 119.87(10)
N1 C2 H2A . . 109.5
N1 C2 H2B . . 109.5
H2A C2 H2B . . 109.5
N1 C2 H2C . . 109.5
H2A C2 H2C . . 109.5
H2B C2 H2C . . 109.5
N1 C3 C4 . . 113.55(16)
N1 C3 H3A . . 108.9
C4 C3 H3A . . 108.9
N1 C3 H3B . . 108.9
C4 C3 H3B . . 108.9
H3A C3 H3B . . 107.7
O1 C4 C3 . . 109.33(17)
O1 C4 H4A . . 109.8
C3 C4 H4A . . 109.8
O1 C4 H4B . . 109.8
C3 C4 H4B . . 109.8
H4A C4 H4B . . 108.3
O1 C5 H5A . . 109.5
O1 C5 H5B . . 109.5
H5A C5 H5B . . 109.5
O1 C5 H5C . . 109.5
H5A C5 H5C . . 109.5
H5B C5 H5C . . 109.5
C7 C6 Sn . . 110.60(19)
C7 C6 H6A . . 109.5
Sn C6 H6A . . 109.5
C7 C6 H6B . . 109.5
Sn C6 H6B . . 109.5
H6A C6 H6B . . 108.1
C6 C7 C8 . . 114.3(3)
C6 C7 H7A . . 108.7
C8 C7 H7A . . 108.7
C6 C7 H7B . . 108.7
C8 C7 H7B . . 108.7
H7A C7 H7B . . 107.6
C9 C8 C7 . . 107.9(4)
C9 C8 H8A . . 110.1
C7 C8 H8A . . 110.1
C9 C8 H8B . . 110.1
C7 C8 H8B . . 110.1
H8A C8 H8B . . 108.4
C8 C9 H9A . . 109.5
C8 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C8 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
C11 C10 Sn . . 114.6(2)
C11 C10 H10A . . 108.6
Sn C10 H10A . . 108.6
C11 C10 H10B . . 108.6
Sn C10 H10B . . 108.6
H10A C10 H10B . . 107.6
C10 C11 C12 . . 112.3(3)
C10 C11 H11A . . 109.2
C12 C11 H11A . . 109.2
C10 C11 H11B . . 109.2
C12 C11 H11B . . 109.2
H11A C11 H11B . . 107.9
C13 C12 C11 . . 112.9(5)
C13 C12 H12A . . 109.0
C11 C12 H12A . . 109.0
C13 C12 H12B . . 109.0
C11 C12 H12B . . 109.0
H12A C12 H12B . . 107.8
C12 C13 H13A . . 109.5
C12 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C12 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
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
Sn S1 . 2.5425(5) y
Sn S2 . 2.9318(5) y
Sn S1 4_565 2.5425(5) n
Sn S2 4_565 2.9318(5) n
Sn C6 . 2.146(3) y
Sn C10 . 2.138(3) y
S1 C1 . 1.7443(18) y
S2 C1 . 1.6974(19) y
O1 C4 . 1.411(2) ?
O1 C5 . 1.421(3) ?
N1 C1 . 1.337(2) ?
N1 C2 . 1.466(2) ?
N1 C3 . 1.476(2) ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
C2 H2C . 0.9800 ?
C3 C4 . 1.508(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 C7 . 1.523(4) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.550(5) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.498(7) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 C11 . 1.511(4) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.545(5) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.521(8) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
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
C4 H4B S2 1_455 0.99 2.96 3.608(2) 124
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
C2 N1 C1 S2 4.5(3)
C3 N1 C1 S2 -176.29(14)
C2 N1 C1 S1 -175.26(14)
C3 N1 C1 S1 3.9(2)
Sn S2 C1 N1 -178.28(16)
Sn S2 C1 S1 1.51(10)
Sn S1 C1 N1 178.07(14)
Sn S1 C1 S2 -1.72(11)
C1 N1 C3 C4 -91.6(2)
C2 N1 C3 C4 87.6(2)
C5 O1 C4 C3 -175.28(18)
N1 C3 C4 O1 -62.2(2)
Sn C6 C7 C8 -170.1(2)
C6 C7 C8 C9 -76.4(5)
Sn C10 C11 C12 -175.9(11)
C10 C11 C12 C13 164.0(11)

_cod_database_fobs_code 2242051
