#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/99/2209959.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_2209959
loop_
_publ_author_name
'Tiekink, Edward R. T.'
'Young, David J.'
_publ_section_title
;A low-temperature refinement of
 tris[N,N'-bis(2-hydroxyethyl)dithiocarbamato-κ²S,S']antimony(III)
;
_journal_coeditor_code           NG2043
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1887
_journal_page_last               m1889
_journal_paper_doi               10.1107/S1600536806027061
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Sb (C5 H10 N1 O2 S2)3]'
_chemical_formula_moiety         'C15 H30 N3 O6 S6 Sb'
_chemical_formula_sum            'C15 H30 N3 O6 S6 Sb'
_chemical_formula_weight         662.53
_chemical_name_systematic
;
tris[N,N'-bis(2-hydroxyethyl)dithiocarbamato-κ²S,S']antimony(III)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.422(4)
_cell_angle_beta                 105.294(4)
_cell_angle_gamma                94.445(3)
_cell_formula_units_Z            2
_cell_length_a                   9.942(2)
_cell_length_b                   11.011(2)
_cell_length_c                   12.458(3)
_cell_measurement_reflns_used    5129
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1259.0(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  AFC12Κ/SATURN724
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_sigmaI/netI    0.018
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31926
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.9
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.630
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.69
_refine_diff_density_min         -0.52
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5694
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.021
_refine_ls_R_factor_gt           0.020
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0275P)²+0.8849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.051
_refine_ls_wR_factor_ref         0.051
_reflns_number_gt                5555
_reflns_number_total             5694
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2043.cif
_cod_data_source_block           I
_cod_original_cell_volume        1258.9(5)
_cod_database_code               2209959
_cod_database_fobs_code          2209959
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
Sb Sb 0.830515(10) 0.765906(9) 0.273618(8) 0.00948(4) Uani d . 1
S S1 0.59487(4) 0.66348(4) 0.14344(3) 0.01142(8) Uani d . 1
S S2 0.76058(4) 0.84048(4) 0.06278(3) 0.01257(8) Uani d . 1
S S3 0.87423(4) 0.55876(4) 0.33946(3) 0.01136(8) Uani d . 1
S S4 0.95162(4) 0.59949(4) 0.13660(3) 0.01173(8) Uani d . 1
S S5 0.74058(4) 0.80162(4) 0.46156(3) 0.01324(8) Uani d . 1
S S6 0.70058(4) 0.98623(4) 0.32316(3) 0.01379(8) Uani d . 1
O O1 0.24787(15) 0.87381(13) 0.02447(13) 0.0235(3) Uani d D 1
H H1O 0.1945 0.8528 -0.0439 0.035 Uiso d D 1
O O2 0.42873(13) 0.66940(12) -0.28984(11) 0.0177(2) Uani d D 1
H H2O 0.4768 0.6100 -0.2960 0.027 Uiso d D 1
O O3 0.93503(16) 0.16688(13) 0.18556(12) 0.0268(3) Uani d D 1
H H3O 1.0069 0.1308 0.1945 0.040 Uiso d D 1
O O4 1.36862(13) 0.48123(13) 0.30191(11) 0.0212(3) Uani d D 1
H H4O 1.3507 0.5279 0.3593 0.032 Uiso d D 1
O O5 0.71861(14) 1.36836(11) 0.52515(11) 0.0184(2) Uani d D 1
H H5O 0.6808 1.3533 0.4535 0.028 Uiso d D 1
O O6 0.85921(15) 0.97901(14) 0.81914(11) 0.0250(3) Uani d D 1
H H6O 0.8297 1.0253 0.8699 0.037 Uiso d D 1
N N1 0.48463(14) 0.75673(13) -0.03231(12) 0.0108(3) Uani d . 1
N N2 1.05289(14) 0.43149(13) 0.24647(11) 0.0108(3) Uani d . 1
N N3 0.67863(14) 1.03285(13) 0.53819(12) 0.0119(3) Uani d . 1
C C1 0.60316(17) 0.75630(14) 0.04770(13) 0.0106(3) Uani d . 1
C C2 0.34908(16) 0.68338(15) -0.04245(14) 0.0123(3) Uani d . 1
H H2A 0.3662 0.6011 -0.0269 0.015 Uiso calc R 1
H H2B 0.2867 0.6654 -0.1228 0.015 Uiso calc R 1
C C3 0.27476(17) 0.75325(16) 0.04130(15) 0.0146(3) Uani d . 1
H H3A 0.1842 0.7006 0.0304 0.017 Uiso calc R 1
H H3B 0.3340 0.7657 0.1219 0.017 Uiso calc R 1
C C4 0.48095(17) 0.83935(15) -0.10991(14) 0.0126(3) Uani d . 1
H H4A 0.5448 0.9201 -0.0659 0.015 Uiso calc R 1
H H4B 0.3841 0.8596 -0.1341 0.015 Uiso calc R 1
C C5 0.52370(17) 0.78141(16) -0.21747(14) 0.0139(3) Uani d . 1
H H5A 0.5254 0.8443 -0.2619 0.017 Uiso calc R 1
H H5B 0.6201 0.7602 -0.1941 0.017 Uiso calc R 1
C C6 0.96942(16) 0.51994(14) 0.24070(13) 0.0095(3) Uani d . 1
C C7 1.06683(17) 0.36063(15) 0.33394(14) 0.0126(3) Uani d . 1
H H7A 1.0661 0.4187 0.4085 0.015 Uiso calc R 1
H H7B 1.1586 0.3288 0.3461 0.015 Uiso calc R 1
C C8 0.94850(18) 0.24930(15) 0.29764(15) 0.0154(3) Uani d . 1
H H8A 0.9669 0.2003 0.3553 0.019 Uiso calc R 1
H H8B 0.8584 0.2820 0.2971 0.019 Uiso calc R 1
C C9 1.13393(17) 0.39747(15) 0.16248(14) 0.0127(3) Uani d . 1
H H9A 1.0758 0.3994 0.0852 0.015 Uiso calc R 1
H H9B 1.1539 0.3097 0.1566 0.015 Uiso calc R 1
C C10 1.27250(18) 0.48633(17) 0.19609(15) 0.0168(3) Uani d . 1
H H10A 1.3174 0.4639 0.1332 0.020 Uiso calc R 1
H H10B 1.2526 0.5743 0.2039 0.020 Uiso calc R 1
C C11 0.70456(16) 0.94978(15) 0.44911(14) 0.0117(3) Uani d . 1
C C12 0.63933(17) 1.15647(15) 0.52768(15) 0.0133(3) Uani d . 1
H H12A 0.5867 1.1875 0.5837 0.016 Uiso calc R 1
H H12B 0.5755 1.1450 0.4488 0.016 Uiso calc R 1
C C13 0.76586(17) 1.25637(15) 0.54952(15) 0.0140(3) Uani d . 1
H H13A 0.8243 1.2768 0.6313 0.017 Uiso calc R 1
H H13B 0.8248 1.2229 0.4994 0.017 Uiso calc R 1
C C14 0.69259(17) 1.00405(15) 0.64920(14) 0.0130(3) Uani d . 1
H H14A 0.6621 0.9121 0.6342 0.016 Uiso calc R 1
H H14B 0.6294 1.0505 0.6882 0.016 Uiso calc R 1
C C15 0.84328(18) 1.04030(16) 0.72932(14) 0.0155(3) Uani d . 1
H H15A 0.9101 1.0145 0.6845 0.019 Uiso calc R 1
H H15B 0.8649 1.1335 0.7636 0.019 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'
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'
Sb Sb -0.5866 1.5461 '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
_geom_angle_publ_flag
S1 Sb S2 67.359(15) y
S1 Sb S3 91.326(16) y
S1 Sb S4 89.770(19) y
S1 Sb S5 92.367(19) y
S1 Sb S6 85.095(18) y
S2 Sb S3 138.619(12) y
S2 Sb S4 78.059(17) y
S2 Sb S5 136.185(15) y
S2 Sb S6 74.674(15) y
S3 Sb S4 66.339(17) y
S3 Sb S5 76.559(14) y
S3 Sb S6 141.007(14) y
S4 Sb S5 142.877(13) y
S4 Sb S6 152.124(12) y
S5 Sb S6 64.852(12) y
Sb S1 C1 92.07(6) y
Sb S2 C1 80.36(5) y
Sb S3 C6 88.54(5) y
Sb S4 C6 85.13(5) y
Sb S5 C11 89.64(5) y
Sb S6 C11 84.54(5) y
C3 O1 H1O 101.7 ?
C5 O2 H2O 106.8 ?
C8 O3 H3O 105.0 ?
C10 O4 H4O 110.9 ?
C13 O5 H5O 109.2 ?
C15 O6 H6O 105.5 ?
C1 N1 C2 122.16(13) ?
C1 N1 C4 120.95(13) ?
C2 N1 C4 116.73(13) ?
C6 N2 C9 120.92(13) ?
C6 N2 C7 122.37(13) ?
C9 N2 C7 116.69(12) ?
C11 N3 C12 120.75(13) ?
C11 N3 C14 120.98(13) ?
C12 N3 C14 118.25(13) ?
N1 C1 S2 123.48(12) ?
N1 C1 S1 117.83(12) ?
S2 C1 S1 118.69(9) ?
N1 C2 C3 112.42(13) ?
N1 C2 H2A 109.1 ?
C3 C2 H2A 109.1 ?
N1 C2 H2B 109.1 ?
C3 C2 H2B 109.1 ?
H2A C2 H2B 107.9 ?
O1 C3 C2 112.13(13) ?
O1 C3 H3A 109.2 ?
C2 C3 H3A 109.2 ?
O1 C3 H3B 109.2 ?
C2 C3 H3B 109.2 ?
H3A C3 H3B 107.9 ?
N1 C4 C5 114.02(13) ?
N1 C4 H4A 108.7 ?
C5 C4 H4A 108.7 ?
N1 C4 H4B 108.7 ?
C5 C4 H4B 108.7 ?
H4A C4 H4B 107.6 ?
O2 C5 C4 111.66(13) ?
O2 C5 H5A 109.3 ?
C4 C5 H5A 109.3 ?
O2 C5 H5B 109.3 ?
C4 C5 H5B 109.3 ?
H5A C5 H5B 107.9 ?
N2 C6 S4 121.84(11) ?
N2 C6 S3 120.54(12) ?
S4 C6 S3 117.61(9) ?
N2 C7 C8 112.06(13) ?
N2 C7 H7A 109.2 ?
C8 C7 H7A 109.2 ?
N2 C7 H7B 109.2 ?
C8 C7 H7B 109.2 ?
H7A C7 H7B 107.9 ?
O3 C8 C7 112.41(14) ?
O3 C8 H8A 109.1 ?
C7 C8 H8A 109.1 ?
O3 C8 H8B 109.1 ?
C7 C8 H8B 109.1 ?
H8A C8 H8B 107.9 ?
N2 C9 C10 112.77(13) ?
N2 C9 H9A 109.0 ?
C10 C9 H9A 109.0 ?
N2 C9 H9B 109.0 ?
C10 C9 H9B 109.0 ?
H9A C9 H9B 107.8 ?
O4 C10 C9 112.98(14) ?
O4 C10 H10A 109.0 ?
C9 C10 H10A 109.0 ?
O4 C10 H10B 109.0 ?
C9 C10 H10B 109.0 ?
H10A C10 H10B 107.8 ?
N3 C11 S6 121.52(12) ?
N3 C11 S5 119.48(12) ?
S6 C11 S5 118.99(9) ?
N3 C12 C13 113.26(13) ?
N3 C12 H12A 108.9 ?
C13 C12 H12A 108.9 ?
N3 C12 H12B 108.9 ?
C13 C12 H12B 108.9 ?
H12A C12 H12B 107.7 ?
O5 C13 C12 109.81(13) ?
O5 C13 H13A 109.7 ?
C12 C13 H13A 109.7 ?
O5 C13 H13B 109.7 ?
C12 C13 H13B 109.7 ?
H13A C13 H13B 108.2 ?
N3 C14 C15 112.41(13) ?
N3 C14 H14A 109.1 ?
C15 C14 H14A 109.1 ?
N3 C14 H14B 109.1 ?
C15 C14 H14B 109.1 ?
H14A C14 H14B 107.9 ?
O6 C15 C14 109.67(14) ?
O6 C15 H15A 109.7 ?
C14 C15 H15A 109.7 ?
O6 C15 H15B 109.7 ?
C14 C15 H15B 109.7 ?
H15A C15 H15B 108.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Sb S1 2.4628(6) y
Sb S2 2.8733(7) y
Sb S3 2.6384(6) y
Sb S4 2.7548(5) y
Sb S5 2.6714(6) y
Sb S6 2.8451(6) y
S1 C1 1.7664(16) y
S2 C1 1.6962(16) y
S3 C6 1.7340(15) y
S4 C6 1.7173(16) y
S5 C11 1.7322(16) y
S6 C11 1.7053(17) y
O1 C3 1.429(2) ?
O1 H1O 0.84 ?
O2 C5 1.429(2) ?
O2 H2O 0.84 ?
O3 C8 1.429(2) ?
O3 H3O 0.84 ?
O4 C10 1.427(2) ?
O4 H4O 0.84 ?
O5 C13 1.4262(19) ?
O5 H5O 0.84 ?
O6 C15 1.426(2) ?
O6 H6O 0.84 ?
N1 C1 1.329(2) y
N1 C2 1.475(2) ?
N1 C4 1.4792(19) ?
N2 C6 1.331(2) y
N2 C9 1.4768(19) ?
N2 C7 1.4751(19) ?
N3 C11 1.348(2) y
N3 C12 1.472(2) ?
N3 C14 1.468(2) ?
C2 C3 1.524(2) ?
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C3 H3A 0.9900 ?
C3 H3B 0.9900 ?
C4 C5 1.517(2) ?
C4 H4A 0.9900 ?
C4 H4B 0.9900 ?
C5 H5A 0.9900 ?
C5 H5B 0.9900 ?
C7 C8 1.520(2) ?
C7 H7A 0.9900 ?
C7 H7B 0.9900 ?
C8 H8A 0.9900 ?
C8 H8B 0.9900 ?
C9 C10 1.521(2) ?
C9 H9A 0.9900 ?
C9 H9B 0.9900 ?
C10 H10A 0.9900 ?
C10 H10B 0.9900 ?
C12 C13 1.524(2) ?
C12 H12A 0.9900 ?
C12 H12B 0.9900 ?
C13 H13A 0.9900 ?
C13 H13B 0.9900 ?
C14 C15 1.523(2) ?
C14 H14A 0.9900 ?
C14 H14B 0.9900 ?
C15 H15A 0.9900 ?
C15 H15B 0.9900 ?
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
O1 H1o O3 2_665 0.84 1.84 2.671(2) 170 y
O2 H2o O4 2_765 0.84 1.91 2.718(2) 162 y
O3 H3o O6 2_766 0.84 1.88 2.701(2) 166 y
O4 H4o O5 2_776 0.84 1.92 2.751(2) 171 y
O5 H5o O2 2_675 0.84 1.99 2.8188(19) 172 y
O6 H6o O1 2_676 0.84 1.87 2.710(2) 176 y
