#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/20/2232030.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_2232030
loop_
_publ_author_name
'Howie, R. Alan'
'de Lima, Geraldo M.'
'Tiekink, Edward R. T.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
_publ_section_title
;
 fac-(2-Amidoethyl-κ²C¹,O)trichlorido(urea-κO)tin(IV)
;
_journal_coeditor_code           QM2029
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1420
_journal_page_last               m1421
_journal_paper_doi               10.1107/S1600536811038281
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Sn (C3 H6 N O) Cl3 (C H4 N2 O)]'
_chemical_formula_moiety         'C4 H10 Cl3 N3 O2 Sn'
_chemical_formula_sum            'C4 H10 Cl3 N3 O2 Sn'
_chemical_formula_weight         357.19
_chemical_name_systematic
;
fac-(2-Amidoethyl-κ²C¹,O)trichlorido-
(urea-κO)tin(IV)
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.1223(2)
_cell_length_b                   12.0180(3)
_cell_length_c                   16.0461(5)
_cell_measurement_reflns_used    2702
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2144.85(9)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker--Nonius APEXII CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12333
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.103
_exptl_absorpt_correction_T_max  0.9127
_exptl_absorpt_correction_T_min  0.7382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.412
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0222
_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)+(0.0000P)²+3.4389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0483
_refine_ls_wR_factor_ref         0.0505
_reflns_number_gt                2242
_reflns_number_total             2451
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qm2029.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2ac 2ab '
_cod_database_code               2232030
_cod_database_fobs_code          2232030
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Sn Sn 0.536685(14) 0.238549(14) 0.600556(10) 0.01156(6) Uani d . 1 1
Cl Cl1 0.40499(6) 0.32834(5) 0.69733(4) 0.02118(14) Uani d . 1 1
Cl Cl2 0.61521(5) 0.11894(5) 0.70850(4) 0.01937(14) Uani d . 1 1
Cl Cl3 0.69075(6) 0.38320(5) 0.62367(4) 0.01866(14) Uani d . 1 1
O O1 0.44877(15) 0.34588(14) 0.50652(10) 0.0147(4) Uani d . 1 1
O O2 0.38496(16) 0.12814(16) 0.57517(11) 0.0202(4) Uani d . 1 1
N N1 0.3982(2) 0.3491(2) 0.37174(14) 0.0194(5) Uani d . 1 1
H H1N 0.360(3) 0.405(3) 0.378(2) 0.023 Uiso d . 1 1
H H2N 0.403(3) 0.321(3) 0.328(2) 0.023 Uiso d . 1 1
N N2 0.2038(2) 0.0487(2) 0.58401(15) 0.0177(5) Uani d . 1 1
H H3N 0.191(3) 0.069(2) 0.531(2) 0.021 Uiso d . 1 1
H H4N 0.160(3) -0.006(3) 0.6044(18) 0.021 Uiso d . 1 1
N N3 0.3448(2) 0.01609(19) 0.68601(14) 0.0182(5) Uani d . 1 1
H H5N 0.296(3) -0.026(2) 0.713(2) 0.022 Uiso d . 1 1
H H6N 0.411(3) 0.024(3) 0.7044(19) 0.022 Uiso d . 1 1
C C1 0.6109(2) 0.1691(2) 0.48944(15) 0.0166(5) Uani d . 1 1
H H1A 0.6918 0.2004 0.4789 0.020 Uiso calc R 1 1
H H1B 0.6183 0.0873 0.4949 0.020 Uiso calc R 1 1
C C2 0.5261(2) 0.1983(2) 0.41798(16) 0.0173(5) Uani d . 1 1
H H2A 0.5736 0.2077 0.3663 0.021 Uiso calc R 1 1
H H2B 0.4694 0.1359 0.4092 0.021 Uiso calc R 1 1
C C3 0.4551(2) 0.3040(2) 0.43435(15) 0.0141(5) Uani d . 1 1
C C4 0.3135(2) 0.0653(2) 0.61521(15) 0.0148(5) Uani d . 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Sn 0.01312(11) 0.01191(10) 0.00966(10) 0.00196(6) 0.00039(6) 0.00036(6)
Cl1 0.0263(3) 0.0240(3) 0.0133(3) 0.0119(3) 0.0043(3) 0.0018(2)
Cl2 0.0177(3) 0.0225(3) 0.0179(3) 0.0042(2) -0.0017(2) 0.0074(2)
Cl3 0.0221(3) 0.0154(3) 0.0185(3) -0.0029(2) -0.0031(2) -0.0013(2)
O1 0.0177(9) 0.0146(9) 0.0119(8) 0.0039(7) 0.0003(7) 0.0000(7)
O2 0.0207(9) 0.0254(10) 0.0145(9) -0.0095(8) -0.0003(7) 0.0025(7)
N1 0.0258(12) 0.0216(13) 0.0107(10) 0.0070(10) -0.0013(9) -0.0022(9)
N2 0.0149(11) 0.0195(12) 0.0187(11) -0.0038(9) 0.0006(9) 0.0023(9)
N3 0.0162(11) 0.0210(12) 0.0175(11) -0.0018(9) 0.0016(9) 0.0041(9)
C1 0.0182(12) 0.0183(13) 0.0132(12) 0.0035(10) 0.0031(10) -0.0027(9)
C2 0.0227(13) 0.0172(13) 0.0120(11) 0.0022(11) 0.0008(10) -0.0027(10)
C3 0.0121(11) 0.0155(13) 0.0148(12) -0.0042(9) 0.0029(9) 0.0018(10)
C4 0.0170(12) 0.0125(12) 0.0148(12) 0.0033(10) 0.0032(9) -0.0018(9)
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'
Cl Cl 0.1484 0.1585 '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'
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
C1 Sn O2 84.59(9)
C1 Sn O1 80.18(8)
O2 Sn O1 83.43(7)
C1 Sn Cl1 162.84(7)
O2 Sn Cl1 85.53(5)
O1 Sn Cl1 84.79(5)
C1 Sn Cl2 103.09(7)
O2 Sn Cl2 92.95(5)
O1 Sn Cl2 174.92(5)
Cl1 Sn Cl2 91.39(2)
C1 Sn Cl3 97.60(7)
O2 Sn Cl3 172.57(5)
O1 Sn Cl3 89.92(5)
Cl1 Sn Cl3 90.56(2)
Cl2 Sn Cl3 93.46(2)
C3 O1 Sn 111.56(15)
C4 O2 Sn 138.58(16)
C3 N1 H1N 121(2)
C3 N1 H2N 119(2)
H1N N1 H2N 120(3)
C4 N2 H3N 117.7(19)
C4 N2 H4N 119(2)
H3N N2 H4N 117(3)
C4 N3 H5N 121(2)
C4 N3 H6N 120(2)
H5N N3 H6N 118(3)
C2 C1 Sn 107.38(16)
C2 C1 H1A 110.2
Sn C1 H1A 110.2
C2 C1 H1B 110.2
Sn C1 H1B 110.2
H1A C1 H1B 108.5
C3 C2 C1 112.6(2)
C3 C2 H2A 109.1
C1 C2 H2A 109.1
C3 C2 H2B 109.1
C1 C2 H2B 109.1
H2A C2 H2B 107.8
O1 C3 N1 120.8(2)
O1 C3 C2 121.4(2)
N1 C3 C2 117.8(2)
O2 C4 N3 122.2(2)
O2 C4 N2 118.1(2)
N3 C4 N2 119.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Sn Cl1 2.3919(6) y
Sn Cl2 2.4144(6) y
Sn Cl3 2.4690(6) y
Sn O1 2.2129(17) y
Sn O2 2.1850(18) y
Sn C1 2.135(2) y
O1 C3 1.265(3) ?
O2 C4 1.271(3) ?
N1 C3 1.305(3) ?
N1 H1N 0.81(3) ?
N1 H2N 0.78(3) ?
N2 C4 1.334(3) ?
N2 H3N 0.90(3) ?
N2 H4N 0.89(3) ?
N3 C4 1.327(3) ?
N3 H5N 0.86(3) ?
N3 H6N 0.80(3) ?
C1 C2 1.526(3) ?
C1 H1A 0.9900 ?
C1 H1B 0.9900 ?
C2 C3 1.519(4) ?
C2 H2A 0.9900 ?
C2 H2B 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
N1 H1n Cl3 5_666 0.81(3) 2.60(3) 3.366(3) 159(3)
N1 H2n Cl1 7_565 0.78(3) 2.76(3) 3.519(3) 164(3)
N2 H3n Cl3 4_456 0.90(3) 2.55(3) 3.435(2) 170(3)
N2 H4n Cl1 8_655 0.89(3) 2.59(3) 3.432(2) 160(3)
N2 H4n O1 8_655 0.89(3) 2.66(3) 3.219(3) 122(2)
N3 H5n Cl1 8_655 0.86(3) 2.85(3) 3.584(3) 145(3)
N3 H5n Cl3 3_646 0.86(3) 2.85(3) 3.469(2) 131(2)
N3 H6n Cl2 . 0.80(3) 2.54(3) 3.272(3) 152(3)
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
C1 Sn O1 C3 16.38(17)
O2 Sn O1 C3 -69.23(16)
Cl1 Sn O1 C3 -155.32(16)
Cl2 Sn O1 C3 -114.0(5)
Cl3 Sn O1 C3 114.11(15)
C1 Sn O2 C4 139.7(3)
O1 Sn O2 C4 -139.6(3)
Cl1 Sn O2 C4 -54.3(3)
Cl2 Sn O2 C4 36.8(3)
Cl3 Sn O2 C4 -112.8(4)
O2 Sn C1 C2 61.74(17)
O1 Sn C1 C2 -22.51(17)
Cl1 Sn C1 C2 6.7(4)
Cl2 Sn C1 C2 153.52(16)
Cl3 Sn C1 C2 -111.11(17)
Sn C1 C2 C3 26.7(3)
Sn O1 C3 N1 173.13(19)
Sn O1 C3 C2 -5.3(3)
C1 C2 C3 O1 -14.9(3)
C1 C2 C3 N1 166.6(2)
Sn O2 C4 N3 -28.6(4)
Sn O2 C4 N2 151.7(2)
