#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:40:12 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178528 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/33/4063362.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4063362
loop_
_publ_author_name
'Li, Hong-Xi'
'Cheng, Mei-Ling'
'Wang, He-Ming'
'Yang, Xiao-Juan'
'Ren, Zhi-Gang'
'Lang, Jian-Ping'
_publ_section_title
;
 Lanthanide(III) 4,6-Dimethylpyrimidine-2-thionate Complexes as Efficient
 Catalysts for Isocyanate Cyclodimerization
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              208
_journal_page_last               214
_journal_paper_doi               10.1021/om100671s
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C13 H13 N3 O S'
_chemical_formula_sum            'C13 H13 N3 O S'
_chemical_formula_weight         259.32
_chemical_name_systematic
; 
 ? 
;
_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                103.00(3)
_cell_angle_beta                 93.27(3)
_cell_angle_gamma                113.14(3)
_cell_formula_units_Z            4
_cell_length_a                   10.070(2)
_cell_length_b                   10.085(2)
_cell_length_c                   14.158(3)
_cell_measurement_reflns_used    4038
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4584
_cell_measurement_theta_min      3.0467
_cell_volume                     1271.2(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_molecular_graphics    'sheltl-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_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  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0893
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10508
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.9525
_exptl_absorpt_correction_T_min  0.9299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0709
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0743P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1602
_refine_ls_wR_factor_ref         0.1848
_reflns_number_gt                3674
_reflns_number_total             5569
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100671s_si_002.cif
_cod_data_source_block           S-(4,6-dimethyl-pyrimidin-2-yl)ester
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1271.2(4)
_cod_database_code               4063362
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.25661(9) 0.24919(11) 0.48237(6) 0.0408(3) Uani 1 1 d . . .
S2 S 0.78364(10) 0.24690(12) 0.99479(6) 0.0469(3) Uani 1 1 d . . .
O1 O 0.3754(3) 0.3279(3) 0.66159(15) 0.0439(6) Uani 1 1 d . . .
O2 O 0.5067(3) 0.1676(3) 0.97680(17) 0.0596(8) Uani 1 1 d . . .
N1 N 0.4578(3) 0.2979(3) 0.35981(18) 0.0346(6) Uani 1 1 d . . .
N2 N 0.2038(3) 0.1819(3) 0.29303(18) 0.0351(6) Uani 1 1 d . . .
N3 N 0.5431(3) 0.3492(3) 0.55645(19) 0.0368(6) Uani 1 1 d . . .
HN3 H 0.5480 0.3293 0.4948 0.044 Uiso 1 1 calc R . .
N4 N 1.0505(3) 0.3213(3) 0.9640(2) 0.0395(7) Uani 1 1 d . . .
N5 N 0.8738(3) 0.2046(3) 0.81748(18) 0.0347(6) Uani 1 1 d . . .
N6 N 0.5835(3) 0.1200(3) 0.82891(18) 0.0385(7) Uani 1 1 d . . .
HN6 H 0.6627 0.1325 0.8048 0.046 Uiso 1 1 calc R . .
C1 C 0.3163(4) 0.2431(4) 0.3659(2) 0.0336(7) Uani 1 1 d . . .
C2 C 0.2390(4) 0.1729(4) 0.2024(2) 0.0380(8) Uani 1 1 d . . .
C3 C 0.3835(4) 0.2236(4) 0.1876(2) 0.0394(8) Uani 1 1 d . . .
H3 H 0.4067 0.2151 0.1244 0.047 Uiso 1 1 calc R . .
C4 C 0.4917(4) 0.2870(4) 0.2685(2) 0.0345(7) Uani 1 1 d . . .
C5 C 0.1141(4) 0.1052(4) 0.1178(2) 0.0471(9) Uani 1 1 d . . .
H5A H 0.0347 0.0240 0.1314 0.071 Uiso 1 1 calc R . .
H5B H 0.1462 0.0686 0.0589 0.071 Uiso 1 1 calc R . .
H5C H 0.0817 0.1801 0.1091 0.071 Uiso 1 1 calc R . .
C6 C 0.6505(4) 0.3450(4) 0.2603(3) 0.0449(9) Uani 1 1 d . . .
H6A H 0.6965 0.4511 0.2897 0.067 Uiso 1 1 calc R . .
H6B H 0.6611 0.3245 0.1922 0.067 Uiso 1 1 calc R . .
H6C H 0.6959 0.2968 0.2935 0.067 Uiso 1 1 calc R . .
C7 C 0.6778(3) 0.4122(4) 0.6223(2) 0.0333(7) Uani 1 1 d . . .
C8 C 0.8039(4) 0.4582(4) 0.5800(2) 0.0427(8) Uani 1 1 d . . .
H8 H 0.7967 0.4439 0.5124 0.051 Uiso 1 1 calc R . .
C9 C 0.9397(4) 0.5252(4) 0.6386(3) 0.0521(10) Uani 1 1 d . . .
H9 H 1.0239 0.5567 0.6103 0.063 Uiso 1 1 calc R . .
C10 C 0.9512(4) 0.5456(4) 0.7389(3) 0.0510(10) Uani 1 1 d . . .
H10 H 1.0427 0.5913 0.7784 0.061 Uiso 1 1 calc R . .
C11 C 0.8261(4) 0.4977(4) 0.7798(2) 0.0433(8) Uani 1 1 d . . .
H11 H 0.8338 0.5098 0.8473 0.052 Uiso 1 1 calc R . .
C12 C 0.6882(4) 0.4314(4) 0.7224(2) 0.0401(8) Uani 1 1 d . . .
H12 H 0.6043 0.4006 0.7511 0.048 Uiso 1 1 calc R . .
C13 C 0.4090(3) 0.3175(3) 0.5806(2) 0.0338(7) Uani 1 1 d . . .
C14 C 0.9141(3) 0.2578(4) 0.9137(2) 0.0349(7) Uani 1 1 d . . .
C15 C 0.9827(3) 0.2195(4) 0.7629(2) 0.0338(7) Uani 1 1 d . . .
C16 C 1.1258(4) 0.2819(4) 0.8080(2) 0.0405(8) Uani 1 1 d . . .
H16 H 1.2005 0.2899 0.7709 0.049 Uiso 1 1 calc R . .
C17 C 1.1575(4) 0.3328(4) 0.9091(2) 0.0382(8) Uani 1 1 d . . .
C18 C 0.9389(4) 0.1651(4) 0.6538(2) 0.0479(9) Uani 1 1 d . . .
H18A H 0.8883 0.0578 0.6347 0.072 Uiso 1 1 calc R . .
H18B H 1.0246 0.1949 0.6232 0.072 Uiso 1 1 calc R . .
H18C H 0.8755 0.2074 0.6335 0.072 Uiso 1 1 calc R . .
C19 C 1.3116(4) 0.4043(5) 0.9625(3) 0.0571(11) Uani 1 1 d . . .
H19A H 1.3120 0.4372 1.0316 0.086 Uiso 1 1 calc R . .
H19B H 1.3679 0.4886 0.9392 0.086 Uiso 1 1 calc R . .
H19C H 1.3537 0.3328 0.9507 0.086 Uiso 1 1 calc R . .
C20 C 0.4525(3) 0.0507(4) 0.7598(2) 0.0341(7) Uani 1 1 d . . .
C21 C 0.4676(4) 0.0163(4) 0.6622(2) 0.0430(8) Uani 1 1 d . . .
H21 H 0.5605 0.0401 0.6454 0.052 Uiso 1 1 calc R . .
C22 C 0.3464(4) -0.0531(4) 0.5890(3) 0.0491(9) Uani 1 1 d . . .
H22 H 0.3581 -0.0752 0.5234 0.059 Uiso 1 1 calc R . .
C23 C 0.2073(4) -0.0895(4) 0.6134(3) 0.0509(9) Uani 1 1 d . . .
H23 H 0.1251 -0.1377 0.5647 0.061 Uiso 1 1 calc R . .
C24 C 0.1930(4) -0.0532(4) 0.7110(3) 0.0507(10) Uani 1 1 d . . .
H24 H 0.1001 -0.0760 0.7277 0.061 Uiso 1 1 calc R . .
C25 C 0.3139(4) 0.0164(4) 0.7850(3) 0.0433(8) Uani 1 1 d . . .
H25 H 0.3023 0.0397 0.8505 0.052 Uiso 1 1 calc R . .
C26 C 0.6000(4) 0.1683(4) 0.9260(2) 0.0394(8) Uani 1 1 d . . .
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'
Li Li -0.0003 0.0001 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C13 111.26(15) . . ?
C14 S2 C26 110.58(15) . . ?
C1 N1 C4 116.3(3) . . ?
C1 N2 C2 115.3(3) . . ?
C13 N3 C7 126.8(3) . . ?
C13 N3 HN3 116.6 . . ?
C7 N3 HN3 116.6 . . ?
C14 N4 C17 115.5(3) . . ?
C14 N5 C15 116.6(3) . . ?
C26 N6 C20 128.5(3) . . ?
C26 N6 HN6 115.7 . . ?
C20 N6 HN6 115.7 . . ?
N1 C1 N2 127.9(3) . . ?
N1 C1 S1 120.8(2) . . ?
N2 C1 S1 111.4(2) . . ?
N2 C2 C3 121.5(3) . . ?
N2 C2 C5 116.8(3) . . ?
C3 C2 C5 121.7(3) . . ?
C4 C3 C2 118.3(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
N1 C4 C3 120.7(3) . . ?
N1 C4 C6 116.9(3) . . ?
C3 C4 C6 122.4(3) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 120.1(3) . . ?
C12 C7 N3 124.1(3) . . ?
C8 C7 N3 115.8(3) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C7 C12 C11 118.9(3) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
O1 C13 N3 127.9(3) . . ?
O1 C13 S1 114.2(2) . . ?
N3 C13 S1 117.9(2) . . ?
N5 C14 N4 127.4(3) . . ?
N5 C14 S2 121.8(2) . . ?
N4 C14 S2 110.9(2) . . ?
N5 C15 C16 120.2(3) . . ?
N5 C15 C18 117.1(3) . . ?
C16 C15 C18 122.7(3) . . ?
C15 C16 C17 119.1(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
N4 C17 C16 121.2(3) . . ?
N4 C17 C19 117.2(3) . . ?
C16 C17 C19 121.6(3) . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 119.6(3) . . ?
C21 C20 N6 116.4(3) . . ?
C25 C20 N6 124.0(3) . . ?
C20 C21 C22 120.9(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 118.9(4) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C25 121.6(3) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C24 C25 C20 119.0(3) . . ?
C24 C25 H25 120.5 . . ?
C20 C25 H25 120.5 . . ?
O2 C26 N6 128.3(3) . . ?
O2 C26 S2 113.9(3) . . ?
N6 C26 S2 117.8(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.784(3) . ?
S1 C13 1.805(3) . ?
S2 C14 1.781(3) . ?
S2 C26 1.814(3) . ?
O1 C13 1.208(3) . ?
O2 C26 1.214(4) . ?
N1 C1 1.326(4) . ?
N1 C4 1.348(4) . ?
N2 C1 1.327(4) . ?
N2 C2 1.344(4) . ?
N3 C13 1.344(4) . ?
N3 C7 1.423(4) . ?
N3 HN3 0.8600 . ?
N4 C14 1.340(4) . ?
N4 C17 1.348(4) . ?
N5 C14 1.321(4) . ?
N5 C15 1.358(3) . ?
N6 C26 1.327(4) . ?
N6 C20 1.416(4) . ?
N6 HN6 0.8600 . ?
C2 C3 1.386(4) . ?
C2 C5 1.506(4) . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.492(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.378(4) . ?
C7 C8 1.391(4) . ?
C8 C9 1.381(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C15 C16 1.371(4) . ?
C15 C18 1.493(4) . ?
C16 C17 1.380(4) . ?
C16 H16 0.9300 . ?
C17 C19 1.497(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.379(4) . ?
C20 C25 1.388(4) . ?
C21 C22 1.383(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.387(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.386(5) . ?
C24 H24 0.9300 . ?
C25 H25 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
_geom_hbond_site_symmetry_A
N3 HN3 N1 0.86 1.97 2.736(4) 147.8 .
N6 HN6 N5 0.86 1.94 2.731(4) 152.3 .
C12 H12 O1 0.93 2.32 2.908(4) 120.9 .
C25 H25 O2 0.93 2.36 2.946(5) 121.0 .
C3 H3 O2 0.93 2.41 3.313(4) 165.4 1_554
C6 H6A O1 0.96 2.57 3.353(4) 139.0 2_666
C16 H16 O1 0.93 2.39 3.307(4) 171.2 1_655
