#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2012437.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_2012437 loop_ _publ_author_name 'Razak, Ibrahim Abdul' 'Usman, Anwar' 'Fun, Hoong-Kun' 'Yamin, Bohari M.' 'Keat, Goh Wooi' _publ_section_title ; Diacetatobis(trimethylenethiourea)zinc(II) monohydrate ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first m31 _journal_page_last m33 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C12 H22 N4 O4 S2 Zn, H2 O' _chemical_formula_sum 'C12 H24 N4 O5 S2 Zn' _chemical_formula_weight 433.84 _chemical_melting_point 400 _chemical_name_systematic ; Diacetatobis(trimethylenethiourea)zinc(II) Monohydrate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _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 90.8370(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.75170(10) _cell_length_b 17.3654(2) _cell_length_c 13.0543(2) _cell_measurement_reflns_used 8192 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.44 _cell_measurement_theta_min 1.95 _cell_volume 1983.74(4) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995), PLATON (Spek, 1990) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type ; Siemens SMART CCD area-detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0972 _diffrn_reflns_av_sigmaI/netI .0936 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 11176 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 1.95 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.476 _exptl_absorpt_correction_T_max .8665 _exptl_absorpt_correction_T_min .7982 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 904 _exptl_crystal_size_max .16 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .10 _refine_diff_density_max .539 _refine_diff_density_min -1.372 _refine_ls_extinction_coef .0165(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_ref .983 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 238 _refine_ls_number_reflns 3495 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all .983 _refine_ls_R_factor_all .0674 _refine_ls_R_factor_gt .0544 _refine_ls_shift/su_max .000 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0693P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .1324 _refine_ls_wR_factor_ref .1384 _reflns_number_gt 2645 _reflns_number_total 3495 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file ln1123.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P21/n _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '400K' was changed to '400' - the value should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2012437 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' 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 Zn1 .57847(4) .250169(19) .53877(3) .0358(2) Uani d . 1 . . Zn S1 .76157(11) .31906(6) .44927(7) .0499(3) Uani d . 1 . . S S2 .34630(11) .24216(5) .44875(8) .0451(3) Uani d . 1 . . S O1 .6330(3) .14138(14) .56550(18) .0507(7) Uani d . 1 . . O O2 .6449(4) .10394(15) .4038(2) .0618(8) Uani d . 1 . . O O3 .5858(3) .27839(14) .68607(17) .0464(6) Uani d . 1 . . O O4 .4660(3) .38806(15) .65645(18) .0536(7) Uani d . 1 . . O N1 .6499(4) .23990(17) .2885(3) .0505(9) Uani d . 1 . . N H1A .6629 .2006 .3277 .061 Uiso calc R 1 . . H N2 .6875(4) .36776(18) .2620(2) .0531(8) Uani d . 1 . . N H2A .7165 .4118 .2855 .064 Uiso calc R 1 . . H N3 .1875(3) .34003(17) .3369(2) .0432(7) Uani d . 1 B . N H3A .1687 .2998 .3005 .052 Uiso calc R 1 . . H N4 .3255(4) .39478(16) .4667(2) .0487(8) Uani d . 1 B . N H4A .3880 .3885 .5175 .058 Uiso calc R 1 . . H C1 .6593(5) .0923(2) .4966(3) .0492(9) Uani d . 1 . . C C2 .7095(7) .0134(2) .5336(4) .0832(16) Uani d . 1 . . C H2B .8057 .0177 .5694 .125 Uiso calc R 1 . . H H2C .7204 -.0203 .4759 .125 Uiso calc R 1 . . H H2D .6343 -.0071 .5789 .125 Uiso calc R 1 . . H C3 .5250(4) .34119(19) .7156(3) .0389(8) Uani d . 1 . . C C4 .5290(5) .3577(3) .8281(3) .0589(11) Uani d . 1 . . C H4B .4762 .3176 .8638 .088 Uiso calc R 1 . . H H4C .4801 .4061 .8408 .088 Uiso calc R 1 . . H H4D .6332 .3599 .8519 .088 Uiso calc R 1 . . H C5 .6940(4) .30764(19) .3243(3) .0419(8) Uani d . 1 . . C C6 .5805(7) .2266(3) .1874(3) .0710(14) Uani d . 1 . . C H6A .4992 .1889 .1925 .085 Uiso calc R 1 . . H H6B .6566 .2067 .1411 .085 Uiso calc R 1 . . H C7 .5176(6) .3007(3) .1467(3) .0680(13) Uani d . 1 . . C H7A .4268 .3147 .1842 .082 Uiso calc R 1 . . H H7B .4888 .2945 .0751 .082 Uiso calc R 1 . . H C8 .6346(6) .3636(3) .1570(3) .0702(13) Uani d . 1 . . C H8A .7199 .3531 .1126 .084 Uiso calc R 1 . . H H8B .5898 .4125 .1367 .084 Uiso calc R 1 . . H C9 .2838(4) .33344(19) .4158(2) .0370(8) Uani d . 1 . . C C10 .1116(5) .4125(2) .3085(3) .0573(10) Uani d . 1 . . C H10A .0151 .4168 .3437 .069 Uiso calc PR .75 A 1 H H10B .0910 .4135 .2353 .069 Uiso calc PR .75 A 1 H H10C .0046 .4031 .2925 .069 Uiso calc PR .25 A 2 H H10D .1591 .4344 .2485 .069 Uiso calc PR .25 A 2 H C11A .2140(8) .4780(3) .3380(5) .0673(17) Uani d P .75 B 1 C H11A .2990 .4797 .2912 .081 Uiso calc PR .75 B 1 H H11B .1576 .5258 .3305 .081 Uiso calc PR .75 B 1 H C11B .1257(18) .4666(9) .3961(13) .049(4) Uani d P .25 B 2 C H11C .0956 .5174 .3725 .059 Uiso calc PR .25 B 2 H H11D .0534 .4510 .4478 .059 Uiso calc PR .25 B 2 H C12 .2750(6) .4727(2) .4445(3) .0680(13) Uani d . 1 . . C H12A .3601 .5080 .4531 .082 Uiso calc PR .75 B 1 H H12B .1962 .4875 .4922 .082 Uiso calc PR .75 B 1 H H12C .2691 .5025 .5072 .082 Uiso calc PR .25 B 2 H H12D .3459 .4980 .3990 .082 Uiso calc PR .25 B 2 H O1W .2152(4) .47623(19) .7228(3) .0646(8) Uani d D 1 . . O H1W1 .182(7) .457(4) .779(4) .14(3) Uiso d D 1 . . H H2W1 .277(6) .446(3) .707(5) .12(2) Uiso d D 1 . . H 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 Zn1 .0469(3) .0312(3) .0292(3) .00422(16) -.0008(2) -.00182(14) S1 .0564(6) .0465(6) .0466(6) -.0130(4) -.0005(4) .0017(4) S2 .0473(6) .0366(5) .0511(7) -.0026(4) -.0114(4) -.0032(4) O1 .0792(19) .0347(13) .0382(15) .0122(12) -.0008(12) -.0029(11) O2 .108(2) .0390(15) .0391(17) -.0013(15) .0103(14) -.0018(11) O3 .0658(17) .0402(14) .0332(14) .0130(13) -.0029(11) -.0062(11) O4 .0799(18) .0445(15) .0358(14) .0166(13) -.0117(12) -.0011(11) N1 .080(3) .0390(18) .0323(19) -.0068(15) .0064(16) .0036(12) N2 .073(2) .0404(18) .046(2) -.0016(16) .0104(16) .0070(14) N3 .0529(18) .0409(17) .0357(17) -.0010(14) -.0077(13) -.0043(13) N4 .069(2) .0394(17) .0375(17) .0030(15) -.0204(14) -.0047(13) C1 .065(2) .0324(19) .050(3) .0035(17) .0095(18) .0001(17) C2 .139(5) .046(3) .065(3) .033(3) .002(3) .004(2) C3 .049(2) .0343(18) .0338(19) -.0006(16) -.0030(15) -.0059(15) C4 .078(3) .066(3) .032(2) .024(2) -.0161(18) -.0139(18) C5 .047(2) .0363(19) .043(2) -.0018(16) .0124(16) .0032(16) C6 .114(4) .057(3) .042(3) -.022(3) .011(2) -.004(2) C7 .075(3) .093(4) .035(2) .000(3) -.007(2) .002(2) C8 .111(4) .051(2) .049(3) .011(3) .017(2) .012(2) C9 .0406(18) .0412(19) .0294(18) -.0015(15) .0044(14) .0004(14) C10 .067(3) .054(3) .051(2) .007(2) -.0092(19) .0046(19) C11A .092(5) .048(3) .062(4) -.005(3) -.032(4) .014(3) C11B .048(9) .047(9) .052(10) .008(7) -.001(7) .005(7) C12 .103(4) .040(2) .060(3) .004(2) -.027(2) -.0026(19) O1W .089(2) .0424(16) .063(2) .0147(16) .0091(17) .0125(15) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn .2839 1.4301 '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 O1 Zn1 O3 93.48(10) yes O1 Zn1 S1 114.42(8) yes O3 Zn1 S1 110.28(8) yes O1 Zn1 S2 103.74(8) yes O3 Zn1 S2 121.17(8) yes S1 Zn1 S2 112.22(4) yes C5 S1 Zn1 100.68(12) ? C9 S2 Zn1 109.89(12) ? C1 O1 Zn1 124.4(2) ? C3 O3 Zn1 119.7(2) ? C5 N1 C6 125.1(3) ? C5 N1 H1A 117.5 ? C6 N1 H1A 117.5 ? C5 N2 C8 123.7(3) ? C5 N2 H2A 118.2 ? C8 N2 H2A 118.2 ? C9 N3 C10 123.4(3) ? C9 N3 H3A 118.3 ? C10 N3 H3A 118.3 ? C9 N4 C12 125.2(3) ? C9 N4 H4A 117.4 ? C12 N4 H4A 117.4 ? O2 C1 O1 124.9(3) ? O2 C1 C2 119.1(4) ? O1 C1 C2 116.0(4) ? C1 C2 H2B 109.5 ? C1 C2 H2C 109.5 ? H2B C2 H2C 109.5 ? C1 C2 H2D 109.5 ? H2B C2 H2D 109.5 ? H2C C2 H2D 109.5 ? O4 C3 O3 123.3(3) ? O4 C3 C4 119.6(3) ? O3 C3 C4 117.1(3) ? C3 C4 H4B 109.5 ? C3 C4 H4C 109.5 ? H4B C4 H4C 109.5 ? C3 C4 H4D 109.5 ? H4B C4 H4D 109.5 ? H4C C4 H4D 109.5 ? N1 C5 N2 118.4(4) ? N1 C5 S1 121.8(3) ? N2 C5 S1 119.8(3) ? N1 C6 C7 109.3(4) ? N1 C6 H6A 109.8 ? C7 C6 H6A 109.8 ? N1 C6 H6B 109.8 ? C7 C6 H6B 109.8 ? H6A C6 H6B 108.3 ? C6 C7 C8 110.3(4) ? C6 C7 H7A 109.6 ? C8 C7 H7A 109.6 ? C6 C7 H7B 109.6 ? C8 C7 H7B 109.6 ? H7A C7 H7B 108.1 ? N2 C8 C7 109.3(3) ? N2 C8 H8A 109.8 ? C7 C8 H8A 109.8 ? N2 C8 H8B 109.8 ? C7 C8 H8B 109.8 ? H8A C8 H8B 108.3 ? N4 C9 N3 119.7(3) ? N4 C9 S2 122.4(3) ? N3 C9 S2 117.9(3) ? N3 C10 C11B 108.4(6) ? N3 C10 C11A 108.7(4) ? N3 C10 H10A 110.0 ? C11A C10 H10A 110.0 ? N3 C10 H10B 110.0 ? C11A C10 H10B 110.0 ? H10A C10 H10B 108.3 ? N3 C10 H10C 110.0 ? C11B C10 H10C 110.0 ? N3 C10 H10D 110.0 ? C11B C10 H10D 110.0 ? H10C C10 H10D 108.4 ? C12 C11A C10 113.6(5) ? C12 C11A H11A 108.9 ? C10 C11A H11A 108.9 ? C12 C11A H11B 108.9 ? C10 C11A H11B 108.9 ? H11A C11A H11B 107.7 ? C12 C11B C10 116.6(11) ? C12 C11B H11C 108.1 ? C10 C11B H11C 108.1 ? C12 C11B H11D 108.1 ? C10 C11B H11D 108.1 ? H11C C11B H11D 107.3 ? C11B C12 N4 106.8(7) ? N4 C12 C11A 110.4(4) ? N4 C12 H12A 109.6 ? C11A C12 H12A 109.6 ? N4 C12 H12B 109.6 ? C11A C12 H12B 109.6 ? H12A C12 H12B 108.1 ? C11B C12 H12C 110.4 ? N4 C12 H12C 110.4 ? C11B C12 H12D 110.4 ? N4 C12 H12D 110.4 ? H12C C12 H12D 108.6 ? H1W1 O1W H2W1 102(6) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Zn1 O1 1.978(2) yes Zn1 O3 1.984(2) yes Zn1 S1 2.3280(10) yes Zn1 S2 2.3370(10) yes S1 C5 1.739(4) yes S2 C9 1.729(3) yes O1 C1 1.263(4) ? O2 C1 1.233(4) ? O3 C3 1.276(4) ? O4 C3 1.230(4) ? N1 C5 1.322(4) yes N1 C6 1.463(6) ? N1 H1A .8600 ? N2 C5 1.324(4) yes N2 C8 1.442(6) ? N2 H2A .8600 ? N3 C9 1.326(4) yes N3 C10 1.468(5) ? N3 H3A .8600 ? N4 C9 1.305(4) yes N4 C12 1.452(5) ? N4 H4A .8600 ? C1 C2 1.516(5) ? C2 H2B .9600 ? C2 H2C .9600 ? C2 H2D .9600 ? C3 C4 1.497(5) ? C4 H4B .9600 ? C4 H4C .9600 ? C4 H4D .9600 ? C6 C7 1.494(7) ? C6 H6A .9700 ? C6 H6B .9700 ? C7 C8 1.502(6) ? C7 H7A .9700 ? C7 H7B .9700 ? C8 H8A .9700 ? C8 H8B .9700 ? C10 C11B 1.484(16) ? C10 C11A 1.496(7) ? C10 H10A .9700 ? C10 H10B .9700 ? C10 H10C .9700 ? C10 H10D .9700 ? C11A C12 1.485(7) ? C11A H11A .9700 ? C11A H11B .9700 ? C11B C12 1.447(16) ? C11B H11C .9700 ? C11B H11D .9700 ? C12 H12A .9700 ? C12 H12B .9700 ? C12 H12C .9700 ? C12 H12D .9700 ? O1W H1W1 .86(4) ? O1W H2W1 .79(4) ? 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 N1 H1A O2 1_555 .86 1.96 2.801(4) 166 yes N4 H4A O4 1_555 .86 1.93 2.752(4) 160 yes O1W H2W1 O4 1_555 .78(5) 2.05(5) 2.823(4) 167(5) yes N2 H2A O1W 3_666 .86 2.04 2.846(5) 156 yes N3 H3A O3 4_565 .86 2.14 2.974(4) 164 yes O1W H1W1 O2 4_566 .86(6) 1.97(6) 2.818(5) 167(6) yes C4 H4D S2 4_666 .96 2.86 3.615(5) 137 yes C10 H10B O1 4_565 .97 2.45 3.315(5) 149 yes 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 O1 Zn1 S1 C5 93.70(15) O3 Zn1 S1 C5 -162.48(14) S2 Zn1 S1 C5 -24.15(13) O1 Zn1 S2 C9 -178.43(13) O3 Zn1 S2 C9 78.81(15) S1 Zn1 S2 C9 -54.40(13) O3 Zn1 O1 C1 -173.9(3) S1 Zn1 O1 C1 -59.8(3) S2 Zn1 O1 C1 62.8(3) O1 Zn1 O3 C3 -164.1(3) S1 Zn1 O3 C3 78.2(3) S2 Zn1 O3 C3 -55.8(3) Zn1 O1 C1 O2 -5.1(6) Zn1 O1 C1 C2 176.0(3) Zn1 O3 C3 O4 -3.1(5) Zn1 O3 C3 C4 177.7(3) C6 N1 C5 N2 -5.9(6) C6 N1 C5 S1 174.8(4) C8 N2 C5 N1 .1(6) C8 N2 C5 S1 179.4(3) Zn1 S1 C5 N1 -46.2(3) Zn1 S1 C5 N2 134.5(3) C5 N1 C6 C7 -19.8(6) N1 C6 C7 C8 48.7(5) C5 N2 C8 C7 30.2(6) C6 C7 C8 N2 -53.9(5) C12 N4 C9 N3 .0(6) C12 N4 C9 S2 -178.7(3) C10 N3 C9 N4 -6.3(5) C10 N3 C9 S2 172.4(3) Zn1 S2 C9 N4 -24.5(3) Zn1 S2 C9 N3 156.8(2) C9 N3 C10 C11B -15.7(9) C9 N3 C10 C11A 30.5(6) N3 C10 C11A C12 -48.8(7) N3 C10 C11B C12 45.8(14) C10 C11B C12 N4 -50.6(14) C9 N4 C12 C11B 27.5(9) C9 N4 C12 C11A -19.4(7) C10 C11A C12 N4 44.0(7)