#------------------------------------------------------------------------------ #$Date: 2015-01-23 13:30:19 +0100 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/88/2008867.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_2008867 loop_ _publ_author_name 'Moers, Oliver' 'Wijaya, Karna' 'Jones, Peter G.' 'Blaschette, Armand' _publ_section_title ; 1,4,7,10-Tetraoxacyclododecane--acetone thiosemicarbazone (1/2) ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1542 _journal_page_last 1545 _journal_paper_doi 10.1107/S0108270199006381 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C8 H16 O4 , 2C5 H9 N3 S' _chemical_formula_sum 'C16 H34 N6 O4 S2' _chemical_formula_weight 438.61 _chemical_name_systematic ; 1,4,7,1O-Tetraoxacyclododecane--acetone thiosemicarbazone (1/2) ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL97 _cell_angle_alpha 115.612(14) _cell_angle_beta 98.079(15) _cell_angle_gamma 104.033(16) _cell_formula_units_Z 1 _cell_length_a 7.847(3) _cell_length_b 8.594(3) _cell_length_c 9.867(3) _cell_measurement_reflns_used 48 _cell_measurement_temperature 143(2) _cell_measurement_theta_max 11.5 _cell_measurement_theta_min 10.0 _cell_volume 558.8(4) _computing_cell_refinement DIF4 _computing_data_collection 'DIF4 (Stoe & Cie, 1992a)' _computing_data_reduction 'REDU4 (Stoe & Cie, 1992b)' _computing_molecular_graphics 'XP (Siemens, 1994)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 143(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Stoe Stadi-4' _diffrn_measurement_method \w/\q-scans _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 0.041 _diffrn_reflns_av_sigmaI/netI 0.035 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 3225 _diffrn_reflns_theta_full 25.02 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 3.12 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 90 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_meas ? _exptl_crystal_description block _exptl_crystal_F_000 236 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.24 _refine_diff_density_min -0.28 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 141 _refine_ls_number_reflns 1975 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.041 _refine_ls_R_factor_gt 0.036 _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/[\s^2^(Fo^2^)+(0.0361P)^2^+0.2808P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.093 _reflns_number_gt 1780 _reflns_number_total 1975 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm1332.cif _[local]_cod_data_source_block foisch _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 558.8(3) _cod_database_code 2008867 _cod_database_fobs_code 2008867 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 S 0.23543(6) 0.24469(6) 0.16670(5) 0.03346(17) Uani d . 1 . . S N1 0.20135(19) 0.4759(2) -0.09760(16) 0.0277(3) Uani d . 1 . . N N2 0.2505(2) 0.4470(2) 0.02807(17) 0.0281(3) Uani d . 1 . . N H01 0.326(3) 0.532(3) 0.116(3) 0.042(6) Uiso d . 1 . . H N3 0.0438(2) 0.1552(2) -0.11624(18) 0.0342(4) Uani d . 1 . . N H02 0.008(3) 0.180(3) -0.190(3) 0.036(6) Uiso d . 1 . . H H03 -0.013(3) 0.055(3) -0.120(3) 0.041(6) Uiso d . 1 . . H C1 0.1703(2) 0.2828(2) 0.01575(19) 0.0262(4) Uani d . 1 . . C C2 0.2734(2) 0.6373(2) -0.0780(2) 0.0281(4) Uani d . 1 . . C C3 0.4037(3) 0.7996(3) 0.0692(2) 0.0382(5) Uani d . 1 . . C H3A 0.3507 0.8172 0.1568 0.046 Uiso calc R 1 . . H H3B 0.4262 0.9094 0.0569 0.046 Uiso calc R 1 . . H H3C 0.5194 0.7786 0.0903 0.046 Uiso calc R 1 . . H C4 0.2245(3) 0.6665(3) -0.2149(2) 0.0385(5) Uani d . 1 . . C H4A 0.1436 0.5502 -0.3053 0.046 Uiso calc R 1 . . H H4B 0.3361 0.7117 -0.2402 0.046 Uiso calc R 1 . . H H4C 0.1617 0.7569 -0.1890 0.046 Uiso calc R 1 . . H O11 0.42287(16) 0.72709(16) 0.36590(13) 0.0290(3) Uani d . 1 . . O C12 0.2569(2) 0.7088(2) 0.4109(2) 0.0316(4) Uani d . 1 . . C H12A 0.2468 0.6302 0.4610 0.038 Uiso calc R 1 . . H H12B 0.1512 0.6483 0.3165 0.038 Uiso calc R 1 . . H C13 0.2514(2) 0.8923(3) 0.5226(2) 0.0330(4) Uani d . 1 . . C H13A 0.1545 0.8768 0.5748 0.040 Uiso calc R 1 . . H H13B 0.3703 0.9668 0.6040 0.040 Uiso calc R 1 . . H O14 0.21409(17) 0.98093(17) 0.43454(14) 0.0356(3) Uani d . 1 . . O C15 0.2510(3) 1.1730(3) 0.5254(2) 0.0375(4) Uani d . 1 . . C H15A 0.2444 1.2023 0.6328 0.045 Uiso calc R 1 . . H H15B 0.1560 1.2073 0.4790 0.045 Uiso calc R 1 . . H C16 0.4360(3) 1.2837(3) 0.5334(2) 0.0359(4) Uani d . 1 . . C H16A 0.4529 1.2371 0.4271 0.043 Uiso calc R 1 . . H H16B 0.4441 1.4134 0.5732 0.043 Uiso calc R 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 S 0.0356(3) 0.0261(3) 0.0298(3) -0.00027(19) -0.00532(19) 0.0159(2) N1 0.0278(8) 0.0292(8) 0.0231(7) 0.0047(6) 0.0031(6) 0.0141(6) N2 0.0308(8) 0.0230(8) 0.0219(7) 0.0004(6) -0.0015(6) 0.0107(6) N3 0.0367(9) 0.0255(8) 0.0275(8) -0.0034(7) -0.0050(7) 0.0135(7) C1 0.0254(8) 0.0235(9) 0.0256(8) 0.0055(7) 0.0036(7) 0.0109(7) C2 0.0283(9) 0.0283(9) 0.0273(9) 0.0063(7) 0.0074(7) 0.0149(7) C3 0.0473(12) 0.0258(10) 0.0317(10) -0.0002(8) 0.0067(8) 0.0136(8) C4 0.0391(11) 0.0415(11) 0.0365(10) 0.0054(9) 0.0052(8) 0.0263(9) O11 0.0254(6) 0.0316(7) 0.0246(6) 0.0025(5) -0.0001(5) 0.0148(5) C12 0.0273(9) 0.0317(10) 0.0275(9) -0.0015(7) 0.0006(7) 0.0155(8) C13 0.0284(9) 0.0375(10) 0.0239(9) 0.0015(8) 0.0018(7) 0.0137(8) O14 0.0356(7) 0.0300(7) 0.0267(6) 0.0033(6) -0.0039(5) 0.0094(5) C15 0.0298(10) 0.0334(10) 0.0372(10) 0.0107(8) 0.0016(8) 0.0093(8) C16 0.0341(10) 0.0330(10) 0.0352(10) 0.0064(8) -0.0031(8) 0.0183(8) 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' 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 _geom_angle_publ_flag C2 N1 N2 . 117.30(14) y C1 N2 N1 . 119.28(15) y N3 C1 N2 . 118.15(16) y N3 C1 S . 122.48(14) y N2 C1 S . 119.36(13) y N1 C2 C4 . 117.14(16) y N1 C2 C3 . 126.07(16) y C4 C2 C3 . 116.79(16) y C16 O11 C12 2_676 112.33(14) ? O11 C12 C13 . 111.08(14) ? O14 C13 C12 . 107.58(14) ? C15 O14 C13 . 114.89(14) ? O14 C15 C16 . 112.06(16) ? O11 C16 C15 2_676 110.59(15) ? 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 S C1 . 1.6958(18) y N1 C2 . 1.280(2) y N1 N2 . 1.388(2) y N2 C1 . 1.342(2) y N3 C1 . 1.326(2) y C2 C4 . 1.493(2) y C2 C3 . 1.497(3) y O11 C16 2_676 1.429(2) ? O11 C12 . 1.429(2) ? C12 C13 . 1.499(3) ? C13 O14 . 1.425(2) ? O14 C15 . 1.424(2) ? C15 C16 . 1.501(3) ? C16 O11 2_676 1.429(2) ? 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 N2 H01 O11 . 0.86(2) 2.18(2) 2.992(2) 158(2) y N3 H02 O14 2_565 0.87(2) 2.35(2) 3.036(2) 136(2) y N3 H02 N1 . 0.87(2) 2.31(2) 2.647(2) 103(2) y N3 H03 S 2 0.85(2) 2.54(2) 3.380(2) 169(2) y C3 H3A O11 . 0.98 2.54 3.238(2) 128 y 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_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 N1 N2 C1 . . . 176.18(16) y N1 N2 C1 N3 . . . -1.2(3) y N1 N2 C1 S . . . 177.90(12) y N2 N1 C2 C4 . . . 178.24(15) y N2 N1 C2 C3 . . . -1.2(3) y O11 C12 C13 O14 . . . 75.21(17) y C12 C13 O14 C15 . . . -164.26(15) y C13 O14 C15 C16 . . . 96.55(19) y O14 C15 C16 O11 . . 2_676 -73.6(2) y C15 C16 O11 C12 . 2_676 2_676 150.52(15) y C16 O11 C12 C13 2_676 2_676 2_676 -90.90(17) y