#------------------------------------------------------------------------------ #$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2015287.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_2015287 loop_ _publ_author_name 'Kasyan, Oleg' 'Thondorf, Iris' 'Bolte, Michael' 'Kalchenko, Vitaly' 'B\"ohmer, Volker' _publ_section_title ; Unusual conformations of 1,3-dialkoxythiacalix[4]arenes in the solid state ; _journal_coeditor_code AV3005 _journal_issue 5 _journal_name_full 'Acta Crystallographica, Section C' _journal_page_first o289 _journal_page_last o294 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C30 H20 N4 O12 S4' _chemical_formula_moiety 'C30 H20 N4 O12 S4' _chemical_formula_sum 'C30 H20 N4 O12 S4' _chemical_formula_weight 756.74 _chemical_name_systematic ; syn-2^2^,4^2^-dihydroxy-1^5^,2^5^,3^5^,4^5^-tetranitro-1^2^,3^2^- bis(prop-2-enoxy)thiacalix[4]arene ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_space_group_name_H-M 'P n m 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 4 _cell_length_a 17.2475(17) _cell_length_b 20.4150(19) _cell_length_c 9.1020(10) _cell_measurement_reflns_used 23347 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.8 _cell_measurement_theta_min 3.4 _cell_volume 3204.9(6) _computing_cell_refinement X-Area _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction X-Area _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type 'STOE IPDS-II two-circle-diffractometer' _diffrn_measurement_method \w _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 0.0982 _diffrn_reflns_av_sigmaI/netI 0.0773 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 44126 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.78 _diffrn_reflns_theta_min 3.40 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.369 _exptl_absorpt_correction_T_max 0.961 _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(MULABS; Spek, 2003; Blessing, 1995)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1552 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.738 _refine_diff_density_min -0.482 _refine_ls_extinction_coef 0.0092(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 239 _refine_ls_number_reflns 3127 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.105 _refine_ls_R_factor_all 0.1145 _refine_ls_R_factor_gt 0.0926 _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/[\s^2^(Fo^2^)+(0.1315P)^2^+3.5315P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2373 _refine_ls_wR_factor_ref 0.2565 _reflns_number_gt 2375 _reflns_number_total 3127 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file av3005.cif _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_database_code 2015287 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' 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_disorder_assembly _atom_site_disorder_group S S1 0.61872(9) 0.61341(8) 0.82180(14) 0.0656(5) Uani d . 1 . . S S2 0.69118(9) 0.61361(8) 0.22341(16) 0.0693(5) Uani d . 1 . . O O12 0.72499(18) 0.62180(17) 0.5518(4) 0.0529(9) Uani d . 1 . . O O22 0.6226(3) 0.7500 0.2025(6) 0.089(2) Uani d S 1 . . H H22 0.6069 0.7888 0.1948 0.133 Uiso d PR 0.50 . . O O25 0.9692(3) 0.6984(3) 0.3656(11) 0.145(3) Uani d . 1 . . O O151 0.3995(2) 0.5491(2) 0.2899(4) 0.0697(11) Uani d . 1 . . O O152 0.3698(2) 0.5563(2) 0.5220(5) 0.0772(13) Uani d . 1 . . O O32 0.5521(3) 0.7500 0.7811(7) 0.090(2) Uani d S 1 . . H H32 0.5362 0.7888 0.7741 0.134 Uiso d PR 0.50 . . O O35 0.8993(3) 0.7006(3) 0.9325(11) 0.157(4) Uani d . 1 . . N N15 0.4162(2) 0.5614(2) 0.4195(5) 0.0540(10) Uani d . 1 . . N N25 0.9362(4) 0.7500 0.3509(11) 0.082(2) Uani d S 1 . . N N35 0.8678(4) 0.7500 0.9116(8) 0.0654(18) Uani d S 1 . . C C11 0.5931(3) 0.6069(2) 0.6329(5) 0.0491(11) Uani d . 1 . . C C12 0.6480(2) 0.6114(2) 0.5186(5) 0.0438(10) Uani d . 1 . . C C13 0.6245(3) 0.6070(2) 0.3721(5) 0.0489(11) Uani d . 1 . . C C14 0.5475(3) 0.5910(2) 0.3386(5) 0.0506(11) Uani d . 1 . . H H14 0.5310 0.5868 0.2395 0.061 Uiso calc R 1 . . C C15 0.4963(2) 0.5814(2) 0.4531(5) 0.0470(11) Uani d . 1 . . C C16 0.5166(3) 0.5907(3) 0.5992(5) 0.0508(11) Uani d . 1 . . H H16 0.4791 0.5860 0.6749 0.061 Uiso calc R 1 . . C C21 0.7377(3) 0.6903(3) 0.2582(5) 0.0575(13) Uani d . 1 . . C C22 0.6982(4) 0.7500 0.2389(7) 0.0552(17) Uani d S 1 . . C C25 0.8531(4) 0.7500 0.3108(9) 0.062(2) Uani d S 1 . . C C26 0.8163(3) 0.6903(3) 0.2952(7) 0.0628(14) Uani d . 1 . . H H26 0.8438 0.6504 0.3091 0.075 Uiso calc R 1 . . C C31 0.6675(3) 0.6902(3) 0.8310(5) 0.0510(12) Uani d . 1 . . C C32 0.6282(4) 0.7500 0.8138(7) 0.0545(18) Uani d S 1 . . C C35 0.7837(4) 0.7500 0.8833(7) 0.0501(16) Uani d S 1 . . C C36 0.7464(3) 0.6904(3) 0.8664(5) 0.0497(11) Uani d . 1 . . H H36 0.7739 0.6505 0.8786 0.060 Uiso calc R 1 . . C C121 0.7672(3) 0.5614(3) 0.5776(8) 0.0747(17) Uani d . 1 A . H H12A 0.7616 0.5317 0.4922 0.090 Uiso calc R 1 . . H H12B 0.7465 0.5389 0.6656 0.090 Uiso calc R 1 . . C C122 0.8506(3) 0.5785(3) 0.6001(7) 0.0703(16) Uani d D 1 . . H H12G 0.8630 0.6168 0.6543 0.084 Uiso calc PR 0.726(15) A 1 H H12H 0.8844 0.5426 0.6181 0.084 Uiso calc PR 0.274(15) A 2 C C123 0.9054(5) 0.5438(4) 0.5499(9) 0.069(3) Uiso d PD 0.726(15) A 1 H H12C 0.9533 0.5637 0.5239 0.083 Uiso calc PR 0.726(15) A 1 H H12D 0.8986 0.4979 0.5381 0.083 Uiso calc PR 0.726(15) A 1 C C124 0.8827(11) 0.6354(7) 0.598(2) 0.058(6) Uiso d PD 0.274(15) A 2 H H12E 0.9344 0.6402 0.5642 0.070 Uiso calc PR 0.274(15) A 2 H H12F 0.8546 0.6727 0.6311 0.070 Uiso calc PR 0.274(15) A 2 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 S1 0.0660(8) 0.0898(11) 0.0411(7) -0.0310(7) -0.0067(5) 0.0057(6) S2 0.0691(9) 0.0859(11) 0.0528(8) -0.0209(7) 0.0181(6) -0.0188(7) O12 0.0364(16) 0.062(2) 0.060(2) -0.0051(14) -0.0038(14) -0.0023(15) O22 0.045(3) 0.169(7) 0.052(3) 0.000 -0.006(2) 0.000 O25 0.050(3) 0.080(3) 0.305(10) 0.010(2) -0.012(4) -0.008(5) O32 0.034(3) 0.160(7) 0.075(4) 0.000 -0.007(2) 0.000 O35 0.059(3) 0.064(3) 0.347(12) 0.010(2) -0.065(5) -0.014(5) O151 0.057(2) 0.084(3) 0.068(2) -0.010(2) -0.0290(18) 0.007(2) O152 0.0428(19) 0.093(3) 0.096(3) -0.0105(19) 0.007(2) -0.021(2) N15 0.041(2) 0.055(2) 0.066(3) 0.0013(18) -0.0107(19) -0.0011(19) N25 0.040(3) 0.067(5) 0.139(7) 0.000 0.010(4) 0.000 N35 0.049(3) 0.050(4) 0.098(5) 0.000 -0.019(3) 0.000 C11 0.045(2) 0.054(3) 0.049(2) -0.004(2) -0.005(2) 0.004(2) C12 0.035(2) 0.046(2) 0.050(2) -0.0041(17) -0.0049(18) -0.0015(19) C13 0.044(2) 0.054(3) 0.049(2) -0.005(2) 0.0015(19) -0.005(2) C14 0.052(3) 0.054(3) 0.045(2) -0.003(2) -0.009(2) -0.001(2) C15 0.036(2) 0.053(3) 0.053(3) -0.0039(19) -0.0097(18) 0.000(2) C16 0.040(2) 0.057(3) 0.055(3) -0.002(2) 0.0004(19) -0.002(2) C21 0.051(3) 0.076(4) 0.046(3) -0.009(2) 0.016(2) -0.007(2) C22 0.052(4) 0.077(5) 0.037(3) 0.000 0.011(3) 0.000 C25 0.041(4) 0.064(5) 0.081(5) 0.000 0.018(3) 0.000 C26 0.048(3) 0.066(3) 0.074(4) 0.002(2) 0.021(2) -0.007(3) C31 0.048(2) 0.076(3) 0.029(2) -0.010(2) 0.0011(18) -0.002(2) C32 0.039(3) 0.088(5) 0.036(3) 0.000 -0.001(3) 0.000 C35 0.039(3) 0.063(4) 0.048(4) 0.000 -0.010(3) 0.000 C36 0.050(3) 0.064(3) 0.035(2) 0.002(2) -0.0040(18) -0.002(2) C121 0.045(3) 0.068(4) 0.110(5) 0.002(3) -0.021(3) 0.005(3) C122 0.047(3) 0.089(4) 0.075(4) 0.007(3) -0.015(3) -0.013(3) 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_site_symmetry_3 _geom_angle C31 S1 C11 . . 103.2(2) C16 C11 C12 . . 119.3(4) C16 C11 S1 . . 117.7(4) C12 C11 S1 . . 122.7(3) O12 C12 C13 . . 119.9(4) O12 C12 C11 . . 119.7(4) C13 C12 C11 . . 120.3(4) C12 C13 C14 . . 119.8(4) C12 C13 S2 . . 122.2(3) C14 C13 S2 . . 117.7(4) C15 C14 C13 . . 118.4(4) C15 C14 H14 . . 120.8 C13 C14 H14 . . 120.8 C14 C15 C16 . . 122.8(4) C14 C15 N15 . . 118.9(4) C16 C15 N15 . . 118.3(4) C15 C16 C11 . . 118.8(4) C15 C16 H16 . . 120.6 C11 C16 H16 . . 120.6 C12 O12 C121 . . 112.8(4) O12 C121 C122 . . 107.9(5) O12 C121 H12A . . 110.1 C122 C121 H12A . . 110.1 O12 C121 H12B . . 110.1 C122 C121 H12B . . 110.1 H12A C121 H12B . . 108.4 C123 C122 C124 . . 100.3(11) C123 C122 C121 . . 122.6(7) C124 C122 C121 . . 128.5(10) C123 C122 H12G . . 118.7 C121 C122 H12G . . 118.7 C124 C122 H12H . . 115.8 C121 C122 H12H . . 115.8 H12G C122 H12H . . 114.1 C122 C123 H12C . . 120.0 C122 C123 H12D . . 120.0 H12C C123 H12D . . 120.0 C122 C124 H12E . . 120.0 C122 C124 H12F . . 120.0 H12E C124 H12F . . 120.0 O152 N15 O151 . . 123.6(4) O152 N15 C15 . . 118.3(4) O151 N15 C15 . . 118.1(4) C13 S2 C21 . . 102.8(2) C26 C21 C22 . . 119.9(5) C26 C21 S2 . . 118.6(5) C22 C21 S2 . . 121.3(4) O22 C22 C21 . 7_575 120.0(3) O22 C22 C21 . . 120.0(3) C21 C22 C21 7_575 . 120.0(7) C26 C25 C26 7_575 . 123.9(7) C26 C25 N25 7_575 . 118.0(4) C26 C25 N25 . . 118.0(4) C25 C26 C21 . . 118.1(6) C25 C26 H26 . . 121.0 C21 C26 H26 . . 121.0 C22 O22 H22 . . 109.5 O25 N25 O25 . 7_575 122.0(8) O25 N25 C25 . . 119.0(4) O25 N25 C25 7_575 . 119.0(4) C36 C31 C32 . . 119.4(5) C36 C31 S1 . . 118.3(4) C32 C31 S1 . . 122.2(4) O32 C32 C31 . . 119.6(3) O32 C32 C31 . 7_575 119.6(3) C31 C32 C31 . 7_575 120.7(6) C36 C35 C36 7_575 . 122.9(6) C36 C35 N35 7_575 . 118.5(3) C36 C35 N35 . . 118.5(3) C35 C36 C31 . . 118.8(5) C35 C36 H36 . . 120.6 C31 C36 H36 . . 120.6 C32 O32 H32 . . 109.5 O35 N35 O35 . 7_575 120.7(7) O35 N35 C35 . . 119.3(4) O35 N35 C35 7_575 . 119.2(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C31 1.780(5) S1 C11 1.780(5) C11 C16 1.394(6) C11 C12 1.410(7) C12 O12 1.378(5) C12 C13 1.397(7) C13 C14 1.402(7) C13 S2 1.781(5) C14 C15 1.380(7) C14 H14 0.9500 C15 C16 1.389(7) C15 N15 1.473(6) C16 H16 0.9500 O12 C121 1.451(7) C121 C122 1.494(8) C121 H12A 0.9900 C121 H12B 0.9900 C122 C123 1.266(9) C122 C124 1.288(12) C122 H12G 0.9500 C122 H12H 0.9500 C123 H12C 0.9500 C123 H12D 0.9500 C124 H12E 0.9500 C124 H12F 0.9500 N15 O152 1.233(6) N15 O151 1.239(5) S2 C21 1.787(6) C21 C26 1.397(8) C21 C22 1.408(7) C22 O22 1.346(9) C25 C26 1.381(7) C25 N25 1.480(10) C26 H26 0.9500 O22 H22 0.8399 N25 O25 1.204(6) C31 C36 1.399(7) C31 C32 1.405(6) C32 O32 1.347(8) C35 C36 1.385(6) C35 N35 1.473(8) C36 H36 0.9500 O32 H32 0.8400 N35 O35 1.162(6) 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 O22 H22 O25 4_465 0.84 2.45 2.915(8) 116 O22 H22 S2 7_575 0.84 2.48 3.031(3) 124 O32 H32 S1 7_575 0.84 2.49 3.039(3) 124 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_1 _geom_torsion_site_symmetry_4 _geom_torsion C31 S1 C11 C16 . . -130.5(4) C31 S1 C11 C12 . . 55.5(5) C16 C11 C12 O12 . . -174.4(4) S1 C11 C12 O12 . . -0.5(6) C16 C11 C12 C13 . . 7.2(7) S1 C11 C12 C13 . . -178.9(4) O12 C12 C13 C14 . . 174.6(4) C11 C12 C13 C14 . . -7.0(7) O12 C12 C13 S2 . . 0.7(7) C11 C12 C13 S2 . . 179.1(4) C12 C13 C14 C15 . . 1.6(7) S2 C13 C14 C15 . . 175.8(4) C13 C14 C15 C16 . . 3.7(8) C13 C14 C15 N15 . . -177.0(4) C14 C15 C16 C11 . . -3.5(8) N15 C15 C16 C11 . . 177.2(4) C12 C11 C16 C15 . . -2.0(7) S1 C11 C16 C15 . . -176.2(4) C13 C12 O12 C121 . . -93.8(6) C11 C12 O12 C121 . . 87.9(6) C12 O12 C121 C122 . . 175.4(5) O12 C121 C122 C123 . . -141.3(7) O12 C121 C122 C124 . . 0.0(14) C14 C15 N15 O152 . . -176.3(5) C16 C15 N15 O152 . . 3.0(7) C14 C15 N15 O151 . . 5.2(7) C16 C15 N15 O151 . . -175.5(5) C12 C13 S2 C21 . . -55.0(5) C14 C13 S2 C21 . . 131.0(4) C13 S2 C21 C26 . . 113.3(4) C13 S2 C21 C22 . . -71.3(5) C26 C21 C22 O22 . . 179.6(5) S2 C21 C22 O22 . . 4.3(8) C26 C21 C22 C21 . 7_575 -0.7(9) S2 C21 C22 C21 . 7_575 -176.0(3) C26 C25 C26 C21 7_575 . 1.4(12) N25 C25 C26 C21 . . 179.6(6) C22 C21 C26 C25 . . -0.3(8) S2 C21 C26 C25 . . 175.1(5) C26 C25 N25 O25 7_575 . 179.7(9) C26 C25 N25 O25 . . 1.4(13) C26 C25 N25 O25 7_575 7_575 -1.4(13) C26 C25 N25 O25 . 7_575 -179.7(9) C11 S1 C31 C36 . . -114.5(4) C11 S1 C31 C32 . . 69.9(5) C36 C31 C32 O32 . . -179.4(5) S1 C31 C32 O32 . . -3.8(8) C36 C31 C32 C31 . 7_575 0.4(9) S1 C31 C32 C31 . 7_575 175.9(3) C36 C35 C36 C31 7_575 . -0.1(9) N35 C35 C36 C31 . . -176.3(5) C32 C31 C36 C35 . . -0.1(7) S1 C31 C36 C35 . . -175.8(4) C36 C35 N35 O35 7_575 . 176.6(8) C36 C35 N35 O35 . . -7.1(12) C36 C35 N35 O35 7_575 7_575 7.1(12) C36 C35 N35 O35 . 7_575 -176.6(8)