#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/05/2010558.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_2010558 loop_ _publ_author_name 'Kansikas, Jarno' 'Sipil\"a, Kaija' _publ_section_title ; Two 9-alkylthiophenanthrenes at 193K (alkyl = dodecyl and tetradecyl) ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 69 _journal_page_last 71 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C26 H34 S' _chemical_formula_weight 378.59 _chemical_melting_point 353 _chemical_name_systematic ; 9-(Dodecylthio)phenanthrene ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 99.28(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.105(2) _cell_length_b 35.679(7) _cell_length_c 6.7840(14) _cell_measurement_reflns_used 25 _cell_measurement_temperature 193(2) _cell_measurement_theta_max 10 _cell_measurement_theta_min 4 _cell_volume 2175.0(8) _computing_cell_refinement 'CAD4 Express' _computing_data_collection 'CAD4 Express (Enraf-Nonius, 1994)' _computing_data_reduction 'WINGX (Farrugia, 1998)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXTL/PC (Sheldrick, 1990)' _diffrn_ambient_temperature 193(2) _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents .0170 _diffrn_reflns_av_sigmaI/netI .0172 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 3928 _diffrn_reflns_theta_max 64.95 _diffrn_reflns_theta_min 2.48 _diffrn_standards_decay_% .8 _diffrn_standards_interval_count 200 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.348 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 824 _exptl_crystal_size_max .31 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .10 _refine_diff_density_max .390 _refine_diff_density_min -.353 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.102 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 244 _refine_ls_number_reflns 3664 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.301 _refine_ls_restrained_S_obs 1.136 _refine_ls_R_factor_all .0655 _refine_ls_R_factor_gt .0493 _refine_ls_shift/esd_mean .000 _refine_ls_shift/su_max -.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ; calc w = 1/[\s^2^(Fo^2^)+(0.0466P)^2^+1.4963P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_wR_factor_all .1444 _refine_ls_wR_factor_ref .1183 _reflns_number_gt 3198 _reflns_number_total 3688 _reflns_observed_criterion I>2\s(I) _[local]_cod_data_source_file os1072.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_geom_bond_publ_flag' value 'Y' changed to 'y' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (12 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_geom_bond_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (12 times). '_geom_angle_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (14 times). '_geom_torsion_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (10 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2010558 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 S .0391(3) .0412(3) .0351(3) -.0050(2) .0110(2) .0077(2) C1 .0371(12) .0363(12) .0301(11) .0033(9) .0039(9) .0043(9) C2 .0324(11) .0381(12) .0389(12) .0009(9) .0054(9) -.0012(10) C3 .0364(12) .0351(12) .0378(12) -.0016(9) .0120(9) .0015(9) C4b .0373(11) .0238(10) .0265(10) .0004(8) .0088(8) -.0016(8) C4a .0328(11) .0242(10) .0273(10) .0019(8) .0074(8) .0000(8) C4 .0386(12) .0294(11) .0328(11) -.0004(9) .0102(9) .0029(9) C5 .0408(12) .0331(11) .0296(11) -.0039(9) .0061(9) .0044(9) C6 .0471(13) .0399(13) .0312(12) -.0014(10) .0025(10) .0058(9) C7 .0354(12) .0456(13) .0344(12) -.0013(10) .0007(9) -.0001(10) C8a .0334(11) .0266(10) .0263(10) .0010(8) .0075(8) -.0015(8) C8 .0375(12) .0355(12) .0334(11) -.0037(9) .0097(9) -.0017(9) C9 .0404(12) .0276(10) .0287(11) -.0005(9) .0141(9) -.0004(8) C10a .0392(12) .0260(10) .0301(11) .0027(9) .0108(9) .0005(8) C10 .0373(12) .0336(11) .0287(11) .0014(9) .0087(9) .0051(9) C12 .0414(12) .0360(12) .0338(12) .0009(10) .0140(9) .0073(9) C13 .0416(12) .0370(12) .0385(12) -.0008(10) .0158(10) .0050(10) C14 .0456(13) .0351(12) .0387(12) -.0006(10) .0165(10) .0058(10) C15 .0438(13) .0385(12) .0448(13) .0003(10) .0184(10) .0080(10) C16 .0441(13) .0377(12) .0417(13) .0015(10) .0168(10) .0066(10) C17 .0458(13) .0384(12) .0441(13) .0010(10) .0168(11) .0088(10) C18 .0483(14) .0356(12) .0428(13) .0023(10) .0179(11) .0062(10) C19 .0481(14) .0409(13) .0450(14) -.0006(11) .0152(11) .0094(11) C20 .0494(14) .0367(12) .0445(13) .0020(10) .0163(11) .0059(10) C21 .0456(13) .0379(12) .0435(13) .0004(10) .0122(10) .0081(10) C22 .0479(13) .0375(12) .0401(13) -.0002(10) .0098(10) .0037(10) C23 .063(2) .052(2) .0465(15) -.0001(13) .0146(13) .0168(12) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol S .78808(6) .13583(2) .33972(8) .0380(2) Uani d . 1 . S C1 1.3331(2) .18312(6) .3556(3) .0347(5) Uani d . 1 . C H1A 1.3585 .17032 .4792 .042 Uiso calc R 1 . H C2 1.4417(2) .20153(6) .2758(3) .0365(5) Uani d . 1 . C H2A 1.5420 .20093 .3418 .044 Uiso calc R 1 . H C3 1.4040(2) .22116(6) .0967(3) .0358(5) Uani d . 1 . C H3A 1.4786 .23451 .0427 .043 Uiso calc R 1 . H C4b .9935(2) .20064(5) -.0272(3) .0288(4) Uani d . 1 . C C4a 1.1466(2) .20193(5) .0741(3) .0278(4) Uani d . 1 . C C4 1.2611(2) .22132(6) -.0012(3) .0331(5) Uani d . 1 . C H4A 1.2378 .23480 -.1230 .040 Uiso calc R 1 . H C5 .9467(2) .21934(6) -.2092(3) .0345(5) Uani d . 1 . C H5A 1.0177 .23298 -.2688 .041 Uiso calc R 1 . H C6 .8024(3) .21844(6) -.3023(3) .0398(5) Uani d . 1 . C H6A .7742 .23135 -.4250 .048 Uiso calc R 1 . H C7 .6961(3) .19855(7) -.2175(3) .0390(5) Uani d . 1 . C H7A .5954 .19803 -.2819 .047 Uiso calc R 1 . H C8a .8853(2) .18045(6) .0590(3) .0285(4) Uani d . 1 . C C8 .7376(2) .17981(6) -.0412(3) .0350(5) Uani d . 1 . C H8A .6650 .16606 .0147 .042 Uiso calc R 1 . H C9 .9297(2) .16113(6) .2480(3) .0313(5) Uani d . 1 . C C10a 1.1852(2) .18284(6) .2584(3) .0312(5) Uani d . 1 . C C10 1.0721(2) .16298(6) .3418(3) .0328(5) Uani d . 1 . C H10A 1.0984 .15076 .4670 .039 Uiso calc R 1 . H C12 .8815(2) .11545(6) .5705(3) .0362(5) Uani d . 1 . C H12A .9660 .09979 .5444 .043 Uiso calc R 1 . H H12B .9206 .13550 .6655 .043 Uiso calc R 1 . H C13 .7692(3) .09148(6) .6587(3) .0380(5) Uani d . 1 . C H13A .6866 .10753 .6878 .046 Uiso calc R 1 . H H13B .7269 .07236 .5598 .046 Uiso calc R 1 . H C14 .8417(3) .07208(6) .8499(3) .0387(5) Uani d . 1 . C H14A .8858 .09136 .9467 .046 Uiso calc R 1 . H H14B .9237 .05599 .8193 .046 Uiso calc R 1 . H C15 .7343(3) .04812(7) .9468(4) .0411(5) Uani d . 1 . C H15A .6539 .06427 .9818 .049 Uiso calc R 1 . H H15B .6881 .02920 .8493 .049 Uiso calc R 1 . H C16 .8106(3) .02825(7) 1.1337(3) .0401(5) Uani d . 1 . C H16A .8904 .01204 1.0974 .048 Uiso calc R 1 . H H16B .8582 .04728 1.2294 .048 Uiso calc R 1 . H C17 .7073(3) .00437(7) 1.2368(4) .0417(5) Uani d . 1 . C H17A .6274 .02050 1.2732 .050 Uiso calc R 1 . H H17B .6600 -.01479 1.1416 .050 Uiso calc R 1 . H C18 .7858(3) -.01514(7) 1.4235(4) .0411(5) Uani d . 1 . C H18A .8659 -.03113 1.3866 .049 Uiso calc R 1 . H H18B .8331 .00411 1.5181 .049 Uiso calc R 1 . H C19 .6850(3) -.03922(7) 1.5292(4) .0438(6) Uani d . 1 . C H19A .6043 -.02334 1.5653 .053 Uiso calc R 1 . H H19B .6385 -.05870 1.4354 .053 Uiso calc R 1 . H C20 .7645(3) -.05813(7) 1.7158(4) .0426(6) Uani d . 1 . C H20A .8127 -.03864 1.8082 .051 Uiso calc R 1 . H H20B .8441 -.07434 1.6789 .051 Uiso calc R 1 . H C21 .6642(3) -.08182(7) 1.8254(4) .0418(5) Uani d . 1 . C H21A .5817 -.06601 1.8568 .050 Uiso calc R 1 . H H21B .6202 -.10224 1.7361 .050 Uiso calc R 1 . H C22 .7453(3) -.09881(7) 2.0174(3) .0415(5) Uani d . 1 . C H22A .7884 -.07842 2.1075 .050 Uiso calc R 1 . H H22B .8285 -.11447 1.9864 .050 Uiso calc R 1 . H C23 .6446(3) -.12269(8) 2.1243(4) .0532(7) Uani d . 1 . C H23A .7021 -.13294 2.2470 .080 Uiso calc R 1 . H H23B .6034 -.14329 2.0370 .080 Uiso calc R 1 . H H23C .5632 -.10722 2.1579 .080 Uiso calc R 1 . H 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 C9 . 1.767(2) y S C12 . 1.809(2) y C1 C2 . 1.370(3) ? C1 C10a . 1.401(3) ? C2 C3 . 1.396(3) ? C3 C4 . 1.362(3) ? C4 C4a . 1.413(3) y C4a C4b . 1.453(3) y C4a C10a . 1.418(3) y C4b C5 . 1.407(3) y C4b C8a . 1.420(3) y C5 C6 . 1.363(3) ? C6 C7 . 1.397(3) ? C7 C8 . 1.369(3) ? C8 C8a . 1.406(3) ? C8a C9 . 1.455(3) y C9 C10 . 1.350(3) y C10 C10a . 1.439(3) y C12 C13 . 1.527(3) y C13 C14 . 1.524(3) y C14 C15 . 1.526(3) ? C15 C16 . 1.520(3) ? C16 C17 . 1.520(3) ? C17 C18 . 1.519(3) ? C18 C19 . 1.518(3) ? C19 C20 . 1.512(4) ? C20 C21 . 1.523(3) ? C21 C22 . 1.516(3) ? C22 C23 . 1.519(3) ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 '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' S S .3331 .5567 '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 C9 S C12 104.01(10) y C2 C1 C10a 121.2(2) ? C1 C2 C3 119.5(2) ? C4 C3 C2 120.5(2) ? C4 C4a C4b 123.5(2) y C4b C4a C10a 119.0(2) y C4a C4b C5 122.1(2) y C4a C4b C8a 119.9(2) y C5 C4b C8a 118.0(2) ? C4 C4a C10a 117.5(2) ? C3 C4 C4a 121.6(2) ? C6 C5 C4b 121.9(2) ? C5 C6 C7 120.1(2) ? C8 C7 C6 119.7(2) ? C8 C8a C4b 118.8(2) ? C8 C8a C9 121.8(2) ? C4b C8a C9 119.4(2) y C7 C8 C8a 121.5(2) ? C8a C9 C10 120.1(2) y C8a C9 S 116.0(2) y C10 C9 S 123.9(2) y C1 C10a C4a 119.6(2) ? C1 C10a C10 120.9(2) ? C9 C10 C10a 122.1(2) y C4a C10a C10 119.5(2) y C13 C12 S 108.2(2) y C12 C13 C14 111.2(2) y C13 C14 C15 113.7(2) y C16 C15 C14 112.5(2) ? C15 C16 C17 114.3(2) ? C16 C17 C18 113.5(2) ? C19 C18 C17 114.5(2) ? C20 C19 C18 113.8(2) ? C19 C20 C21 114.4(2) ? C22 C21 C20 113.2(2) ? C21 C22 C23 112.7(2) ? 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 _geom_torsion_publ_flag C10a C1 C2 C3 1.6(3) ? C1 C2 C3 C4 -1.7(3) ? C5 C4b C4a C4 -.9(3) ? C8a C4b C4a C4 180.0(2) ? C5 C4b C4a C10a 179.1(2) ? C8a C4b C4a C10a .0(3) y C2 C3 C4 C4a .2(3) ? C10a C4a C4 C3 1.4(3) ? C4b C4a C4 C3 -178.6(2) ? C8a C4b C5 C6 .0(3) ? C4a C4b C5 C6 -179.1(2) ? C4b C5 C6 C7 .0(3) ? C5 C6 C7 C8 -.4(3) ? C5 C4b C8a C8 .4(3) ? C4a C4b C8a C8 179.6(2) ? C5 C4b C8a C9 -179.4(2) ? C4a C4b C8a C9 -.2(3) y C6 C7 C8 C8a .8(3) ? C4b C8a C8 C7 -.9(3) ? C9 C8a C8 C7 178.9(2) ? C8 C8a C9 C10 -178.7(2) y C4b C8a C9 C10 1.1(3) y C8 C8a C9 S 1.8(3) y C4b C8a C9 S -178.44(15) y C12 S C9 C10 -.1(2) y C12 S C9 C8a 179.4(2) y C2 C1 C10a C4a .0(3) ? C2 C1 C10a C10 179.1(2) ? C4 C4a C10a C1 -1.4(3) ? C4b C4a C10a C1 178.6(2) ? C4 C4a C10a C10 179.5(2) ? C4b C4a C10a C10 -.6(3) ? C8a C9 C10 C10a -1.7(3) y S C9 C10 C10a 177.8(2) y C1 C10a C10 C9 -177.6(2) ? C4a C10a C10 C9 1.5(3) ? C9 S C12 C13 -177.79(15) ? S C12 C13 C14 177.7(2) ? C12 C13 C14 C15 179.2(2) ? C13 C14 C15 C16 178.3(2) ? C14 C15 C16 C17 179.3(2) ? C15 C16 C17 C18 -179.8(2) ? C16 C17 C18 C19 -179.9(2) ? C17 C18 C19 C20 -179.4(2) ? C18 C19 C20 C21 178.9(2) ? C19 C20 C21 C22 -177.1(2) ? C20 C21 C22 C23 -179.4(2) ? _cod_database_fobs_code 2010558 _journal_paper_doi 10.1107/S0108270199012871