#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2012482.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_2012482 loop_ _publ_author_name 'Nesterov, Vladimir N.' 'Montoya, Nicole G.' 'Antipin, Mikhail Yu.' 'Sanghadasa, Mohan' 'Clark, Ronald D.' 'Timofeeva, Tatiana V.' _publ_section_title ; Three polar derivatives of N-ethylcarbazole: materials for optical applications ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o72 _journal_page_last o75 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C18 H15 N3 S' _chemical_formula_sum 'C18 H15 N3 S' _chemical_formula_weight 305.39 _chemical_name_systematic ; 2-cyano-3-(9-ethyl-9H-carbazol-3-yl)thioacrylamide ; _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 SHELXL97 _cell_angle_alpha 79.82(3) _cell_angle_beta 76.82(3) _cell_angle_gamma 63.76(3) _cell_formula_units_Z 2 _cell_length_a 8.4370(17) _cell_length_b 8.7500(17) _cell_length_c 12.300(3) _cell_measurement_reflns_used 24 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 12 _cell_measurement_theta_min 11 _cell_volume 790.0(4) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1994)' _computing_molecular_graphics SHELXTL-Plus _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full .996 _diffrn_measured_fraction_theta_max .996 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \q/2\q _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 .013 _diffrn_reflns_av_sigmaI/netI .018 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 2971 _diffrn_reflns_theta_full 24.97 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_min 1.71 _diffrn_standards_decay_% 3 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .204 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'parallelepiped prism' _exptl_crystal_F_000 320 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .35 _exptl_crystal_size_min .30 _refine_diff_density_max .33 _refine_diff_density_min -.19 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 2762 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all .051 _refine_ls_R_factor_gt .039 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.06P)^2^+0.24P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .106 _refine_ls_wR_factor_ref .114 _reflns_number_gt 2257 _reflns_number_total 2762 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm1472.cif _[local]_cod_data_source_block IIIb _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 790.0(3) _cod_database_code 2012482 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_type_symbol S1 .41428(8) .37861(7) .89386(4) .0599(2) Uani d . 1 S N1 .0770(2) .5525(2) .26053(12) .0453(4) Uani d . 1 N N2 .2878(3) .9276(3) .64142(18) .0721(6) Uani d . 1 N N3 .4516(2) .6662(2) .85720(13) .0565(5) Uani d . 1 N H3A .4438 .7603 .8181 .068 Uiso calc R 1 H H3B .4880 .6413 .9206 .068 Uiso calc R 1 H C1 .1080(3) .7126(2) .39735(15) .0482(4) Uani d . 1 C H1A .0477 .8207 .3629 .058 Uiso calc R 1 H C2 .1753(3) .6928(2) .49317(15) .0475(4) Uani d . 1 C H2A .1617 .7895 .5226 .057 Uiso calc R 1 H C3 .2644(2) .5304(2) .54832(13) .0409(4) Uani d . 1 C C4 .2851(2) .3853(2) .50360(14) .0414(4) Uani d . 1 C H4A .3405 .2775 .5400 .050 Uiso calc R 1 H C5 .2230(2) .4016(2) .40500(13) .0385(4) Uani d . 1 C C6 .2251(2) .2815(2) .33690(14) .0420(4) Uani d . 1 C C7 .2969(3) .1045(3) .34141(18) .0565(5) Uani d . 1 C H7A .3554 .0374 .4001 .068 Uiso calc R 1 H C8 .2804(4) .0297(3) .2577(2) .0702(6) Uani d . 1 C H8A .3288 -.0889 .2597 .084 Uiso calc R 1 H C9 .1920(4) .1294(3) .1701(2) .0707(7) Uani d . 1 C H9A .1837 .0755 .1142 .085 Uiso calc R 1 H C10 .1163(3) .3055(3) .16378(17) .0561(5) Uani d . 1 C H10A .0557 .3713 .1057 .067 Uiso calc R 1 H C11 .1346(2) .3806(2) .24809(14) .0427(4) Uani d . 1 C C12 -.0334(3) .6954(3) .19076(17) .0569(5) Uani d . 1 C H12A -.1117 .7893 .2364 .068 Uiso calc R 1 H H12B -.1081 .6606 .1608 .068 Uiso calc R 1 H C13 .0772(4) .7543(4) .0971(2) .0844(8) Uani d . 1 C H13A .0004 .8491 .0535 .127 Uiso calc R 1 H H13B .1522 .6625 .0505 .127 Uiso calc R 1 H H13C .1508 .7894 .1265 .127 Uiso calc R 1 H C14 .1327(2) .5660(2) .35335(14) .0402(4) Uani d . 1 C C15 .3292(2) .5051(2) .65209(14) .0431(4) Uani d . 1 C H15A .3658 .3937 .6856 .052 Uiso calc R 1 H C16 .3463(2) .6140(2) .70918(14) .0426(4) Uani d . 1 C C17 .3106(3) .7882(3) .66844(16) .0502(5) Uani d . 1 C C18 .4077(2) .5594(3) .81966(14) .0445(4) Uani d . 1 C 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 .0807(4) .0756(4) .0394(3) -.0425(3) -.0283(2) .0058(2) N1 .0520(9) .0510(9) .0372(8) -.0203(7) -.0196(7) -.0021(6) N2 .0845(14) .0540(12) .0779(13) -.0146(10) -.0425(11) -.0081(9) N3 .0723(11) .0784(12) .0355(8) -.0440(10) -.0190(8) .0010(8) C1 .0533(11) .0451(10) .0448(10) -.0132(8) -.0228(8) -.0019(8) C2 .0527(11) .0491(10) .0427(10) -.0161(9) -.0188(8) -.0089(8) C3 .0401(9) .0528(10) .0296(8) -.0185(8) -.0083(7) -.0031(7) C4 .0452(10) .0479(10) .0308(8) -.0198(8) -.0092(7) .0015(7) C5 .0400(9) .0472(10) .0300(8) -.0203(8) -.0066(7) -.0015(7) C6 .0470(10) .0510(10) .0333(9) -.0258(8) -.0068(7) -.0023(7) C7 .0732(14) .0504(12) .0528(11) -.0301(10) -.0191(10) .0013(9) C8 .0951(18) .0534(13) .0728(15) -.0348(13) -.0231(13) -.0099(11) C9 .0991(18) .0702(15) .0619(13) -.0448(14) -.0225(13) -.0156(11) C10 .0708(13) .0679(13) .0434(10) -.0363(11) -.0200(9) -.0052(9) C11 .0461(10) .0529(11) .0351(9) -.0252(8) -.0083(7) -.0048(7) C12 .0641(13) .0597(12) .0519(11) -.0215(10) -.0300(10) -.0026(9) C13 .102(2) .0909(19) .0746(17) -.0514(17) -.0369(15) .0167(14) C14 .0398(9) .0497(10) .0326(8) -.0181(8) -.0117(7) -.0019(7) C15 .0424(9) .0554(11) .0306(8) -.0189(8) -.0088(7) -.0026(7) C16 .0372(9) .0550(11) .0321(8) -.0147(8) -.0077(7) -.0056(7) C17 .0480(11) .0588(13) .0422(10) -.0128(9) -.0179(8) -.0135(9) C18 .0384(9) .0653(12) .0315(9) -.0212(9) -.0064(7) -.0094(8) 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' S S .1246 .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_publ_flag C14 N1 C11 108.64(15) no C14 N1 C12 125.48(16) no C11 N1 C12 125.79(15) no C18 N3 H3A 120.0 no C18 N3 H3B 120.0 no H3A N3 H3B 120.0 no C2 C1 C14 118.06(17) no C2 C1 H1A 121.0 no C14 C1 H1A 121.0 no C1 C2 C3 122.13(17) no C1 C2 H2A 118.9 no C3 C2 H2A 118.9 no C4 C3 C2 118.78(15) no C4 C3 C15 117.50(16) no C2 C3 C15 123.66(17) yes C5 C4 C3 120.19(16) no C5 C4 H4A 119.9 no C3 C4 H4A 119.9 no C4 C5 C14 119.26(16) no C4 C5 C6 134.19(17) no C14 C5 C6 106.53(15) no C7 C6 C11 119.55(17) no C7 C6 C5 134.28(17) no C11 C6 C5 106.15(16) no C8 C7 C6 118.9(2) no C8 C7 H7A 120.5 no C6 C7 H7A 120.5 no C7 C8 C9 120.8(2) no C7 C8 H8A 119.6 no C9 C8 H8A 119.6 no C10 C9 C8 121.9(2) no C10 C9 H9A 119.0 no C8 C9 H9A 119.0 no C9 C10 C11 117.1(2) no C9 C10 H10A 121.4 no C11 C10 H10A 121.4 no N1 C11 C10 129.15(18) no N1 C11 C6 109.16(15) no C10 C11 C6 121.68(18) no N1 C12 C13 111.69(19) no N1 C12 H12A 109.3 no C13 C12 H12A 109.3 no N1 C12 H12B 109.3 no C13 C12 H12B 109.3 no H12A C12 H12B 107.9 no C12 C13 H13A 109.5 no C12 C13 H13B 109.5 no H13A C13 H13B 109.5 no C12 C13 H13C 109.5 no H13A C13 H13C 109.5 no H13B C13 H13C 109.5 no N1 C14 C1 128.98(17) no N1 C14 C5 109.49(15) no C1 C14 C5 121.53(15) no C16 C15 C3 131.64(18) yes C16 C15 H15A 114.2 no C3 C15 H15A 114.2 no C15 C16 C17 123.41(16) yes C15 C16 C18 121.76(17) yes C17 C16 C18 114.82(16) yes N2 C17 C16 175.4(2) yes N3 C18 C16 115.93(17) yes N3 C18 S1 121.89(14) yes C16 C18 S1 122.14(14) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C18 1.665(2) yes N1 C11 1.387(2) no N1 C12 1.457(2) no N1 C14 1.371(2) no N2 C17 1.146(3) yes N3 C18 1.327(2) yes N3 H3A .8600 no N3 H3B .8600 no C1 C2 1.374(2) no C1 C14 1.393(3) no C1 H1A .9300 no C2 C3 1.411(3) no C2 H2A .9300 no C3 C4 1.397(3) no C3 C15 1.445(2) yes C4 C5 1.388(2) no C4 H4A .9300 no C5 C14 1.408(2) no C5 C6 1.447(2) no C6 C7 1.387(3) no C6 C11 1.410(3) no C7 C8 1.375(3) no C7 H7A .9300 no C8 C9 1.392(3) no C8 H8A .9300 no C9 C10 1.378(3) no C9 H9A .9300 no C10 C11 1.391(3) no C10 H10A .9300 no C12 C13 1.480(3) no C12 H12A .9700 no C12 H12B .9700 no C13 H13A .9600 no C13 H13B .9600 no C13 H13C .9600 no C15 C16 1.351(3) yes C15 H15A .9300 no C16 C17 1.435(3) yes C16 C18 1.488(2) yes 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 N3 H3B S1 2_667 .86 2.55 3.402(2) 170 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 C14 C1 C2 C3 -1.2(3) no C1 C2 C3 C4 .2(3) no C1 C2 C3 C15 -176.91(18) no C2 C3 C4 C5 1.7(3) no C15 C3 C4 C5 179.03(15) no C3 C4 C5 C14 -2.6(3) no C3 C4 C5 C6 178.88(17) no C4 C5 C6 C7 -3.6(4) no C14 C5 C6 C7 177.8(2) no C4 C5 C6 C11 178.26(19) no C14 C5 C6 C11 -.37(19) no C11 C6 C7 C8 1.0(3) no C5 C6 C7 C8 -176.9(2) no C6 C7 C8 C9 -.5(4) no C7 C8 C9 C10 -.6(4) no C8 C9 C10 C11 1.1(4) no C14 N1 C11 C10 -176.94(19) no C12 N1 C11 C10 6.4(3) no C14 N1 C11 C6 1.7(2) no C12 N1 C11 C6 -174.96(17) no C9 C10 C11 N1 177.9(2) no C9 C10 C11 C6 -.5(3) no C7 C6 C11 N1 -179.26(17) no C5 C6 C11 N1 -.78(19) no C7 C6 C11 C10 -.5(3) no C5 C6 C11 C10 177.96(17) no C14 N1 C12 C13 90.9(2) no C11 N1 C12 C13 -93.0(2) yes C11 N1 C14 C1 179.08(18) no C12 N1 C14 C1 -4.3(3) no C11 N1 C14 C5 -1.9(2) no C12 N1 C14 C5 174.73(17) no C2 C1 C14 N1 179.17(18) no C2 C1 C14 C5 .3(3) no C4 C5 C14 N1 -177.47(15) no C6 C5 C14 N1 1.41(19) no C4 C5 C14 C1 1.6(3) no C6 C5 C14 C1 -179.51(16) no C4 C3 C15 C16 172.01(18) no C2 C3 C15 C16 -10.9(3) no C3 C15 C16 C17 -4.8(3) no C3 C15 C16 C18 176.30(17) no C15 C16 C18 N3 167.64(17) no C17 C16 C18 N3 -11.3(2) no C15 C16 C18 S1 -14.4(2) no C17 C16 C18 S1 166.67(14) no