#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2012481.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_2012481 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 H13 N3' _chemical_formula_sum 'C18 H13 N3' _chemical_formula_weight 271.31 _chemical_name_systematic ; 2-(9-ethyl-9H-carbazol-3-ylmethylene)malononitrile ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 96.87(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.731(3) _cell_length_b 4.2160(8) _cell_length_c 26.640(5) _cell_measurement_reflns_used 24 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 12 _cell_measurement_theta_min 11 _cell_volume 1419.6(5) _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 .024 _diffrn_reflns_av_sigmaI/netI .081 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 2575 _diffrn_reflns_theta_full 24.98 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_min 1.54 _diffrn_standards_decay_% 3 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .077 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ; ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 568 _exptl_crystal_size_max .5 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .1 _refine_diff_density_max .17 _refine_diff_density_min -.21 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 2458 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.004 _refine_ls_R_factor_all .125 _refine_ls_R_factor_gt .062 _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^)+(0.062P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .131 _refine_ls_wR_factor_ref .156 _reflns_number_gt 1280 _reflns_number_total 2458 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm1472.cif _[local]_cod_data_source_block IIIa _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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_database_code 2012481 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_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 N1 .24263(18) .2665(6) .12782(9) .0432(7) Uani d . 1 N N2 .7266(3) .2384(9) .01848(13) .0812(11) Uani d . 1 N N3 .9166(2) -.3603(10) .12600(12) .0877(12) Uani d . 1 N C1 .4002(2) .2588(8) .08033(12) .0487(9) Uani d . 1 C H1A .3686 .3770 .0521 .058 Uiso calc R 1 H C2 .5028(2) .1540(8) .08266(11) .0502(9) Uani d . 1 C H2A .5425 .2047 .0557 .060 Uiso calc R 1 H C3 .5512(2) -.0260(8) .12358(11) .0447(8) Uani d . 1 C C4 .4921(2) -.1046(8) .16329(11) .0452(9) Uani d . 1 C H4A .5230 -.2311 .1907 .054 Uiso calc R 1 H C5 .3892(2) .0020(8) .16249(10) .0418(8) Uani d . 1 C C6 .3086(2) -.0295(8) .19616(11) .0416(8) Uani d . 1 C C7 .3045(2) -.1738(8) .24234(12) .0497(9) Uani d . 1 C H7A .3637 -.2884 .2581 .060 Uiso calc R 1 H C8 .2135(3) -.1496(9) .26530(12) .0559(9) Uani d . 1 C H8A .2103 -.2450 .2974 .067 Uiso calc R 1 H C9 .1260(3) .0143(9) .24167(13) .0565(10) Uani d . 1 C H9A .0635 .0243 .2579 .068 Uiso calc R 1 H C10 .1272(2) .1612(8) .19584(12) .0495(9) Uani d . 1 C H10A .0674 .2727 .1800 .059 Uiso calc R 1 H C11 .2202(2) .1390(8) .17366(11) .0416(8) Uani d . 1 C C12 .1706(2) .4617(9) .09390(12) .0533(9) Uani d . 1 C H12A .2127 .6077 .0751 .064 Uiso calc R 1 H H12B .1269 .5921 .1143 .064 Uiso calc R 1 H C13 .0992(3) .2686(10) .05679(13) .0719(12) Uani d . 1 C H13A .0530 .4105 .0349 .108 Uiso calc R 1 H H13B .0559 .1276 .0751 .108 Uiso calc R 1 H H13C .1420 .1416 .0361 .108 Uiso calc R 1 H C14 .3439(2) .1862(8) .12072(11) .0415(8) Uani d . 1 C C15 .6578(2) -.1410(8) .12851(12) .0513(9) Uani d . 1 C H15A .6763 -.2702 .1574 .062 Uiso calc R 1 H C16 .7369(2) -.0986(8) .09939(11) .0466(9) Uani d . 1 C C17 .7297(2) .0886(10) .05432(14) .0563(10) Uani d . 1 C C18 .8373(3) -.2418(10) .11382(13) .0595(10) 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 N1 .0349(14) .0495(18) .0444(15) .0088(13) .0006(11) .0012(14) N2 .076(2) .101(3) .069(2) .019(2) .0201(18) .015(2) N3 .0536(19) .124(3) .088(2) .028(2) .0153(17) .017(2) C1 .0421(19) .059(2) .0440(18) .0069(17) .0025(14) .0087(18) C2 .0402(18) .063(2) .0472(19) .0058(19) .0053(14) .0010(19) C3 .0355(17) .052(2) .0460(18) .0026(17) .0033(14) -.0014(17) C4 .0433(19) .048(2) .0413(18) .0024(17) -.0054(14) .0005(16) C5 .0359(17) .045(2) .0429(18) .0005(16) -.0008(13) -.0013(17) C6 .0392(18) .045(2) .0390(17) .0020(16) -.0007(14) -.0013(16) C7 .050(2) .049(2) .049(2) .0031(18) .0030(15) .0026(18) C8 .056(2) .066(3) .0459(19) -.004(2) .0076(16) .0047(19) C9 .047(2) .068(3) .057(2) -.006(2) .0145(16) -.007(2) C10 .0415(18) .053(2) .054(2) .0055(17) .0042(15) -.0012(18) C11 .0400(17) .045(2) .0394(18) .0051(16) .0040(14) -.0034(16) C12 .0494(19) .057(2) .0526(19) .0165(19) .0040(15) .0107(19) C13 .068(2) .078(3) .064(2) .025(2) -.0192(19) -.001(2) C14 .0347(17) .045(2) .0439(18) .0042(16) -.0014(13) -.0045(16) C15 .0411(18) .063(2) .0493(19) .0054(18) .0018(15) -.0008(18) C16 .0395(18) .055(2) .0452(19) .0041(17) .0038(14) -.0072(18) C17 .044(2) .072(3) .054(2) .0055(19) .0118(17) -.002(2) C18 .043(2) .078(3) .059(2) .010(2) .0114(17) .007(2) 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' 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 108.7(2) no C14 N1 C12 125.8(3) no C11 N1 C12 125.4(2) no C2 C1 C14 117.9(3) no C2 C1 H1A 121.1 no C14 C1 H1A 121.1 no C1 C2 C3 122.3(3) no C1 C2 H2A 118.9 no C3 C2 H2A 118.9 no C2 C3 C4 119.0(3) no C2 C3 C15 125.1(3) yes C4 C3 C15 115.9(3) no C5 C4 C3 120.1(3) no C5 C4 H4A 119.9 no C3 C4 H4A 119.9 no C4 C5 C14 119.0(3) no C4 C5 C6 134.5(3) no C14 C5 C6 106.5(2) no C7 C6 C11 119.4(3) no C7 C6 C5 134.3(3) no C11 C6 C5 106.3(3) no C8 C7 C6 119.1(3) no C8 C7 H7A 120.4 no C6 C7 H7A 120.4 no C7 C8 C9 120.4(3) no C7 C8 H8A 119.8 no C9 C8 H8A 119.8 no C10 C9 C8 122.1(3) no C10 C9 H9A 119.0 no C8 C9 H9A 119.0 no C9 C10 C11 116.8(3) no C9 C10 H10A 121.6 no C11 C10 H10A 121.6 no C10 C11 N1 128.4(3) no C10 C11 C6 122.2(3) no N1 C11 C6 109.3(3) no N1 C12 C13 112.8(3) no N1 C12 H12A 109.0 no C13 C12 H12A 109.0 no N1 C12 H12B 109.0 no C13 C12 H12B 109.0 no H12A C12 H12B 107.8 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 129.2(3) no N1 C14 C5 109.1(3) no C1 C14 C5 121.7(3) no C16 C15 C3 131.6(3) yes C16 C15 H15A 114.2 no C3 C15 H15A 114.2 no C15 C16 C18 119.6(3) yes C15 C16 C17 125.2(3) yes C18 C16 C17 115.2(3) yes N2 C17 C16 178.3(4) yes N3 C18 C16 178.6(4) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C11 1.395(4) no N1 C12 1.461(4) no N1 C14 1.368(3) no N2 C17 1.142(4) yes N3 C18 1.138(4) yes C1 C2 1.372(4) no C1 C14 1.396(4) no C1 H1A .9500 no C2 C3 1.408(4) no C2 H2A .9500 no C3 C4 1.409(4) no C3 C15 1.432(4) yes C4 C5 1.383(4) no C4 H4A .9500 no C5 C14 1.421(4) no C5 C6 1.448(4) no C6 C7 1.379(4) no C6 C11 1.403(4) no C7 C8 1.377(4) no C7 H7A .9500 no C8 C9 1.396(4) no C8 H8A .9500 no C9 C10 1.371(4) no C9 H9A .9500 no C10 C11 1.387(4) no C10 H10A .9500 no C12 C13 1.501(4) no C12 H12A .9900 no C12 H12B .9900 no C13 H13A .9800 no C13 H13B .9800 no C13 H13C .9800 no C15 C16 1.355(4) yes C15 H15A .9500 no C16 C18 1.424(5) yes C16 C17 1.431(5) 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 _geom_torsion_publ_flag C14 C1 C2 C3 1.1(5) no C1 C2 C3 C4 .7(5) no C1 C2 C3 C15 -179.6(3) no C2 C3 C4 C5 -1.8(5) no C15 C3 C4 C5 178.5(3) no C3 C4 C5 C14 1.1(5) no C3 C4 C5 C6 -179.2(3) no C4 C5 C6 C7 1.3(7) no C14 C5 C6 C7 -178.9(4) no C4 C5 C6 C11 179.4(4) no C14 C5 C6 C11 -.8(3) no C11 C6 C7 C8 .1(5) no C5 C6 C7 C8 178.0(3) no C6 C7 C8 C9 1.1(5) no C7 C8 C9 C10 -1.3(5) no C8 C9 C10 C11 .2(5) no C9 C10 C11 N1 -179.6(3) no C9 C10 C11 C6 1.1(5) no C14 N1 C11 C10 -180.0(3) no C12 N1 C11 C10 1.7(5) no C14 N1 C11 C6 -.7(4) no C12 N1 C11 C6 -178.9(3) no C7 C6 C11 C10 -1.3(5) no C5 C6 C11 C10 -179.7(3) no C7 C6 C11 N1 179.3(3) no C5 C6 C11 N1 .9(4) no C14 N1 C12 C13 94.2(4) no C11 N1 C12 C13 -87.8(4) yes C11 N1 C14 C1 179.6(3) no C12 N1 C14 C1 -2.2(5) no C11 N1 C14 C5 .1(3) no C12 N1 C14 C5 178.4(3) no C2 C1 C14 N1 178.8(3) no C2 C1 C14 C5 -1.8(5) no C4 C5 C14 N1 -179.8(3) no C6 C5 C14 N1 .4(3) no C4 C5 C14 C1 .8(5) no C6 C5 C14 C1 -179.1(3) no C2 C3 C15 C16 3.9(6) no C4 C3 C15 C16 -176.5(3) no C3 C15 C16 C18 179.5(4) no C3 C15 C16 C17 .9(6) no