#------------------------------------------------------------------------------ #$Date: 2012-02-03 18:16:24 +0100 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/14/2011467.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_2011467 loop_ _publ_author_name 'Shaban, Mohammed A. E.' 'Morgaan, Ali, E. A.' 'Chun, Hyungphil' 'Bernal, Ivan' _publ_section_title 10-Ethyl-3-(4-methoxyphenyl)-1,2,4-triazolo[4',3':2,3]-1,2,4-triazino[5,6-b]indole _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e472 _journal_page_last e473 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C19 H16 N6 O' _chemical_formula_sum 'C19 H16 N6 O' _chemical_formula_weight 344.38 _chemical_name_systematic ;10-Ethyl-3-(4-methoxyphenyl)-1,2,4-triazolo[4'3':2,3]1,2,4- triazino[5,6-b]indole ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 114.55(4) _cell_angle_beta 114.67(4) _cell_angle_gamma 91.03(3) _cell_formula_units_Z 2 _cell_length_a 9.420(3) _cell_length_b 9.805(4) _cell_length_c 11.228(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 16.45 _cell_measurement_theta_min 2.97 _cell_volume 833.9(8) _computing_cell_refinement CAD-4-PC _computing_data_collection 'CAD-4-PC Software (Enraf-Nonius, 1989)' _computing_data_reduction 'NRCVAX DATRD2 (Le Page & Gabe, 1979)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .000 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 2935 _diffrn_reflns_theta_max 24.97 _diffrn_standards_decay_% 1.27 _diffrn_standards_interval_time 240 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .091 _exptl_absorpt_correction_T_max .996 _exptl_absorpt_correction_T_min .777 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(NRCVAX ABSORP; Gabe et al., 1989)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 360 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .31 _exptl_crystal_size_min .07 _refine_diff_density_max .191 _refine_diff_density_min -.242 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all .831 _refine_ls_goodness_of_fit_ref 1.223 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 2935 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .831 _refine_ls_restrained_S_obs 1.223 _refine_ls_R_factor_all .208 _refine_ls_R_factor_gt .053 _refine_ls_shift/su_max .005 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0706P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .145 _refine_ls_wR_factor_ref .115 _reflns_number_gt 1005 _reflns_number_total 2935 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file qd0026.cif _[local]_cod_data_source_block I _cod_original_cell_volume 834.0(8) _cod_database_code 2011467 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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 .2446(4) -.3329(3) -.3136(3) .0725(9) Uani d . 1 . O N1 -.1436(3) .6069(3) .1793(3) .0524(9) Uani d . 1 . N N2 -.3057(3) .3585(3) -.0108(3) .0503(9) Uani d . 1 . N N3 .0058(3) .2897(3) .0251(3) .0418(8) Uani d . 1 . N N4 -.1388(3) .1865(3) -.0751(3) .0417(8) Uani d . 1 . N N5 -.4024(4) .0917(4) -.1913(4) .0606(10) Uani d . 1 . N N6 -.3248(4) -.0222(3) -.2422(3) .0564(10) Uani d . 1 . N C1 .0214(4) .6701(4) .2675(4) .0471(11) Uani d . 1 . C C2 .0996(5) .8177(4) .3845(4) .0609(12) Uani d . 1 . C H2 .0429 .8903 .4136 .073 Uiso calc R 1 . H C3 .2644(5) .8511(5) .4547(4) .0660(13) Uani d . 1 . C H3 .3198 .9490 .5331 .079 Uiso calc R 1 . H C4 .3526(5) .7435(5) .4132(4) .0644(13) Uani d . 1 . C H4 .4643 .7706 .4643 .077 Uiso calc R 1 . H C5 .2740(4) .5973(4) .2964(4) .0534(11) Uani d . 1 . C H5 .3311 .5251 .2676 .064 Uiso calc R 1 . H C6 .1075(4) .5617(4) .2236(4) .0403(10) Uani d . 1 . C C7 -.0119(4) .4235(4) .1048(4) .0389(10) Uani d . 1 . C C8 -.1666(4) .4570(4) .0838(4) .0426(10) Uani d . 1 . C C9 -.2880(4) .2163(4) -.0908(4) .0493(11) Uani d . 1 . C C10 -.1707(4) .0326(4) -.1744(4) .0462(11) Uani d . 1 . C C11 -.0529(4) -.0537(4) -.2007(4) .0444(10) Uani d . 1 . C C12 .1101(4) .0048(4) -.1304(4) .0566(12) Uani d . 1 . C H12 .1518 .1070 -.0573 .068 Uiso calc R 1 . H C13 .2153(5) -.0829(4) -.1643(4) .0621(12) Uani d . 1 . C H13 .3250 -.0399 -.1151 .074 Uiso calc R 1 . H C14 .1534(5) -.2355(4) -.2728(4) .0543(12) Uani d . 1 . C C15 -.0082(5) -.2966(4) -.3430(4) .0634(13) Uani d . 1 . C H15 -.0495 -.3992 -.4151 .076 Uiso calc R 1 . H C16 -.1107(5) -.2080(4) -.3080(4) .0551(12) Uani d . 1 . C H16 -.2201 -.2518 -.3569 .066 Uiso calc R 1 . H C17 .4115(5) -.2754(5) -.2433(6) .091(2) Uani d . 1 . C H17A .4605 -.3557 -.2825 .136 Uiso calc R 1 . H H17B .4542 -.2398 -.1388 .136 Uiso calc R 1 . H H17C .4338 -.1914 -.2606 .136 Uiso calc R 1 . H C18 -.2738(5) .6873(5) .1877(5) .0790(15) Uani d . 1 . C H18A -.2421 .7915 .2055 .095 Uiso calc R 1 . H H18B -.3696 .6349 .0927 .095 Uiso calc R 1 . H C19 -.3139(6) .6951(6) .3044(5) .103(2) Uani d . 1 . C H19A -.3986 .7484 .3030 .154 Uiso calc R 1 . H H19B -.2207 .7493 .3994 .154 Uiso calc R 1 . H H19C -.3483 .5926 .2864 .154 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 O1 .082(2) .049(2) .094(2) .021(2) .055(2) .026(2) N1 .041(2) .043(2) .063(2) .017(2) .027(2) .012(2) N2 .045(2) .042(2) .050(2) .008(2) .017(2) .013(2) N3 .039(2) .041(2) .038(2) .007(2) .013(2) .017(2) N4 .035(2) .035(2) .038(2) .000(2) .008(2) .012(2) N5 .048(2) .050(2) .062(2) .002(2) .016(2) .017(2) N6 .047(2) .041(2) .056(2) .001(2) .014(2) .011(2) C1 .044(2) .043(3) .045(3) .003(2) .022(2) .013(2) C2 .062(3) .043(3) .059(3) .012(2) .025(2) .011(2) C3 .066(3) .051(3) .045(3) -.005(2) .017(2) .001(2) C4 .051(3) .064(3) .051(3) .003(2) .013(2) .014(3) C5 .054(3) .040(3) .047(3) .006(2) .016(2) .011(2) C6 .038(2) .038(2) .030(2) .002(2) .010(2) .009(2) C7 .034(2) .041(3) .038(2) .008(2) .016(2) .016(2) C8 .045(3) .038(2) .042(3) .010(2) .021(2) .015(2) C9 .041(2) .050(3) .040(3) -.001(2) .011(2) .014(2) C10 .051(3) .032(2) .042(3) -.003(2) .014(2) .014(2) C11 .049(2) .035(2) .038(2) .004(2) .015(2) .013(2) C12 .055(3) .029(2) .058(3) .003(2) .014(2) .009(2) C13 .058(3) .045(3) .069(3) .011(2) .026(2) .018(3) C14 .065(3) .041(3) .058(3) .014(2) .031(2) .022(2) C15 .079(3) .032(2) .057(3) .006(2) .033(3) .002(2) C16 .058(3) .049(3) .044(3) .002(2) .019(2) .015(2) C17 .089(4) .065(3) .148(5) .029(3) .079(4) .051(3) C18 .079(3) .067(3) .075(4) .018(2) .027(3) .029(3) C19 .109(4) .127(5) .104(5) .039(3) .075(4) .054(4) 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 O1 C14 . 1.363(4) yes O1 C17 . 1.405(4) yes N1 C8 . 1.357(4) yes N1 C1 . 1.396(4) yes N1 C18 . 1.485(4) yes N2 C8 . 1.311(4) yes N2 C9 . 1.368(4) yes N3 C7 . 1.307(4) yes N3 N4 . 1.368(4) yes N4 C10 . 1.384(4) yes N4 C9 . 1.394(4) yes N5 C9 . 1.311(4) yes N5 N6 . 1.398(4) yes N6 C10 . 1.298(4) yes C1 C2 . 1.392(5) no C1 C6 . 1.401(4) yes C2 C3 . 1.373(5) no C3 C4 . 1.402(5) no C4 C5 . 1.383(5) no C5 C6 . 1.386(4) no C6 C7 . 1.439(4) yes C7 C8 . 1.442(4) yes C10 C11 . 1.461(5) yes C11 C12 . 1.375(5) no C11 C16 . 1.394(4) no C12 C13 . 1.392(5) no C13 C14 . 1.387(5) no C14 C15 . 1.368(5) no C15 C16 . 1.380(5) no C18 C19 . 1.482(5) no 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' O O .0106 .0060 '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 O1 C17 118.3(3) yes C8 N1 C1 108.5(3) yes C8 N1 C18 125.0(3) yes C1 N1 C18 126.6(3) yes C8 N2 C9 111.6(3) yes C7 N3 N4 111.6(3) yes N3 N4 C10 129.3(3) yes N3 N4 C9 125.3(3) yes C10 N4 C9 105.3(3) yes C9 N5 N6 105.5(3) yes C10 N6 N5 110.8(3) yes C2 C1 N1 128.3(4) yes C2 C1 C6 121.3(3) no N1 C1 C6 110.5(3) yes C3 C2 C1 116.8(4) no C2 C3 C4 122.7(4) no C5 C4 C3 120.1(4) no C4 C5 C6 118.1(3) no C5 C6 C1 121.0(3) no C5 C6 C7 133.5(3) yes C1 C6 C7 105.4(3) yes N3 C7 C6 129.7(3) yes N3 C7 C8 123.2(3) yes C6 C7 C8 107.0(3) yes N2 C8 N1 125.9(3) yes N2 C8 C7 125.6(3) yes N1 C8 C7 108.5(3) yes N5 C9 N2 127.0(4) yes N5 C9 N4 110.4(3) yes N2 C9 N4 122.6(3) yes N6 C10 N4 108.0(3) yes N6 C10 C11 125.6(3) yes N4 C10 C11 126.4(3) yes C12 C11 C16 117.1(3) no C12 C11 C10 125.6(3) no C16 C11 C10 117.3(3) no C11 C12 C13 122.6(3) no C14 C13 C12 118.8(4) no O1 C14 C15 116.3(4) no O1 C14 C13 124.0(4) no C15 C14 C13 119.6(4) no C14 C15 C16 120.8(4) no C15 C16 C11 121.1(4) no C19 C18 N1 114.4(4) no