#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2011710.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_2011710 loop_ _publ_author_name 'Janes, Robert W.' 'Potter, Brian S.' 'Naylor, Matthew A.' 'Ferguson, Amanda C.' 'Patel, Kantilal B.' 'Stratford, Michael R. L.' 'Wardman, Peter' 'Everett, Steven A.' _publ_section_title ; 1-Methylindole-3-carboxaldehyde oxime derivatives ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 58 _journal_page_last 61 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C10 H10 N2 O' _chemical_formula_sum 'C10 H10 N2 O' _chemical_formula_weight 174.20 _chemical_name_systematic ; 1-Methylindole-3-carboxyaldehyde oxime ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90.00(4) _cell_angle_beta 111.53(4) _cell_angle_gamma 90.00(4) _cell_formula_units_Z 4 _cell_length_a 13.462(4) _cell_length_b 5.079(4) _cell_length_c 14.127(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 38.7 _cell_measurement_theta_min 11.3 _cell_volume 898.5(8) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'CAD77 and CADRAL (Korber, 1982), and CADSHEL (Cooper, 1990)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full .996 _diffrn_measured_fraction_theta_max .996 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _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 1.54180 _diffrn_reflns_av_R_equivalents .052 _diffrn_reflns_av_sigmaI/netI .0921 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 3706 _diffrn_reflns_theta_full 74.24 _diffrn_reflns_theta_max 74.24 _diffrn_reflns_theta_min 3.88 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 200 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .693 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 368 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .15 _refine_diff_density_max .172 _refine_diff_density_min -.203 _refine_ls_extinction_coef .0043(7) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 240 _refine_ls_number_reflns 2045 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.001 _refine_ls_R_factor_all .144 _refine_ls_R_factor_gt .049 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0453P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_ref .129 _reflns_number_gt 1039 _reflns_number_total 2045 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd1087.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21' _cod_original_cell_volume 898.4(8) _cod_database_code 2011710 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -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 C3A .5915(4) -.0522(12) .4021(4) .0574(16) Uani d . 1 C H3A .6174 -.1859 .4498 .069 Uiso calc R 1 H C4A .5035(5) .0968(12) .4003(4) .0592(16) Uani d . 1 C H4A .4727 .0612 .4481 .071 Uiso calc R 1 H C5A .4612(4) .2920(11) .3312(4) .0521(14) Uani d . 1 C H5A .4019 .3881 .3300 .062 Uiso calc R 1 H C6A .5111(4) .3404(10) .2627(3) .0430(12) Uani d . 1 C C7A .5993(4) .1984(11) .2623(3) .0422(12) Uani d . 1 C C8A .6398(4) -.0019(11) .3337(3) .0495(14) Uani d . 1 C H8A .6987 -.0998 .3349 .059 Uiso calc R 1 H N9A .4862(3) .5222(9) .1848(3) .0480(11) Uani d . 1 N C10A .3985(4) .7108(13) .1589(4) .0634(16) Uani d . 1 C H10A .3318 .6180 .1356 .076 Uiso calc R 1 H H10B .4015 .8258 .1061 .076 Uiso calc R 1 H H10C .4046 .8128 .2180 .076 Uiso calc R 1 H C11A .5579(4) .4987(12) .1386(4) .0511(14) Uani d . 1 C H11A .5582 .6018 .0843 .061 Uiso calc R 1 H C12A .6292(4) .3043(11) .1822(4) .0446(12) Uani d . 1 C C13A .7159(4) .2069(12) .1558(4) .0541(14) Uani d . 1 C H13A .7419 .0429 .1830 .065 Uiso calc R 1 H N14A .7636(4) .3104(10) .1005(3) .0555(12) Uani d . 1 N O15A .7183(3) .5535(8) .0633(3) .0619(11) Uani d . 1 O H15A .7547 .6282 .0359 .074 Uiso calc R 1 H C3B .2078(5) -.0388(13) .4410(4) .0666(18) Uani d . 1 C H3B .2502 -.1742 .4793 .080 Uiso calc R 1 H C4B .1470(5) .1116(14) .4822(4) .0633(18) Uani d . 1 C H4B .1502 .0758 .5478 .076 Uiso calc R 1 H C5B .0828(4) .3106(12) .4281(4) .0566(15) Uani d . 1 C H5B .0426 .4110 .4559 .068 Uiso calc R 1 H C6B .0796(4) .3584(11) .3296(4) .0470(14) Uani d . 1 C C7B .1405(4) .2096(11) .2868(3) .0422(12) Uani d . 1 C C8B .2059(4) .0100(12) .3445(4) .0552(15) Uani d . 1 C H8B .2478 -.0891 .3182 .066 Uiso calc R 1 H N9B .0238(3) .5404(9) .2585(3) .0494(11) Uani d . 1 N C10B -.0516(4) .7270(13) .2715(4) .0624(17) Uani d . 1 C H10D -.1132 .6345 .2728 .075 Uiso calc R 1 H H10E -.0728 .8498 .2160 .075 Uiso calc R 1 H H10F -.0186 .8203 .3344 .075 Uiso calc R 1 H C11B .0479(4) .5174(12) .1741(4) .0483(13) Uani d . 1 C H11B .0199 .6216 .1162 .058 Uiso calc R 1 H C12B .1203(4) .3157(12) .1870(3) .0442(12) Uani d . 1 C C13B .1646(4) .2138(12) .1169(4) .0532(14) Uani d . 1 C H13B .1941 .0467 .1334 .064 Uiso calc R 1 H N14B .1714(3) .3096(9) .0351(3) .0528(12) Uani d . 1 N O15B .1212(3) .5558(8) .0115(3) .0604(11) Uani d . 1 O H15B .1402 .6307 -.0304 .073 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 C3A .073(4) .050(4) .055(3) .000(3) .030(3) .008(3) C4A .072(4) .060(4) .056(3) -.009(4) .036(3) -.006(3) C5A .063(3) .048(4) .057(3) .001(3) .035(3) -.008(3) C6A .055(3) .035(3) .042(3) -.002(3) .022(2) -.002(3) C7A .049(3) .037(3) .043(3) -.005(3) .020(2) .001(3) C8A .060(3) .047(4) .047(3) .001(3) .025(3) .005(3) N9A .056(3) .040(3) .050(2) .009(3) .021(2) .001(2) C10A .061(4) .048(4) .078(4) .009(3) .022(3) .004(3) C11A .062(3) .046(4) .050(3) -.003(3) .026(3) .000(3) C12A .057(3) .037(3) .045(3) .000(3) .026(3) -.004(3) C13A .071(4) .043(3) .055(3) .001(3) .032(3) .004(3) N14A .069(3) .051(3) .053(3) -.004(3) .030(2) -.008(3) O15A .083(3) .052(3) .067(2) -.006(2) .047(2) .005(2) C3B .070(4) .066(5) .058(3) -.006(4) .017(3) .013(3) C4B .072(4) .074(5) .042(3) -.014(4) .020(3) .002(3) C5B .069(4) .059(4) .047(3) -.014(4) .027(3) -.015(3) C6B .053(3) .041(4) .050(3) -.011(3) .024(3) -.005(3) C7B .052(3) .037(3) .041(3) -.006(3) .021(2) .002(2) C8B .057(3) .048(4) .064(3) .000(3) .026(3) -.002(3) N9B .047(3) .048(3) .059(3) .005(3) .026(2) -.008(3) C10B .060(4) .061(4) .069(4) .004(3) .027(3) -.018(3) C11B .059(3) .048(3) .043(3) -.006(3) .025(3) -.006(3) C12B .053(3) .040(3) .046(3) .001(3) .026(3) .000(3) C13B .073(4) .034(3) .062(3) .007(3) .037(3) .001(3) N14B .063(3) .046(3) .056(3) .000(3) .030(2) -.009(3) O15B .081(3) .051(3) .065(3) .010(2) .046(2) .011(2) 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' O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 '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 C8A C3A C4A 120.3(5) no C5A C4A C3A 122.4(5) no C4A C5A C6A 116.6(5) no N9A C6A C5A 129.5(5) no N9A C6A C7A 107.6(4) no C5A C6A C7A 122.9(5) no C6A C7A C8A 118.9(4) no C6A C7A C12A 107.2(4) no C8A C7A C12A 133.9(5) no C3A C8A C7A 118.9(5) no C11A N9A C6A 108.5(4) no C11A N9A C10A 126.2(5) no C6A N9A C10A 125.2(4) no N9A C11A C12A 110.8(5) no C11A C12A C7A 105.9(4) yes C11A C12A C13A 129.7(5) yes C7A C12A C13A 124.4(5) yes N14A C13A C12A 130.4(5) yes C13A N14A O15A 110.1(5) yes C8B C3B C4B 121.0(6) no C5B C4B C3B 121.2(5) no C4B C5B C6B 117.9(5) no N9B C6B C5B 131.0(5) no N9B C6B C7B 107.3(4) no C5B C6B C7B 121.7(5) no C8B C7B C6B 118.9(4) no C8B C7B C12B 134.2(5) no C6B C7B C12B 106.9(5) no C3B C8B C7B 119.3(5) no C11B N9B C6B 110.2(4) no C11B N9B C10B 125.1(5) no C6B N9B C10B 124.7(4) no N9B C11B C12B 109.6(5) no C11B C12B C13B 129.3(5) yes C11B C12B C7B 106.1(4) yes C13B C12B C7B 124.6(5) yes N14B C13B C12B 132.2(5) yes C13B N14B O15B 111.2(4) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C3A C8A 1.372(6) yes C3A C4A 1.398(7) yes C4A C5A 1.361(7) yes C5A C6A 1.388(6) yes C6A N9A 1.380(6) yes C6A C7A 1.390(6) yes C7A C8A 1.395(7) yes C7A C12A 1.438(6) yes N9A C11A 1.355(6) yes N9A C10A 1.459(6) yes C11A C12A 1.357(7) yes C12A C13A 1.437(7) yes C13A N14A 1.292(6) yes N14A O15A 1.392(6) yes C3B C8B 1.377(6) no C3B C4B 1.393(8) no C4B C5B 1.367(8) no C5B C6B 1.397(7) no C6B N9B 1.369(6) no C6B C7B 1.404(7) no C7B C8B 1.393(7) no C7B C12B 1.439(6) no N9B C11B 1.349(5) no N9B C10B 1.449(6) no C11B C12B 1.380(7) no C12B C13B 1.427(6) no C13B N14B 1.288(6) yes N14B O15B 1.402(6) 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 O15A H15A N14B 2_655 .82 1.89 2.709(5) 175.5 O15B H15B N14A 2_655 .82 2.11 2.895(6) 161.8 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 C8A C3A C4A C5A 1.0(9) no C3A C4A C5A C6A -1.1(8) no C4A C5A C6A N9A 179.6(5) no C4A C5A C6A C7A .5(7) no N9A C6A C7A C8A -179.2(4) no C5A C6A C7A C8A .0(7) no N9A C6A C7A C12A 1.2(5) no C5A C6A C7A C12A -179.6(5) no C4A C3A C8A C7A -.4(8) no C6A C7A C8A C3A -.1(7) no C12A C7A C8A C3A 179.3(5) no C5A C6A N9A C11A 179.6(5) no C7A C6A N9A C11A -1.3(5) no C5A C6A N9A C10A .8(8) no C7A C6A N9A C10A 179.9(4) no C6A N9A C11A C12A .8(6) no C10A N9A C11A C12A 179.6(5) no N9A C11A C12A C7A -.1(6) no N9A C11A C12A C13A 177.8(5) no C6A C7A C12A C11A -.7(6) no C8A C7A C12A C11A 179.8(5) no C6A C7A C12A C13A -178.8(5) no C8A C7A C12A C13A 1.8(9) no C11A C12A C13A N14A 17.2(9) no C7A C12A C13A N14A -165.3(5) no C12A C13A N14A O15A -.4(8) no C8B C3B C4B C5B .6(9) no C3B C4B C5B C6B .2(8) no C4B C5B C6B N9B 179.9(5) no C4B C5B C6B C7B -.4(7) no N9B C6B C7B C8B 179.5(4) no C5B C6B C7B C8B -.2(7) no N9B C6B C7B C12B 1.3(5) no C5B C6B C7B C12B -178.4(5) no C4B C3B C8B C7B -1.3(8) no C6B C7B C8B C3B 1.1(7) no C12B C7B C8B C3B 178.7(5) no C5B C6B N9B C11B 178.5(5) no C7B C6B N9B C11B -1.2(6) no C5B C6B N9B C10B -2.5(8) no C7B C6B N9B C10B 177.8(4) no C6B N9B C11B C12B .6(6) no C10B N9B C11B C12B -178.4(5) no N9B C11B C12B C13B 177.1(5) no N9B C11B C12B C7B .3(6) no C8B C7B C12B C11B -178.8(6) no C6B C7B C12B C11B -1.0(5) no C8B C7B C12B C13B 4.3(9) no C6B C7B C12B C13B -178.0(5) no C11B C12B C13B N14B 18.70(10) no C7B C12B C13B N14B -165.1(5) no C12B C13B N14B O15B -2.9(8) no