#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/34/2203407.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_2203407 loop_ _publ_author_name 'Yavuz K\"oysal' '\,Samil I\,s\?ik' 'Nursabah Sar\?ikavakl\?i' 'Fatih Erduran' _publ_section_title ; anti-1-(Benzylamino)glyoxime ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o515 _journal_page_last o516 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C9 H11 N3 O2' _chemical_formula_moiety 'C9 H11 N3 O2' _chemical_formula_sum 'C9 H11 N3 O2' _chemical_formula_weight 193.21 _chemical_name_systematic ; anti-1-(Benzylamino)glyoxime ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 11.6618(9) _cell_length_b 8.8584(7) _cell_length_c 19.163(2) _cell_measurement_reflns_used 7310 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.39 _cell_measurement_theta_min 1.75 _cell_volume 1979.6(3) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie,2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material 'WinGX (Farrugia, 1997) and PARST (Nardelli, 1995)' _computing_structure_refinement SHELXL97 _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'STOE IPDS-II' _diffrn_measurement_method '\w scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0736 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 18058 _diffrn_reflns_theta_full 26.01 _diffrn_reflns_theta_max 26.01 _diffrn_reflns_theta_min 2.13 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_process_details '(X-RED32; Stoe & Cie, 2002)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism. _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.277 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.138 _refine_diff_density_min -0.106 _refine_ls_extinction_coef 0.0139(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 0.799 _refine_ls_hydrogen_treatment 'see text' _refine_ls_matrix_type full _refine_ls_number_parameters 128 _refine_ls_number_reflns 1935 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.799 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0341 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0489P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0776 _refine_ls_wR_factor_ref 0.0853 _reflns_number_gt 1037 _reflns_number_total 1935 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cv6275.cif _[local]_cod_data_source_block I _cod_database_code 2203407 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O2 0.14330(9) 0.00228(13) -0.51572(7) 0.0697(4) Uani d . 1 O H2 0.1043 -0.0725 -0.5242 0.105 Uiso calc R 1 H N3 0.47068(10) 0.24966(14) -0.54691(7) 0.0514(4) Uani d . 1 N C8 0.42702(13) 0.12017(18) -0.56430(8) 0.0460(4) Uani d . 1 C O1 0.58211(9) 0.26497(13) -0.57423(7) 0.0685(4) Uani d . 1 O H1 0.6085 0.3472 -0.5629 0.103 Uiso calc R 1 H N2 0.24940(11) -0.01170(14) -0.54828(7) 0.0512(4) Uani d . 1 N N1 0.48424(11) 0.01693(15) -0.60172(7) 0.0573(4) Uani d . 1 N H1A 0.5550 0.0369 -0.6102 0.069 Uiso calc R 1 H C6 0.53391(14) -0.19577(18) -0.67379(8) 0.0503(4) Uani d . 1 C C9 0.31152(14) 0.10144(19) -0.53772(9) 0.0564(5) Uani d . 1 C H9 0.2813 0.1792 -0.5108 0.068 Uiso calc R 1 H C7 0.44121(14) -0.12495(18) -0.62975(10) 0.0619(5) Uani d . 1 C H7A 0.3735 -0.1067 -0.6579 0.074 Uiso calc R 1 H H7B 0.4204 -0.1923 -0.5919 0.074 Uiso calc R 1 H C5 0.55686(16) -0.1436(2) -0.74013(10) 0.0669(5) Uani d . 1 C H5 0.5127 -0.0660 -0.7587 0.080 Uiso calc R 1 H C1 0.59996(17) -0.3114(2) -0.64838(10) 0.0703(5) Uani d . 1 C H1B 0.5858 -0.3489 -0.6039 0.084 Uiso calc R 1 H C3 0.70875(19) -0.3178(3) -0.75312(14) 0.0837(7) Uani d . 1 C H3 0.7681 -0.3580 -0.7797 0.100 Uiso calc R 1 H C4 0.64410(19) -0.2048(3) -0.77915(11) 0.0769(6) Uani d . 1 C H4 0.6586 -0.1681 -0.8237 0.092 Uiso calc R 1 H C2 0.68741(18) -0.3730(3) -0.68810(13) 0.0873(7) Uani d . 1 C H2A 0.7314 -0.4518 -0.6704 0.105 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 O2 0.0516(7) 0.0558(7) 0.1019(10) -0.0096(6) 0.0264(6) -0.0264(7) N3 0.0402(7) 0.0501(8) 0.0640(9) -0.0032(6) 0.0020(7) -0.0112(7) C8 0.0441(9) 0.0436(9) 0.0504(9) 0.0023(8) -0.0034(7) -0.0055(7) O1 0.0457(7) 0.0647(8) 0.0952(9) -0.0119(6) 0.0088(6) -0.0231(7) N2 0.0438(7) 0.0482(8) 0.0614(8) -0.0004(7) 0.0066(6) -0.0069(7) N1 0.0446(8) 0.0517(8) 0.0756(10) -0.0027(7) 0.0056(7) -0.0224(7) C6 0.0500(10) 0.0482(9) 0.0528(10) -0.0033(8) 0.0012(8) -0.0128(8) C9 0.0539(10) 0.0445(9) 0.0707(12) -0.0014(9) 0.0105(9) -0.0152(9) C7 0.0569(11) 0.0515(10) 0.0772(12) -0.0030(9) 0.0072(9) -0.0203(9) C5 0.0728(13) 0.0650(12) 0.0630(12) 0.0011(10) -0.0022(10) 0.0004(9) C1 0.0807(14) 0.0699(12) 0.0604(11) 0.0133(11) 0.0041(10) -0.0016(10) C3 0.0726(15) 0.0826(15) 0.0958(18) -0.0039(13) 0.0240(12) -0.0328(14) C4 0.0899(15) 0.0836(15) 0.0573(12) -0.0155(13) 0.0173(11) -0.0119(11) C2 0.0770(15) 0.0814(15) 0.1034(18) 0.0280(12) 0.0000(13) -0.0105(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O2 N2 1.3912(16) yes O2 H2 0.8200 ? N3 C8 1.2986(18) yes N3 O1 1.4075(16) yes C8 N1 1.3400(19) yes C8 C9 1.449(2) ? O1 H1 0.8200 ? N2 C9 1.2532(19) yes N1 C7 1.456(2) yes N1 H1A 0.8600 ? C6 C1 1.371(2) ? C6 C5 1.379(2) ? C6 C7 1.508(2) ? C9 H9 0.9300 ? C7 H7A 0.9700 ? C7 H7B 0.9700 ? C5 C4 1.374(3) ? C5 H5 0.9300 ? C1 C2 1.385(3) ? C1 H1B 0.9300 ? C3 C4 1.349(3) ? C3 C2 1.362(3) ? C3 H3 0.9300 ? C4 H4 0.9300 ? C2 H2A 0.9300 ? 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 N2 O2 H2 109.5 ? C8 N3 O1 110.59(12) yes N3 C8 N1 123.02(14) ? N3 C8 C9 112.04(14) ? N1 C8 C9 124.94(15) ? N3 O1 H1 109.5 ? C9 N2 O2 111.75(13) yes C8 N1 C7 127.94(13) yes C8 N1 H1A 116.0 ? C7 N1 H1A 116.0 ? C1 C6 C5 117.96(16) ? C1 C6 C7 120.98(16) ? C5 C6 C7 121.04(16) ? N2 C9 C8 124.89(15) ? N2 C9 H9 117.6 ? C8 C9 H9 117.6 ? N1 C7 C6 108.57(13) ? N1 C7 H7A 110.0 ? C6 C7 H7A 110.0 ? N1 C7 H7B 110.0 ? C6 C7 H7B 110.0 ? H7A C7 H7B 108.4 ? C4 C5 C6 120.88(19) ? C4 C5 H5 119.6 ? C6 C5 H5 119.6 ? C6 C1 C2 120.87(19) ? C6 C1 H1B 119.6 ? C2 C1 H1B 119.6 ? C4 C3 C2 120.2(2) ? C4 C3 H3 119.9 ? C2 C3 H3 119.9 ? C3 C4 C5 120.4(2) ? C3 C4 H4 119.8 ? C5 C4 H4 119.8 ? C3 C2 C1 119.7(2) ? C3 C2 H2A 120.1 ? C1 C2 H2A 120.1 ? 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 O1 N3 C8 N1 1.5(2) yes O1 N3 C8 C9 -179.26(13) yes N3 C8 N1 C7 -173.74(16) ? C9 C8 N1 C7 7.2(3) yes O2 N2 C9 C8 179.56(15) yes N3 C8 C9 N2 178.43(15) ? N1 C8 C9 N2 -2.4(3) ? C8 N1 C7 C6 174.75(15) yes C1 C6 C7 N1 101.08(18) ? C5 C6 C7 N1 -77.2(2) ? C1 C6 C5 C4 -0.7(3) ? C7 C6 C5 C4 177.63(16) ? C5 C6 C1 C2 0.4(3) ? C7 C6 C1 C2 -177.93(17) ? C2 C3 C4 C5 0.6(3) ? C6 C5 C4 C3 0.2(3) ? C4 C3 C2 C1 -0.8(3) ? C6 C1 C2 C3 0.4(3) ? 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 O1 H1 O2 3_554 0.82 2.05 2.7805(16) 148 O2 H2 N3 7_655 0.82 1.85 2.6705(17) 174 N1 H1A O1 . 0.86 2.16 2.5314(17) 106 _cod_database_fobs_code 2203407 _journal_paper_doi 10.1107/S1600536804004799