#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/25/2202508.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_2202508 loop_ _publ_author_name 'C. R. Girija' 'Noor Shahina Begum' 'G. Nagendrappa' _publ_section_title ; 1-(4-Chlorophenyl)propane-1,2-dione 2-oxime ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1666 _journal_page_last o1667 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C9 H8 Cl N O2' _chemical_formula_moiety 'C9 H8 Cl N O2' _chemical_formula_sum 'C9 H8 Cl N O2' _chemical_formula_weight 197.61 _chemical_name_systematic ; 1-(4-chlorophenyl)propane-1,2-dione 2-oxime ; _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 _cell_angle_alpha 90 _cell_angle_beta 102.809(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.066(2) _cell_length_b 5.9348(13) _cell_length_c 14.075(3) _cell_measurement_reflns_used 7478 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.03 _cell_measurement_theta_min 1.89 _cell_volume 901.4(3) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material PLATON _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 0.3 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.968 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _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 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 7478 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 28.03 _diffrn_reflns_theta_min 1.89 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.387 _exptl_absorpt_correction_T_max 0.964 _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description Plate _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.213 _refine_diff_density_min -0.241 _refine_ls_extinction_coef 0.043(5) _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 0.950 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 140 _refine_ls_number_reflns 2116 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.950 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0418 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0784P)^2^+0.2853P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1185 _refine_ls_wR_factor_ref 0.1249 _reflns_number_gt 1827 _reflns_number_total 2116 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6277.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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_enum 1527 2010-12-29 10:47:43Z saulius 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 2202508 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl1 0.05231(5) 0.20157(11) 0.58546(4) 0.0719(2) Uani d . 1 . . Cl O1 0.28572(13) 0.7137(2) 1.00137(10) 0.0594(4) Uani d . 1 . . O O2 0.50727(12) 0.0870(2) 1.10942(8) 0.0489(3) Uani d . 1 . . O N2 0.43038(12) 0.2005(2) 1.03279(9) 0.0396(3) Uani d . 1 . . N C1 0.30377(14) 0.5182(2) 0.98319(11) 0.0409(3) Uani d . 1 . . C C2 0.38269(13) 0.3775(2) 1.06140(10) 0.0393(3) Uani d . 1 . . C C3 0.40766(17) 0.4612(3) 1.16376(12) 0.0533(4) Uani d . 1 . . C H3A 0.3959 0.3408 1.2063 0.080 Uiso calc R 1 . . H H3B 0.3517 0.5822 1.1686 0.080 Uiso calc R 1 . . H H3C 0.4915 0.5147 1.1823 0.080 Uiso calc R 1 . . H C4 0.12963(14) 0.2871(3) 0.70064(12) 0.0451(4) Uani d . 1 . . C C5 0.13464(14) 0.1433(3) 0.77855(13) 0.0448(4) Uani d . 1 . . C C6 0.19671(14) 0.2102(2) 0.87075(12) 0.0414(3) Uani d . 1 . . C C7 0.24950(13) 0.4241(2) 0.88476(11) 0.0383(3) Uani d . 1 . . C C8 0.24267(15) 0.5652(3) 0.80475(12) 0.0458(4) Uani d . 1 . . C C9 0.18444(16) 0.4970(3) 0.71215(12) 0.0504(4) Uani d . 1 . . C H2 0.535(2) -0.009(4) 1.0783(16) 0.069(7) Uiso d . 1 . . H H5 0.0959(18) 0.009(4) 0.7711(14) 0.053(5) Uiso d . 1 . . H H6 0.2013(18) 0.116(3) 0.9252(15) 0.052(5) Uiso d . 1 . . H H8 0.2786(19) 0.713(4) 0.8168(15) 0.055(5) Uiso d . 1 . . H H9 0.187(2) 0.593(4) 0.6565(18) 0.084(7) Uiso d . 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 Cl1 0.0710(4) 0.0893(4) 0.0486(3) -0.0117(3) -0.0016(2) -0.0149(2) O1 0.0765(9) 0.0363(6) 0.0614(8) 0.0058(5) 0.0069(7) -0.0092(5) O2 0.0620(7) 0.0442(6) 0.0351(6) 0.0078(5) -0.0011(5) -0.0014(5) N2 0.0469(7) 0.0348(6) 0.0344(6) -0.0007(5) 0.0032(5) -0.0001(5) C1 0.0437(7) 0.0337(7) 0.0456(8) -0.0023(6) 0.0107(6) -0.0028(6) C2 0.0424(7) 0.0374(7) 0.0383(7) -0.0056(6) 0.0093(6) -0.0048(6) C3 0.0591(10) 0.0594(10) 0.0403(8) 0.0021(8) 0.0090(7) -0.0134(7) C4 0.0369(7) 0.0521(9) 0.0442(8) 0.0016(6) 0.0043(6) -0.0067(6) C5 0.0411(8) 0.0374(7) 0.0552(9) -0.0048(6) 0.0094(7) -0.0070(6) C6 0.0439(8) 0.0345(7) 0.0460(8) -0.0028(6) 0.0101(6) 0.0005(6) C7 0.0375(7) 0.0337(7) 0.0427(7) 0.0015(5) 0.0067(6) -0.0010(5) C8 0.0494(8) 0.0352(7) 0.0504(9) -0.0035(6) 0.0058(7) 0.0034(6) C9 0.0531(9) 0.0499(9) 0.0457(8) -0.0017(7) 0.0055(7) 0.0072(7) 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 Cl1 C4 . 1.7330(16) y O1 C1 . 1.2138(19) y O2 N2 . 1.3906(16) y O2 H2 . 0.82(2) ? N2 C2 . 1.2801(19) y C1 C7 . 1.491(2) y C1 C2 . 1.499(2) y C2 C3 . 1.491(2) y C3 H3A . 0.96 ? C3 H3B . 0.96 ? C3 H3C . 0.96 ? C4 C9 . 1.379(2) ? C4 C5 . 1.381(2) ? C5 C6 . 1.385(2) ? C5 H5 . 0.90(2) ? C6 C7 . 1.393(2) ? C6 H6 . 0.94(2) ? C7 C8 . 1.392(2) ? C8 C9 . 1.381(2) ? C8 H8 . 0.96(2) ? C9 H9 . 0.97(3) ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 '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' C C 0.0033 0.0016 '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 N2 O2 H2 99.2(16) ? C2 N2 O2 112.17(12) y O1 C1 C7 120.18(15) ? O1 C1 C2 118.30(14) ? C7 C1 C2 121.52(12) ? N2 C2 C3 125.21(14) y N2 C2 C1 116.11(13) y C3 C2 C1 118.49(14) y C2 C3 H3A 109.5 ? C2 C3 H3B 109.5 ? H3A C3 H3B 109.5 ? C2 C3 H3C 109.5 ? H3A C3 H3C 109.5 ? H3B C3 H3C 109.5 ? C9 C4 C5 121.71(15) ? C9 C4 Cl1 119.18(14) ? C5 C4 Cl1 119.11(13) ? C4 C5 C6 119.43(15) ? C4 C5 H5 121.4(13) ? C6 C5 H5 119.2(13) ? C5 C6 C7 119.94(15) ? C5 C6 H6 121.2(12) ? C7 C6 H6 118.8(12) ? C8 C7 C6 119.21(14) ? C8 C7 C1 117.69(13) ? C6 C7 C1 122.88(13) ? C9 C8 C7 121.16(15) ? C9 C8 H8 121.5(13) ? C7 C8 H8 117.3(13) ? C4 C9 C8 118.49(16) ? C4 C9 H9 121.7(15) ? C8 C9 H9 119.7(15) ? 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 _geom_hbond_publ_flag O2 H2 N2 3_657 0.82(2) 2.04(2) 2.830(2) 163(2) yes O2 H2 O2 3_657 0.82(2) 2.62(2) 3.219(2) 131(2) yes C3 H3B O1 1_555 0.96 2.43 2.815(2) 103 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 O2 N2 C2 C3 1.8(2) O2 N2 C2 C1 176.77(12) O1 C1 C2 N2 -159.49(15) C7 C1 C2 N2 19.7(2) O1 C1 C2 C3 15.8(2) C7 C1 C2 C3 -164.99(14) C9 C4 C5 C6 -0.3(2) Cl1 C4 C5 C6 179.73(12) C4 C5 C6 C7 2.3(2) C5 C6 C7 C8 -2.2(2) C5 C6 C7 C1 172.17(14) O1 C1 C7 C8 35.9(2) C2 C1 C7 C8 -143.27(15) O1 C1 C7 C6 -138.57(17) C2 C1 C7 C6 42.3(2) C6 C7 C8 C9 0.1(2) C1 C7 C8 C9 -174.57(15) C5 C4 C9 C8 -1.8(3) Cl1 C4 C9 C8 178.20(13) C7 C8 C9 C4 1.8(3) _journal_paper_doi 10.1107/S1600536803021664