#------------------------------------------------------------------------------ #$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $ #$Revision: 202017 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/17/7201766.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7201766 loop_ _publ_author_name 'Marten, J.' 'Seichter, W.' 'Weber, E.' 'B\"ohme, U.' _publ_section_title ; Crystalline packings of diketoarylhydrazones controlled by a methyl for trifluoromethyl structural change ; _journal_issue 5 _journal_name_full CrystEngComm _journal_page_first 541 _journal_paper_doi 10.1039/b715090c _journal_volume 10 _journal_year 2008 _chemical_formula_sum 'C11 H11 I N2 O2' _chemical_formula_weight 330.12 _chemical_name_systematic ; ? ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 88.762(2) _cell_angle_beta 81.264(2) _cell_angle_gamma 61.6120(10) _cell_formula_units_Z 2 _cell_length_a 7.9355(3) _cell_length_b 7.9685(3) _cell_length_c 11.1563(5) _cell_measurement_temperature 298(2) _cell_volume 612.39(4) _computing_cell_refinement 'SAINT-NT (Bruker, 2003)' _computing_data_collection 'SMART APEX2 (Bruker-AXS)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _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 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 23617 _diffrn_reflns_theta_full 34.84 _diffrn_reflns_theta_max 34.84 _diffrn_reflns_theta_min 1.85 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 2.602 _exptl_absorpt_correction_T_max 0.8780 _exptl_absorpt_correction_T_min 0.6320 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.790 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _refine_diff_density_max 2.042 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.120 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 147 _refine_ls_number_reflns 5306 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.093 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0491 _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1781 _refine_ls_wR_factor_ref 0.1973 _reflns_number_gt 3282 _reflns_number_total 5306 _reflns_threshold_expression >2sigma(I) _cod_data_source_file b715090c.txt _cod_data_source_block jama13new _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'multi scan' changed to 'multi-scan' 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 ; _cod_database_code 7201766 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.32193(4) -0.46677(4) 1.30451(2) 0.07499(16) Uani 1 1 d . . . O1 O 0.2666(6) 0.2499(6) 0.5124(3) 0.0876(10) Uani 1 1 d . . . O2 O 0.1451(8) 0.4860(5) 0.8655(3) 0.0950(12) Uani 1 1 d . . . N1 N 0.2345(4) 0.1102(4) 0.8073(2) 0.0499(5) Uani 1 1 d . . . N2 N 0.2257(5) 0.1460(4) 0.9218(2) 0.0549(6) Uani 1 1 d . . . H2 H 0.2028 0.2597 0.9473 0.066 Uiso 1 1 calc R . . C1 C 0.2331(9) -0.0173(8) 0.5807(4) 0.0839(14) Uani 1 1 d . . . H1A H 0.2228 -0.0327 0.4957 0.126 Uiso 1 1 calc R . . H1B H 0.1201 -0.0125 0.6336 0.126 Uiso 1 1 calc R . . H1C H 0.3518 -0.1256 0.6002 0.126 Uiso 1 1 calc R . . C2 C 0.2401(5) 0.1646(5) 0.6002(3) 0.0563(7) Uani 1 1 d . . . C3 C 0.2123(5) 0.2403(5) 0.7271(3) 0.0527(6) Uani 1 1 d . . . C4 C 0.1646(7) 0.4370(6) 0.7581(4) 0.0645(9) Uani 1 1 d . . . C5 C 0.1273(8) 0.5846(7) 0.6646(4) 0.0780(13) Uani 1 1 d . . . H5A H 0.0693 0.7117 0.7056 0.117 Uiso 1 1 calc R . . H5B H 0.0382 0.5806 0.6142 0.117 Uiso 1 1 calc R . . H5C H 0.2501 0.5574 0.6132 0.117 Uiso 1 1 calc R . . C6 C 0.2522(5) 0.0064(5) 1.0037(3) 0.0512(6) Uani 1 1 d . . . C7 C 0.2502(6) -0.1634(5) 0.9732(3) 0.0571(7) Uani 1 1 d . . . H7 H 0.2343 -0.1859 0.8934 0.068 Uiso 1 1 calc R . . C8 C 0.2713(6) -0.2967(5) 1.0583(3) 0.0583(7) Uani 1 1 d . . . H8 H 0.2673 -0.4097 1.0378 0.070 Uiso 1 1 calc R . . C9 C 0.2985(5) -0.2655(5) 1.1752(3) 0.0545(7) Uani 1 1 d . . . C10 C 0.3014(6) -0.0995(6) 1.2064(3) 0.0616(8) Uani 1 1 d . . . H10 H 0.3188 -0.0787 1.2861 0.074 Uiso 1 1 calc R . . C11 C 0.2787(6) 0.0365(6) 1.1210(3) 0.0624(8) Uani 1 1 d . . . H11 H 0.2813 0.1500 1.1424 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0704(2) 0.0872(3) 0.0620(2) 0.03980(15) -0.01725(13) -0.03298(17) O1 0.111(3) 0.101(2) 0.0490(14) 0.0321(15) -0.0122(15) -0.051(2) O2 0.165(4) 0.082(2) 0.0620(18) 0.0203(15) -0.036(2) -0.074(3) N1 0.0534(14) 0.0593(14) 0.0390(11) 0.0179(10) -0.0112(9) -0.0281(12) N2 0.0688(17) 0.0600(15) 0.0415(11) 0.0159(10) -0.0147(11) -0.0340(14) C1 0.121(4) 0.092(3) 0.051(2) 0.012(2) -0.013(2) -0.061(3) C2 0.0640(18) 0.0636(18) 0.0401(13) 0.0165(12) -0.0107(12) -0.0294(16) C3 0.0556(16) 0.0633(18) 0.0429(13) 0.0189(12) -0.0141(12) -0.0302(14) C4 0.080(2) 0.071(2) 0.0585(19) 0.0232(16) -0.0193(17) -0.048(2) C5 0.106(4) 0.079(3) 0.070(2) 0.037(2) -0.025(2) -0.059(3) C6 0.0544(16) 0.0607(17) 0.0386(12) 0.0147(12) -0.0100(11) -0.0274(14) C7 0.071(2) 0.0581(17) 0.0395(13) 0.0111(12) -0.0134(13) -0.0277(16) C8 0.068(2) 0.0587(18) 0.0434(14) 0.0148(13) -0.0132(13) -0.0252(16) C9 0.0495(15) 0.0701(19) 0.0362(12) 0.0186(12) -0.0081(10) -0.0226(14) C10 0.071(2) 0.080(2) 0.0361(13) 0.0157(14) -0.0123(13) -0.0378(19) C11 0.081(2) 0.075(2) 0.0389(13) 0.0147(14) -0.0161(14) -0.042(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' H H 0.0000 0.0000 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C3 121.5(3) . . ? N1 N2 C6 120.4(3) . . ? N1 N2 H2 119.8 . . ? C6 N2 H2 119.8 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 121.1(4) . . ? O1 C2 C1 119.9(3) . . ? C3 C2 C1 119.0(3) . . ? N1 C3 C4 124.2(3) . . ? N1 C3 C2 112.3(3) . . ? C4 C3 C2 123.5(3) . . ? O2 C4 C3 118.7(4) . . ? O2 C4 C5 118.8(4) . . ? C3 C4 C5 122.4(4) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 C11 118.7(3) . . ? N2 C6 C7 122.0(3) . . ? C11 C6 C7 119.3(3) . . ? C8 C7 C6 120.4(3) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 119.9(3) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 C8 120.4(3) . . ? C10 C9 I1 120.5(2) . . ? C8 C9 I1 119.1(3) . . ? C9 C10 C11 120.0(3) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C6 120.1(4) . . ? C10 C11 H11 120.0 . . ? C6 C11 H11 120.0 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C9 2.094(3) . ? O1 C2 1.230(4) . ? O2 C4 1.233(5) . ? N1 N2 1.299(4) . ? N1 C3 1.319(4) . ? N2 C6 1.382(4) . ? N2 H2 0.8800 . ? C1 C2 1.498(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.494(5) . ? C3 C4 1.462(6) . ? C4 C5 1.506(6) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C11 1.400(4) . ? C6 C7 1.410(5) . ? C7 C8 1.376(5) . ? C7 H7 0.9500 . ? C8 C9 1.400(5) . ? C8 H8 0.9500 . ? C9 C10 1.386(6) . ? C10 C11 1.392(5) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 N2 C6 -179.1(3) . . . . ? N2 N1 C3 C4 -4.0(5) . . . . ? N2 N1 C3 C2 176.5(3) . . . . ? O1 C2 C3 N1 -164.1(4) . . . . ? C1 C2 C3 N1 16.6(5) . . . . ? O1 C2 C3 C4 16.3(6) . . . . ? C1 C2 C3 C4 -163.0(4) . . . . ? N1 C3 C4 O2 0.7(7) . . . . ? C2 C3 C4 O2 -179.8(4) . . . . ? N1 C3 C4 C5 -175.7(4) . . . . ? C2 C3 C4 C5 3.8(7) . . . . ? N1 N2 C6 C11 168.0(3) . . . . ? N1 N2 C6 C7 -13.0(5) . . . . ? N2 C6 C7 C8 -178.0(3) . . . . ? C11 C6 C7 C8 1.0(6) . . . . ? C6 C7 C8 C9 -1.2(6) . . . . ? C7 C8 C9 C10 1.0(6) . . . . ? C7 C8 C9 I1 178.2(3) . . . . ? C8 C9 C10 C11 -0.5(6) . . . . ? I1 C9 C10 C11 -177.7(3) . . . . ? C9 C10 C11 C6 0.3(6) . . . . ? N2 C6 C11 C10 178.6(3) . . . . ? C7 C6 C11 C10 -0.5(6) . . . . ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 839404