#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/33/2003349.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_2003349 loop_ _publ_author_name '\"Ozbey, S.' 'Kendi, E.' '\.Ide, S.' 'Mak, T. C. W.' _publ_section_title ; 2-Methyl-2-(2-methylphenylazo)-1,3-indandione ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 707 _journal_page_last 709 _journal_paper_doi 10.1107/S010827019400867X _journal_volume 51 _journal_year 1995 _chemical_compound_source 'Phillips (1959)' _chemical_formula_moiety 'C17 H14 N2 O2' _chemical_formula_sum 'C17 H14 N2 O2' _chemical_formula_weight 278.3 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _atom_type_scat_source IntTabIV _cell_angle_alpha 90. _cell_angle_beta 107.73(2) _cell_angle_gamma 90. _cell_formula_units_Z 4 _cell_length_a 8.205(2) _cell_length_b 14.321(5) _cell_length_c 12.838(4) _cell_measurement_reflns_used 15 _cell_measurement_temperature 293 _cell_measurement_theta_max 20 _cell_measurement_theta_min 6 _cell_volume 1436.9(8) _diffrn_measurement_device 'Nicolet R3m/V' _diffrn_measurement_method \w-2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 1174 _diffrn_reflns_theta_max 22.5 _diffrn_standards_decay_% 0.5 _diffrn_standards_interval_time 125 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.08 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_correction_T_min 0.959 _exptl_absorpt_correction_type empirical _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.287 _exptl_crystal_description plate _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.16 _refine_diff_density_min -0.21 _refine_ls_extinction_method none _refine_ls_hydrogen_treatment refxyz _refine_ls_number_parameters 232 _refine_ls_number_reflns 991 _refine_ls_R_factor_obs 0.0529 _refine_ls_shift/esd_max 0.186 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 2.7065/[\s^2^(F) + 0.000846F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.0565 _reflns_number_observed 1079 _reflns_number_total 1174 _reflns_observed_criterion F>4\s(F) _cod_data_source_file hr1008.cif _cod_data_source_block hr1008a _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '2.7065/[\s^2^(F) + 0.000846F^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 2.7065/[\s^2^(F) + 0.000846F^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/a' _cod_database_code 2003349 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,1/2-y,z -x,-y,-z 1/2-x,1/2+y,-z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv O2 .0821(4) .2828(2) .3834(3) .074(2) O1 .0899(5) -.0437(2) .3887(3) .086(2) N2 .1614(4) .1170(3) .2506(3) .060(1) N1 .0758(4) .1331(2) .1564(3) .060(2) C1 .1308(6) .2032(3) .4055(4) .056(3) C2 .0615(5) .1186(3) .3303(3) .055(2) C3 .1350(6) .0364(3) .4065(4) .059(3) C4 .2679(6) .0724(3) .5040(4) .051(3) C9 .2634(6) .1700(3) .5035(4) .054(3) C1' .1708(6) .1307(3) .0792(4) .058(2) C2' .0745(7) .1251(3) -.0296(4) .078(2) C5 .3879(7) .0254(4) .5889(4) .063(3) C6 .5001(7) .0757(4) .6697(5) .073(3) C7 .4913(7) .1728(4) .6695(5) .076(3) C8 .3734(7) .2206(3) .5874(5) .065(3) C10 -.1301(6) .1179(4) .2813(5) .075(2) C11 -.1170(10) .1239(4) -.0637(6) .113(3) C3' .1678(13) .1172(4) -.1072(5) .104(4) C4' .3421(13) .1166(5) -.0737(6) .107(4) C5' .4344(9) .1255(4) .0355(5) .092(3) C6' .3502(7) .1321(3) .1100(4) .067(2) H5 .389(5) -.034(3) .584(3) .050 H6 .595(5) .044(3) .729(3) .065 H7 .572(5) .200(3) .727(3) .065 H8 .365(5) .286(3) .585(3) .060 H101 -.182(5) .124(3) .336(3) .070 H102 -.166(5) .064(3) .234(3) .070 H103 -.175(5) .179(3) .233(3) .070 H111 -.152(5) .124(3) -.140(4) .070 H112 -.154(6) .172(3) -.079(4) .070 H113 -.156(5) .073(3) -.043(4) .070 H3' .088(6) .114(3) -.169(4) .090 H4' .384(6) .114(3) -.133(5) .100 H5' .566(6) .136(3) .053(4) .090 H6' .404(6) .139(3) .176(4) .060 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 N1 N2 C2 113.9(3) yes N2 N1 C1' 114.2(4) yes O2 C1 C9 127.6(4) yes O2 C1 C2 123.9(4) yes C2 C1 C9 108.5(4) yes N2 C2 C1 105.4(3) yes C1 C2 C10 113.9(4) yes C1 C2 C3 101.8(4) yes N2 C2 C10 115.8(4) yes N2 C2 C3 103.6(4) yes C3 C2 C10 114.8(4) yes O1 C3 C2 124.9(4) yes C2 C3 C4 108.5(4) yes O1 C3 C4 126.6(6) yes C5 C6 C7 120.2(6) yes C6 C7 C8 121.5(5) yes C9 C8 C7 118.4(5) yes C4 C5 C6 119.4(5) yes C3 C4 C5 130.8(4) yes C3 C4 C9 109.4(4) yes C9 C4 C5 119.7(4) yes C1 C9 C4 109.8(4) yes C4 C9 C8 120.7(5) yes C1 C9 C8 129.5(4) yes N1 C1' C6' 123.3(4) yes N1 C1' C2' 115.8(5) yes C2' C1' C6' 120.9(5) yes C1' C2' C3' 116.4(6) yes C1' C2' C11 121.5(6) yes C11 C2' C3' 122.1(5) yes C3' C4' C5' 121.2(9) yes C4' C5' C6' 119.2(7) yes C1' C6' C5' 121.4(5) yes C2' C3' C4' 120.8(6) yes C4 C5 H5 116.(3) no C6 C6 H5 124.(3) no C5 C6 H6 121.(2) no C7 C6 H6 119.(2) no C6 C7 H7 114.(3) no C8 C7 H7 125.(3) no C7 C8 H8 123.(2) no C9 C8 H8 118.(2) no C2 C10 H103 112.(2) no C2 C10 H102 110.(3) no C2 C10 H101 110.(3) no C2' C11 H113 112.(3) no C2' C11 H112 111.(4) no C2' C11 H111 105.(3) no C2' C3' H3' 104.(4) no C4' C3' H3' 136.(4) no C3' C4' H4' 111.(4) no C5' C4' H4' 127.(3) no C4' C5' H5' 118.(3) no C6' C5' H5' 122.(3) no C5' C6' H6' 121.(3) no C1' C6' H6' 118.(3) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O2 C1 1.212(5) yes O1 C3 1.205(5) yes N2 N1 1.221(4) yes N2 C2 1.493(6) yes N1 C1' 1.436(7) yes C1 C2 1.546(6) yes C1 C9 1.469(6) yes C2 C3 1.532(6) yes C2 C10 1.505(6) yes C3 C4 1.479(6) yes C4 C9 1.398(6) yes C4 C5 1.400(6) yes C5 C6 1.364(7) yes C6 C7 1.392(8) yes C7 C8 1.376(7) yes C9 C8 1.381(7) yes C1' C6' 1.403(7) yes C2' C11 1.497(10) yes C2' C3' 1.434(12) yes C9 C8 1.381(7) yes C3' C4' 1.362(14) yes C4' C5' 1.382(9) yes C5' C6' 1.343(10) yes C1' C2' 1.382(6) yes C5 H5 0.85(4) no C6 H6 1.02(4) no C7 H7 0.91(4) no C8 H8 0.95(4) no C10 H101 0.93(5) no C10 H102 0.97(4) no C10 H103 1.06(4) no C11 H111 0.93(4) no C11 H112 0.76(4) no C11 H113 0.87(5) no C3' H3' 0.86(5) no C4' H4' 0.93(6) no C5' H5' 1.04(4) no C6' H6' 0.84(4) no 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 C2 N2 N1 C1' -179.4(4) yes N2 N1 C1' C2' -14.5(6) yes N2 N1 C1' C2' 164.4(4) yes N1 N2 C2 C1 -113.7(4) yes N1 N2 C2 C3 139.7(4) yes C3 C2 C1 C9 12.8(5) yes C2 C1 C9 C4 -7.9(5) yes C1 C9 C4 C3 -0.9(5) yes C9 C4 C3 C2 9.5(5) yes C4 C3 C2 C1 -13.3(5) yes N1 N2 C2 C10 13.2(5) yes C6' C1' C2' C11 -179.8(5) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 85654288