#------------------------------------------------------------------------------ #$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/66/2206681.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_2206681 loop_ _publ_author_name 'Takahashi, Hajime' 'Takechi, Haruko' 'Kubo, Kanji' 'Matsumoto, Taisuke' _publ_section_title ; 7-Diethylamino-3-dimethylamino-2H-1-benzopyran-2-one ; _journal_coeditor_code DN6246 _journal_issue 9 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o3041 _journal_page_last o3043 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C15 H20 N2 O2' _chemical_formula_moiety 'C15 H20 N2 O2' _chemical_formula_sum 'C15 H20 N2 O2' _chemical_formula_weight 260.34 _chemical_name_systematic ; 7-Diethylamino-3-dimethylamino-2H-1-benzopyran-2-one ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_formula_units_Z 4 _cell_length_a 6.596(3) _cell_length_b 14.360(6) _cell_length_c 14.549(6) _cell_measurement_reflns_used 4379 _cell_measurement_temperature 123.1 _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.1 _cell_volume 1378.0(10) _computing_cell_refinement 'Crystal Clear' _computing_data_collection 'Crystal Clear (Rigaku, 1999)' _computing_data_reduction 'Crystal Structure (Rigaku/MSC & Rigaku, 2004)' _computing_molecular_graphics ; ORTEPIII (Burnett & Johnson, 1996) and ORTEPIII for Windows (Farrugia, 1997) ; _computing_publication_material CrystalStructure _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_detector_area_resol_mean 7.31 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_reflns_av_R_equivalents 0.138 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 11200 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.48 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(REQAB; Jacobson, 1998)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 560.00 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.31 _refine_diff_density_min -0.31 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 194 _refine_ls_number_reflns 1817 _refine_ls_R_factor_gt 0.0566 _refine_ls_shift/su_max 0.0001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[0.9370\s(Fo^2^)]/(4Fo^2^)' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1625 _reflns_number_gt 1467 _reflns_number_total 1823 _reflns_threshold_expression F^2^>2\s(F^2^) _[local]_cod_data_source_file dn6246.cif loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +x,+y,+z 2 1/2+x,1/2-y,-z 3 -x,1/2+y,1/2-z 4 1/2-x,-y,1/2+z loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, 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 O1 0.3225(2) 0.81266(12) 0.61901(13) 0.0199(4) Uani d . 1.00 O O2 0.4480(3) 0.70325(14) 0.70694(16) 0.0285(5) Uani d . 1.00 O N1 0.0639(3) 0.62869(14) 0.74974(14) 0.0195(5) Uani d . 1.00 N N2 0.1079(3) 1.05384(17) 0.41548(17) 0.0229(5) Uani d . 1.00 N C1 0.2947(4) 0.73664(19) 0.67543(19) 0.0197(6) Uani d . 1.00 C C2 0.0864(4) 0.70677(18) 0.69226(19) 0.0171(5) Uani d . 1.00 C C3 -0.0671(4) 0.74784(17) 0.64592(18) 0.0156(5) Uani d . 1.00 C C4 -0.0313(4) 0.82297(19) 0.58296(18) 0.0160(5) Uani d . 1.00 C C5 -0.1815(4) 0.86916(18) 0.53231(18) 0.0182(5) Uani d . 1.00 C C6 -0.1366(4) 0.94350(19) 0.47660(19) 0.0190(6) Uani d . 1.00 C C7 0.0650(4) 0.97726(18) 0.46916(18) 0.0181(6) Uani d . 1.00 C C8 0.2170(4) 0.93009(18) 0.51819(18) 0.0185(6) Uani d . 1.00 C C9 0.1664(4) 0.85518(18) 0.57280(18) 0.0165(5) Uani d . 1.00 C C10 0.1576(5) 0.6327(2) 0.8426(2) 0.0295(7) Uani d . 1.00 C C11 -0.1400(4) 0.5923(2) 0.7563(2) 0.0258(7) Uani d . 1.00 C C12 0.3145(4) 1.0897(2) 0.4088(2) 0.0232(6) Uani d . 1.00 C C13 0.3738(5) 1.1489(2) 0.4919(2) 0.0304(7) Uani d . 1.00 C C14 -0.0515(4) 1.1073(2) 0.3710(2) 0.0270(7) Uani d . 1.00 C C15 -0.1177(5) 1.0672(2) 0.2778(2) 0.0409(9) Uani d . 1.00 C H1 -0.2020 0.7267 0.6553 0.019 Uiso c R 1.00 H H2 -0.3180 0.8486 0.5367 0.022 Uiso c R 1.00 H H3 -0.2418 0.9725 0.4425 0.023 Uiso c R 1.00 H H4 0.3543 0.9497 0.5137 0.022 Uiso c R 1.00 H H5 0.0627 0.6577 0.8851 0.035 Uiso c R 1.00 H H6 0.1955 0.5718 0.8615 0.035 Uiso c R 1.00 H H7 0.2744 0.6713 0.8406 0.036 Uiso c R 1.00 H H8 -0.1967 0.5874 0.6964 0.031 Uiso c R 1.00 H H9 -0.2205 0.6331 0.7924 0.031 Uiso c R 1.00 H H10 -0.1369 0.5325 0.7842 0.031 Uiso c R 1.00 H H11 0.3249 1.1268 0.3550 0.028 Uiso c R 1.00 H H12 0.4053 1.0385 0.4044 0.028 Uiso c R 1.00 H H13 0.4324 1.1101 0.5376 0.037 Uiso c R 1.00 H H14 0.4695 1.1946 0.4734 0.037 Uiso c R 1.00 H H15 0.2569 1.1787 0.5162 0.037 Uiso c R 1.00 H H16 -0.0033 1.1690 0.3619 0.032 Uiso c R 1.00 H H17 -0.1662 1.1086 0.4104 0.032 Uiso c R 1.00 H H18 -0.1330 1.0015 0.2823 0.049 Uiso c R 1.00 H H19 -0.0179 1.0813 0.2328 0.049 Uiso c R 1.00 H H20 -0.2433 1.0943 0.2604 0.049 Uiso c R 1.00 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 O1 0.0138(8) 0.0187(8) 0.0273(10) 0.0002(7) -0.0025(8) 0.0043(7) O2 0.0146(9) 0.0304(10) 0.0403(12) 0.0006(9) -0.0049(9) 0.0105(9) N1 0.0202(11) 0.0178(10) 0.0206(10) 0.0007(10) -0.0015(10) 0.0050(9) N2 0.0180(11) 0.0204(11) 0.0302(12) -0.0025(10) -0.0021(10) 0.0085(9) C1 0.0195(13) 0.0181(12) 0.0216(13) -0.0007(11) -0.0001(11) 0.0005(10) C2 0.0172(12) 0.0141(10) 0.0201(12) 0.0002(10) 0.0017(10) -0.0036(10) C3 0.0129(11) 0.0153(11) 0.0185(11) -0.0020(9) 0.0031(10) -0.0020(9) C4 0.0144(11) 0.0170(11) 0.0167(11) 0.0006(10) 0.0001(10) -0.0003(10) C5 0.0157(11) 0.0177(11) 0.0212(11) -0.0001(10) 0.0010(10) 0.0009(10) C6 0.0141(12) 0.0205(12) 0.0224(12) 0.0028(11) -0.0018(10) 0.0012(10) C7 0.0190(13) 0.0151(11) 0.0203(11) -0.0003(10) 0.0016(11) -0.0005(10) C8 0.0147(12) 0.0162(11) 0.0245(12) 0.0006(10) 0.0012(10) 0.0005(10) C9 0.0141(11) 0.0168(11) 0.0188(11) 0.0024(10) -0.0012(10) -0.0011(9) C10 0.0301(16) 0.0324(15) 0.0261(14) -0.0027(14) -0.0066(13) 0.0077(12) C11 0.0269(15) 0.0205(12) 0.0299(14) -0.0045(12) 0.0007(13) 0.0056(11) C12 0.0174(12) 0.0219(13) 0.0303(14) -0.0017(11) 0.0007(11) 0.0048(11) C13 0.0281(16) 0.0254(14) 0.0377(16) -0.0065(13) -0.0004(14) -0.0040(12) C14 0.0228(14) 0.0191(12) 0.0391(16) 0.0005(11) -0.0036(14) 0.0095(12) C15 0.047(2) 0.0391(17) 0.0370(17) -0.0129(17) -0.0148(16) 0.0211(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.378(3) no O1 C9 1.373(3) no O2 C1 1.209(3) no N1 C2 1.407(3) no N1 C10 1.486(3) no N1 C11 1.446(3) no N2 C7 1.378(3) no N2 C12 1.459(3) no N2 C14 1.455(3) no C1 C2 1.460(3) no C2 C3 1.352(3) no C3 C4 1.435(3) no C4 C5 1.401(3) no C4 C9 1.392(3) no C5 C6 1.373(3) no C6 C7 1.419(3) no C7 C8 1.405(3) no C8 C9 1.378(3) no C12 C13 1.529(4) no C14 C15 1.536(4) no C3 H1 0.950 ? C5 H2 0.950 ? C6 H3 0.950 ? C8 H4 0.950 ? C10 H5 0.950 ? C10 H6 0.950 ? C10 H7 0.950 ? C11 H8 0.950 ? C11 H9 0.950 ? C11 H10 0.950 ? C12 H11 0.950 ? C12 H12 0.950 ? C13 H13 0.950 ? C13 H14 0.950 ? C13 H15 0.950 ? C14 H16 0.950 ? C14 H17 0.950 ? C15 H18 0.950 ? C15 H19 0.950 ? C15 H20 0.950 ? 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 C1 O1 C9 123.0(2) no C2 N1 C10 117.8(2) no C2 N1 C11 115.2(2) no C10 N1 C11 109.9(2) no C7 N2 C12 120.7(2) no C7 N2 C14 121.7(2) no C12 N2 C14 117.3(2) no O1 C1 O2 115.4(2) no O1 C1 C2 117.3(2) ? O2 C1 C2 127.4(2) ? N1 C2 C1 115.7(2) ? N1 C2 C3 124.4(2) ? C1 C2 C3 119.5(2) ? C2 C3 C4 121.5(2) ? C3 C4 C5 125.1(2) ? C3 C4 C9 118.2(2) ? C5 C4 C9 116.7(2) ? C4 C5 C6 121.7(2) ? C5 C6 C7 120.9(2) ? N2 C7 C6 120.6(2) ? N2 C7 C8 121.7(2) ? C6 C7 C8 117.7(2) ? C7 C8 C9 119.7(2) ? O1 C9 C4 120.2(2) ? O1 C9 C8 116.6(2) ? C4 C9 C8 123.2(2) ? N2 C12 C13 112.5(2) ? N2 C14 C15 113.6(2) ? C2 C3 H1 119.4 ? C4 C3 H1 119.1 ? C4 C5 H2 119.2 ? C6 C5 H2 119.1 ? C5 C6 H3 119.5 ? C7 C6 H3 119.7 ? C7 C8 H4 120.2 ? C9 C8 H4 120.1 ? N1 C10 H5 109.4 ? N1 C10 H6 109.7 ? N1 C10 H7 109.3 ? H5 C10 H6 109.5 ? H5 C10 H7 109.5 ? H6 C10 H7 109.5 ? N1 C11 H8 109.4 ? N1 C11 H9 109.5 ? N1 C11 H10 109.5 ? H8 C11 H9 109.5 ? H8 C11 H10 109.5 ? H9 C11 H10 109.5 ? N2 C12 H11 108.7 ? N2 C12 H12 108.7 ? C13 C12 H11 108.7 ? C13 C12 H12 108.8 ? H11 C12 H12 109.5 ? C12 C13 H13 109.4 ? C12 C13 H14 109.3 ? C12 C13 H15 109.7 ? H13 C13 H14 109.5 ? H13 C13 H15 109.5 ? H14 C13 H15 109.5 ? N2 C14 H16 108.2 ? N2 C14 H17 108.5 ? C15 C14 H16 108.8 ? C15 C14 H17 108.3 ? H16 C14 H17 109.4 ? C14 C15 H18 109.9 ? C14 C15 H19 109.3 ? C14 C15 H20 109.2 ? H18 C15 H19 109.5 ? H18 C15 H20 109.5 ? H19 C15 H20 109.5 ? 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 C1 O1 C9 C4 1.1(3) C1 O1 C9 C8 -179.5(2) C9 O1 C1 O2 175.6(2) C9 O1 C1 C2 -5.8(3) C10 N1 C2 C1 55.5(3) C10 N1 C2 C3 -131.6(2) C11 N1 C2 C1 -172.2(2) C11 N1 C2 C3 0.7(3) C7 N2 C12 C13 -79.4(3) C12 N2 C7 C6 179.0(2) C12 N2 C7 C8 -0.9(3) C7 N2 C14 C15 -85.0(3) C14 N2 C7 C6 5.2(3) C14 N2 C7 C8 -174.7(2) C12 N2 C14 C15 101.0(3) C14 N2 C12 C13 94.7(3) O1 C1 C2 N1 179.7(2) O1 C1 C2 C3 6.4(3) O2 C1 C2 N1 -1.9(4) O2 C1 C2 C3 -175.2(2) N1 C2 C3 C4 -175.2(2) C1 C2 C3 C4 -2.5(3) C2 C3 C4 C5 179.95(18) C2 C3 C4 C9 -2.2(3) C3 C4 C5 C6 176.8(2) C3 C4 C9 O1 3.0(3) C3 C4 C9 C8 -176.4(2) C5 C4 C9 O1 -179.0(2) C5 C4 C9 C8 1.7(3) C9 C4 C5 C6 -1.1(3) C4 C5 C6 C7 -0.8(4) C5 C6 C7 N2 -177.8(2) C5 C6 C7 C8 2.1(3) N2 C7 C8 C9 178.4(2) C6 C7 C8 C9 -1.5(3) C7 C8 C9 O1 -179.7(2) C7 C8 C9 C4 -0.4(4) 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 C3 H1 O2 1_455 0.95 2.45 3.380(3) 166.0(2) yes C5 H2 O1 1_455 0.95 2.71 3.599(3) 156.9(2) yes C11 H9 O2 1_455 0.95 2.71 3.230(4) 115.3(2) yes C15 H19 O1 4_574 0.95 2.59 3.479(4) 155.4(2) yes C5 H2 Cp 2_466 0.95 3.09 3.44 104 yes _cod_database_code 2206681