#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/65/2006520.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_2006520 loop_ _publ_author_name 'Ko\cis-6,10b,11,12-Tetrahydro-12-hydroxypyrrolo[1',2':2,3]pyridazino[6,1-a]isoindol-6-one _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1362 _journal_page_last 1363 _journal_paper_doi 10.1107/S0108270197004800 _journal_volume 53 _journal_year 1997 _chemical_formula_sum 'C14 H12 N2 O2' _chemical_formula_weight 240.26 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 99.04(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.386(2) _cell_length_b 8.149(2) _cell_length_c 17.267(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 21.6 _cell_measurement_theta_min 17.3 _cell_volume 1165.3(5) _computing_cell_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_data_collection 'Enraf-Nonius SDP-Plus Structure Determination Package (Frenz, 1985)' _computing_data_reduction 'REDU4 (Stoe & Cie, 1988)' _computing_molecular_graphics 'ORTEPII (Johnson, 1971)' _computing_publication_material 'PARST (Nardelli, 1983)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 298(2) _diffrn_measurement_device STOE-STADI4 _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0123 _diffrn_reflns_av_sigmaI/netI 0.0134 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 2573 _diffrn_reflns_theta_max 23.05 _diffrn_reflns_theta_min 2.39 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method none _exptl_crystal_description block _exptl_crystal_F_000 504 _exptl_crystal_size_max 1.32 _exptl_crystal_size_mid 0.80 _exptl_crystal_size_min 0.57 _refine_diff_density_max 0.11 _refine_diff_density_min -0.12 _refine_ls_extinction_coef 0.039(3) _refine_ls_extinction_method 'SHELXL (Sheldrick, 1993)' _refine_ls_goodness_of_fit_all 1.045 _refine_ls_goodness_of_fit_obs 1.046 _refine_ls_hydrogen_treatment 'H-atom parameters refined only for H21' _refine_ls_matrix_type full _refine_ls_number_parameters 168 _refine_ls_number_reflns 1601 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_restrained_S_obs 1.046 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_obs .0325 _refine_ls_shift/esd_max 0.054 _refine_ls_shift/esd_mean 0.010 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.3151P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0898 _refine_ls_wR_factor_obs .0843 _reflns_number_observed 1454 _reflns_number_total 1603 _reflns_observed_criterion >2sigma(I) _cod_data_source_file mu1289.cif _cod_data_source_block koz16 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2006520 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 .0459(7) .0778(9) .0991(10) -.0133(6) .0035(7) .0122(8) O2 .0534(8) .0688(8) .0693(8) -.0053(6) .0189(6) .0146(6) N1 .0485(8) .0492(8) .0536(8) -.0044(6) -.0010(6) -.0062(6) N2 .0445(7) .0485(8) .0516(8) -.0061(6) .0034(6) -.0010(6) C1 .0527(10) .0871(14) .0548(11) -.0028(10) .0015(8) -.0135(10) C2 .0702(13) .0809(14) .0721(14) -.0079(11) -.0082(10) -.0287(11) C3 .0632(11) .0537(11) .0783(13) -.0104(9) -.0099(9) -.0115(10) C4 .0390(9) .0485(10) .0707(11) .0015(8) .0054(8) .0144(8) C5 .0613(11) .0702(13) .0772(14) .0247(10) .0257(10) .0276(11) C6 .099(2) .0790(14) .0597(12) .0419(13) .0310(11) .0180(11) C7 .094(2) .0707(13) .0540(11) .0265(12) .0125(10) .0019(9) C8 .0660(11) .0598(11) .0535(11) .0113(9) .0049(8) -.0028(9) C9 .0460(9) .0478(9) .0501(9) .0119(7) .0059(7) .0031(7) C10 .0339(8) .0477(9) .0536(9) .0010(7) .0028(6) -.0059(7) C11 .0410(8) .0462(9) .0570(10) -.0037(7) .0098(7) -.0053(7) C12 .0339(8) .0567(10) .0575(10) -.0006(7) .0107(7) -.0006(8) C13 .0349(8) .0567(10) .0523(9) .0024(7) .0031(7) -.0043(8) C14 .0468(9) .0522(10) .0601(10) .0145(8) .0118(8) .0144(8) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 .22906(14) .0062(2) .33126(8) .0751(4) Uani d . 1 . O O2 .5967(2) .4433(2) .16316(7) .0628(4) Uani d . 1 . O H21 .493(3) .465(3) .1577(13) .096(8) Uiso d . 1 . H N1 .4783(2) .0553(2) .23782(8) .0514(4) Uani d . 1 . N N2 .48472(15) .0889(2) .31696(7) .0486(4) Uani d . 1 . N C1 .5235(2) .0801(3) .11720(11) .0656(5) Uani d . 1 . C H1 .5548(2) .1204(3) .07148(11) .079 Uiso calc R 1 . H C2 .4492(2) -.0714(3) .12522(13) .0764(6) Uani d . 1 . C H2 .4222(2) -.1485(3) .08565(13) .092 Uiso calc R 1 . H C3 .4234(2) -.0866(2) .20057(12) .0673(5) Uani d . 1 . C H3 .3775(2) -.1757(2) .22247(12) .081 Uiso calc R 1 . H C4 .3562(2) .0749(2) .35662(10) .0531(4) Uani d . 1 . C C5 .3375(2) .1602(2) .49956(12) .0680(6) Uani d . 1 . C H5 .2386(2) .1097(2) .50114(12) .082 Uiso calc R 1 . H C6 .4184(3) .2426(3) .56392(12) .0771(6) Uani d . 1 . C H6 .3725(3) .2479(3) .60952(12) .093 Uiso calc R 1 . H C7 .5655(3) .3172(3) .56222(11) .0729(6) Uani d . 1 . C H7 .6176(3) .3706(3) .60670(11) .087 Uiso calc R 1 . H C8 .6356(2) .3136(2) .49552(10) .0602(5) Uani d . 1 . C H8A .7343(2) .3647(2) .49422(10) .072 Uiso calc R 1 . H C9 .5565(2) .2323(2) .43036(9) .0481(4) Uani d . 1 . C C10 .6071(2) .2070(2) .35190(9) .0455(4) Uani d . 1 . C H10 .7153(2) .1586(2) .35760(9) .055 Uiso calc R 1 . H C11 .5957(2) .3579(2) .29906(9) .0478(4) Uani d . 1 . C H11A .4887(2) .4054(2) .29521(9) .057 Uiso calc R 1 . H H11B .6734(2) .4394(2) .32193(9) .057 Uiso calc R 1 . H C12 .6286(2) .3130(2) .21769(9) .0490(4) Uani d . 1 . C H12 .7444(2) .2896(2) .22274(9) .059 Uiso calc R 1 . H C13 .5422(2) .1590(2) .18791(9) .0484(4) Uani d . 1 . C C14 .4095(2) .1555(2) .43232(10) .0526(4) Uani d . 1 . C 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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C12 O2 H21 107.6(15) C3 N1 C13 111.13(15) C3 N1 N2 126.07(15) C13 N1 N2 122.54(13) C4 N2 N1 124.36(13) C4 N2 C10 113.84(13) N1 N2 C10 116.85(12) C13 C1 C2 108.5(2) C13 C1 H1 125.77(12) C2 C1 H1 125.77(12) C3 C2 C1 108.4(2) C3 C2 H2 125.79(12) C1 C2 H2 125.79(12) C2 C3 N1 106.3(2) C2 C3 H3 126.84(12) N1 C3 H3 126.84(11) O1 C4 N2 124.7(2) O1 C4 C14 130.6(2) N2 C4 C14 104.72(14) C6 C5 C14 117.5(2) C6 C5 H5 121.25(12) C14 C5 H5 121.25(12) C7 C6 C5 121.7(2) C7 C6 H6 119.18(12) C5 C6 H6 119.17(12) C8 C7 C6 120.7(2) C8 C7 H7 119.66(13) C6 C7 H7 119.66(12) C7 C8 C9 118.6(2) C7 C8 H8A 120.69(13) C9 C8 H8A 120.69(11) C8 C9 C14 120.7(2) C8 C9 C10 129.40(15) C14 C9 C10 109.85(14) N2 C10 C9 100.54(12) N2 C10 C11 108.00(12) C9 C10 C11 115.47(13) N2 C10 H10 110.77(8) C9 C10 H10 110.77(8) C11 C10 H10 110.77(8) C12 C11 C10 110.84(13) C12 C11 H11A 109.47(9) C10 C11 H11A 109.47(8) C12 C11 H11B 109.47(8) C10 C11 H11B 109.47(8) H11A C11 H11B 108.1 O2 C12 C13 111.65(13) O2 C12 C11 113.05(13) C13 C12 C11 111.76(13) O2 C12 H12 106.63(8) C13 C12 H12 106.63(8) C11 C12 H12 106.63(9) C1 C13 N1 105.7(2) C1 C13 C12 133.0(2) N1 C13 C12 120.98(14) C9 C14 C5 120.8(2) C9 C14 C4 109.13(14) C5 C14 C4 130.1(2) 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 O1 C4 . 1.223(2) ? O2 C12 . 1.416(2) ? O2 H21 . .87(2) ? N1 C3 . 1.367(2) ? N1 C13 . 1.375(2) ? N1 N2 . 1.386(2) ? N2 C4 . 1.370(2) ? N2 C10 . 1.466(2) ? C1 C13 . 1.367(2) ? C1 C2 . 1.399(3) ? C1 H1 . .93 ? C2 C3 . 1.358(3) ? C2 H2 . .93 ? C3 H3 . .93 ? C4 C14 . 1.469(3) ? C5 C6 . 1.382(3) ? C5 C14 . 1.391(2) ? C5 H5 . .93 ? C6 C7 . 1.380(3) ? C6 H6 . .93 ? C7 C8 . 1.373(3) ? C7 H7 . .93 ? C8 C9 . 1.382(2) ? C8 H8A . .93 ? C9 C14 . 1.387(2) ? C9 C10 . 1.497(2) ? C10 C11 . 1.525(2) ? C10 H10 . .98 ? C11 C12 . 1.519(2) ? C11 H11A . .97 ? C11 H11B . .97 ? C12 C13 . 1.499(2) ? C12 H12 . .98 ? 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 C3 N1 N2 C4 -53.1(2) ? C13 N1 N2 C4 133.2(2) ? C3 N1 N2 C10 153.4(2) ? C13 N1 N2 C10 -20.3(2) yes C13 C1 C2 C3 -0.5(2) ? C1 C2 C3 N1 1.2(2) ? C13 N1 C3 C2 -1.5(2) ? N2 N1 C3 C2 -175.78(15) ? N1 N2 C4 O1 12.7(2) ? C10 N2 C4 O1 166.94(15) ? N1 N2 C4 C14 -168.19(13) ? C10 N2 C4 C14 -14.0(2) ? C14 C5 C6 C7 -0.3(3) ? C5 C6 C7 C8 0.8(3) ? C6 C7 C8 C9 -0.5(3) ? C7 C8 C9 C14 -0.3(2) ? C7 C8 C9 C10 -178.5(2) ? C4 N2 C10 C9 13.9(2) ? N1 N2 C10 C9 170.16(12) ? C4 N2 C10 C11 -107.46(14) yes N1 N2 C10 C11 48.8(2) yes C8 C9 C10 N2 170.3(2) ? C14 C9 C10 N2 -8.1(2) ? C8 C9 C10 C11 -73.8(2) ? C14 C9 C10 C11 107.8(2) ? N2 C10 C11 C12 -61.0(2) yes C9 C10 C11 C12 -172.55(12) yes C10 C11 C12 O2 171.38(12) yes C10 C11 C12 C13 44.4(2) yes C2 C1 C13 N1 -0.4(2) ? C2 C1 C13 C12 172.0(2) ? C3 N1 C13 C1 1.2(2) ? N2 N1 C13 C1 175.73(13) ? C3 N1 C13 C12 -172.37(14) ? N2 N1 C13 C12 2.2(2) ? O2 C12 C13 C1 45.6(2) ? C11 C12 C13 C1 173.3(2) yes O2 C12 C13 N1 -142.92(14) ? C11 C12 C13 N1 -15.2(2) yes C8 C9 C14 C5 0.8(2) ? C10 C9 C14 C5 179.39(14) ? C8 C9 C14 C4 -178.07(14) ? C10 C9 C14 C4 0.5(2) ? C6 C5 C14 C9 -0.5(2) ? C6 C5 C14 C4 178.1(2) ? O1 C4 C14 C9 -173.1(2) ? N2 C4 C14 C9 8.0(2) ? O1 C4 C14 C5 8.2(3) ? N2 C4 C14 C5 -170.8(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 3384645 2 PubChem 15182482