#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202108.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_2202108 loop_ _publ_author_name 'Mizuguchi, Jin' 'Senju, Takatoshi' _publ_section_title ; Reinvestigation of 5,12-dihydro-5,12-dimethylquino[2,3-b]acridine-7,4-dione ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o232 _journal_page_last o233 _journal_paper_doi 10.1107/S1600536803001612 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C22 H16 N2 O2' _chemical_formula_moiety 'C22 H16 N2 O2' _chemical_formula_sum 'C22 H16 N2 O2' _chemical_formula_weight 340.38 _chemical_name_common trans-N,N'-dimethylquinacridone _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' _cell_angle_alpha 90 _cell_angle_beta 98.39(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 4.928(3) _cell_length_b 11.103(3) _cell_length_c 14.462(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 223.2 _cell_measurement_theta_max 14.9 _cell_measurement_theta_min 14.7 _cell_volume 782.8(5) _computing_cell_refinement PROCESS-AUTO _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction ; TEXSAN (Molecular Structure Corporation, 2001) ; _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SIR88 (Burla et al., 1989)' _diffrn_measured_fraction_theta_full 0.9972 _diffrn_measured_fraction_theta_max 0.9972 _diffrn_measurement_device_type 'Rigaku AFC-7R' _diffrn_measurement_method \w-2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.013 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 2107 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_standards_decay_% 1.31 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_correction_T_min 0.947 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_description platelet _exptl_crystal_F_000 356 _exptl_crystal_size_max 1.180 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.070 _refine_diff_density_max 0.21 _refine_diff_density_min -0.17 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.589 _refine_ls_hydrogen_treatment noref _refine_ls_number_parameters 118 _refine_ls_number_reflns 1747 _refine_ls_R_factor_gt 0.0441 _refine_ls_shift/su_max 0.0014 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + {0.05[Max(Fo^2^,0) + 2Fc^2^]/3}^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1263 _reflns_number_gt 1349 _reflns_number_total 1797 _reflns_threshold_expression F^2^>2\s(F^2^) _cod_data_source_file ob6210.cif _cod_data_source_block I _cod_original_cell_volume 782.8(4) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2202108 _cod_database_fobs_code 2202108 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 O1 0.3115(3) 0.73650(10) -0.12444(7) 0.0480(3) Uani d . 1.00 . . O N1 0.4143(2) 0.58724(9) 0.13854(7) 0.0237(2) Uani d . 1.00 . . N C1 0.7310(3) 0.82620(10) 0.01053(10) 0.0338(3) Uani d . 1.00 . . C C2 0.9407(3) 0.86480(10) 0.07730(10) 0.0358(3) Uani d . 1.00 . . C C3 0.9722(3) 0.81100(10) 0.16559(9) 0.0317(3) Uani d . 1.00 . . C C4 0.7988(3) 0.72140(10) 0.18705(8) 0.0273(3) Uani d . 1.00 . . C C5 0.5848(2) 0.67940(10) 0.11876(8) 0.0226(3) Uani d . 1.00 . . C C6 0.5536(2) 0.73320(10) 0.02929(8) 0.0260(3) Uani d . 1.00 . . C C7 0.3424(3) 0.69220(10) -0.04536(9) 0.0296(3) Uani d . 1.00 . . C C8 0.1689(2) 0.59330(10) -0.02056(8) 0.0231(3) Uani d . 1.00 . . C C9 0.2095(2) 0.54360(10) 0.07058(7) 0.0217(3) Uani d . 1.00 . . C C10 0.0369(2) 0.45000(10) 0.08876(8) 0.0241(3) Uani d . 1.00 . . C C11 0.4437(3) 0.53550(10) 0.23233(9) 0.0384(4) Uani d . 1.00 . . C H1 0.7050 0.8634 -0.0492 0.0405 Uiso calc . 1.00 . . H H2 1.0619 0.9267 0.0637 0.0425 Uiso calc . 1.00 . . H H3 1.1173 0.8367 0.2120 0.0377 Uiso calc . 1.00 . . H H4 0.8226 0.6877 0.2480 0.0327 Uiso calc . 1.00 . . H H5 0.0570 0.4141 0.1491 0.0287 Uiso calc . 1.00 . . H H6 0.5907 0.5734 0.2710 0.0458 Uiso calc . 1.00 . . H H7 0.2784 0.5468 0.2578 0.0458 Uiso calc . 1.00 . . H H8 0.4802 0.4514 0.2289 0.0458 Uiso calc . 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 0.0575(7) 0.0550(7) 0.0267(5) -0.0296(6) -0.0096(4) 0.0124(5) N1 0.0256(5) 0.0249(5) 0.0189(4) -0.0038(4) -0.0025(3) -0.0004(4) C1 0.0369(7) 0.0327(7) 0.0303(6) -0.0106(5) -0.0002(5) 0.0024(5) C2 0.0362(7) 0.0331(7) 0.0368(7) -0.0132(5) 0.0006(5) -0.0028(5) C3 0.0291(6) 0.0320(6) 0.0319(6) -0.0067(5) -0.0020(5) -0.0083(5) C4 0.0268(6) 0.0290(6) 0.0245(5) -0.0020(4) -0.0019(4) -0.0054(4) C5 0.0220(5) 0.0218(5) 0.0230(5) -0.0002(4) -0.0003(4) -0.0040(4) C6 0.0270(6) 0.0261(6) 0.0238(5) -0.0046(5) 0.0000(4) -0.0011(4) C7 0.0318(6) 0.0324(6) 0.0233(5) -0.0088(5) -0.0008(5) 0.0019(5) C8 0.0238(5) 0.0243(5) 0.0204(5) -0.0027(4) 0.0008(4) -0.0015(4) C9 0.0220(5) 0.0222(5) 0.0197(5) -0.0001(4) -0.0012(4) -0.0030(4) C10 0.0255(5) 0.0260(6) 0.0197(5) -0.0023(4) -0.0008(4) -0.0003(4) C11 0.0460(8) 0.0417(8) 0.0231(6) -0.0140(6) -0.0092(5) 0.0060(5) 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 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 N1 C9 . . 120.89(10) no C5 N1 C11 . . 120.21(10) no C9 N1 C11 . . 118.90(10) no C2 C1 C6 . . 121.20(10) no C2 C1 H1 . . 119.4 no C6 C1 H1 . . 119.4 no C1 C2 C3 . . 118.70(10) no C1 C2 H2 . . 120.8 no C3 C2 H2 . . 120.6 no C2 C3 C4 . . 121.70(10) no C2 C3 H3 . . 119.2 no C4 C3 H3 . . 119.1 no C3 C4 C5 . . 120.30(10) no C3 C4 H4 . . 119.8 no C5 C4 H4 . . 119.8 no N1 C5 C4 . . 120.90(10) no N1 C5 C6 . . 120.98(10) no C4 C5 C6 . . 118.10(10) no C1 C6 C5 . . 120.00(10) no C1 C6 C7 . . 118.90(10) no C5 C6 C7 . . 121.10(10) no O1 C7 C6 . . 122.70(10) no O1 C7 C8 . . 121.80(10) no C6 C7 C8 . . 115.50(10) no C7 C8 C9 . . 120.70(10) no C7 C8 C10 . 3_565 118.30(10) no C9 C8 C10 . 3_565 120.90(10) no N1 C9 C8 . . 120.80(10) no N1 C9 C10 . . 121.90(10) no C8 C9 C10 . . 117.40(10) no C8 C10 C9 3_565 . 121.70(10) no C8 C10 H5 3_565 . 118.2 no C9 C10 H5 . . 120.1 no N1 C11 H6 . . 109.7 no N1 C11 H7 . . 109.5 no N1 C11 H8 . . 109.3 no H6 C11 H7 . . 109.7 no H6 C11 H8 . . 109.4 no H7 C11 H8 . . 109.2 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C7 . . 1.234(2) yes N1 C5 . . 1.380(2) yes N1 C9 . . 1.3890(10) yes N1 C11 . . 1.461(2) yes C1 C2 . . 1.376(2) yes C1 C6 . . 1.405(2) yes C1 H1 . . 0.950 no C2 C3 . . 1.398(2) yes C2 H2 . . 0.949 no C3 C4 . . 1.376(2) yes C3 H3 . . 0.950 no C4 C5 . . 1.414(2) yes C4 H4 . . 0.949 no C5 C6 . . 1.413(2) yes C6 C7 . . 1.459(2) yes C7 C8 . . 1.468(2) yes C8 C9 . . 1.416(2) yes C8 C10 . 3_565 1.393(2) yes C9 C10 . . 1.392(2) yes C10 H5 . . 0.951 no C11 H6 . . 0.947 no C11 H7 . . 0.950 no C11 H8 . . 0.953 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 O1 C3 3.288(2) 4_464 O1 C11 3.394(2) 4_564 O1 C4 3.468(2) 4_464 N1 C3 3.364(2) 1_455 N1 C8 3.489(2) 3_665 N1 C4 3.540(2) 1_455 N1 C10 3.592(2) 1_655 C1 C8 3.439(2) 1_655 C1 C7 3.557(2) 1_655 C2 C7 3.430(2) 1_655 C2 C6 3.515(2) 1_655 C2 C8 3.581(2) 1_655 C3 C5 3.507(2) 1_655 C3 C9 3.541(2) 1_655 C4 C9 3.439(2) 1_655 C5 C10 3.453(2) 1_655 C5 C9 3.587(2) 1_655 C6 C10 3.482(2) 3_665 C6 C8 3.572(2) 1_655 C7 C9 3.478(2) 3_665 C7 C10 3.578(2) 3_665 C8 C9 3.586(2) 3_665 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 2844779