#------------------------------------------------------------------------------ #$Date: 2016-02-19 15:29:56 +0100 (Fri, 19 Feb 2016) $ #$Revision: 176759 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/88/2008897.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_2008897 loop_ _publ_author_name 'R. Sankaranarayanan' 'S. Shanmuga Sundara Raj' 'D. Velmurugan' 'Hoong-Kun Fun' _publ_section_title ; 1,2,3,4,5,6,7,8-Octahydro-3,3,6,6-tetramethylacridine-1,8-dione ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1513 _journal_page_last 1514 _journal_paper_doi 10.1107/S0108270199006149 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C17 H21 N O2' _chemical_formula_weight 271.35 _chemical_name_systematic ; 1,2,3,4,5,6,7,8-Octahydro-3,3,6,6-tetramethylacridine-1,8-dione ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.9887(2) _cell_length_b 10.7123(2) _cell_length_c 20.4198(4) _cell_measurement_reflns_used 39 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.51 _cell_measurement_theta_min 5.38 _cell_volume 1528.73(6) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction XSCANS _computing_molecular_graphics 'ZORTEP (Zsolnai, 1997)' _computing_publication_material 'SHELXL97 and PARST (Nardelli, 1983b, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997b)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Siemens P4' _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 0.71073 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.038 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 9982 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.76 _diffrn_standards_decay_% <3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 584 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.29 _refine_diff_density_max 0.14 _refine_diff_density_min -0.17 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2024 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.094 _refine_ls_R_factor_all 0.078 _refine_ls_R_factor_gt 0.051 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0394P)^2^+0.3749P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.118 _reflns_number_gt 1501 _reflns_number_total 2024 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1186.cif _cod_data_source_block anishyd4 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0394P)^2^+0.3749P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0394P)^2^+0.3749P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2008897 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' '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 C1 0.5753(4) 0.8577(3) 0.20063(12) 0.0437(7) Uani d . 1 . . C H1A 0.4406 0.8360 0.2009 0.052 Uiso calc R 1 . . H H1B 0.5870 0.9405 0.1818 0.052 Uiso calc R 1 . . H C2 0.6480(4) 0.8615(2) 0.27183(13) 0.0399(6) Uani d . 1 . . C C3 0.8671(4) 0.8744(3) 0.27058(15) 0.0465(7) Uani d . 1 . . C H3A 0.9005 0.9542 0.2513 0.056 Uiso calc R 1 . . H H3B 0.9147 0.8739 0.3152 0.056 Uiso calc R 1 . . H O4 1.1163(3) 0.7279(3) 0.24960(12) 0.0821(8) Uani d . 1 . . O C4 0.9637(4) 0.7725(3) 0.23286(15) 0.0480(7) Uani d . 1 . . C C4A 0.8657(4) 0.7269(2) 0.17278(12) 0.0393(6) Uani d . 1 . . C C5 0.9557(4) 0.6436(3) 0.13016(14) 0.0437(7) Uani d . 1 . . C H5 1.0788 0.6154 0.1390 0.052 Uiso calc R 1 . . H O6 1.1066(4) 0.4678(3) 0.04059(14) 0.0871(9) Uani d . 1 . . O C6 0.9527(4) 0.5164(3) 0.02730(16) 0.0506(8) Uani d . 1 . . C C6A 0.8605(4) 0.6035(2) 0.07464(13) 0.0389(6) Uani d . 1 . . C C7 0.8499(5) 0.4932(3) -0.03550(14) 0.0536(8) Uani d . 1 . . C H7A 0.8966 0.4161 -0.0546 0.064 Uiso calc R 1 . . H H7B 0.8787 0.5603 -0.0658 0.064 Uiso calc R 1 . . H C8 0.6317(5) 0.4841(3) -0.02685(14) 0.0473(7) Uani d . 1 . . C C9 0.5617(5) 0.6065(3) 0.00444(14) 0.0521(8) Uani d . 1 . . C H9A 0.5676 0.6722 -0.0282 0.063 Uiso calc R 1 . . H H9B 0.4288 0.5964 0.0170 0.063 Uiso calc R 1 . . H C9A 0.6742(4) 0.6467(2) 0.06353(12) 0.0386(6) Uani d . 1 . . C N10 0.5851(3) 0.7275(2) 0.10389(10) 0.0395(5) Uani d . 1 . . N C10 0.6801(4) 0.7667(2) 0.15764(12) 0.0379(6) Uani d . 1 . . C C11 0.5620(5) 0.9751(3) 0.30690(14) 0.0524(8) Uani d . 1 . . C H11A 0.5966 1.0498 0.2838 0.079 Uiso calc R 1 . . H H11B 0.6104 0.9790 0.3509 0.079 Uiso calc R 1 . . H H11C 0.4252 0.9674 0.3080 0.079 Uiso calc R 1 . . H C12 0.5923(5) 0.7429(3) 0.30882(14) 0.0518(8) Uani d . 1 . . C H12A 0.4554 0.7351 0.3095 0.078 Uiso calc R 1 . . H H12B 0.6395 0.7475 0.3529 0.078 Uiso calc R 1 . . H H12C 0.6468 0.6717 0.2873 0.078 Uiso calc R 1 . . H C13 0.5328(6) 0.4679(4) -0.09382(17) 0.0844(13) Uani d . 1 . . C H13A 0.5628 0.5379 -0.1213 0.127 Uiso calc R 1 . . H H13B 0.3968 0.4633 -0.0876 0.127 Uiso calc R 1 . . H H13C 0.5772 0.3925 -0.1141 0.127 Uiso calc R 1 . . H C14 0.5827(5) 0.3717(3) 0.01606(16) 0.0586(8) Uani d . 1 . . C H14A 0.4465 0.3664 0.0214 0.088 Uiso calc R 1 . . H H14B 0.6422 0.3811 0.0582 0.088 Uiso calc R 1 . . H H14C 0.6288 0.2968 -0.0044 0.088 Uiso calc R 1 . . 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 C1 0.0467(16) 0.0466(15) 0.0378(14) 0.0142(15) -0.0007(13) -0.0015(12) C2 0.0433(15) 0.0407(14) 0.0357(13) 0.0045(14) -0.0009(12) 0.0007(11) C3 0.0474(16) 0.0447(16) 0.0475(16) -0.0040(14) -0.0026(14) -0.0082(13) O4 0.0484(13) 0.113(2) 0.0856(18) 0.0251(15) -0.0237(14) -0.0358(16) C4 0.0370(15) 0.0542(18) 0.0528(17) -0.0001(15) -0.0022(14) -0.0041(15) C4A 0.0404(15) 0.0357(13) 0.0416(14) 0.0022(13) 0.0026(12) 0.0011(11) C5 0.0358(14) 0.0408(15) 0.0546(17) 0.0016(13) 0.0033(13) -0.0020(13) O6 0.0489(13) 0.105(2) 0.108(2) 0.0233(15) -0.0021(15) -0.0504(17) C6 0.0404(16) 0.0503(17) 0.0610(19) -0.0034(15) 0.0147(15) -0.0120(15) C6A 0.0419(16) 0.0323(13) 0.0425(14) 0.0008(13) 0.0063(13) 0.0008(11) C7 0.064(2) 0.0510(17) 0.0462(17) 0.0019(17) 0.0152(16) -0.0061(14) C8 0.0509(17) 0.0489(16) 0.0421(15) 0.0084(15) -0.0005(14) -0.0060(13) C9 0.063(2) 0.0499(17) 0.0439(16) 0.0180(16) -0.0116(15) -0.0052(13) C9A 0.0475(16) 0.0312(13) 0.0372(14) 0.0052(13) 0.0012(12) 0.0059(11) N10 0.0462(13) 0.0376(11) 0.0345(11) 0.0112(11) -0.0037(10) -0.0003(10) C10 0.0426(15) 0.0344(13) 0.0366(14) 0.0055(13) 0.0035(12) 0.0055(11) C11 0.0603(19) 0.0536(17) 0.0432(16) 0.0124(16) 0.0021(15) -0.0078(13) C12 0.0562(19) 0.0528(17) 0.0463(16) 0.0016(16) 0.0017(15) 0.0048(13) C13 0.100(3) 0.096(3) 0.057(2) 0.033(3) -0.027(2) -0.033(2) C14 0.0504(19) 0.0515(18) 0.074(2) -0.0037(16) 0.0059(17) -0.0107(16) 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' 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 C10 C1 C2 114.1(2) ? C10 C1 H1A 108.7 ? C2 C1 H1A 108.7 ? C10 C1 H1B 108.7 ? C2 C1 H1B 108.7 ? H1A C1 H1B 107.6 ? C12 C2 C11 109.2(2) ? C12 C2 C3 109.7(2) ? C11 C2 C3 109.1(2) ? C12 C2 C1 111.1(2) ? C11 C2 C1 109.4(2) ? C3 C2 C1 108.4(2) ? C4 C3 C2 113.1(2) ? C4 C3 H3A 109.0 ? C2 C3 H3A 109.0 ? C4 C3 H3B 109.0 ? C2 C3 H3B 109.0 ? H3A C3 H3B 107.8 ? O4 C4 C4A 120.4(3) ? O4 C4 C3 122.5(3) ? C4A C4 C3 117.1(3) ? C5 C4A C10 118.3(3) ? C5 C4A C4 121.1(3) ? C10 C4A C4 120.6(2) ? C6A C5 C4A 119.5(3) yes C6A C5 H5 120.2 ? C4A C5 H5 120.2 ? O6 C6 C6A 120.1(3) ? O6 C6 C7 122.9(3) ? C6A C6 C7 117.0(3) ? C5 C6A C9A 118.5(2) ? C5 C6A C6 121.2(3) ? C9A C6A C6 120.3(3) ? C6 C7 C8 112.9(2) ? C6 C7 H7A 109.0 ? C8 C7 H7A 109.0 ? C6 C7 H7B 109.0 ? C8 C7 H7B 109.0 ? H7A C7 H7B 107.8 ? C14 C8 C9 111.2(2) ? C14 C8 C7 109.7(3) ? C9 C8 C7 108.0(3) ? C14 C8 C13 108.6(3) ? C9 C8 C13 108.8(3) ? C7 C8 C13 110.5(3) ? C9A C9 C8 114.3(2) ? C9A C9 H9A 108.7 ? C8 C9 H9A 108.7 ? C9A C9 H9B 108.7 ? C8 C9 H9B 108.7 ? H9A C9 H9B 107.6 ? N10 C9A C6A 122.9(3) ? N10 C9A C9 115.7(2) ? C6A C9A C9 121.4(3) ? C9A N10 C10 118.1(2) yes N10 C10 C4A 122.7(2) ? N10 C10 C1 116.0(2) ? C4A C10 C1 121.3(2) ? C2 C11 H11A 109.5 ? C2 C11 H11B 109.5 ? H11A C11 H11B 109.5 ? C2 C11 H11C 109.5 ? H11A C11 H11C 109.5 ? H11B C11 H11C 109.5 ? C2 C12 H12A 109.5 ? C2 C12 H12B 109.5 ? H12A C12 H12B 109.5 ? C2 C12 H12C 109.5 ? H12A C12 H12C 109.5 ? H12B C12 H12C 109.5 ? C8 C13 H13A 109.5 ? C8 C13 H13B 109.5 ? H13A C13 H13B 109.5 ? C8 C13 H13C 109.5 ? H13A C13 H13C 109.5 ? H13B C13 H13C 109.5 ? C8 C14 H14A 109.5 ? C8 C14 H14B 109.5 ? H14A C14 H14B 109.5 ? C8 C14 H14C 109.5 ? H14A C14 H14C 109.5 ? H14B C14 H14C 109.5 ? 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 C1 C10 . 1.502(4) yes C1 C2 . 1.541(3) ? C1 H1A . 0.9700 ? C1 H1B . 0.9700 ? C2 C12 . 1.529(4) ? C2 C11 . 1.534(4) ? C2 C3 . 1.538(4) ? C3 C4 . 1.497(4) ? C3 H3A . 0.9700 ? C3 H3B . 0.9700 ? O4 C4 . 1.218(3) ? C4 C4A . 1.488(4) yes C4A C5 . 1.396(4) yes C4A C10 . 1.400(4) ? C5 C6A . 1.383(4) yes C5 H5 . 0.9300 ? O6 C6 . 1.225(4) ? C6 C6A . 1.490(4) yes C6 C7 . 1.491(4) ? C6A C9A . 1.400(4) yes C7 C8 . 1.538(4) ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C8 C14 . 1.529(4) ? C8 C9 . 1.538(4) ? C8 C13 . 1.542(4) ? C9 C9A . 1.503(4) yes C9 H9A . 0.9700 ? C9 H9B . 0.9700 ? C9A N10 . 1.347(3) yes N10 C10 . 1.350(3) ? C11 H11A . 0.9600 ? C11 H11B . 0.9600 ? C11 H11C . 0.9600 ? C12 H12A . 0.9600 ? C12 H12B . 0.9600 ? C12 H12C . 0.9600 ? C13 H13A . 0.9600 ? C13 H13B . 0.9600 ? C13 H13C . 0.9600 ? C14 H14A . 0.9600 ? C14 H14B . 0.9600 ? C14 H14C . 0.9600 ? 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 C10 C1 C2 C12 -71.3(3) ? C10 C1 C2 C11 168.1(2) ? C10 C1 C2 C3 49.2(3) ? C12 C2 C3 C4 64.8(3) yes C11 C2 C3 C4 -175.7(2) yes C1 C2 C3 C4 -56.6(3) ? C2 C3 C4 O4 -143.3(3) ? C2 C3 C4 C4A 37.0(4) ? O4 C4 C4A C5 -7.8(5) ? C3 C4 C4A C5 171.9(3) ? O4 C4 C4A C10 172.2(3) ? C3 C4 C4A C10 -8.1(4) ? C10 C4A C5 C6A 0.2(4) ? C4 C4A C5 C6A -179.8(3) ? C4A C5 C6A C9A -0.9(4) ? C4A C5 C6A C6 178.9(3) ? O6 C6 C6A C5 8.3(4) ? C7 C6 C6A C5 -171.4(3) ? O6 C6 C6A C9A -171.9(3) ? C7 C6 C6A C9A 8.4(4) ? O6 C6 C7 C8 141.7(3) ? C6A C6 C7 C8 -38.7(4) ? C6 C7 C8 C14 -63.6(3) yes C6 C7 C8 C9 57.8(3) ? C6 C7 C8 C13 176.7(3) yes C14 C8 C9 C9A 71.7(3) ? C7 C8 C9 C9A -48.7(3) ? C13 C8 C9 C9A -168.7(3) ? C5 C6A C9A N10 1.3(4) ? C6 C6A C9A N10 -178.6(2) ? C5 C6A C9A C9 -179.7(3) ? C6 C6A C9A C9 0.5(4) ? C8 C9 C9A N10 -159.6(2) ? C8 C9 C9A C6A 21.2(4) ? C6A C9A N10 C10 -0.8(4) ? C9 C9A N10 C10 -179.9(2) ? C9A N10 C10 C4A 0.0(4) ? C9A N10 C10 C1 179.4(2) ? C5 C4A C10 N10 0.3(4) ? C4 C4A C10 N10 -179.7(2) ? C5 C4A C10 C1 -179.1(2) ? C4 C4A C10 C1 0.9(4) ? C2 C1 C10 N10 157.7(2) ? C2 C1 C10 C4A -22.9(4) ?