#------------------------------------------------------------------------------ #$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/02/2200230.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_2200230 loop_ _publ_author_name 'Kubo, Kanji' 'Tsujimoto, Teppei' 'Kato, Nobuo' 'Mori, Akira' _publ_section_title ; 2,3-Cyclohexanopyrrolo[2,3-b]tropone ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o370 _journal_page_last o371 _journal_paper_doi 10.1107/S1600536801005001 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C13 H13 N O' _chemical_formula_moiety 'C13 H13 N O' _chemical_formula_sum 'C13 H13 N O' _chemical_formula_weight 199.24 _chemical_name_systematic ; ? ; _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 113.590(18) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.778(2) _cell_length_b 15.3778(19) _cell_length_c 8.442(2) _cell_measurement_reflns_used 16 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 18.2 _cell_measurement_theta_min 8.9 _cell_volume 1044.3(4) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_molecular_graphics 'Xtal_GX (Hall & du Boulay, 1995)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full .000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .7107 _diffrn_reflns_av_R_equivalents .059 _diffrn_reflns_av_sigmaI/netI .181 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 2677 _diffrn_reflns_theta_full 28.0 _diffrn_reflns_theta_max 27.96 _diffrn_reflns_theta_min 2.63 _diffrn_standards_decay_% .6 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .080 _exptl_absorpt_correction_T_max .999 _exptl_absorpt_correction_T_min .962 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 424 _exptl_crystal_size_max .23 _exptl_crystal_size_mid .13 _exptl_crystal_size_min .13 _refine_diff_density_max .20 _refine_diff_density_min -.24 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .939 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 140 _refine_ls_number_reflns 2519 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .939 _refine_ls_R_factor_all .257 _refine_ls_R_factor_gt .062 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0777P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .194 _reflns_number_gt 828 _reflns_number_total 2519 _reflns_threshold_expression I>2\s(I) _cod_data_source_file tk6011.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/a' _cod_database_code 2200230 _cod_database_fobs_code 2200230 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 N1 .8866(3) .47307(18) .6722(3) .0523(7) Uani d . 1 . . N O1 .8557(3) .58737(16) .4107(3) .0838(9) Uani d . 1 . . O C1 .7595(4) .5952(2) .4868(4) .0588(9) Uani d . 1 . . C C2 .7684(4) .5361(2) .6203(4) .0500(8) Uani d . 1 . . C C3 .6758(4) .5282(2) .7237(4) .0516(8) Uani d . 1 . . C C4 .5378(4) .5784(3) .7150(5) .0655(10) Uani d . 1 . . C H4 .4864 .5609 .7870 .079 Uiso calc R 1 . . H C5 .4711(4) .6489(3) .6148(5) .0689(10) Uani d . 1 . . C H5 .3799 .6741 .6268 .083 Uiso calc R 1 . . H C6 .5230(4) .6883(2) .4956(4) .0676(10) Uani d . 1 . . C H6 .4651 .7386 .4453 .081 Uiso calc R 1 . . H C7 .6434(4) .6659(2) .4407(4) .0653(10) Uani d . 1 . . C H7 .6521 .7032 .3580 .078 Uiso calc R 1 . . H C8 .8752(4) .4257(2) .8049(4) .0520(8) Uani d . 1 . . C C9 .7453(4) .4580(2) .8372(4) .0553(9) Uani d . 1 . . C C10 .6976(5) .4197(3) .9737(4) .0717(10) Uani d . 1 . . C H10A .5885 .3933 .9194 .086 Uiso calc R 1 . . H H10B .6907 .4657 1.0491 .086 Uiso calc R 1 . . H C11 .8205(6) .3520(3) 1.0807(5) .0959(14) Uani d . 1 . . C H11A .9062 .3812 1.1773 .115 Uiso calc R 1 . . H H11B .7631 .3126 1.1280 .115 Uiso calc R 1 . . H C12 .9011(6) .3004(3) .9919(5) .1015(15) Uani d . 1 . . C H12A .8185 .2625 .9101 .122 Uiso calc R 1 . . H H12B .9839 .2637 1.0763 .122 Uiso calc R 1 . . H C13 .9855(4) .3520(2) .8948(4) .0621(9) Uani d . 1 . . C H13A 1.0921 .3738 .9753 .075 Uiso calc R 1 . . H H13B 1.0042 .3149 .8114 .075 Uiso calc R 1 . . H H1 .963(4) .458(2) .629(4) .080(11) Uiso d . 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 N1 .0469(16) .0591(17) .0578(17) -.0025(15) .0282(14) -.0001(15) O1 .0821(18) .0977(19) .102(2) .0229(15) .0681(17) .0341(16) C1 .050(2) .066(2) .066(2) -.0004(19) .0287(18) .0047(19) C2 .0423(17) .0536(19) .056(2) -.0035(18) .0217(15) -.0046(17) C3 .0502(18) .060(2) .052(2) -.0061(18) .0279(16) -.0071(18) C4 .059(2) .083(3) .066(2) -.002(2) .0376(19) -.010(2) C5 .064(2) .083(3) .068(2) .009(2) .035(2) -.006(2) C6 .054(2) .074(2) .070(2) .0123(19) .020(2) .003(2) C7 .059(2) .067(2) .072(2) .006(2) .028(2) .015(2) C8 .054(2) .055(2) .0496(19) -.0090(17) .0241(16) -.0038(17) C9 .057(2) .066(2) .053(2) -.0098(19) .0322(17) -.0071(18) C10 .078(3) .087(3) .062(2) -.005(2) .040(2) .001(2) C11 .114(3) .103(3) .087(3) .000(3) .057(3) .021(3) C12 .133(4) .095(3) .099(3) .021(3) .069(3) .032(3) C13 .056(2) .063(2) .064(2) -.0055(19) .0216(18) -.0009(19) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 C2 N1 C8 110.2(3) C2 N1 H1 130(2) C8 N1 H1 120(2) O1 C1 C2 120.5(3) O1 C1 C7 119.1(3) C2 C1 C7 120.4(3) N1 C2 C3 107.0(3) N1 C2 C1 120.2(3) C3 C2 C1 132.8(3) C9 C3 C4 125.6(3) C9 C3 C2 106.6(3) C4 C3 C2 127.7(3) C5 C4 C3 128.1(3) C5 C4 H4 116.0 C3 C4 H4 116.0 C4 C5 C6 127.7(3) C4 C5 H5 116.2 C6 C5 H5 116.2 C7 C6 C5 131.2(3) C7 C6 H6 114.4 C5 C6 H6 114.4 C6 C7 C1 131.8(3) C6 C7 H7 114.1 C1 C7 H7 114.1 C9 C8 N1 108.0(3) C9 C8 C13 126.9(3) N1 C8 C13 125.1(3) C8 C9 C3 108.1(3) C8 C9 C10 121.6(3) C3 C9 C10 130.3(3) C9 C10 C11 112.3(3) C9 C10 H10A 109.2 C11 C10 H10A 109.2 C9 C10 H10B 109.2 C11 C10 H10B 109.2 H10A C10 H10B 107.9 C12 C11 C10 116.5(3) C12 C11 H11A 108.2 C10 C11 H11A 108.2 C12 C11 H11B 108.2 C10 C11 H11B 108.2 H11A C11 H11B 107.3 C11 C12 C13 115.7(3) C11 C12 H12A 108.4 C13 C12 H12A 108.4 C11 C12 H12B 108.4 C13 C12 H12B 108.4 H12A C12 H12B 107.4 C8 C13 C12 108.2(3) C8 C13 H13A 110.1 C12 C13 H13A 110.1 C8 C13 H13B 110.1 C12 C13 H13B 110.1 H13A C13 H13B 108.4 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 N1 C2 . 1.358(4) no N1 C8 . 1.374(4) no N1 H1 . .91(3) no O1 C1 . 1.254(4) no C1 C2 . 1.426(4) no C1 C7 . 1.432(4) no C2 C3 . 1.416(4) no C3 C4 . 1.414(4) no C3 C9 . 1.410(4) no C4 C5 . 1.356(5) no C4 H4 . .9300 ? C5 C6 . 1.398(4) no C5 H5 . .9300 ? C6 C7 . 1.358(4) no C6 H6 . .9300 ? C7 H7 . .9300 ? C8 C9 . 1.367(4) no C8 C13 . 1.487(4) ? C9 C10 . 1.495(4) ? C10 C11 . 1.511(5) ? C10 H10A . .9700 ? C10 H10B . .9700 ? C11 C12 . 1.455(5) ? C11 H11A . .9700 ? C11 H11B . .9700 ? C12 C13 . 1.528(5) ? C12 H12A . .9700 ? C12 H12B . .9700 ? C13 H13A . .9700 ? C13 H13B . .9700 ? 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 N1 H1 O1 3_766 .91(3) 1.89(4) 2.781(4) 166.53 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 C8 N1 C2 C3 -.6(3) C8 N1 C2 C1 178.2(3) O1 C1 C2 N1 3.1(5) C7 C1 C2 N1 -175.2(3) O1 C1 C2 C3 -178.5(3) C7 C1 C2 C3 3.2(6) N1 C2 C3 C9 .0(3) C1 C2 C3 C9 -178.6(3) N1 C2 C3 C4 -178.7(3) C1 C2 C3 C4 2.8(6) C9 C3 C4 C5 176.5(3) C2 C3 C4 C5 -5.1(6) C3 C4 C5 C6 .3(6) C4 C5 C6 C7 4.1(7) C5 C6 C7 C1 -.9(6) O1 C1 C7 C6 177.4(4) C2 C1 C7 C6 -4.2(6) C2 N1 C8 C9 1.0(3) C2 N1 C8 C13 -179.4(3) N1 C8 C9 C3 -1.0(3) C13 C8 C9 C3 179.5(3) N1 C8 C9 C10 179.1(3) C13 C8 C9 C10 -.4(5) C4 C3 C9 C8 179.3(3) C2 C3 C9 C8 .6(3) C4 C3 C9 C10 -.8(6) C2 C3 C9 C10 -179.5(3) C8 C9 C10 C11 7.3(5) C3 C9 C10 C11 -172.6(3) C9 C10 C11 C12 -33.0(5) C10 C11 C12 C13 52.8(5) C9 C8 C13 C12 16.7(5) N1 C8 C13 C12 -162.8(3) C11 C12 C13 C8 -41.6(5)