#------------------------------------------------------------------------------ #$Date: 2017-10-13 07:09:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201973 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/02/2200248.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_2200248 loop_ _publ_author_name 'Kubo, Kanji ' ' Tsujimoto, Teppei ' 'Mori, Akira' _publ_section_title ; 3-Phenylpyrrolo[2,3-b]tropone ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o225 _journal_page_last o227 _journal_paper_doi 10.1107/S1600536801002021 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C15 H11 N O' _chemical_formula_moiety 'C15 H11 N O' _chemical_formula_sum 'C15 H11 N O' _chemical_formula_weight 221.25 _chemical_name_systematic ; 3-Phenylpyrrolo[2,3-b]tropone ; _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 90.00 _cell_angle_beta 101.980(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.2145(10) _cell_length_b 7.7681(5) _cell_length_c 10.3928(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 18.2 _cell_measurement_theta_min 11.0 _cell_volume 1122.58(13) _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 .71073 _diffrn_reflns_av_R_equivalents .022 _diffrn_reflns_av_sigmaI/netI .030 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 2851 _diffrn_reflns_theta_full 28.0 _diffrn_reflns_theta_max 28.0 _diffrn_reflns_theta_min 2.9 _diffrn_standards_decay_% 3.9 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .082 _exptl_absorpt_correction_T_max .999 _exptl_absorpt_correction_T_min .978 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ' (North et al., 1968)' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 464 _exptl_crystal_size_max .47 _exptl_crystal_size_mid .47 _exptl_crystal_size_min .43 _refine_diff_density_max .18 _refine_diff_density_min -.22 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 158 _refine_ls_number_reflns 2700 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.03 _refine_ls_R_factor_all .074 _refine_ls_R_factor_gt .042 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.2047P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .116 _reflns_number_gt 1921 _reflns_number_total 2700 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ya6009.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value ' psi-scan' changed to 'psi-scan' 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 ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2200248 _cod_database_fobs_code 2200248 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 .11507(8) .24901(15) -.12642(11) .0408(3) Uani d . 1 . . N H1 .0638(12) .229(2) -.2009(17) .059(5) Uiso d . 1 . . H O1 .01425(8) .53883(15) -.20816(11) .0581(3) Uani d . 1 . . O C1 .07444(10) .54791(19) -.10252(15) .0429(3) Uani d . 1 . . C C2 .13198(9) .39801(17) -.05691(13) .0367(3) Uani d . 1 . . C C3 .20964(9) .36788(16) .05017(13) .0345(3) Uani d . 1 . . C C4 .25393(10) .48854(18) .14654(14) .0423(3) Uani d . 1 . . C H4 .3087 .4508 .2051 .051 Uiso calc R 1 . . H C5 .22584(12) .6521(2) .16325(15) .0489(4) Uani d . 1 . . C H5 .2629 .7120 .2333 .059 Uiso calc R 1 . . H C6 .14712(12) .74387(19) .08764(16) .0512(4) Uani d . 1 . . C H6 .1370 .8516 .1213 .061 Uiso calc R 1 . . H C7 .08409(11) .70298(19) -.02457(16) .0502(4) Uani d . 1 . . C H7 .0398 .7888 -.0567 .060 Uiso calc R 1 . . H C8 .17702(10) .12603(18) -.06909(14) .0398(3) Uani d . 1 . . C H8 .1783 .0133 -.0988 .048 Uiso calc R 1 . . H C9 .23780(9) .19225(17) .03951(13) .0361(3) Uani d . 1 . . C C10 .31509(9) .09397(17) .12569(13) .0375(3) Uani d . 1 . . C C11 .32669(10) .09459(19) .26228(14) .0431(3) Uani d . 1 . . C H11 .2870 .1634 .3015 .052 Uiso calc R 1 . . H C12 .39655(11) -.0060(2) .34035(17) .0539(4) Uani d . 1 . . C H12 .4032 -.0047 .4313 .065 Uiso calc R 1 . . H C13 .45612(11) -.1079(2) .28404(19) .0608(5) Uani d . 1 . . C H13 .5032 -.1748 .3366 .073 Uiso calc R 1 . . H C14 .44574(12) -.1101(2) .1495(2) .0619(5) Uani d . 1 . . C H14 .4858 -.1791 .1112 .074 Uiso calc R 1 . . H C15 .37617(11) -.0105(2) .07085(17) .0503(4) Uani d . 1 . . C H15 .3700 -.0132 -.0200 .060 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 N1 .0399(6) .0405(6) .0377(6) -.0053(5) -.0020(5) .0007(5) O1 .0530(6) .0540(7) .0580(7) .0037(5) -.0102(5) .0132(5) C1 .0378(7) .0419(8) .0474(8) -.0013(6) .0053(6) .0121(6) C2 .0349(6) .0367(7) .0369(7) -.0044(5) .0041(5) .0034(5) C3 .0344(6) .0338(6) .0348(7) -.0025(5) .0058(5) .0031(5) C4 .0433(7) .0391(7) .0404(7) -.0053(6) -.0009(6) .0015(6) C5 .0606(9) .0383(7) .0452(8) -.0101(7) .0048(7) -.0041(6) C6 .0646(10) .0333(7) .0581(9) -.0009(7) .0182(8) .0014(6) C7 .0506(8) .0363(7) .0629(10) .0047(6) .0102(7) .0106(7) C8 .0436(7) .0341(7) .0407(7) -.0027(6) .0063(6) -.0003(6) C9 .0369(6) .0348(6) .0356(7) -.0019(5) .0056(5) .0013(5) C10 .0350(6) .0341(6) .0415(7) -.0014(5) .0040(5) .0007(6) C11 .0430(7) .0419(7) .0422(7) .0037(6) .0038(6) -.0006(6) C12 .0509(9) .0536(9) .0494(9) .0022(7) -.0075(7) .0055(7) C13 .0440(8) .0537(10) .0767(12) .0105(7) -.0056(8) .0123(9) C14 .0486(9) .0572(10) .0811(13) .0166(8) .0161(9) .0008(9) C15 .0499(8) .0506(9) .0514(9) .0066(7) .0129(7) -.0004(7) 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 C8 N1 C2 109.92(11) C8 N1 H1 123.7(10) C2 N1 H1 126.2(10) O1 C1 C7 120.67(13) O1 C1 C2 118.80(14) C7 C1 C2 120.49(13) N1 C2 C3 107.47(11) N1 C2 C1 119.09(12) C3 C2 C1 133.42(12) C2 C3 C4 127.22(12) C2 C3 C9 106.36(11) C4 C3 C9 126.38(12) C5 C4 C3 127.63(14) C5 C4 H4 116.2 C3 C4 H4 116.2 C4 C5 C6 128.33(14) C4 C5 H5 115.8 C6 C5 H5 115.8 C7 C6 C5 131.65(15) C7 C6 H6 114.2 C5 C6 H6 114.2 C6 C7 C1 130.47(14) C6 C7 H7 114.8 C1 C7 H7 114.8 N1 C8 C9 109.84(12) N1 C8 H8 125.1 C9 C8 H8 125.1 C8 C9 C3 106.41(11) C8 C9 C10 124.56(12) C3 C9 C10 129.03(12) C15 C10 C11 117.78(13) C15 C10 C9 120.06(13) C11 C10 C9 122.08(12) C12 C11 C10 120.86(14) C12 C11 H11 119.6 C10 C11 H11 119.6 C13 C12 C11 120.33(16) C13 C12 H12 119.8 C11 C12 H12 119.8 C12 C13 C14 119.62(15) C12 C13 H13 120.2 C14 C13 H13 120.2 C13 C14 C15 120.47(16) C13 C14 H14 119.8 C15 C14 H14 119.8 C14 C15 C10 120.94(15) C14 C15 H15 119.5 C10 C15 H15 119.5 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 N1 C2 . 1.3591(17) yes N1 C8 . 1.3510(18) yes N1 H1 . .959(17) yes O1 C1 . 1.2460(17) yes C1 C2 . 1.4452(19) yes C1 C7 . 1.442(2) yes C2 C3 . 1.4149(18) yes C3 C4 . 1.4199(19) yes C3 C9 . 1.4326(19) yes C4 C5 . 1.354(2) yes C4 H4 . .9300 ? C5 C6 . 1.419(2) yes C5 H5 . .9300 ? C6 C7 . 1.353(2) yes C6 H6 . .9300 ? C7 H7 . .9300 ? C8 C9 . 1.3712(18) yes C8 H8 . .9300 ? C9 C10 . 1.4777(18) yes C10 C11 . 1.3948(19) yes C10 C15 . 1.394(2) yes C11 C12 . 1.386(2) yes C11 H11 . .9300 ? C12 C13 . 1.375(3) yes C12 H12 . .9300 ? C13 C14 . 1.375(3) yes C13 H13 . .9300 ? C14 C15 . 1.382(2) yes C14 H14 . .9300 ? C15 H15 . .9300 ? 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 2_544 .959(17) 1.968(16) 2.773(2) 140.38(10) yes 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 C8 N1 C2 C3 .43(16) ? C8 N1 C2 C1 179.03(12) ? O1 C1 C2 N1 -3.7(2) ? C7 C1 C2 N1 173.98(13) ? O1 C1 C2 C3 174.47(15) ? C7 C1 C2 C3 -7.9(2) ? N1 C2 C3 C4 177.89(13) ? C1 C2 C3 C4 -.4(3) ? N1 C2 C3 C9 .18(15) ? C1 C2 C3 C9 -178.14(14) ? C2 C3 C4 C5 6.6(2) ? C9 C3 C4 C5 -176.15(15) ? C3 C4 C5 C6 -1.5(3) ? C4 C5 C6 C7 -5.9(3) ? C5 C6 C7 C1 2.4(3) ? O1 C1 C7 C6 -175.93(16) ? C2 C1 C7 C6 6.4(3) ? C2 N1 C8 C9 -.91(16) ? N1 C8 C9 C3 .99(15) ? N1 C8 C9 C10 -179.72(12) ? C2 C3 C9 C8 -.71(15) ? C4 C3 C9 C8 -178.44(14) ? C2 C3 C9 C10 -179.96(13) ? C4 C3 C9 C10 2.3(2) ? C8 C9 C10 C15 45.5(2) ? C3 C9 C10 C11 48.0(2) yes C3 C9 C10 C15 -135.37(15) yes C8 C9 C10 C11 -131.13(15) ? C15 C10 C11 C12 -.2(2) ? C9 C10 C11 C12 176.50(13) ? C10 C11 C12 C13 .3(2) ? C11 C12 C13 C14 -.3(3) ? C12 C13 C14 C15 .2(3) ? C13 C14 C15 C10 -.1(3) ? C11 C10 C15 C14 .1(2) ? C9 C10 C15 C14 -176.71(14) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21132953