#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:48:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/19/2011967.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_2011967 loop_ _publ_author_name 'Kubo, Kanji' 'Yamamoto, Emi' 'Mori, Akira' _publ_section_title ; 5-Cyanotropolone and 5-nitrotropolone ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 611 _journal_page_last 613 _journal_paper_doi 10.1107/S0108270101002463 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C7 H5 N O4' _chemical_formula_sum 'C7 H5 N O4' _chemical_formula_weight 167.12 _chemical_name_systematic ; ? ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.751(14) _cell_angle_beta 104.796(8) _cell_angle_gamma 94.410(13) _cell_formula_units_Z 4 _cell_length_a 7.5701(10) _cell_length_b 14.496(3) _cell_length_c 6.4945(7) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 18.3 _cell_measurement_theta_min 10.8 _cell_volume 686.61(19) _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 .999 _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _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 .0092 _diffrn_reflns_av_sigmaI/netI .0242 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 3438 _diffrn_reflns_theta_full .50 _diffrn_reflns_theta_max 27.97 _diffrn_reflns_theta_min 2.79 _diffrn_standards_decay_% .5 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .136 _exptl_absorpt_correction_T_max .969 _exptl_absorpt_correction_T_min .914 _exptl_absorpt_correction_type \y _exptl_absorpt_process_details 'via \y scans (North et al., 1968)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 344 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .23 _refine_diff_density_max .288 _refine_diff_density_min -.177 _refine_ls_extinction_coef .141(9) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 3309 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all .0616 _refine_ls_R_factor_gt .0388 _refine_ls_shift/su_max .000 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0603P)^2^+0.1579P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1191 _reflns_number_gt 2493 _reflns_number_total 3309 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1319.cif _cod_data_source_block II _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_cell_volume 686.7(2) _cod_database_code 2011967 _cod_database_fobs_code 2011967 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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 -.25178(18) .30941(10) .1946(2) .0470(3) Uani d . 1 . . N O1 .28301(16) .47812(9) .94339(18) .0542(3) Uani d . 1 . . O O2 .48839(15) .43210(10) .70233(19) .0569(3) Uani d . 1 . . O H2 .5094 .4555 .8227 .085 Uiso calc R 1 . . H O3 -.23379(19) .28045(13) .0255(2) .0798(5) Uani d . 1 . . O O4 -.40023(17) .31145(12) .2321(2) .0768(5) Uani d . 1 . . O C1 .1988(2) .43735(10) .7734(2) .0379(3) Uani d . 1 . . C C2 .30936(19) .41137(11) .6274(2) .0390(3) Uani d . 1 . . C C3 .2522(2) .37069(11) .4275(2) .0408(3) Uani d . 1 . . C H3 .3455 .3612 .3620 .049 Uiso calc R 1 . . H C4 .0752(2) .34116(10) .3061(2) .0380(3) Uani d . 1 . . C H4 .0671 .3158 .1714 .046 Uiso calc R 1 . . H C5 -.08634(19) .34488(10) .3604(2) .0358(3) Uani d . 1 . . C C6 -.1194(2) .37814(10) .5509(2) .0390(3) Uani d . 1 . . C H6 -.2410 .3724 .5577 .047 Uiso calc R 1 . . H C7 .0037(2) .41758(11) .7260(2) .0396(3) Uani d . 1 . . C H7 -.0479 .4349 .8347 .048 Uiso calc R 1 . . H N11 .13714(17) .18383(9) .7945(2) .0407(3) Uani d . 1 . . N O11 .31610(16) .02160(9) .05243(17) .0510(3) Uani d . 1 . . O O12 .63329(15) .08343(10) .28423(19) .0543(3) Uani d . 1 . . O H12 .5973 .0556 .1685 .081 Uiso calc R 1 . . H O13 -.02239(17) .15694(10) .7807(2) .0636(4) Uani d . 1 . . O O14 .22838(18) .23618(9) .9379(2) .0575(4) Uani d . 1 . . O C11 .31226(19) .06151(10) .2222(2) .0369(3) Uani d . 1 . . C C12 .49053(19) .09777(11) .3617(2) .0388(3) Uani d . 1 . . C C13 .52839(19) .14325(11) .5555(2) .0426(4) Uani d . 1 . . C H13 .6519 .1609 .6151 .051 Uiso calc R 1 . . H C14 .4102(2) .16753(10) .6789(2) .0387(3) Uani d . 1 . . C H14 .4652 .1985 .8084 .046 Uiso calc R 1 . . H C15 .22434(19) .15096(9) .6306(2) .0338(3) Uani d . 1 . . C C16 .10273(18) .10841(10) .4486(2) .0368(3) Uani d . 1 . . C H16 -.0207 .1052 .4476 .044 Uiso calc R 1 . . H C17 .14100(19) .07114(11) .2729(2) .0396(3) Uani d . 1 . . C H17 .0384 .0480 .1678 .048 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 .0367(7) .0564(8) .0448(7) -.0021(6) .0076(6) -.0126(6) O1 .0455(6) .0709(8) .0417(6) .0002(5) .0053(5) -.0168(5) O2 .0321(6) .0888(9) .0468(7) .0026(6) .0064(5) -.0165(6) O3 .0514(8) .1265(13) .0560(8) -.0107(8) .0112(6) -.0454(8) O4 .0333(6) .1205(13) .0739(9) -.0065(7) .0144(6) -.0332(9) C1 .0394(7) .0410(8) .0325(7) .0047(6) .0078(6) -.0023(6) C2 .0293(6) .0474(8) .0404(8) .0061(6) .0082(6) .0004(6) C3 .0324(7) .0537(9) .0396(7) .0088(6) .0137(6) -.0049(6) C4 .0374(7) .0443(8) .0336(7) .0064(6) .0109(6) -.0069(6) C5 .0320(7) .0383(7) .0360(7) .0022(5) .0072(5) -.0049(6) C6 .0332(7) .0464(8) .0402(7) .0033(6) .0149(6) -.0038(6) C7 .0391(7) .0476(8) .0354(7) .0041(6) .0156(6) -.0050(6) N11 .0404(7) .0466(7) .0370(6) .0103(5) .0118(5) -.0059(5) O11 .0456(6) .0713(8) .0372(6) .0120(5) .0111(5) -.0135(5) O12 .0345(6) .0798(9) .0508(7) .0045(5) .0162(5) -.0179(6) O13 .0396(6) .0951(10) .0600(8) .0035(6) .0219(6) -.0199(7) O14 .0568(7) .0658(8) .0497(7) .0027(6) .0154(6) -.0263(6) C11 .0353(7) .0445(8) .0307(7) .0068(6) .0073(5) -.0025(6) C12 .0303(7) .0471(8) .0407(7) .0060(6) .0116(6) -.0010(6) C13 .0271(6) .0548(9) .0433(8) .0005(6) .0055(6) -.0089(7) C14 .0345(7) .0454(8) .0336(7) .0022(6) .0050(5) -.0083(6) C15 .0338(7) .0366(7) .0323(7) .0055(5) .0101(5) -.0035(5) C16 .0275(6) .0453(8) .0372(7) .0034(5) .0079(5) -.0044(6) C17 .0310(7) .0512(8) .0336(7) .0011(6) .0040(5) -.0089(6) 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 O4 N1 O3 122.57(14) O4 N1 C5 118.62(13) O3 N1 C5 118.81(13) C2 O2 H2 109.5 O1 C1 C7 120.24(13) O1 C1 C2 116.69(14) C7 C1 C2 123.07(13) O2 C2 C3 116.53(13) O2 C2 C1 114.40(13) C3 C2 C1 129.06(13) C2 C3 C4 130.09(13) C2 C3 H3 115.0 C4 C3 H3 115.0 C5 C4 C3 128.22(13) C5 C4 H4 115.9 C3 C4 H4 115.9 C4 C5 C6 129.51(13) C4 C5 N1 115.29(13) C6 C5 N1 115.20(12) C7 C6 C5 128.31(14) C7 C6 H6 115.8 C5 C6 H6 115.8 C6 C7 C1 131.63(13) C6 C7 H7 114.2 C1 C7 H7 114.2 O13 N11 O14 123.05(13) O13 N11 C15 118.43(12) O14 N11 C15 118.52(13) C12 O12 H12 109.5 O11 C11 C17 120.36(13) O11 C11 C12 116.42(13) C17 C11 C12 123.22(12) O12 C12 C13 116.56(13) O12 C12 C11 114.07(13) C13 C12 C11 129.37(13) C12 C13 C14 130.18(14) C12 C13 H13 114.9 C14 C13 H13 114.9 C15 C14 C13 127.50(14) C15 C14 H14 116.3 C13 C14 H14 116.3 C14 C15 C16 129.92(13) C14 C15 N11 115.11(12) C16 C15 N11 114.97(12) C17 C16 C15 128.69(13) C17 C16 H16 115.7 C15 C16 H16 115.7 C16 C17 C11 131.05(13) C16 C17 H17 114.5 C11 C17 H17 114.5 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 O4 . 1.2117(18) yes N1 O3 . 1.2139(18) yes N1 C5 . 1.4800(19) yes O1 C1 . 1.2411(17) yes O2 C2 . 1.3268(18) yes O2 H2 . .8200 ? C1 C7 . 1.435(2) yes C1 C2 . 1.478(2) yes C2 C3 . 1.370(2) yes C3 C4 . 1.401(2) yes C3 H3 . .9300 ? C4 C5 . 1.361(2) yes C4 H4 . .9300 ? C5 C6 . 1.4096(19) yes C6 C7 . 1.359(2) yes C6 H6 . .9300 ? C7 H7 . .9300 ? N11 O13 . 1.2205(17) yes N11 O14 . 1.2220(17) yes N11 C15 . 1.4796(17) yes O11 C11 . 1.2463(17) yes O12 C12 . 1.3317(17) yes O12 H12 . .8200 ? C11 C17 . 1.433(2) yes C11 C12 . 1.474(2) yes C12 C13 . 1.366(2) yes C13 C14 . 1.405(2) yes C13 H13 . .9300 ? C14 C15 . 1.3626(19) yes C14 H14 . .9300 ? C15 C16 . 1.4012(19) yes C16 C17 . 1.3620(19) yes C16 H16 . .9300 ? C17 H17 . .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 O2 H2 O1 2_667 .82 2.05 2.743(2) 142 yes O2 H2 O1 . .82 2.10 2.586(2) 117 yes O12 H12 O11 2_655 .82 2.07 2.771(2) 143 yes O12 H12 O11 . .82 2.09 2.573(2) 118 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 O1 C1 C2 O2 2.6(2) C7 C1 C2 O2 -177.42(15) O1 C1 C2 C3 -176.34(16) C7 C1 C2 C3 3.6(3) O2 C2 C3 C4 -179.91(16) C1 C2 C3 C4 -1.0(3) C2 C3 C4 C5 -.9(3) C3 C4 C5 C6 -.6(3) C3 C4 C5 N1 178.94(15) O4 N1 C5 C4 -179.41(16) O3 N1 C5 C4 -.3(2) O4 N1 C5 C6 .2(2) O3 N1 C5 C6 179.31(16) C4 C5 C6 C7 2.2(3) N1 C5 C6 C7 -177.32(15) C5 C6 C7 C1 -.2(3) O1 C1 C7 C6 176.81(16) C2 C1 C7 C6 -3.1(3) O11 C11 C12 O12 .7(2) C17 C11 C12 O12 -178.70(14) O11 C11 C12 C13 -179.38(16) C17 C11 C12 C13 1.2(3) O12 C12 C13 C14 -179.17(17) C11 C12 C13 C14 .9(3) C12 C13 C14 C15 -.4(3) C13 C14 C15 C16 -1.6(3) C13 C14 C15 N11 179.16(15) O13 N11 C15 C14 -166.88(15) O14 N11 C15 C14 12.7(2) O13 N11 C15 C16 13.8(2) O14 N11 C15 C16 -166.65(14) C14 C15 C16 C17 1.1(3) N11 C15 C16 C17 -179.65(15) C15 C16 C17 C11 1.9(3) O11 C11 C17 C16 177.43(16) C12 C11 C17 C16 -3.2(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 387713