#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/14/2011476.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_2011476 loop_ _publ_author_name 'Ooms, Fr\'ed\'eric' 'Norberg, Bernadette' 'Isin, Emre M.' 'Castagnoli, Neal Jr' 'Van der Schyf, Cornelis J.' 'Wouters, Johan' _publ_section_title ; 7-Nitroindazole ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e474 _journal_page_last e475 _journal_paper_doi 10.1107/S0108270100011975 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C7 H5 N3 O2' _chemical_formula_sum 'C7 H5 N3 O2' _chemical_formula_weight 163.14 _chemical_name_common 7-nitroindazole _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 98.232(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.0200(10) _cell_length_b 9.6360(10) _cell_length_c 14.5060(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 45 _cell_measurement_theta_min 40 _cell_volume 694.46(16) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1989)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .939 _diffrn_measured_fraction_theta_max .939 _diffrn_measurement_device_type Enraf-Nonius _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents .010 _diffrn_reflns_av_sigmaI/netI .013 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 1877 _diffrn_reflns_theta_full 71.87 _diffrn_reflns_theta_max 71.87 _diffrn_reflns_theta_min 5.53 _diffrn_standards_decay_% 2 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.013 _exptl_absorpt_correction_T_max .839 _exptl_absorpt_correction_T_min .537 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(Spek, 1997)' _exptl_crystal_colour orange--yellow _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 336 _exptl_crystal_size_max .70 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .18 _refine_diff_density_max .199 _refine_diff_density_min -.151 _refine_ls_extinction_coef .0079(12) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 110 _refine_ls_number_reflns 1355 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.097 _refine_ls_R_factor_all .041 _refine_ls_R_factor_gt .037 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0544P)^2^+0.1541P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .109 _reflns_number_gt 1223 _reflns_number_total 1355 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file qd0040.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 'Monoclinic-' changed to 'monoclinic' 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^)+(0.0544P)^2^+0.1541P] 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^)+(0.0544P)^2^+0.1541P] 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 2011476 _cod_database_fobs_code 2011476 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 C7 .4179(3) .28020(14) .04060(9) .0407(3) Uani d . 1 . . C C6 .2458(3) .33636(16) .09695(11) .0474(4) Uani d . 1 . . C H6 .1338 .4098 .0753 .057 Uiso calc R 1 . . H C5 .2390(3) .28378(17) .18587(11) .0503(4) Uani d . 1 . . C H5 .1229 .3232 .2230 .060 Uiso calc R 1 . . H C4 .4001(3) .17484(16) .22000(10) .0470(4) Uani d . 1 . . C H4 .3930 .1403 .2795 .056 Uiso calc R 1 . . H C3A .5750(3) .11678(15) .16378(10) .0418(3) Uani d . 1 . . C C3 .7637(3) .00659(17) .17263(11) .0499(4) Uani d . 1 . . C H3 .8028 -.0486 .2254 .060 Uiso calc R 1 . . H N2 .8762(2) -.00789(13) .09720(9) .0511(4) Uani d . 1 . . N N1 .7668(2) .09196(12) .03689(8) .0447(3) Uani d . 1 . . N H1 .8091 .1041 -.0179 .054 Uiso calc R 1 . . H C1A .5843(3) .16938(14) .07349(9) .0384(3) Uani d . 1 . . C N8 .4260(3) .33609(13) -.05120(9) .0500(3) Uani d . 1 . . N O9 .5911(3) .28690(14) -.09639(8) .0706(4) Uani d . 1 . . O O10 .2714(3) .43003(14) -.08015(9) .0680(4) Uani d . 1 . . O 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 C7 .0403(7) .0418(7) .0409(7) -.0041(5) .0088(5) -.0035(5) C6 .0426(7) .0463(8) .0543(8) .0037(6) .0109(6) -.0070(6) C5 .0459(8) .0571(9) .0519(8) .0004(7) .0205(6) -.0123(7) C4 .0475(8) .0561(9) .0402(7) -.0043(6) .0157(6) -.0047(6) C3A .0384(7) .0456(7) .0426(7) -.0033(6) .0100(5) -.0038(6) C3 .0453(8) .0523(8) .0532(8) .0037(6) .0101(6) .0029(7) N2 .0438(7) .0503(7) .0608(8) .0064(5) .0128(5) -.0042(6) N1 .0421(6) .0480(7) .0470(6) .0008(5) .0169(5) -.0066(5) C1A .0340(6) .0417(7) .0415(7) -.0054(5) .0120(5) -.0085(5) N8 .0553(7) .0507(7) .0449(7) -.0056(6) .0102(5) -.0012(5) O9 .0865(9) .0781(9) .0549(7) .0056(7) .0357(6) .0059(6) O10 .0755(8) .0666(8) .0594(7) .0098(6) .0011(6) .0119(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 '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 .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 '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 C6 C7 C1A 119.42(13) C6 C7 N8 120.17(13) C1A C7 N8 120.41(12) C7 C6 C5 120.42(14) C7 C6 H6 119.8 C5 C6 H6 119.8 C4 C5 C6 121.42(13) C4 C5 H5 119.3 C6 C5 H5 119.3 C5 C4 C3A 118.83(13) C5 C4 H4 120.6 C3A C4 H4 120.6 C4 C3A C1A 120.32(13) C4 C3A C3 135.63(14) C1A C3A C3 104.04(12) N2 C3 C3A 111.54(14) N2 C3 H3 124.2 C3A C3 H3 124.2 C3 N2 N1 106.21(12) C1A N1 N2 111.85(11) C1A N1 H1 124.1 N2 N1 H1 124.1 N1 C1A C7 134.06(13) N1 C1A C3A 106.35(12) C7 C1A C3A 119.58(12) O9 N8 O10 123.12(14) O9 N8 C7 117.43(13) O10 N8 C7 119.45(13) 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 C7 C6 . 1.3818(19) ? C7 C1A . 1.3970(19) ? C7 N8 . 1.4425(18) ? C6 C5 . 1.391(2) ? C6 H6 . .9300 ? C5 C4 . 1.374(2) ? C5 H5 . .9300 ? C4 C3A . 1.3975(19) ? C4 H4 . .9300 ? C3A C1A . 1.4115(19) ? C3A C3 . 1.417(2) ? C3 N2 . 1.309(2) ? C3 H3 . .9300 ? N2 N1 . 1.3620(18) ? N1 C1A . 1.3480(17) ? N1 H1 . .8600 ? N8 O9 . 1.2234(17) ? N8 O10 . 1.2265(18) ? 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 N2 3_755 .86 2.280 2.941(2) 133.74 yes N1 H1 O9 . .86 2.289 2.749(2) 113.65 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 C1A C7 C6 C5 .4(2) N8 C7 C6 C5 -179.38(13) C7 C6 C5 C4 -.4(2) C6 C5 C4 C3A .3(2) C5 C4 C3A C1A -.2(2) C5 C4 C3A C3 -179.04(16) C4 C3A C3 N2 178.86(16) C1A C3A C3 N2 -.13(17) C3A C3 N2 N1 .27(17) C3 N2 N1 C1A -.31(16) N2 N1 C1A C7 -179.01(14) N2 N1 C1A C3A .23(15) C6 C7 C1A N1 178.93(14) N8 C7 C1A N1 -1.3(2) C6 C7 C1A C3A -.2(2) N8 C7 C1A C3A 179.54(12) C4 C3A C1A N1 -179.25(12) C3 C3A C1A N1 -.06(15) C4 C3A C1A C7 .1(2) C3 C3A C1A C7 179.31(12) C6 C7 N8 O9 176.57(14) C1A C7 N8 O9 -3.2(2) C6 C7 N8 O10 -2.9(2) C1A C7 N8 O10 177.36(12)