#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/18/2011801.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_2011801 loop_ _publ_author_name 'Zaleski, Jacek' 'Daszkiewicz, Zdzis\/law' 'Kyzio\/l, Janusz B.' _publ_section_title ; 1-Nitroindoline ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 304 _journal_page_last 305 _journal_paper_doi 10.1107/S0108270100019144 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C8 H8 N2 O2' _chemical_formula_sum 'C8 H8 N2 O2' _chemical_formula_weight 164.16 _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 116.80(3) _cell_angle_beta 104.04(3) _cell_angle_gamma 92.53(3) _cell_formula_units_Z 2 _cell_length_a 5.886(2) _cell_length_b 8.402(3) _cell_length_c 8.923(3) _cell_measurement_reflns_used 19 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26 _cell_measurement_theta_min 15 _cell_volume 376.1(3) _computing_cell_refinement 'KUMA Diffraction Software (KUMA, 1997)' _computing_data_reduction 'KUMA Diffraction Software' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1990)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full .976 _diffrn_measured_fraction_theta_max .938 _diffrn_measurement_device_type 'KUMA KM4 diffractometer' _diffrn_measurement_method \w _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 .0063 _diffrn_reflns_av_sigmaI/netI .0101 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 2196 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 30.06 _diffrn_reflns_theta_min 2.68 _diffrn_standards_decay_% 4.05 _diffrn_standards_interval_count 50 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu .107 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plates _exptl_crystal_F_000 172 _exptl_crystal_size_max .6 _exptl_crystal_size_mid .5 _exptl_crystal_size_min .25 _refine_diff_density_max .247 _refine_diff_density_min -.167 _refine_ls_extinction_coef .042(10) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 142 _refine_ls_number_reflns 2063 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.0012 _refine_ls_R_factor_all .0487 _refine_ls_R_factor_gt .0368 _refine_ls_shift/su_max .010 _refine_ls_shift/su_mean .002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.0575P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1098 _reflns_number_gt 1643 _reflns_number_total 2063 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gd1117.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 'Triclinic' changed to 'triclinic' 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^)+(0.0555P)^2^+0.0575P] 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^)+(0.0555P)^2^+0.0575P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 376.1(2) _cod_original_sg_symbol_H-M P-1 _cod_database_code 2011801 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 C1 .03253(18) .76359(13) .46292(13) .0372(2) Uani d . 1 . . C C2 -.12229(18) .70046(14) .52725(13) .0382(2) Uani d . 1 . . C C3 -.0669(2) .75623(19) .70445(15) .0511(3) Uani d . 1 . . C C4 .1423(3) .8750(2) .81636(16) .0586(3) Uani d . 1 . . C C5 .2939(2) .93635(18) .75082(17) .0564(3) Uani d . 1 . . C C6 .2431(2) .88204(16) .57318(17) .0494(3) Uani d . 1 . . C N7 -.06979(17) .68569(14) .28014(12) .0463(2) Uani d . 1 . . N C8 -.3063(2) .57703(19) .21843(15) .0490(3) Uani d . 1 . . C C9 -.3355(2) .57295(17) .38166(15) .0458(3) Uani d . 1 . . C O11 .21270(19) .81134(16) .22450(14) .0695(3) Uani d . 1 . . O O12 -.1192(2) .65732(15) .01832(12) .0685(3) Uani d . 1 . . O N10 .0130(2) .72110(15) .16956(13) .0514(3) Uani d . 1 . . N H3 -.175(3) .716(2) .753(2) .082(5) Uiso d . 1 . . H H4 .185(3) .911(3) .936(3) .088(6) Uiso d . 1 . . H H5 .439(3) 1.016(2) .823(2) .067(4) Uiso d . 1 . . H H6 .342(3) .920(2) .525(2) .065(4) Uiso d . 1 . . H H9A -.484(3) .614(2) .401(2) .066(4) Uiso d . 1 . . H H8A -.414(3) .642(2) .181(2) .063(4) Uiso d . 1 . . H H9B -.338(3) .448(2) .366(2) .062(4) Uiso d . 1 . . H H8B -.304(3) .458(2) .126(2) .071(5) 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 C1 .0391(5) .0382(5) .0365(5) .0059(4) .0108(4) .0199(4) C2 .0392(5) .0419(5) .0365(5) .0063(4) .0115(4) .0211(4) C3 .0562(7) .0624(7) .0393(6) .0082(5) .0157(5) .0276(5) C4 .0661(8) .0635(8) .0348(6) .0095(6) .0053(5) .0189(5) C5 .0521(7) .0481(6) .0487(7) -.0018(5) -.0026(5) .0158(5) C6 .0446(6) .0461(6) .0551(7) -.0021(5) .0104(5) .0252(5) N7 .0487(5) .0566(6) .0360(5) -.0001(4) .0124(4) .0248(4) C8 .0462(6) .0561(7) .0384(5) .0002(5) .0041(4) .0222(5) C9 .0393(5) .0525(6) .0448(6) -.0001(4) .0102(4) .0242(5) O11 .0711(6) .0838(7) .0789(7) .0095(5) .0390(5) .0518(6) O12 .1010(8) .0766(7) .0429(5) .0260(6) .0270(5) .0373(5) N10 .0677(7) .0572(6) .0478(5) .0199(5) .0291(5) .0337(5) 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 C6 C1 C2 121.40(10) C6 C1 N7 131.30(10) C2 C1 N7 107.20(10) C3 C2 C1 119.80(10) C3 C2 C9 129.10(10) C1 C2 C9 111.10(10) C2 C3 C4 119.40(10) C5 C4 C3 120.10(10) C4 C5 C6 121.70(10) C1 C6 C5 117.50(10) N10 N7 C1 126.60(10) N10 N7 C8 119.80(10) C1 N7 C8 113.00(10) N7 C8 C9 103.50(10) C2 C9 C8 104.70(10) O11 N10 O12 125.20(10) O11 N10 N7 118.40(10) O12 N10 N7 116.40(10) C2 C3 H3 121.0(10) C4 C3 H3 119.0(10) C3 C4 H4 121.0(10) C5 C4 H4 119.0(10) C4 C5 H5 123.0(10) C6 C5 H5 116.0(10) C1 C6 H6 119.0(10) C5 C6 H6 124.0(10) N7 C8 H8A 106.0(10) C9 C8 H8A 112.0(10) N7 C8 H8B 107.0(10) C9 C8 H8B 113.0(10) H8A C8 H8B 114.0(10) C2 C9 H9A 112.0(10) C8 C9 H9A 109.0(10) C2 C9 H9B 111.0(10) C8 C9 H9B 110.0(10) H9A C9 H9B 110.0(10) 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 C6 . 1.383(2) y C1 C2 . 1.3880(10) y C1 N7 . 1.4060(10) y C2 C3 . 1.376(2) y C2 C9 . 1.499(2) y C3 C4 . 1.381(2) y C4 C5 . 1.374(2) y C5 C6 . 1.384(2) y N7 N10 . 1.3360(10) y N7 C8 . 1.462(2) y C8 C9 . 1.523(2) y O11 N10 . 1.226(2) y O12 N10 . 1.231(2) y C3 H3 . .98(2) ? C4 H4 . .93(2) ? C5 H5 . .94(2) ? C6 H6 . .92(2) ? C8 H8A . .95(2) ? C8 H8B . .97(2) ? C9 H9A . .98(2) ? C9 H9B . .99(2) ? 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 C3 H3 O12 1_556 .98(2) 2.57(2) 3.335(2) 134.0(10) 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 C6 C1 C2 C3 .1(2) ? N7 C1 C2 C3 -179.70(10) ? C6 C1 C2 C9 -179.40(10) ? N7 C1 C2 C9 .90(10) ? C1 C2 C3 C4 .2(2) ? C9 C2 C3 C4 179.60(10) ? C2 C3 C4 C5 -.2(2) ? C3 C4 C5 C6 .0(2) ? C2 C1 C6 C5 -.3(2) ? N7 C1 C6 C5 179.40(10) ? C4 C5 C6 C1 .3(2) ? C6 C1 N7 N10 -4.9(2) ? C2 C1 N7 N10 174.80(10) ? C6 C1 N7 C8 -175.60(10) ? C2 C1 N7 C8 4.00(10) ? N10 N7 C8 C9 -178.40(10) ? C1 N7 C8 C9 -7.00(10) y C3 C2 C9 C8 175.50(10) y C1 C2 C9 C8 -5.00(10) y N7 C8 C9 C2 6.90(10) y C1 N7 N10 O11 10.4(2) y C8 N7 N10 O11 -179.40(10) y C1 N7 N10 O12 -170.40(10) y C8 N7 N10 O12 -.3(2) y