#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/25/2012556.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_2012556 loop_ _publ_author_name 'Saha, Satyen' _publ_section_title ; 4-Amino derivatives of 7-nitro-2,1,3-benzoxadiazole: the effect of the amino moiety on the structure of fluorophores ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o174 _journal_page_last o177 _journal_paper_doi 10.1107/S0108270102000173 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C12 H14 N4 O3' _chemical_formula_sum 'C12 H14 N4 O3' _chemical_formula_weight 262.27 _chemical_name_common 7NBD _chemical_name_systematic ; 4-(azepan-1-yl)-7-nitro-2,1,3-benzoxadiazole ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 98.958(14) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.4909(16) _cell_length_b 10.8002(14) _cell_length_c 15.1001(19) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 10.59 _cell_measurement_theta_min 9.34 _cell_volume 1206.7(3) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'Xtal3.5 (Hall et al., 1995)' _computing_molecular_graphics 'ORTEX6.0 (McArdle, 1995)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .945 _diffrn_measured_fraction_theta_max .945 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\w scans' _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 .000 _diffrn_reflns_av_sigmaI/netI .046 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2115 _diffrn_reflns_theta_full 24.96 _diffrn_reflns_theta_max 24.96 _diffrn_reflns_theta_min 2.33 _diffrn_standards_decay_% none _diffrn_standards_interval_time 90 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .107 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 552 _exptl_crystal_size_max .32 _exptl_crystal_size_mid .21 _exptl_crystal_size_min .10 _refine_diff_density_max .22 _refine_diff_density_min -.20 _refine_ls_extinction_coef .010(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2115 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all .106 _refine_ls_R_factor_gt .051 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0918P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .125 _refine_ls_wR_factor_ref .174 _reflns_number_gt 1043 _reflns_number_total 2115 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm1482.cif _[local]_cod_data_source_block III _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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. '_geom_bond_publ_flag' value 'Y' changed to 'y' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times). 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. '_geom_bond_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times). '_geom_angle_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (3 times). '_geom_torsion_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 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_database_code 2012556 _cod_database_fobs_code 2012556 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 O2 .8728(4) -.1494(2) .06047(15) .0596(7) Uani d . 1 . . O O3 .4812(4) -.0492(2) -.27555(16) .0706(8) Uani d . 1 . . O O4 .6308(4) -.1977(2) -.20052(18) .0749(9) Uani d . 1 . . O N1 .7892(4) -.1647(2) -.02781(18) .0523(8) Uani d . 1 . . N N3 .8594(4) -.0311(2) .09053(17) .0503(8) Uani d . 1 . . N N4 .7419(4) .2345(2) .08964(17) .0465(7) Uani d . 1 . . N N5 .5748(4) -.0910(3) -.20698(18) .0533(8) Uani d . 1 . . N C1 .7237(4) -.0540(3) -.0513(2) .0398(7) Uani d . 1 . . C C3 .7682(4) .0303(3) .02302(19) .0382(7) Uani d . 1 . . C C4 .7099(4) .1577(3) .0190(2) .0426(8) Uani d . 1 . . C C5 .6087(5) .1927(3) -.0638(2) .0493(9) Uani d . 1 . . C H5 .5680 .2739 -.0710 .059 Uiso calc R 1 . . H C6 .5672(4) .1114(3) -.1349(2) .0483(8) Uani d . 1 . . C H6 .4989 .1408 -.1875 .058 Uiso calc R 1 . . H C7 .6217(4) -.0107(3) -.13214(19) .0446(8) Uani d . 1 . . C C8 .6450(5) .3529(3) .0889(3) .0588(10) Uani d . 1 . . C H8A .6238 .3713 .1493 .071 Uiso calc R 1 . . H H8B .5283 .3447 .0513 .071 Uiso calc R 1 . . H C9 .7461(6) .4605(3) .0551(3) .0702(12) Uani d . 1 . . C H9A .7917 .4345 .0013 .084 Uiso calc R 1 . . H H9B .6616 .5277 .0385 .084 Uiso calc R 1 . . H C10 .9029(6) .5090(3) .1219(3) .0740(12) Uani d . 1 . . C H10A .9660 .5715 .0926 .089 Uiso calc R 1 . . H H10B .8548 .5490 .1706 .089 Uiso calc R 1 . . H C11 1.0379(5) .4115(3) .1611(3) .0688(11) Uani d . 1 . . C H11A 1.1400 .4523 .1968 .083 Uiso calc R 1 . . H H11B 1.0825 .3688 .1124 .083 Uiso calc R 1 . . H C12 .9609(5) .3161(3) .2194(3) .0620(10) Uani d . 1 . . C H12A 1.0582 .2871 .2646 .074 Uiso calc R 1 . . H H12B .8734 .3572 .2503 .074 Uiso calc R 1 . . H C13 .8711(5) .2050(3) .1709(2) .0560(9) Uani d . 1 . . C H13A .9640 .1511 .1543 .067 Uiso calc R 1 . . H H13B .8079 .1594 .2120 .067 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 O2 .0781(17) .0429(13) .0536(14) .0124(12) -.0033(13) .0003(11) O3 .0793(19) .0814(19) .0446(14) -.0087(15) -.0110(14) .0003(13) O4 .096(2) .0536(16) .0683(18) .0026(15) -.0074(15) -.0182(13) N1 .0625(19) .0471(17) .0459(16) .0037(14) .0039(14) -.0012(13) N3 .0648(19) .0384(15) .0454(15) .0111(14) .0014(14) .0014(12) N4 .0513(16) .0389(15) .0475(15) .0031(12) .0022(13) -.0007(12) N5 .0519(18) .062(2) .0448(17) -.0109(15) .0033(14) -.0028(14) C1 .0383(17) .0390(17) .0432(17) .0035(14) .0101(14) .0004(14) C3 .0399(17) .0365(16) .0383(16) .0024(14) .0062(14) .0044(13) C4 .0427(18) .0406(17) .0449(17) .0007(14) .0085(14) .0017(15) C5 .054(2) .0419(18) .049(2) .0092(16) -.0005(16) .0076(15) C6 .048(2) .0496(19) .0441(18) -.0006(16) -.0020(15) .0089(15) C7 .0399(18) .0536(19) .0390(17) -.0024(15) .0025(14) .0027(15) C8 .052(2) .0454(19) .076(2) .0111(17) .0037(19) -.0055(18) C9 .078(3) .044(2) .085(3) .011(2) .004(2) .0040(19) C10 .073(3) .047(2) .106(3) -.006(2) .024(2) -.014(2) C11 .058(2) .058(2) .090(3) -.007(2) .008(2) -.018(2) C12 .067(2) .058(2) .060(2) .0007(19) .0033(19) -.0159(18) C13 .067(2) .053(2) .0459(19) .0031(18) .0000(18) .0011(16) 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 _geom_angle_publ_flag N3 O2 N1 112.6(2) ? C1 N1 O2 104.0(2) ? C3 N3 O2 105.7(2) ? C4 N4 C8 120.3(3) y C4 N4 C13 122.7(3) y C8 N4 C13 117.0(3) y O4 N5 O3 123.4(3) ? O4 N5 C7 118.1(3) ? O3 N5 C7 118.5(3) ? N1 C1 C7 131.2(3) ? N1 C1 C3 109.3(3) ? C7 C1 C3 119.4(3) ? N3 C3 C4 129.1(3) ? N3 C3 C1 108.3(3) ? C4 C3 C1 122.5(3) ? N4 C4 C5 122.9(3) ? N4 C4 C3 122.7(3) ? C5 C4 C3 114.3(3) ? C6 C5 C4 122.9(3) ? C6 C5 H5 118.6 ? C4 C5 H5 118.6 ? C7 C6 C5 123.6(3) ? C7 C6 H6 118.2 ? C5 C6 H6 118.2 ? C6 C7 C1 117.4(3) ? C6 C7 N5 121.5(3) ? C1 C7 N5 121.1(3) ? N4 C8 C9 113.4(3) ? N4 C8 H8A 108.9 ? C9 C8 H8A 108.9 ? N4 C8 H8B 108.9 ? C9 C8 H8B 108.9 ? H8A C8 H8B 107.7 ? C10 C9 C8 114.5(3) ? C10 C9 H9A 108.6 ? C8 C9 H9A 108.6 ? C10 C9 H9B 108.6 ? C8 C9 H9B 108.6 ? H9A C9 H9B 107.6 ? C11 C10 C9 114.9(3) ? C11 C10 H10A 108.6 ? C9 C10 H10A 108.6 ? C11 C10 H10B 108.6 ? C9 C10 H10B 108.6 ? H10A C10 H10B 107.5 ? C10 C11 C12 113.9(3) ? C10 C11 H11A 108.8 ? C12 C11 H11A 108.8 ? C10 C11 H11B 108.8 ? C12 C11 H11B 108.8 ? H11A C11 H11B 107.7 ? C13 C12 C11 116.0(3) ? C13 C12 H12A 108.3 ? C11 C12 H12A 108.3 ? C13 C12 H12B 108.3 ? C11 C12 H12B 108.3 ? H12A C12 H12B 107.4 ? N4 C13 C12 114.6(3) ? N4 C13 H13A 108.6 ? C12 C13 H13A 108.6 ? N4 C13 H13B 108.6 ? C12 C13 H13B 108.6 ? H13A C13 H13B 107.6 ? 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 O2 N3 . 1.365(3) ? O2 N1 . 1.392(4) ? O3 N5 . 1.242(3) ? O4 N5 . 1.226(4) ? N1 C1 . 1.320(4) ? N3 C3 . 1.314(4) ? N4 C4 . 1.344(4) y N4 C8 . 1.469(4) ? N4 C13 . 1.475(4) ? N5 C7 . 1.424(4) y C1 C7 . 1.415(4) ? C1 C3 . 1.443(4) ? C3 C4 . 1.442(4) ? C4 C5 . 1.409(4) ? C5 C6 . 1.384(4) ? C5 H5 . .9300 ? C6 C7 . 1.379(4) ? C6 H6 . .9300 ? C8 C9 . 1.518(5) ? C8 H8A . .9700 ? C8 H8B . .9700 ? C9 C10 . 1.518(6) ? C9 H9A . .9700 ? C9 H9B . .9700 ? C10 C11 . 1.515(5) ? C10 H10A . .9700 ? C10 H10B . .9700 ? C11 C12 . 1.526(5) ? C11 H11A . .9700 ? C11 H11B . .9700 ? C12 C13 . 1.508(5) ? C12 H12A . .9700 ? C12 H12B . .9700 ? C13 H13A . .9700 ? C13 H13B . .9700 ? 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 N3 O2 N1 C1 -.2(4) ? N1 O2 N3 C3 .1(4) ? O2 N1 C1 C7 -178.6(3) ? O2 N1 C1 C3 .3(3) ? O2 N3 C3 C4 177.5(3) ? O2 N3 C3 C1 .1(3) ? N1 C1 C3 N3 -.3(4) ? C7 C1 C3 N3 178.8(3) ? N1 C1 C3 C4 -177.9(3) ? C7 C1 C3 C4 1.1(4) ? C8 N4 C4 C5 10.9(5) y C13 N4 C4 C5 -169.9(3) ? C8 N4 C4 C3 -165.7(3) ? C13 N4 C4 C3 13.4(5) ? N3 C3 C4 N4 -1.1(5) ? C1 C3 C4 N4 176.0(3) ? N3 C3 C4 C5 -178.0(3) ? C1 C3 C4 C5 -.9(4) ? N4 C4 C5 C6 -176.3(3) ? C3 C4 C5 C6 .6(5) ? C4 C5 C6 C7 -.6(5) ? C5 C6 C7 C1 .7(5) ? C5 C6 C7 N5 179.7(3) ? N1 C1 C7 C6 177.8(3) ? C3 C1 C7 C6 -1.0(4) ? N1 C1 C7 N5 -1.1(5) ? C3 C1 C7 N5 -179.9(3) ? O4 N5 C7 C6 178.5(3) ? O3 N5 C7 C6 -.7(5) y O4 N5 C7 C1 -2.6(5) ? O3 N5 C7 C1 178.2(3) ? C4 N4 C8 C9 -93.0(4) ? C13 N4 C8 C9 87.8(4) ? N4 C8 C9 C10 -76.2(4) ? C8 C9 C10 C11 52.7(5) ? C9 C10 C11 C12 -65.6(5) ? C10 C11 C12 C13 87.6(4) ? C4 N4 C13 C12 150.0(3) ? C8 N4 C13 C12 -30.8(4) ? C11 C12 C13 N4 -47.6(5) ?