#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/82/2008275.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_2008275 loop_ _publ_author_name 'H\"okelek, Tuncer' 'K\?il\?i\,c, Emine' 'Aktan, Selami' _publ_section_title ; 1-Nitrobenzo[c]cinnoline ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 383 _journal_page_last 385 _journal_paper_doi 10.1107/S0108270198013560 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C12 H7 N3 O2' _chemical_formula_sum 'C12 H7 N3 O2' _chemical_formula_weight 225.206 _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' _atom_type_scat_source IntTabIV _cell_angle_alpha 90 _cell_angle_beta 103.28(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.8940(10) _cell_length_b 13.8920(10) _cell_length_c 9.5560(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298 _cell_measurement_theta_max 18 _cell_measurement_theta_min 9 _cell_volume 1019.9(2) _computing_cell_refinement MolEN _computing_data_collection 'MolEN (Fair, 1990)' _computing_data_reduction MolEN _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material MolEN _computing_structure_refinement MolEN _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 2312 _diffrn_reflns_theta_max 26.3 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.1044 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_type 'empirical via \y scans (MolEN; Fair, 1990)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.4666 _exptl_crystal_density_method none _exptl_crystal_description block-like _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.22 _refine_diff_density_min -0.25 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.68 _refine_ls_hydrogen_treatment 'see text' _refine_ls_number_parameters 170 _refine_ls_number_reflns 1715 _refine_ls_R_factor_obs 0.048 _refine_ls_shift/esd_max 0.01 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1 / [\s(F)^2^ + (0.02 F)^2^ + 1.0]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.060 _reflns_number_observed 1715 _reflns_number_total 2062 _reflns_observed_criterion F>2.0\s(F) _[local]_cod_data_source_file ka1302.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: '_refine_ls_weighting_scheme' value ' w = 1 / [\s(F)^2^ + (0.02 F)^2^ + 1.0] ' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1 / [\s(F)^2^ + (0.02 F)^2^ + 1.0]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2008275 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_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 O1 0.0918(7) 0.0602(7) 0.1136(9) 0.0231(6) 0.0544(6) 0.0124(7) O2 0.1180(10) 0.0612(8) 0.1000(10) -0.0192(8) 0.0348(8) -0.0279(7) N7 0.0579(7) 0.0448(7) 0.0792(9) -0.0065(6) 0.0095(7) 0.0072(7) N6 0.0592(7) 0.0421(7) 0.0727(9) -0.0032(6) 0.0128(6) 0.0001(7) N8 0.0854(9) 0.0399(7) 0.0679(8) 0.0031(7) 0.0296(6) 0.0038(6) C13 0.0364(6) 0.0494(8) 0.0518(8) 0.0019(6) 0.0043(6) 0.0051(7) C12 0.0594(9) 0.0630(10) 0.0562(8) 0.0088(8) 0.0140(7) 0.0050(8) C11 0.0660(10) 0.0930(10) 0.0538(9) 0.0180(10) 0.0149(7) 0.0090(10) C10 0.0536(9) 0.1080(10) 0.0644(9) 0.0090(10) 0.0174(7) 0.0280(10) C9 0.0493(8) 0.0750(10) 0.0730(10) -0.0038(8) 0.0084(8) 0.0257(9) C8 0.0378(7) 0.0552(8) 0.0619(9) -0.0022(7) 0.0036(6) 0.0133(8) C5 0.0393(7) 0.0406(7) 0.0573(8) -0.0003(6) 0.0025(6) -0.0008(7) C4 0.0517(8) 0.0518(9) 0.0579(8) 0.0026(7) 0.0089(7) -0.0084(7) C3 0.0574(8) 0.0630(10) 0.0518(8) 0.0023(8) 0.0154(6) 0.0014(8) C2 0.0626(9) 0.0464(8) 0.0601(9) 0.0022(7) 0.0163(7) 0.0080(7) C1 0.0497(7) 0.0403(7) 0.0549(8) 0.0029(6) 0.0113(6) 0.0013(7) C14 0.0348(6) 0.0402(7) 0.0513(7) 0.0010(6) 0.0047(5) 0.0017(6) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv O1 0.1188(2) 0.27780(10) 0.4184(2) 0.0836(3) O2 0.3879(2) 0.31960(10) 0.4678(2) 0.0915(4) C1 0.3156(2) 0.17430(10) 0.3545(2) 0.0484(3) C2 0.3692(2) 0.18490(10) 0.2288(2) 0.0560(4) C3 0.4012(2) 0.10370(10) 0.1537(2) 0.0569(4) C4 0.3734(2) 0.01450(10) 0.2032(2) 0.0545(3) C5 0.3183(2) 0.00390(10) 0.3323(2) 0.0472(3) N6 0.2888(2) -0.09020(10) 0.3690(2) 0.0584(3) N7 0.2337(2) -0.10750(10) 0.4829(2) 0.0617(3) N8 0.2715(2) 0.26370(10) 0.4197(2) 0.0625(3) C8 0.2128(2) -0.03310(10) 0.5746(2) 0.0530(3) C9 0.1589(2) -0.0607(2) 0.6993(2) 0.0669(4) C10 0.1435(2) 0.0066(2) 0.7988(2) 0.0747(5) C11 0.1844(3) 0.1026(2) 0.7794(2) 0.0709(4) C12 0.2353(2) 0.13090(10) 0.6573(2) 0.0595(4) C13 0.2467(2) 0.06430(10) 0.5496(2) 0.0469(3) C14 0.2923(2) 0.08430(10) 0.4150(2) 0.0430(3) H21 0.376(2) 0.2460(10) 0.185(2) 0.0697(4) H31 0.435(2) 0.1100(10) 0.065(2) 0.0647(4) H41 0.389(2) -0.0420(10) 0.156(2) 0.0647(4) H91 0.134 -0.126 0.714 0.0837 H101 0.104 -0.012 0.882 0.0900 H111 0.178 0.149 0.851 0.0849 H121 0.263(2) 0.1980(10) 0.649(2) 0.0761(5) 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 C5 C14 C13 116.50(10) yes C5 C14 C1 115.2(2) yes C13 C14 C1 128.40(10) yes C14 C5 N6 123.4(2) yes C14 C5 C4 121.40(10) yes N6 C5 C4 115.2(2) yes C5 N6 N7 120.0(2) yes C13 C8 C9 120.7(2) yes C13 C8 N7 123.5(2) yes C9 C8 N7 115.9(2) yes C14 C13 C8 115.60(10) yes C14 C13 C12 126.9(2) yes C8 C13 C12 117.5(2) yes C5 C4 C3 120.5(2) yes C5 C4 H41 116.0(10) no C3 C4 H41 123.0(10) no C8 C9 C10 120.0(2) yes C8 C9 H91 120.1(2) no C10 C9 H91 120.0(2) no N6 N7 C8 120.60(10) yes C1 C2 C3 119.6(2) yes C1 C2 H21 123.0(10) no C3 C2 H21 117.0(10) no C14 C1 C2 123.5(2) yes C14 C1 N8 120.8(2) yes C2 C1 N8 115.60(10) yes C4 C3 C2 119.7(2) yes C4 C3 H31 120.0(10) no C2 C3 H31 120.0(10) no C13 C12 C11 121.0(2) yes C13 C12 H121 122.0(10) no C11 C12 H121 117.0(10) no C1 N8 O1 117.60(10) yes C1 N8 O2 118.1(2) yes O1 N8 O2 124.2(2) yes C9 C10 C11 120.3(2) yes C9 C10 H101 119.8(2) no C11 C10 H101 119.9(2) no C12 C11 C10 120.4(2) yes C12 C11 H111 119.9(2) no C10 C11 H111 119.6(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C14 C5 . . 1.411(2) yes C14 C13 . . 1.441(2) yes C14 C1 . . 1.407(2) yes C5 N6 . . 1.386(2) yes C4 C5 . . 1.408(3) yes N6 N7 . . 1.284(3) yes C8 C13 . . 1.412(2) yes C8 C9 . . 1.408(3) yes C8 N7 . . 1.388(2) yes C13 C12 . . 1.403(3) yes C3 C4 . . 1.362(3) yes C4 H41 . . 0.92(2) no C9 C10 . . 1.359(3) yes C9 H91 . . 0.950(2) no C1 C2 . . 1.370(3) yes C2 C3 . . 1.391(3) yes C2 H21 . . 0.95(2) no C1 N8 . . 1.467(2) yes C3 H31 . . 0.95(2) no C11 C12 . . 1.377(3) yes C12 H121 . . 0.96(2) no N8 O1 . . 1.218(2) yes N8 O2 . . 1.211(2) yes C10 C11 . . 1.395(3) yes C10 H101 . . 0.950(2) no C11 H111 . . 0.950(2) no 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 C13 C14 C5 N6 5.2(2) yes C13 C14 C5 C4 -176.2(2) yes C1 C14 C5 N6 -175.1(2) yes C1 C14 C5 C4 3.6(2) yes C5 C14 C13 C8 -7.3(2) yes C5 C14 C13 C12 171.6(2) no C1 C14 C13 C8 173.0(2) no C1 C14 C13 C12 -8.0(3) no C5 C14 C1 C2 -3.6(2) no C5 C14 C1 N8 172.20(10) no C13 C14 C1 C2 176.1(2) no C13 C14 C1 N8 -8.1(3) yes C14 C5 N6 N7 0.6(3) no C4 C5 N6 N7 -178.2(2) no C14 C5 C4 C3 -0.8(3) yes N6 C5 C4 C3 177.9(2) no C5 N6 N7 C8 -3.8(2) no C9 C8 C13 C14 -176.9(2) no C9 C8 C13 C12 4.0(3) yes N7 C8 C13 C14 4.7(2) no N7 C8 C13 C12 -174.4(2) no C13 C8 C9 C10 -1.8(3) no N7 C8 C9 C10 176.7(2) no C13 C8 N7 N6 1.1(3) no C9 C8 N7 N6 -177.4(2) no C14 C13 C12 C11 177.8(2) no C8 C13 C12 C11 -3.3(3) no C5 C4 C3 C2 -2.2(3) no C8 C9 C10 C11 -1.3(3) no C3 C2 C1 C14 0.8(3) no C3 C2 C1 N8 -175.2(2) no C1 C2 C3 C4 2.2(3) no C14 C1 N8 O1 -65.7(2) yes C14 C1 N8 O2 116.1(2) yes C2 C1 N8 O1 110.4(2) yes C2 C1 N8 O2 -67.8(2) yes C13 C12 C11 C10 0.3(3) no C9 C10 C11 C12 2.1(3) no