#------------------------------------------------------------------------------ #$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $ #$Revision: 176798 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/23/45/2234543.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_2234543 loop_ _publ_author_name 'Thies, Steffen' 'N\"ather, Christian' 'Herges, Rainer' _publ_section_title ; Bis(4-methoxypyridin-3-yl)diazene ; _journal_coeditor_code BT5885 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1568 _journal_paper_doi 10.1107/S1600536812018326 _journal_volume 68 _journal_year 2012 _chemical_formula_iupac 'C12 H12 N4 O2' _chemical_formula_moiety 'C12 H12 N4 O2' _chemical_formula_sum 'C12 H12 N4 O2' _chemical_formula_weight 244.26 _chemical_name_systematic ; Bis(4-methoxypyridin-3-yl)diazene ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.3976(8) _cell_length_b 6.2101(6) _cell_length_c 13.6079(9) _cell_measurement_reflns_used 4972 _cell_measurement_temperature 220(2) _cell_measurement_theta_max 28.8 _cell_measurement_theta_min 4.7 _cell_volume 1132.18(15) _computing_cell_refinement 'X-AREA (Stoe & Cie, 2008)' _computing_data_collection 'X-AREA (Stoe & Cie, 2008)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2008)' _computing_molecular_graphics 'XP in SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 220(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Stoe IPDS-1' _diffrn_measurement_method 'Phi scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 5829 _diffrn_reflns_theta_full 27.10 _diffrn_reflns_theta_max 27.10 _diffrn_reflns_theta_min 2.99 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 512 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.264 _refine_diff_density_min -0.190 _refine_ls_extinction_coef 0.030(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)' _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 84 _refine_ls_number_reflns 1235 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0385 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0625P)^2^+0.2040P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0980 _refine_ls_wR_factor_ref 0.1049 _reflns_number_gt 1002 _reflns_number_total 1235 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt5885.cif _cod_data_source_block I _cod_database_code 2234543 _cod_database_fobs_code 2234543 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' loop_ _atom_site_type_symbol _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_symmetry_multiplicity N N1 0.66974(9) 0.6358(2) 0.34371(9) 0.0314(3) Uani d . 1 1 C C1 0.62249(10) 0.7907(2) 0.39360(9) 0.0263(3) Uani d . 1 1 H H1 0.6591 0.9134 0.4119 0.032 Uiso calc R 1 1 C C2 0.52211(9) 0.7811(2) 0.42010(8) 0.0211(3) Uani d . 1 1 C C3 0.46546(10) 0.60269(19) 0.38987(8) 0.0205(3) Uani d . 1 1 C C4 0.51423(10) 0.4414(2) 0.33786(9) 0.0250(3) Uani d . 1 1 H H4 0.4794 0.3190 0.3161 0.030 Uiso calc R 1 1 C C5 0.61506(11) 0.4644(2) 0.31870(10) 0.0301(3) Uani d . 1 1 H H5 0.6475 0.3513 0.2857 0.036 Uiso calc R 1 1 N N2 0.47208(8) 0.94965(17) 0.47068(7) 0.0228(3) Uani d . 1 1 O O1 0.36924(7) 0.60036(15) 0.41627(7) 0.0277(3) Uani d . 1 1 C C6 0.30947(11) 0.4230(2) 0.38338(11) 0.0321(4) Uani d . 1 1 H H6A 0.3032 0.4284 0.3124 0.048 Uiso calc R 1 1 H H6B 0.2438 0.4320 0.4130 0.048 Uiso calc R 1 1 H H6C 0.3410 0.2888 0.4024 0.048 Uiso calc R 1 1 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 0.0230(6) 0.0348(6) 0.0364(7) -0.0008(5) 0.0067(5) -0.0042(5) C1 0.0237(7) 0.0271(7) 0.0280(6) -0.0044(5) 0.0010(5) -0.0020(5) C2 0.0227(6) 0.0202(6) 0.0203(5) 0.0000(5) -0.0014(4) -0.0006(4) C3 0.0200(6) 0.0208(6) 0.0205(6) 0.0011(5) -0.0014(4) 0.0011(4) C4 0.0273(7) 0.0216(6) 0.0261(6) -0.0009(5) -0.0004(5) -0.0045(5) C5 0.0292(7) 0.0283(7) 0.0329(7) 0.0039(6) 0.0052(5) -0.0058(5) N2 0.0231(5) 0.0202(5) 0.0251(5) -0.0017(4) -0.0012(4) -0.0022(4) O1 0.0193(5) 0.0241(5) 0.0396(6) -0.0030(4) 0.0020(4) -0.0086(4) C6 0.0230(7) 0.0288(7) 0.0444(8) -0.0068(6) -0.0037(6) -0.0068(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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_site_symmetry_1 _geom_angle C5 N1 C1 . 116.29(12) N1 C1 C2 . 123.89(12) N1 C1 H1 . 118.1 C2 C1 H1 . 118.1 C1 C2 C3 . 118.65(11) C1 C2 N2 . 123.30(11) C3 C2 N2 . 117.91(11) O1 C3 C4 . 125.58(11) O1 C3 C2 . 116.77(11) C4 C3 C2 . 117.62(12) C5 C4 C3 . 118.73(12) C5 C4 H4 . 120.6 C3 C4 H4 . 120.6 N1 C5 C4 . 124.74(13) N1 C5 H5 . 117.6 C4 C5 H5 . 117.6 N2 N2 C2 5_676 113.10(14) C3 O1 C6 . 117.56(10) O1 C6 H6A . 109.5 O1 C6 H6B . 109.5 H6A C6 H6B . 109.5 O1 C6 H6C . 109.5 H6A C6 H6C . 109.5 H6B C6 H6C . 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance N1 C5 . 1.3360(19) N1 C1 . 1.3369(18) C1 C2 . 1.3936(18) C1 H1 . 0.9400 C2 C3 . 1.4044(17) C2 N2 . 1.4209(16) C3 O1 . 1.3384(16) C3 C4 . 1.3897(17) C4 C5 . 1.3832(19) C4 H4 . 0.9400 C5 H5 . 0.9400 N2 N2 5_676 1.260(2) O1 C6 . 1.4333(16) C6 H6A . 0.9700 C6 H6B . 0.9700 C6 H6C . 0.9700