#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2222329.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_2222329 loop_ _publ_author_name 'Khan, Misbahul Ain' 'Tahir, M. Nawaz' 'Ather, Abdul Qayyum' 'Shaheen, Maryam' 'Khan, Rauf Ahmad' _publ_section_title ; 4-Methyl-3-nitropyridin-2-amine ; _journal_coeditor_code HB5007 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1615 _journal_volume 65 _journal_year 2009 _chemical_formula_iupac 'C6 H7 N3 O2' _chemical_formula_moiety 'C6 H7 N3 O2' _chemical_formula_sum 'C6 H7 N3 O2' _chemical_formula_weight 153.15 _chemical_name_systematic ; 4-Methyl-3-nitropyridin-2-amine ; _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_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 104.364(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.3776(6) _cell_length_b 12.8673(11) _cell_length_c 7.3884(6) _cell_measurement_reflns_used 1677 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.31 _cell_measurement_theta_min 3.17 _cell_volume 679.45(10) _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material 'WinGx (Farrugia, 1999) and PLATON (Spek, 2009)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 7.40 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker Kappa APEXII CCD' _diffrn_measurement_method \w _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 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0709 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 7483 _diffrn_reflns_theta_full 28.31 _diffrn_reflns_theta_max 28.31 _diffrn_reflns_theta_min 3.17 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_correction_T_min 0.985 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2005)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.392 _refine_diff_density_min -0.315 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 107 _refine_ls_number_reflns 1677 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.003 _refine_ls_R_factor_all 0.1515 _refine_ls_R_factor_gt 0.0555 _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^)+(0.0745P)^2^+0.0769P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1321 _refine_ls_wR_factor_ref 0.1730 _reflns_number_gt 759 _reflns_number_total 1677 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hb5007.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2222329 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z 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 0.0667(16) 0.0497(16) 0.127(2) -0.0025(12) -0.0035(14) 0.0240(14) O2 0.0609(15) 0.0759(19) 0.110(2) 0.0105(13) -0.0247(14) 0.0200(14) N1 0.0373(12) 0.0424(14) 0.0475(13) 0.0041(11) 0.0096(10) -0.0006(11) N2 0.0399(13) 0.0506(17) 0.0639(16) -0.0020(13) 0.0048(12) 0.0097(14) N3 0.0416(14) 0.0502(17) 0.0506(14) 0.0091(12) 0.0110(12) 0.0076(12) C1 0.0355(14) 0.0427(16) 0.0394(14) 0.0019(13) 0.0126(11) -0.0016(12) C2 0.0356(15) 0.0404(16) 0.0378(14) 0.0070(12) 0.0101(11) 0.0004(12) C3 0.0361(14) 0.0500(18) 0.0354(14) 0.0038(13) 0.0090(11) -0.0046(12) C4 0.0493(18) 0.0399(17) 0.0547(17) -0.0042(14) 0.0126(14) -0.0032(14) C5 0.0495(18) 0.0421(17) 0.0492(16) 0.0105(14) 0.0110(13) -0.0001(13) C6 0.0391(16) 0.066(2) 0.0589(18) -0.0051(14) 0.0077(13) -0.0058(16) 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_thermal_displace_type _atom_site_occupancy O O1 0.9915(3) -0.20091(18) 0.2978(3) 0.0860(10) Uani 1.000 O O2 1.2249(3) -0.11801(19) 0.4483(4) 0.0904(10) Uani 1.000 N N1 0.7197(3) 0.06783(18) 0.0831(3) 0.0426(8) Uani 1.000 N N2 0.6845(4) -0.1039(2) 0.1310(3) 0.0529(9) Uani 1.000 N N3 1.0759(3) -0.11908(19) 0.3358(3) 0.0475(9) Uani 1.000 C C1 0.8004(4) -0.0221(2) 0.1552(3) 0.0386(8) Uani 1.000 C C2 0.9935(3) -0.0238(2) 0.2507(3) 0.0378(9) Uani 1.000 C C3 1.1041(3) 0.0656(2) 0.2608(3) 0.0405(9) Uani 1.000 C C4 1.0135(4) 0.1542(2) 0.1803(4) 0.0480(10) Uani 1.000 C C5 0.8246(4) 0.1511(2) 0.0979(4) 0.0472(10) Uani 1.000 C C6 1.3108(4) 0.0719(3) 0.3480(4) 0.0555(10) Uani 1.000 H H2A 0.570(5) -0.089(2) 0.066(4) 0.0635 Uiso 1.000 H H2B 0.730(4) -0.164(2) 0.156(4) 0.0635 Uiso 1.000 H H4 1.07986 0.21582 0.18170 0.0576 Uiso 1.000 H H5 0.76702 0.21275 0.04899 0.0566 Uiso 1.000 H H6A 1.35738 0.13785 0.31888 0.0666 Uiso 1.000 H H6B 1.37365 0.01708 0.29973 0.0666 Uiso 1.000 H H6C 1.33334 0.06475 0.48107 0.0666 Uiso 1.000 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 _geom_angle_publ_flag C1 N1 C5 118.4(2) n O1 N3 O2 119.7(2) n O1 N3 C2 119.9(2) n O2 N3 C2 120.4(2) n H2A N2 H2B 126(3) no C1 N2 H2A 113.3(18) no C1 N2 H2B 119(2) no N1 C1 N2 114.6(3) n N1 C1 C2 119.9(2) n N2 C1 C2 125.5(2) n N3 C2 C1 119.4(2) n N3 C2 C3 119.9(2) n C1 C2 C3 120.8(2) no C2 C3 C6 125.6(2) no C2 C3 C4 116.2(2) no C4 C3 C6 118.2(3) no C3 C4 C5 119.7(2) no N1 C5 C4 125.0(3) n C3 C4 H4 120.00 no C5 C4 H4 120.00 no N1 C5 H5 118.00 no C4 C5 H5 118.00 no C3 C6 H6A 109.00 no C3 C6 H6B 109.00 no C3 C6 H6C 109.00 no H6A C6 H6B 109.00 no H6A C6 H6C 109.00 no H6B C6 H6C 109.00 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 N3 1.220(3) n O2 N3 1.203(3) n N1 C1 1.349(3) n N1 C5 1.310(4) n N2 C1 1.340(4) n N3 C2 1.442(3) n N2 H2B 0.85(3) no N2 H2A 0.88(3) no C1 C2 1.425(4) no C2 C3 1.402(4) no C3 C4 1.380(4) no C3 C6 1.503(4) no C4 C5 1.376(4) no C4 H4 0.9300 no C5 H5 0.9300 no C6 H6A 0.9600 no C6 H6B 0.9600 no C6 H6C 0.9600 no 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 N2 H2A N1 3_655 0.88(3) 2.17(4) 3.045(4) 174(3) yes N2 H2B O1 . 0.85(3) 2.01(3) 2.612(4) 127(2) yes N3 O2 Cg1 3_756 1.203(3) 3.2743(3) 3.681(12) 100.16(17) 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 _geom_torsion_publ_flag C5 N1 C1 N2 -178.7(2) no C5 N1 C1 C2 2.3(4) no C1 N1 C5 C4 0.8(4) no O1 N3 C2 C1 13.3(3) no O1 N3 C2 C3 -166.0(2) no O2 N3 C2 C1 -164.5(2) no O2 N3 C2 C3 16.2(4) no N1 C1 C2 N3 176.7(2) no N1 C1 C2 C3 -4.0(3) no N2 C1 C2 N3 -2.1(4) no N2 C1 C2 C3 177.2(2) no N3 C2 C3 C4 -178.3(2) no N3 C2 C3 C6 2.8(4) no C1 C2 C3 C4 2.4(3) no C1 C2 C3 C6 -176.4(2) no C2 C3 C4 C5 0.5(4) no C6 C3 C4 C5 179.5(3) no C3 C4 C5 N1 -2.3(5) no