#------------------------------------------------------------------------------ #$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176789 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/22/23/2222329.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_paper_doi 10.1107/S1600536809022582 _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) _cod_data_source_file hb5007.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2222329 _cod_database_fobs_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_calc_flag _atom_site_refinement_flags _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_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_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_site_symmetry_1 _geom_bond_site_symmetry_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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_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