#------------------------------------------------------------------------------ #$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/00/2200042.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_2200042 loop_ _publ_author_name 'Lynch, Daniel E.' 'McClenaghan, Ian' _publ_section_title ; 4-Methoxy-3-nitropyridinium chloride ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o83 _journal_page_last o84 _journal_paper_doi 10.1107/S1600536800020729 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C6 H7 N2 O3 1+, Cl 1-' _chemical_formula_moiety 'C6 H7 N2 O3 1+, Cl 1-' _chemical_formula_sum 'C6 H7 Cl N2 O3' _chemical_formula_weight 190.59 _chemical_name_systematic ; 4-Methoxy-3-nitropyridinium chloride ; _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 111.523(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.6185(4) _cell_length_b 7.1517(4) _cell_length_c 11.3701(5) _cell_measurement_reflns_used 4004 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.9 _cell_volume 803.24(7) _computing_cell_refinement 'DENZO and COLLECT' _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO and COLLECT' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full .992 _diffrn_measured_fraction_theta_max .992 _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .042 _diffrn_reflns_av_sigmaI/netI .052 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 5993 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 3.3 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .44 _exptl_absorpt_correction_T_max .957 _exptl_absorpt_correction_T_min .937 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.576 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 392 _exptl_crystal_size_max .15 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .10 _refine_diff_density_max .25 _refine_diff_density_min -.26 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.00 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 114 _refine_ls_number_reflns 1835 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.00 _refine_ls_R_factor_all .078 _refine_ls_R_factor_gt .043 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0664P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .121 _reflns_number_gt 1219 _reflns_number_total 1835 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cf6034.cif _cod_data_source_block I _cod_original_cell_volume 803.24(6) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2200042 _cod_database_fobs_code 2200042 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_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 Cl1 .14928(5) -.48448(7) .68197(5) .0504(2) Uani d . 1 . . Cl N1 .29721(17) -.4262(3) .95746(18) .0483(5) Uani d . 1 . . N H1 .245(2) -.426(4) .870(3) .078(8) Uiso d . 1 . . H C2 .3021(2) -.2817(3) 1.03233(19) .0455(5) Uani d . 1 . . C H2 .2585 -.1676 .9975 .057 Uiso calc R 1 . . H C3 .37018(18) -.2979(3) 1.15977(17) .0387(5) Uani d . 1 . . C N31 .36643(19) -.1332(2) 1.23515(17) .0500(5) Uani d . 1 . . N O31 .29498(18) -.0033(2) 1.18145(18) .0687(5) Uani d . 1 . . O O32 .4352(2) -.1318(2) 1.34665(16) .0872(6) Uani d . 1 . . O C4 .43571(18) -.4643(3) 1.21323(18) .0377(5) Uani d . 1 . . C O41 .49836(15) -.47804(18) 1.33625(13) .0460(4) Uani d . 1 . . O C42 .5523(2) -.6580(3) 1.3888(2) .0584(6) Uani d . 1 . . C H421 .4788 -.7501 1.3661 .073 Uiso calc R 1 . . H H422 .5939 -.6482 1.4811 .073 Uiso calc R 1 . . H H423 .6205 -.6977 1.3549 .073 Uiso calc R 1 . . H C5 .42871(19) -.6114(3) 1.12890(18) .0426(5) Uani d . 1 . . C H5 .4727 -.7268 1.1597 .053 Uiso calc R 1 . . H C6 .35892(19) -.5873(3) 1.00372(19) .0462(5) Uani d . 1 . . C H6 .3537 -.6877 .9474 .058 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 Cl1 .0667(4) .0442(4) .0359(3) -.0050(2) .0138(3) .0012(2) N1 .0532(10) .0567(12) .0342(10) -.0028(9) .0150(9) -.0030(9) C2 .0552(12) .0428(12) .0408(12) .0066(10) .0203(10) .0073(9) C3 .0499(11) .0323(10) .0374(11) -.0019(8) .0199(9) -.0027(8) N31 .0715(12) .0371(10) .0475(12) -.0018(9) .0289(10) -.0029(8) O31 .0751(11) .0511(11) .0778(13) .0212(8) .0255(10) -.0042(8) O32 .1658(19) .0456(11) .0422(10) .0023(11) .0285(11) -.0065(8) C4 .0420(10) .0394(11) .0328(11) -.0050(8) .0149(9) -.0020(8) O41 .0550(8) .0447(9) .0331(8) .0060(6) .0101(7) .0010(6) C42 .0693(14) .0559(14) .0452(13) .0136(12) .0152(11) .0104(11) C5 .0498(11) .0343(11) .0448(12) -.0022(9) .0187(10) -.0014(9) C6 .0543(12) .0438(12) .0440(12) -.0107(10) .0223(10) -.0109(10) 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' Cl Cl .1484 .1585 '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 C2 N1 C6 121.42(19) C2 N1 H1 123.0(16) C6 N1 H1 115.4(16) N1 C2 C3 119.7(2) N1 C2 H2 120.2 C3 C2 H2 120.2 C2 C3 C4 121.19(17) C2 C3 N31 115.77(18) C4 C3 N31 123.02(17) O32 N31 O31 123.16(18) O32 N31 C3 118.99(18) O31 N31 C3 117.85(18) O41 C4 C3 120.20(17) O41 C4 C5 123.30(17) C3 C4 C5 116.50(18) C4 O41 C42 118.42(16) O41 C42 H421 109.5 O41 C42 H422 109.5 H421 C42 H422 109.5 O41 C42 H423 109.5 H421 C42 H423 109.5 H422 C42 H423 109.5 C6 C5 C4 119.58(18) C6 C5 H5 120.2 C4 C5 H5 120.2 N1 C6 C5 121.63(19) N1 C6 H6 119.2 C5 C6 H6 119.2 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 N1 C2 . 1.328(3) ? N1 C6 . 1.335(3) ? N1 H1 . .94(3) ? C2 C3 . 1.366(3) ? C2 H2 . .95 ? C3 C4 . 1.400(3) ? C3 N31 . 1.466(2) ? N31 O32 . 1.209(2) ? N31 O31 . 1.213(2) ? C4 O41 . 1.314(2) ? C4 C5 . 1.407(3) ? O41 C42 . 1.446(2) ? C42 H421 . .98 ? C42 H422 . .98 ? C42 H423 . .98 ? C5 C6 . 1.353(3) ? C5 H5 . .95 ? C6 H6 . .95 ? 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 N1 H1 Cl1 . .94(3) 2.05(3) 2.974(2) 167(2) yes C5 H5 Cl1 2_535 .95 2.74 3.629(2) 157 yes C6 H6 Cl1 4_657 .95 2.58 3.521(2) 173 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 C6 N1 C2 C3 -.8(3) N1 C2 C3 C4 .3(3) N1 C2 C3 N31 -178.12(16) C2 C3 N31 O32 -172.9(2) C4 C3 N31 O32 8.7(3) C2 C3 N31 O31 6.2(3) C4 C3 N31 O31 -172.20(18) C2 C3 C4 O41 -178.69(17) N31 C3 C4 O41 -.4(3) C2 C3 C4 C5 .7(3) N31 C3 C4 C5 178.98(16) C3 C4 O41 C42 173.49(18) C5 C4 O41 C42 -5.8(3) O41 C4 C5 C6 178.18(18) C3 C4 C5 C6 -1.2(3) C2 N1 C6 C5 .3(3) C4 C5 C6 N1 .7(3)