############################################################################## # # # This CIF contains the data in a paper accepted for publication in # # Acta Crystallographica Section E. It conforms to the requirements of # # Notes for Authors for Acta Crystallographica Section E, and has been # # peer reviewed under the auspices of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. # # # # Software is freely available for graphical display of the structure(s) # # in this CIF. For information consult the CIF software page # # http://www.iucr.org/resources/cif/software. # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Carboxypyridinium nitrate ; _chemical_name_common ; Nicotinium nitrate ; _chemical_formula_moiety 'C6 H6 N O2 +, N O3 -' _chemical_formula_sum 'C6 H6 N2 O5' _chemical_formula_iupac 'C6 H6 N O2 +, N O3 -' _chemical_formula_weight 186.13 _chemical_melting_point ? _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7530(4) _cell_length_b 7.5024(4) _cell_length_c 8.4439(5) _cell_angle_alpha 81.895(2) _cell_angle_beta 82.2150(10) _cell_angle_gamma 66.769(2) _cell_volume 387.69(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 963 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 293(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 192 _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrystalClear; Rigaku, 2007)' _exptl_absorpt_correction_T_min 0.9455 _exptl_absorpt_correction_T_max 0.9860 _exptl_special_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.0 _diffrn_reflns_number 15468 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 1760 _reflns_number_gt 1102 _reflns_threshold_expression I>2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_gt 0.1245 _refine_ls_wR_factor_ref 0.1448 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _refine_ls_number_reflns 1760 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0739P)^2^+0.0250P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.189 _refine_diff_density_min -0.351 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'CrystalClear (Rigaku, 2007)' _computing_cell_refinement 'CrystalClear (Rigaku, 2007)' _computing_data_reduction 'CrystalClear (Rigaku, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2004)' _computing_publication_material 'publCIF (Westrip, 2010)' 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 _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.2671(2) -0.1191(2) 0.48174(17) 0.0528(4) Uani d . 1 2 . . H H1O 0.277(4) -0.232(4) 0.443(3) 0.079(8) Uiso d . 1 2 . . N N1 0.2399(3) 0.3328(2) 0.7169(2) 0.0461(5) Uani d . 1 2 . . H H1N 0.245(4) 0.449(4) 0.654(3) 0.086(9) Uiso d . 1 2 . . C C1 0.2321(3) -0.1404(3) 0.6385(2) 0.0405(5) Uani d . 1 2 . . O O2 0.2000(3) -0.2778(2) 0.71433(17) 0.0570(5) Uani d . 1 2 . . N N2 0.2859(3) 0.5132(2) 0.2675(2) 0.0461(4) Uani d . 1 2 . . C C2 0.2350(3) 0.0215(2) 0.7207(2) 0.0366(4) Uani d . 1 2 . . O O3 0.2861(3) 0.3523(2) 0.2502(2) 0.0723(6) Uani d . 1 2 . . C C3 0.2385(3) 0.1913(3) 0.6360(2) 0.0416(5) Uani d . 1 2 . . H H3 0.2399 0.2079 0.5247 0.050 Uiso calc R 1 2 . . O O4 0.2781(3) 0.5540(2) 0.40863(18) 0.0698(5) Uani d . 1 2 . . C C4 0.2393(3) 0.3167(3) 0.8764(3) 0.0483(5) Uani d . 1 2 . . H H4 0.2410 0.4182 0.9273 0.058 Uiso calc R 1 2 . . C C5 0.2361(3) 0.1507(3) 0.9645(2) 0.0497(5) Uani d . 1 2 . . H H5 0.2348 0.1381 1.0758 0.060 Uiso calc R 1 2 . . O O5 0.2917(3) 0.6324(3) 0.1555(2) 0.0817(6) Uani d . 1 2 . . C C6 0.2350(3) 0.0018(3) 0.8862(2) 0.0439(5) Uani d . 1 2 . . H H6 0.2341 -0.1126 0.9449 0.053 Uiso calc R 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 0.0802(11) 0.0451(9) 0.0395(9) -0.0309(8) 0.0008(7) -0.0094(6) N1 0.0598(11) 0.0313(9) 0.0518(11) -0.0232(8) -0.0029(8) -0.0032(7) C1 0.0501(11) 0.0346(10) 0.0389(11) -0.0185(9) -0.0027(8) -0.0052(8) O2 0.0937(12) 0.0416(8) 0.0482(9) -0.0412(8) -0.0003(8) -0.0045(7) N2 0.0578(11) 0.0445(10) 0.0380(9) -0.0205(8) -0.0065(7) -0.0053(7) C2 0.0447(10) 0.0304(9) 0.0364(10) -0.0171(8) -0.0010(8) -0.0033(7) O3 0.1120(14) 0.0623(11) 0.0602(11) -0.0464(10) -0.0100(9) -0.0208(8) C3 0.0533(12) 0.0346(10) 0.0390(10) -0.0202(9) -0.0018(8) -0.0025(8) O4 0.1353(15) 0.0522(10) 0.0359(9) -0.0481(10) -0.0118(9) -0.0077(7) C4 0.0580(13) 0.0421(11) 0.0514(13) -0.0237(10) -0.0038(9) -0.0126(9) C5 0.0660(14) 0.0477(12) 0.0408(12) -0.0264(11) -0.0052(10) -0.0077(9) O5 0.1135(15) 0.0740(12) 0.0513(10) -0.0380(11) -0.0075(9) 0.0208(9) C6 0.0585(12) 0.0352(10) 0.0419(11) -0.0230(9) -0.0024(9) -0.0031(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O1 C1 . 1.311(2) ? O1 H1O . 0.92(3) ? N1 C4 . 1.335(3) ? N1 C3 . 1.344(3) ? N1 H1N . 0.96(3) ? C1 O2 . 1.213(2) ? C1 C2 . 1.489(3) ? N2 O5 . 1.214(2) ? N2 O3 . 1.236(2) ? N2 O4 . 1.261(2) ? C2 C3 . 1.377(2) ? C2 C6 . 1.385(3) ? C3 H3 . 0.9300 ? C4 C5 . 1.364(3) ? C4 H4 . 0.9300 ? C5 C6 . 1.379(3) ? C5 H5 . 0.9300 ? C6 H6 . 0.9300 ? 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_3 _geom_angle _geom_angle_publ_flag C1 O1 H1O . . 107.7(16) ? C4 N1 C3 . . 123.13(17) ? C4 N1 H1N . . 120.2(16) ? C3 N1 H1N . . 116.7(16) ? O2 C1 O1 . . 124.77(18) ? O2 C1 C2 . . 121.11(18) ? O1 C1 C2 . . 114.11(16) ? O5 N2 O3 . . 123.04(18) ? O5 N2 O4 . . 119.22(18) ? O3 N2 O4 . . 117.74(17) ? C3 C2 C6 . . 118.80(17) ? C3 C2 C1 . . 121.64(17) ? C6 C2 C1 . . 119.56(16) ? N1 C3 C2 . . 118.93(18) ? N1 C3 H3 . . 120.5 ? C2 C3 H3 . . 120.5 ? N1 C4 C5 . . 119.72(18) ? N1 C4 H4 . . 120.1 ? C5 C4 H4 . . 120.1 ? C4 C5 C6 . . 119.0(2) ? C4 C5 H5 . . 120.5 ? C6 C5 H5 . . 120.5 ? C5 C6 C2 . . 120.39(18) ? C5 C6 H6 . . 119.8 ? C2 C6 H6 . . 119.8 ? 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 O1 H1O O4 1_545 0.92(3) 1.67(3) 2.5833(19) 169(2) N1 H1N O2 1_565 0.96(3) 2.08(3) 2.824(2) 133(2) N1 H1N O4 . 0.96(3) 2.12(3) 2.921(2) 139(2) C3 H3 O3 . 0.93 2.45 3.330(3) 157.7 C6 H6 O5 1_546 0.93 2.37 3.259(2) 159.9 C5 H5 O3 1_556 0.93 2.47 3.142(2) 128.9 _iucr_refine_instructions_details ; TITL MG571 IN P-1 CELL 0.71075 6.75300 7.50242 8.44392 81.89500 82.21500 66.76900 ZERR 2 0.00039 0.00039 0.00051 0.00200 0.00100 0.00200 LATT 1 SFAC C H N O UNIT 12 12 4 10 L.S. 15 FMAP 2 PLAN 10 BOND $H EQIV $1_X,-1+Y,Z EQIV $2_X,1+Y,Z EQIV $3_X,-1+Y,1+Z EQIV $4_X,Y,1+Z HTAB O1 O4_$1 HTAB N1 O2_$2 HTAB N1 O4 HTAB C3 O3 HTAB C6 O5_$3 HTAB C5 O3_$4 MPLA O1 O2 C1 C2 C3 N1 C4 C5 C6 OMIT -1 7 1 OMIT -1 7 2 OMIT 2 8 4 MPLA 8 O2 C1 C2 C3 N1 C4 C5 C6 O1 ACTA SIZE 0.400 0.200 0.100! COLORLESS BLOCK WGHT 0.073900 0.025000 FVAR 0.55766 0.00000 O1 4 0.267092 -0.119122 0.481741 11.00000 0.08023 0.04513 = 0.03951 -0.00942 0.00076 -0.03091 H1O 2 0.277375 -0.231698 0.442887 11.00000 0.07862 N1 3 0.239878 0.332813 0.716941 11.00000 0.05975 0.03132 = 0.05179 -0.00324 -0.00291 -0.02324 H1N 2 0.244560 0.448806 0.653703 11.00000 0.08577 C1 1 0.232145 -0.140437 0.638517 11.00000 0.05012 0.03460 = 0.03895 -0.00516 -0.00266 -0.01847 O2 4 0.200048 -0.277754 0.714332 11.00000 0.09371 0.04164 = 0.04824 -0.00448 -0.00029 -0.04120 N2 3 0.285947 0.513232 0.267482 11.00000 0.05775 0.04447 = 0.03796 -0.00532 -0.00650 -0.02046 C2 1 0.235018 0.021519 0.720698 11.00000 0.04471 0.03041 = 0.03641 -0.00331 -0.00104 -0.01708 O3 4 0.286111 0.352310 0.250215 11.00000 0.11203 0.06232 = 0.06024 -0.02076 -0.01000 -0.04644 C3 1 0.238520 0.191347 0.636046 11.00000 0.05333 0.03459 = 0.03896 -0.00251 -0.00177 -0.02025 AFIX 43 H3 2 0.239922 0.207873 0.524712 11.00000 -1.20000 AFIX 0 O4 4 0.278084 0.553956 0.408627 11.00000 0.13527 0.05217 = 0.03588 -0.00770 -0.01178 -0.04809 C4 1 0.239292 0.316672 0.876444 11.00000 0.05802 0.04213 = 0.05136 -0.01255 -0.00377 -0.02369 AFIX 43 H4 2 0.241034 0.418173 0.927280 11.00000 -1.20000 AFIX 0 C5 1 0.236129 0.150717 0.964541 11.00000 0.06602 0.04774 = 0.04075 -0.00771 -0.00522 -0.02635 AFIX 43 H5 2 0.234778 0.138136 1.075798 11.00000 -1.20000 AFIX 0 O5 4 0.291705 0.632378 0.155527 11.00000 0.11346 0.07401 = 0.05126 0.02076 -0.00750 -0.03803 C6 1 0.234963 0.001784 0.886222 11.00000 0.05850 0.03523 = 0.04192 -0.00310 -0.00243 -0.02301 AFIX 43 H6 2 0.234134 -0.112559 0.944944 11.00000 -1.20000 HKLF 4 REM MG571 IN P-1 REM R1 = 0.0497 for 1102 Fo > 4sig(Fo) and 0.0768 for all 1760 data REM 127 parameters refined using 0 restraints END WGHT 0.0746 0.0235 REM Highest difference peak 0.189, deepest hole -0.351, 1-sigma level 0.061 Q1 1 0.4448 -0.0749 0.3661 11.00000 0.05 0.19 Q2 1 0.3650 0.0621 1.2876 11.00000 0.05 0.18 Q3 1 0.2365 0.5804 0.4638 11.00000 0.05 0.17 Q4 1 0.0353 -0.2546 0.8791 11.00000 0.05 0.17 Q5 1 0.4494 0.1613 0.2739 11.00000 0.05 0.17 Q6 1 0.0997 -0.0735 0.9677 11.00000 0.05 0.17 Q7 1 0.5064 0.1857 0.7834 11.00000 0.05 0.16 Q8 1 0.2407 0.4578 0.1423 11.00000 0.05 0.16 Q9 1 0.2028 0.1384 1.1301 11.00000 0.05 0.16 Q10 1 0.4020 0.5375 0.6039 11.00000 0.05 0.15 ; data_global _journal_date_recd_electronic 2012-04-11 _journal_date_accepted 2012-06-23 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2012 _journal_volume 68 _journal_issue 7 _journal_page_first o2246 _journal_page_last o2246 _journal_paper_category QO _journal_paper_doi 10.1107/S1600536812028565 _journal_coeditor_code LX2240 _publ_contact_author_name 'Mohamed Ghazzali' _publ_contact_author_address ; Department of Chemistry, college of science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia ; _publ_contact_author_email 'mghazzali@ksu.edu.sa' _publ_contact_author_fax '0096614673922' _publ_contact_author_phone '0096614673734' _publ_section_title ; 3-Carboxypyridinium nitrate ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Al-Farhan, Khalid' . ; Department of Chemistry, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia ; 'Khair, Miftahul' . ; Department of Chemistry, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia ; 'Ghazzali, Mohamed' . ; Department of Chemistry, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia ;