#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/03/2200394.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_2200394 loop_ _publ_author_name 'Ishida, Hiroyuki' 'Rahman, Bilkish' 'Kashino, Setsuo' _publ_section_title ; Imidazolium 2-chloro-4-nitrobenzoate ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o744 _journal_page_last o745 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C3 H5 N2 1+, C7 H3 Cl N O4 1-' _chemical_formula_moiety 'C3 H5 N2 1+, C7 H3 Cl N O4 1-' _chemical_formula_sum 'C10 H8 Cl N3 O4' _chemical_formula_weight 269.64 _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90 _cell_angle_beta 98.998(17) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.078(2) _cell_length_b 5.928(2) _cell_length_c 10.7711(18) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298 _cell_measurement_theta_max 12.4 _cell_measurement_theta_min 11.9 _cell_volume 572.5(3) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990) ; _computing_data_reduction 'TEXSAN for Windows (MSC, 1997-1999)' _computing_publication_material 'TEXSAN for Windows' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 298 _diffrn_measured_fraction_theta_full 1.0 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measurement_device 'Rigaku AFC-5R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0141 _diffrn_reflns_av_sigmaI/netI .0309 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 3945 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_theta_min 1.91 _diffrn_standards_decay_% -3.35 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .344 _exptl_absorpt_correction_T_max .934 _exptl_absorpt_correction_T_min .874 _exptl_absorpt_correction_type '\y scans' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 276.0 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .20 _refine_diff_density_max .192 _refine_diff_density_min -.229 _refine_ls_abs_structure_details 'Flack, 1983' _refine_ls_abs_structure_Flack .02(6) _refine_ls_extinction_coef .012(3) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 186 _refine_ls_number_reflns 2652 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.04 _refine_ls_R_factor_all .050 _refine_ls_R_factor_gt .032 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0320P)^2^+0.0911P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .076 _reflns_number_gt 2141 _reflns_number_total 2652 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt6065.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21' _[local]_cod_chemical_formula_sum_orig 'C10 H8 Cl N3 O4 ' _cod_original_cell_volume 572.5(2) _cod_database_code 2200394 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y, -z' 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 Cl .45183(6) .0000 .29755(5) .04751(16) Uani d . 1 . . Cl O1 .74535(15) .4499(4) .22182(14) .0495(5) Uani d . 1 . . O O2 .62065(16) .4708(4) .38425(13) .0537(5) Uani d . 1 . . O O3 .01305(18) .1510(4) -.06683(15) .0621(6) Uani d . 1 . . O O4 .07838(19) .4224(4) -.17668(15) .0594(5) Uani d . 1 . . O N1 .09824(19) .2993(4) -.08466(16) .0395(5) Uani d . 1 . . N N2 1.02363(19) .4034(4) .34032(16) .0415(5) Uani d . 1 . . N N3 1.2021(2) .2496(4) .46630(17) .0472(5) Uani d . 1 . . N C1 .4868(2) .3989(4) .18143(16) .0277(4) Uani d . 1 . . C C2 .3997(2) .2080(4) .18574(16) .0305(4) Uani d . 1 . . C C3 .2705(2) .1727(4) .09930(18) .0323(4) Uani d . 1 . . C C4 .2327(2) .3355(4) .00901(17) .0303(4) Uani d . 1 . . C C5 .3142(2) .5281(4) .00019(17) .0331(5) Uani d . 1 . . C C6 .4427(2) .5574(4) .08744(18) .0321(5) Uani d . 1 . . C C7 .6310(2) .4420(4) .27148(17) .0334(5) Uani d . 1 . . C C8 1.0628(3) .2256(5) .4102(2) .0456(6) Uani d . 1 . . C C9 1.2542(2) .4500(5) .4300(2) .0510(7) Uani d . 1 . . C C10 1.1424(2) .5479(5) .3511(2) .0473(6) Uani d . 1 . . C H1 .218(2) .046(4) .1032(19) .038(6) Uiso d . 1 . . H H2 .282(2) .639(4) -.063(2) .041(6) Uiso d . 1 . . H H3 .502(2) .690(5) .083(2) .038(6) Uiso d . 1 . . H H4 .924(3) .417(6) .286(3) .076(9) Uiso d . 1 . . H H5 1.000(3) .103(4) .419(2) .047(7) Uiso d . 1 . . H H6 1.259(3) .133(6) .526(3) .083(10) Uiso d . 1 . . H H7 1.354(3) .509(5) .458(2) .061(7) Uiso d . 1 . . H H8 1.142(3) .688(6) .304(2) .056(8) Uiso d . 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 Cl .0582(3) .0378(3) .0403(2) -.0027(3) -.0116(2) .0075(3) O1 .0226(6) .0747(16) .0480(8) -.0026(8) -.0050(6) -.0020(9) O2 .0458(8) .0766(15) .0350(6) -.0165(9) -.0053(6) -.0144(9) O3 .0396(9) .0869(15) .0543(10) -.0306(10) -.0096(7) .0041(10) O4 .0554(10) .0678(14) .0451(8) -.0080(10) -.0227(7) .0114(8) N1 .0270(8) .0523(13) .0354(9) -.0035(8) -.0071(7) -.0043(8) N2 .0296(9) .0551(13) .0360(8) .0028(9) -.0063(7) .0021(8) N3 .0396(10) .0612(16) .0373(9) .0118(10) -.0054(8) .0080(9) C1 .0223(8) .0315(11) .0282(8) -.0019(8) .0003(6) -.0072(8) C2 .0303(9) .0316(11) .0279(8) .0012(9) -.0004(7) .0004(8) C3 .0281(9) .0345(12) .0327(9) -.0081(9) .0000(7) -.0023(9) C4 .0199(8) .0398(12) .0289(8) .0004(8) -.0031(7) -.0037(8) C5 .0294(9) .0380(13) .0303(8) .0012(9) -.0007(7) .0025(9) C6 .0288(9) .0327(13) .0340(9) -.0057(8) .0021(7) -.0004(8) C7 .0276(9) .0335(13) .0352(9) -.0039(9) -.0073(7) -.0020(8) C8 .0413(12) .0552(17) .0377(10) -.0010(12) -.0019(9) .0067(11) C9 .0304(10) .075(2) .0437(10) -.0055(12) -.0066(8) .0092(12) C10 .0387(12) .0556(19) .0434(11) -.0013(11) -.0065(9) .0089(11) 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 Cl C2 . 1.737(2) yes O1 C7 . 1.241(2) yes O2 C7 . 1.245(2) yes O3 N1 . 1.206(3) yes O4 N1 . 1.221(2) yes N1 C4 . 1.473(2) yes N2 C8 . 1.311(3) yes N2 C10 . 1.368(3) yes N2 H4 . 1.00(3) ? N3 C8 . 1.321(3) yes N3 C9 . 1.358(4) yes N3 H6 . 1.03(3) ? C1 C2 . 1.385(3) yes C1 C6 . 1.393(3) yes C1 C7 . 1.524(2) yes C2 C3 . 1.395(2) yes C3 C4 . 1.375(3) yes C3 H1 . .89(3) ? C4 C5 . 1.372(3) yes C5 C6 . 1.390(3) yes C5 H2 . .96(2) ? C6 H3 . .96(2) ? C8 H5 . .94(3) ? C9 C10 . 1.349(3) yes C9 H7 . .97(3) ? C10 H8 . .97(3) ? 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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 -2 0 0 -2 -2 1 -2 1 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 O3 N1 O4 123.23(17) ? O3 N1 C4 118.70(18) ? O4 N1 C4 118.07(19) ? C8 N2 C10 108.37(19) yes C8 N2 H4 123(2) ? C10 N2 H4 128.9(19) ? C8 N3 C9 108.3(2) yes C8 N3 H6 124.6(18) ? C9 N3 H6 127.0(17) ? C2 C1 C6 118.37(16) ? C2 C1 C7 123.59(18) ? C6 C1 C7 118.01(18) ? C1 C2 C3 121.66(18) ? C1 C2 Cl 120.56(14) ? C3 C2 Cl 117.75(17) ? C4 C3 C2 117.24(19) ? C4 C3 H1 123.2(14) ? C2 C3 H1 119.6(14) ? C5 C4 C3 123.74(17) ? C5 C4 N1 118.14(18) ? C3 C4 N1 118.11(18) ? C4 C5 C6 117.50(19) ? C4 C5 H2 120.8(14) ? C6 C5 H2 121.7(14) ? C5 C6 C1 121.5(2) ? C5 C6 H3 119.4(14) ? C1 C6 H3 119.2(14) ? O1 C7 O2 127.68(17) ? O1 C7 C1 115.17(16) ? O2 C7 C1 117.12(17) ? N2 C8 N3 109.3(2) yes N2 C8 H5 124.6(15) ? N3 C8 H5 126.1(15) ? C10 C9 N3 107.2(2) yes C10 C9 H7 127.9(17) ? N3 C9 H7 124.9(17) ? C9 C10 N2 106.8(2) yes C9 C10 H8 129.6(16) ? N2 C10 H8 123.5(15) ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 N2 2.661(2) . no O1 N1 3.024(3) 2_655 no O1 O3 3.188(3) 2_655 no O2 N3 2.665(3) 2_756 no O3 N1 2.923(3) 2_545 no O3 C4 3.049(3) 2_545 no O3 O4 3.176(3) 2_545 no O3 N2 3.261(3) 2_645 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 H4 O1 . 1.00(3) 1.67(3) 2.661(2) 169(3) yes N3 H6 O2 2_746 1.03(3) 1.65(3) 2.665(3) 169(3) yes C5 H2 O1 2_655 .96(2) 2.50(2) 3.444(3) 168.0(15) yes C10 H8 O4 2_655 .97(3) 2.64(3) 3.361(3) 131(2) 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 C1 C2 C3 -.3(3) C7 C1 C2 C3 -178.3(2) C6 C1 C2 Cl 177.95(15) C7 C1 C2 Cl -.1(3) C1 C2 C3 C4 .1(3) Cl C2 C3 C4 -178.18(15) C2 C3 C4 C5 -.2(3) C2 C3 C4 N1 178.84(19) O3 N1 C4 C5 -168.3(2) O4 N1 C4 C5 11.4(3) O3 N1 C4 C3 12.5(3) O4 N1 C4 C3 -167.7(2) C3 C4 C5 C6 .6(3) N1 C4 C5 C6 -178.51(19) C4 C5 C6 C1 -.8(3) C2 C1 C6 C5 .6(3) C7 C1 C6 C5 178.75(19) C2 C1 C7 O1 116.0(2) C6 C1 C7 O1 -62.1(3) C2 C1 C7 O2 -65.9(3) C6 C1 C7 O2 116.1(2) C10 N2 C8 N3 .3(3) C9 N3 C8 N2 -.5(3) C8 N3 C9 C10 .5(3) N3 C9 C10 N2 -.3(3) C8 N2 C10 C9 .0(3)