#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/23/2012388.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_2012388 loop_ _publ_author_name 'Ishida, Hiroyuki' 'Rahman, Bilkish' Kashino,Setsuo _publ_section_title ; Morpholinium 2-chloro-4-nitrobenzoate, 2-chloro-5-nitrobenzoate and 4-chloro-3-nitrobenzoate ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1450 _journal_page_last 1453 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C4 H10 N O 1+, C7 H3 Cl N O4 1-' _chemical_formula_moiety 'C4 H10 N O 1+, C7 H3 Cl N O4 1-' _chemical_formula_sum 'C11 H13 Cl N2 O5' _chemical_formula_weight 288.69 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 93.35(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 18.680(6) _cell_length_b 10.498(3) _cell_length_c 13.125(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298 _cell_measurement_theta_max 12.5 _cell_measurement_theta_min 11.2 _cell_volume 2569.4(13) _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 (Molecular Structure Corporation, 1997-1999)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'TEXSAN for Windows' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _diffrn_ambient_temperature 298 _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _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 .025 _diffrn_reflns_av_sigmaI/netI .092 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 3215 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.18 _diffrn_standards_decay_% 1.47 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .316 _exptl_absorpt_correction_T_max .940 _exptl_absorpt_correction_T_min .884 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 1200 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .20 _refine_diff_density_max .26 _refine_diff_density_min -.24 _refine_ls_extinction_coef .0240(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.00 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 225 _refine_ls_number_reflns 2945 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.00 _refine_ls_R_factor_all .111 _refine_ls_R_factor_gt .046 _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^)+(0.0219P)^2^+1.0240P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .101 _refine_ls_wR_factor_ref .121 _reflns_number_gt 1741 _reflns_number_total 2945 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ob1046.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M 'C 2/c' _[local]_cod_chemical_formula_sum_orig 'C11 H13 Cl N2 O5 ' _cod_original_cell_volume 2569.5(13) _cod_database_code 2012388 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, +y,1/2-z' ' -x, -y, -z' ' +x, -y,1/2+z' '1/2+x,1/2+y, +z' 1/2-x,1/2+y,1/2-z '1/2-x,1/2-y, -z' 1/2+x,1/2-y,1/2+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 .58105(4) .37294(7) .32979(6) .0559(3) Uani d . 1 . . Cl O1 .61609(11) .00193(18) .36764(15) .0556(5) Uani d . 1 . . O O2 .58973(9) .14191(18) .48707(14) .0506(5) Uani d . 1 . . O O3 .92286(11) .2335(3) .30218(17) .0784(8) Uani d . 1 . . O O4 .89280(11) .0791(2) .3986(2) .0720(7) Uani d . 1 . . O O5 .31960(10) .29981(19) .43692(15) .0550(5) Uani d . 1 . . O N1 .87919(12) .1750(3) .34898(18) .0527(6) Uani d . 1 . . N N2 .44683(12) .1719(2) .50853(18) .0432(6) Uani d . 1 . . N C1 .68165(12) .1917(2) .37796(17) .0335(5) Uani d . 1 . . C C2 .66822(13) .3131(2) .33920(18) .0377(6) Uani d . 1 . . C C3 .72200(16) .3875(3) .3022(2) .0472(7) Uani d . 1 . . C C4 .79118(16) .3433(3) .3050(2) .0477(7) Uani d . 1 . . C C5 .80519(13) .2243(2) .34609(18) .0392(6) Uani d . 1 . . C C6 .75198(13) .1480(2) .38116(18) .0371(6) Uani d . 1 . . C C7 .62345(12) .1057(2) .41338(18) .0373(6) Uani d . 1 . . C C8 .41171(17) .1445(3) .4057(2) .0527(7) Uani d . 1 . . C C9 .33271(16) .1724(3) .4082(2) .0523(7) Uani d . 1 . . C C10 .35140(16) .3231(3) .5362(2) .0524(7) Uani d . 1 . . C C11 .43096(15) .3038(3) .5412(2) .0475(7) Uani d . 1 . . C H1 .7123(15) .460(3) .275(2) .057(9) Uiso d . 1 . . H H2 .8270(15) .390(2) .283(2) .048(8) Uiso d . 1 . . H H3 .7624(12) .062(3) .4072(18) .040(7) Uiso d . 1 . . H H4 .4906(16) .161(3) .503(2) .049(8) Uiso d . 1 . . H H5 .4300(17) .108(3) .558(3) .080(10) Uiso d . 1 . . H H6 .4323(18) .197(3) .361(3) .073(10) Uiso d . 1 . . H H7 .4214(15) .055(3) .387(2) .064(9) Uiso d . 1 . . H H8 .3075(16) .159(3) .336(2) .062(9) Uiso d . 1 . . H H9 .3098(14) .117(3) .454(2) .051(8) Uiso d . 1 . . H H10 .3438(15) .411(3) .550(2) .060(9) Uiso d . 1 . . H H11 .3310(16) .268(3) .584(2) .061(9) Uiso d . 1 . . H H12 .4530(14) .359(2) .495(2) .045(8) Uiso d . 1 . . H H13 .4546(16) .311(3) .610(2) .064(9) 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 .0463(4) .0548(4) .0658(5) .0102(3) -.0024(3) .0033(4) O1 .0674(13) .0458(11) .0557(12) -.0179(10) .0207(10) -.0075(9) O2 .0397(10) .0620(12) .0520(11) -.0028(9) .0180(9) -.0051(9) O3 .0406(11) .132(2) .0645(13) -.0101(13) .0187(10) .0137(14) O4 .0443(12) .0661(15) .1056(19) .0073(11) .0033(12) .0037(14) O5 .0477(11) .0564(12) .0596(12) .0025(10) -.0091(9) .0078(10) N1 .0351(12) .0757(18) .0477(14) -.0077(12) .0049(11) -.0124(13) N2 .0307(12) .0499(14) .0497(13) -.0009(10) .0084(10) .0079(11) C1 .0343(12) .0373(13) .0293(11) -.0034(10) .0042(10) -.0035(10) C2 .0350(12) .0415(14) .0365(13) .0023(11) .0006(10) -.0030(11) C3 .0600(18) .0366(15) .0451(15) -.0056(14) .0029(13) .0048(13) C4 .0477(16) .0530(17) .0433(15) -.0184(14) .0092(13) -.0019(13) C5 .0341(13) .0498(15) .0338(13) -.0044(12) .0026(10) -.0076(12) C6 .0368(13) .0413(15) .0335(12) -.0042(11) .0043(10) -.0028(11) C7 .0331(12) .0429(14) .0360(13) -.0009(11) .0032(10) .0008(11) C8 .0596(19) .054(2) .0457(16) -.0022(15) .0125(14) .0003(14) C9 .0526(17) .0575(19) .0457(16) -.0119(15) -.0055(14) .0068(14) C10 .0476(17) .0522(18) .0571(19) .0045(14) .0013(15) -.0034(16) C11 .0407(15) .0492(17) .0522(17) -.0043(13) -.0017(13) .0008(14) 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 . 1.743(3) yes O1 C7 . 1.247(3) yes O2 C7 . 1.244(3) yes O3 N1 . 1.216(3) yes O4 N1 . 1.218(3) yes C1 C2 . 1.389(3) no C1 C6 . 1.390(3) no C1 C7 . 1.508(3) no C2 C3 . 1.383(4) no C3 C4 . 1.372(4) no C3 H1 . .86(3) ? C4 C5 . 1.379(4) no C4 H2 . .89(3) ? C5 C6 . 1.376(3) no C6 H3 . .98(3) ? O5 C9 . 1.415(4) no O5 C10 . 1.421(3) no N1 C5 . 1.474(3) no N2 C11 . 1.484(4) no N2 C8 . 1.494(4) no N2 H4 . .83(3) ? N2 H5 . .99(4) ? C8 C9 . 1.507(4) no C8 H6 . .91(3) ? C8 H7 . .99(3) ? C9 H8 . 1.04(3) ? C9 H9 . .96(3) ? C10 C11 . 1.497(4) no C10 H10 . .95(3) ? C10 H11 . .95(3) ? C11 H12 . .95(3) ? C11 H13 . .99(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 -3 1 0 -2 3 -2 -2 -3 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 124.2(3) ? O3 N1 C5 117.7(3) ? O4 N1 C5 118.0(2) ? C11 N2 H4 111.3(19) ? C8 N2 H4 107(2) ? C11 N2 H5 111.1(19) ? C8 N2 H5 108.7(19) ? H4 N2 H5 108(3) ? C2 C1 C6 117.6(2) ? C2 C1 C7 123.0(2) ? C6 C1 C7 119.4(2) ? C3 C2 C1 121.8(2) ? C3 C2 Cl 117.8(2) ? C1 C2 Cl 120.29(19) ? C4 C3 C2 120.2(3) ? C4 C3 H1 119(2) ? C2 C3 H1 121(2) ? C3 C4 C5 118.3(3) ? C3 C4 H2 122.0(17) ? C5 C4 H2 119.7(17) ? C6 C5 C4 122.2(2) ? C6 C5 N1 118.8(2) ? C4 C5 N1 118.9(2) ? C5 C6 C1 119.8(2) ? C5 C6 H3 121.4(14) ? C1 C6 H3 118.8(14) ? O2 C7 O1 126.5(2) ? O2 C7 C1 117.6(2) ? O1 C7 C1 115.9(2) ? N2 C8 H6 107(2) ? C9 C8 H6 110(2) ? N2 C8 H7 109.2(17) ? C9 C8 H7 112.5(17) ? H6 C8 H7 109(3) ? O5 C9 C8 112.0(2) no O5 C9 H8 107.0(16) ? C8 C9 H8 110.3(17) ? O5 C9 H9 108.6(16) ? C8 C9 H9 111.6(16) ? H8 C9 H9 107(2) ? O5 C10 C11 112.2(3) no O5 C10 H10 106.2(17) ? C11 C10 H10 106.3(17) ? O5 C10 H11 109.8(17) ? C11 C10 H11 108.9(18) ? H10 C10 H11 113(3) ? N2 C8 C9 108.8(2) no N2 C11 C10 109.2(2) no N2 C11 H12 106.3(15) ? C10 C11 H12 110.8(16) ? N2 C11 H13 104.4(17) ? C10 C11 H13 114.7(18) ? H12 C11 H13 111(2) ? C8 N2 C11 110.8(2) no C9 O5 C10 109.7(2) no 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 2.753(3) 3_656 no O2 N2 2.719(3) . no O2 N1 2.918(3) 7_656 no O2 O3 3.081(3) 7_656 no O2 C5 3.181(3) 7_656 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 O2 . .83(3) 1.89(3) 2.719(3) 178(2) yes N2 H5 O1 3_656 1.00(4) 1.77(3) 2.753(3) 169(3) yes C4 H2 O1 6_655 .89(3) 2.58(3) 3.371(4) 148(2) yes C11 H13 O3 7_656 .98(3) 2.55(3) 3.344(4) 138(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 _geom_torsion_publ_flag C6 C1 C2 C3 1.8(4) ? C7 C1 C2 C3 -176.5(2) ? C6 C1 C2 Cl 178.40(18) ? C7 C1 C2 Cl .1(3) ? C1 C2 C3 C4 -1.4(4) ? Cl C2 C3 C4 -178.1(2) ? C2 C3 C4 C5 -.5(4) ? C3 C4 C5 C6 1.9(4) ? C3 C4 C5 N1 179.6(2) ? O3 N1 C5 C6 167.6(2) yes O4 N1 C5 C6 -13.0(4) yes O3 N1 C5 C4 -10.1(4) ? O4 N1 C5 C4 169.3(2) ? C4 C5 C6 C1 -1.5(4) ? N1 C5 C6 C1 -179.1(2) ? C2 C1 C6 C5 -.3(3) ? C7 C1 C6 C5 178.0(2) ? C2 C1 C7 O2 -63.1(3) yes C6 C1 C7 O2 118.7(3) ? C2 C1 C7 O1 119.8(3) yes C6 C1 C7 O1 -58.5(3) ? C11 N2 C8 C9 -54.4(3) ? C10 O5 C9 C8 -60.5(3) ? N2 C8 C9 O5 57.7(3) ? C9 O5 C10 C11 60.4(3) ? C8 N2 C11 C10 54.5(3) ? O5 C10 C11 N2 -57.6(3) ? _cod_database_fobs_code 2012388 _journal_paper_doi 10.1107/S0108270101016389