#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/23/2012387.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_2012387 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 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.304(2) _cell_length_b 19.557(6) _cell_length_c 6.4387(13) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298 _cell_measurement_theta_max 12.4 _cell_measurement_theta_min 11.3 _cell_volume 1297.5(5) _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 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 298 _diffrn_measured_fraction_theta_full .993 _diffrn_measured_fraction_theta_max .993 _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 .058 _diffrn_reflns_av_sigmaI/netI .113 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -3 _diffrn_reflns_number 4209 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_full 29.0 _diffrn_reflns_theta_max 29.0 _diffrn_reflns_theta_min 2.08 _diffrn_standards_decay_% 1.74 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .313 _exptl_absorpt_correction_T_max .940 _exptl_absorpt_correction_T_min .885 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 600 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .20 _refine_diff_density_max .28 _refine_diff_density_min -.23 _refine_ls_abs_structure_details '(Flack, 1983), 1102 Friedel pairs' _refine_ls_abs_structure_Flack .02(8) _refine_ls_extinction_coef .0053(9) _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 1.04 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 173 _refine_ls_number_reflns 3101 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.04 _refine_ls_R_factor_all .140 _refine_ls_R_factor_gt .053 _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^)+0.4754P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .062 _refine_ls_wR_factor_ref .075 _reflns_number_gt 1769 _reflns_number_total 3101 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ob1046.cif _[local]_cod_data_source_block I _cod_database_code 2012387 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x, -y,1/2+z' '1/2+x,1/2-y, -z' ' -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 .92033(9) .26987(5) 1.07561(13) .0527(3) Uani d . 1 . . Cl O1 .7367(2) .42775(11) .8920(4) .0563(7) Uani d . 1 . . O O2 .6418(2) .35904(11) 1.1175(4) .0533(7) Uani d . 1 . . O O3 .8873(2) .10450(12) .4440(4) .0564(7) Uani d . 1 . . O O4 .7277(3) .13867(12) .2498(4) .0608(8) Uani d . 1 . . O O5 1.1351(2) .45873(13) .3723(3) .0529(7) Uani d . 1 . . O N1 .7982(3) .14421(14) .4035(5) .0438(7) Uani d . 1 . . N N2 .8939(2) .46701(12) .5821(4) .0379(6) Uani d . 1 . . N C1 .7295(3) .30998(15) .8115(4) .0312(8) Uani d . 1 . . C C2 .8235(3) .26118(16) .8542(4) .0334(8) Uani d . 1 . . C C3 .8469(3) .20654(15) .7258(5) .0354(8) Uani d . 1 . . C C4 .7744(3) .20165(15) .5466(5) .0347(8) Uani d . 1 . . C C5 .6818(3) .24974(19) .4936(5) .0402(8) Uani d . 1 . . C C6 .6616(3) .30375(16) .6263(5) .0389(8) Uani d . 1 . . C C7 .7010(3) .36942(16) .9559(5) .0343(8) Uani d . 1 . . C C8 .9174(3) .41577(16) .4179(5) .0456(8) Uani d . 1 . . C C9 1.0180(4) .4435(2) .2674(5) .0544(11) Uani d . 1 . . C C10 1.1129(3) .51107(19) .5230(5) .0527(10) Uani d . 1 . . C C11 1.0167(3) .48916(19) .6842(4) .0452(10) Uani d . 1 . . C H1 .9094 .1740 .7585 .042 Uiso calc R 1 . . H H2 .6345 .2457 .3712 .048 Uiso calc R 1 . . H H3 .6008 .3370 .5912 .047 Uiso calc R 1 . . H H4 .8410 .4493 .6773 .057 Uiso calc R 1 . . H H5 .8548 .5033 .5269 .057 Uiso calc R 1 . . H H6 .8372 .4062 .3446 .055 Uiso calc R 1 . . H H7 .9483 .3735 .4794 .055 Uiso calc R 1 . . H H8 1.0346 .4099 .1598 .065 Uiso calc R 1 . . H H9 .9849 .4845 .2016 .065 Uiso calc R 1 . . H H10 1.0811 .5518 .4536 .063 Uiso calc R 1 . . H H11 1.1944 .5225 .5901 .063 Uiso calc R 1 . . H H12 1.0522 .4517 .7649 .054 Uiso calc R 1 . . H H13 .9991 .5269 .7779 .054 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 Cl .0537(5) .0565(6) .0478(5) .0121(5) -.0151(5) -.0085(5) O1 .0744(17) .0293(13) .0652(16) -.0018(13) .0380(15) -.0009(13) O2 .0655(17) .0484(15) .0460(15) -.0015(13) .0206(14) .0016(12) O3 .0496(16) .0448(15) .0748(17) .0084(13) .0070(15) -.0168(14) O4 .0779(19) .0534(17) .0512(15) -.0068(15) -.0110(17) -.0165(13) O5 .0399(14) .0707(19) .0482(15) -.0027(13) .0086(12) .0011(14) N1 .0463(18) .0379(18) .0473(18) -.0112(15) .0133(18) -.0075(16) N2 .0385(15) .0374(15) .0377(14) .0023(12) .0026(14) .0060(14) C1 .0290(17) .0276(18) .0368(18) .0002(15) .0049(15) .0029(14) C2 .0335(17) .0354(19) .0312(16) -.0033(16) .0021(14) .0026(15) C3 .0347(18) .0318(19) .0396(18) .0034(15) .0024(17) .0005(15) C4 .0368(17) .0309(18) .0364(18) -.0022(15) .0074(17) -.0028(15) C5 .0394(19) .045(2) .0358(17) -.0006(16) -.0063(14) .0000(14) C6 .0365(18) .037(2) .043(2) .0073(16) -.0022(18) .0048(16) C7 .0333(17) .0306(18) .039(2) .0036(15) .0011(17) .0012(16) C8 .048(2) .0439(19) .0448(19) -.0063(18) .006(2) -.0027(19) C9 .066(3) .062(3) .036(2) -.002(2) .013(2) -.005(2) C10 .041(2) .059(3) .058(2) -.0123(19) -.0015(18) -.0005(19) C11 .054(2) .049(2) .0324(19) .0052(18) -.0076(18) -.0005(17) 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 . 1.748(3) yes O1 C7 . 1.267(3) yes O2 C7 . 1.223(4) yes O3 N1 . 1.230(3) yes O4 N1 . 1.232(3) yes N1 C4 . 1.474(4) no C1 C2 . 1.387(4) no C1 C6 . 1.388(4) no C1 C7 . 1.517(4) no C2 C3 . 1.372(4) no C3 C4 . 1.378(4) no C3 H1 . .93 ? C4 C5 . 1.382(4) no C5 C6 . 1.375(4) no C5 H2 . .93 ? C6 H3 . .93 ? O5 C9 . 1.414(4) no O5 C10 . 1.429(4) no N2 C8 . 1.477(4) no N2 C11 . 1.490(4) no N2 H4 . .89 ? N2 H5 . .89 ? C8 C9 . 1.519(4) no C8 H6 . .97 ? C8 H7 . .97 ? C9 H8 . .97 ? C9 H9 . .97 ? C10 C11 . 1.499(4) no C10 H10 . .97 ? C10 H11 . .97 ? C11 H12 . .97 ? C11 H13 . .97 ? 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 -2 -4 0 -1 -5 -1 1 -6 0 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 123.7(3) ? O3 N1 C4 118.2(3) ? O4 N1 C4 118.1(3) ? C2 C1 C6 117.5(3) ? C2 C1 C7 122.8(3) ? C6 C1 C7 119.7(3) ? C3 C2 C1 122.6(3) ? C3 C2 Cl 117.9(2) ? C1 C2 Cl 119.6(2) ? C2 C3 C4 117.6(3) ? C2 C3 H1 121.2 ? C4 C3 H1 121.2 ? C3 C4 C5 122.3(3) ? C3 C4 N1 119.1(3) ? C5 C4 N1 118.6(3) ? C6 C5 C4 118.3(3) ? C6 C5 H2 120.9 ? C4 C5 H2 120.9 ? C5 C6 C1 121.7(3) ? C5 C6 H3 119.2 ? C1 C6 H3 119.2 ? O2 C7 O1 124.8(3) ? O2 C7 C1 119.4(3) ? O1 C7 C1 115.7(3) ? H6 C8 H7 108.3 ? O5 C9 C8 110.6(3) no O5 C9 H8 109.5 ? C8 C9 H8 109.5 ? O5 C9 H9 109.5 ? C8 C9 H9 109.5 ? H8 C9 H9 108.1 ? O5 C10 C11 111.8(3) no O5 C10 H10 109.3 ? C11 C10 H10 109.3 ? O5 C10 H11 109.3 ? C11 C10 H11 109.3 ? H10 C10 H11 107.9 ? N2 C8 C9 109.1(2) no N2 C8 H6 109.9 ? C9 C8 H6 109.9 ? N2 C8 H7 109.9 ? C9 C8 H7 109.9 ? N2 C11 C10 109.8(2) no N2 C11 H12 109.7 ? C10 C11 H12 109.7 ? N2 C11 H13 109.7 ? C10 C11 H13 109.7 ? H12 C11 H13 108.2 ? C8 N2 C11 112.0(2) no C8 N2 H4 109.2 ? C11 N2 H4 109.2 ? C8 N2 H5 109.2 ? C11 N2 H5 109.2 ? H4 N2 H5 107.9 ? C9 O5 C10 109.8(3) 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 2.682(3) . no O1 N2 2.747(3) 2_665 no O5 N1 2.994(4) 3_556 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 . .89 1.80 2.682(3) 170 yes N2 H5 O1 2_664 .89 1.86 2.747(3) 174 yes C6 H3 O3 3_456 .93 2.49 3.378(4) 160 yes C10 H11 O5 2_765 .97 2.55 3.486(4) 161 yes C11 H12 O4 3_556 .97 2.53 3.340(4) 141 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 -2.8(4) ? C7 C1 C2 C3 178.3(3) ? C6 C1 C2 Cl 175.3(2) ? C7 C1 C2 Cl -3.5(4) ? C1 C2 C3 C4 1.1(4) ? Cl C2 C3 C4 -177.1(2) ? C2 C3 C4 C5 .6(4) ? C2 C3 C4 N1 179.1(3) ? O3 N1 C4 C3 -3.9(4) yes O4 N1 C4 C3 176.2(3) yes O3 N1 C4 C5 174.6(3) ? O4 N1 C4 C5 -5.3(4) ? C3 C4 C5 C6 -.6(5) ? N1 C4 C5 C6 -179.0(3) ? C4 C5 C6 C1 -1.3(5) ? C2 C1 C6 C5 2.9(4) ? C7 C1 C6 C5 -178.2(3) ? C2 C1 C7 O2 -74.1(4) yes C6 C1 C7 O2 107.1(4) ? C2 C1 C7 O1 108.9(3) yes C6 C1 C7 O1 -69.9(4) ? C11 N2 C8 C9 -53.3(3) ? C10 O5 C9 C8 -62.5(4) ? N2 C8 C9 O5 58.6(4) ? C9 O5 C10 C11 61.3(4) ? C8 N2 C11 C10 52.0(4) ? O5 C10 C11 N2 -55.2(4) ? _cod_database_fobs_code 2012387 _journal_paper_doi 10.1107/S0108270101016389