# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 2012 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_cambridge 1326 loop_ _publ_author_name _publ_author_address 'Tobu, Yasuhiro' ; Department of Chemistry University of Tukuba Tukuba 305-8571 Japan ; 'Ikeda, Ryuichi' ; Department of Chemistry University of Tukuba Tukuba 305-8571 Japan ; 'Nihei, Taka-aki' ; Department of Chemistry and Biochemistry Numazu National College of Technology Numazu 410-8501 Japan ; 'Gotoh, Kazuma' ; Department of Chemistry Faculty of Science Okayama University Okayama 700-8530 Japan ; 'Ishida, Hiroyuki' ; Department of Chemistry Faculty of Science Okayama University Okayama 700-8530 Japan ; 'Asaji, Tetsuo' ; Department of Chemistry College of Humanities and Sciences Nihon University, Sakurajosui, Setagaya-ku, 3-25-40 Tokyo 156-8550 Japan ; _publ_contact_author_email ishidah@cc.okayama-u.ac.jp #TrackingRef '12023_web_deposit_cif_file_0_HiroyukiIshida_1340178346.338K.cif' _publ_contact_author_name 'Ishida, Hiroyuki' data_114K _database_code_depnum_ccdc_archive 'CCDC 876320' _chemical_name_common 'morpholinium hydrogen chloranilete' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Cl2 N O5' _chemical_formula_weight 296.10 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.61998(16) _cell_length_b 9.10428(16) _cell_length_c 9.19040(17) _cell_angle_alpha 91.9088(7) _cell_angle_beta 116.6760(7) _cell_angle_gamma 114.0492(7) _cell_volume 567.491(19) _cell_formula_units_Z 2 _cell_measurement_temperature 114(1) _cell_measurement_reflns_used 15964 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 30.1 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_preparation ; Single crystals suitable for X-ray diffraction were prepared by slow evaporation from an acetonitrile solution of chloranilic acid with morpholine (molar ration 1:1). ; _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.733 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.585 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; (NUMABS; Higashi, 1999) ; _exptl_absorpt_correction_T_min 0.828 _exptl_absorpt_correction_T_max 0.900 _exptl_special_details ; ? ; _diffrn_ambient_temperature 114(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16837 _diffrn_reflns_av_R_equivalents 0.0147 _diffrn_reflns_av_sigmaI/netI 0.0084 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 30.03 _reflns_number_total 3303 _reflns_number_gt 3200 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0332P)^2^+0.2192P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3303 _refine_ls_number_parameters 178 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0232 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0607 _refine_ls_wR_factor_gt 0.0603 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.76393(3) 0.16885(2) 0.70482(3) 0.01338(6) Uani 1 1 d . . . Cl2 Cl -0.00105(3) 0.11695(3) 0.18027(3) 0.01557(6) Uani 1 1 d . . . O1 O 1.17759(9) 0.32545(8) 0.98011(8) 0.01312(12) Uani 1 1 d . . . O2 O 0.61736(9) 0.40882(8) 0.76686(8) 0.01287(12) Uani 1 1 d D . . H2 H 0.544(3) 0.318(2) 0.696(3) 0.019 Uiso 0.63(2) 1 d PD . . O3 O -0.34222(10) -0.07795(9) 0.22394(8) 0.01554(13) Uani 1 1 d . . . O4 O 0.34827(9) 0.18429(8) 0.50812(8) 0.01280(12) Uani 1 1 d D . . H4 H 0.431(5) 0.239(4) 0.609(3) 0.019 Uiso 0.37(2) 1 d PD . . O5 O 0.82780(10) 0.41780(9) 0.26557(9) 0.01592(13) Uani 1 1 d . . . N1 N 0.48576(11) 0.31963(10) 0.29314(10) 0.01313(14) Uani 1 1 d . . . C1 C 1.09085(12) 0.40211(10) 0.98585(10) 0.00996(14) Uani 1 1 d . . . C2 C 0.88668(12) 0.34900(10) 0.86453(10) 0.01032(15) Uani 1 1 d . . . C3 C 0.79678(12) 0.43975(10) 0.87166(10) 0.01029(15) Uani 1 1 d . . . C4 C -0.18299(12) -0.04153(10) 0.34759(11) 0.01061(15) Uani 1 1 d . . . C5 C 0.00320(12) 0.05465(10) 0.35657(10) 0.01109(15) Uani 1 1 d . . . C6 C 0.17975(12) 0.09817(10) 0.49733(11) 0.01066(15) Uani 1 1 d . . . C7 C 0.50796(14) 0.19813(11) 0.19937(12) 0.01513(16) Uani 1 1 d . . . H7A H 0.3772 0.1155 0.1044 0.018 Uiso 1 1 calc R . . H7B H 0.5652 0.1375 0.2760 0.018 Uiso 1 1 calc R . . C8 C 0.64084(14) 0.29151(12) 0.13270(12) 0.01604(17) Uani 1 1 d . . . H8A H 0.6603 0.2121 0.0755 0.019 Uiso 1 1 calc R . . H8B H 0.5771 0.3435 0.0484 0.019 Uiso 1 1 calc R . . C9 C 0.80378(14) 0.53754(11) 0.34589(12) 0.01521(16) Uani 1 1 d . . . H9A H 0.7381 0.5883 0.2614 0.018 Uiso 1 1 calc R . . H9B H 0.9348 0.6274 0.4336 0.018 Uiso 1 1 calc R . . C10 C 0.68187(13) 0.45656(12) 0.42620(11) 0.01400(16) Uani 1 1 d . . . H10A H 0.7503 0.4108 0.5152 0.017 Uiso 1 1 calc R . . H10B H 0.6641 0.5405 0.4790 0.017 Uiso 1 1 calc R . . H1A H 0.415(2) 0.2660(19) 0.3417(19) 0.026(4) Uiso 1 1 d . . . H1B H 0.420(2) 0.3636(18) 0.2199(19) 0.022(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01185(10) 0.01133(10) 0.01297(10) -0.00023(7) 0.00413(8) 0.00476(7) Cl2 0.01238(10) 0.01986(11) 0.01170(10) 0.00730(8) 0.00592(8) 0.00525(8) O1 0.0126(3) 0.0146(3) 0.0140(3) 0.0041(2) 0.0064(2) 0.0084(2) O2 0.0079(3) 0.0134(3) 0.0129(3) 0.0012(2) 0.0024(2) 0.0046(2) O3 0.0098(3) 0.0194(3) 0.0128(3) 0.0049(2) 0.0035(2) 0.0055(2) O4 0.0078(3) 0.0148(3) 0.0113(3) 0.0020(2) 0.0044(2) 0.0023(2) O5 0.0116(3) 0.0173(3) 0.0182(3) 0.0017(2) 0.0084(3) 0.0055(2) N1 0.0113(3) 0.0166(3) 0.0147(3) 0.0067(3) 0.0079(3) 0.0075(3) C1 0.0099(3) 0.0104(3) 0.0098(3) 0.0039(3) 0.0055(3) 0.0043(3) C2 0.0091(3) 0.0099(3) 0.0094(3) 0.0013(3) 0.0037(3) 0.0034(3) C3 0.0091(3) 0.0109(3) 0.0100(3) 0.0033(3) 0.0049(3) 0.0039(3) C4 0.0099(3) 0.0101(3) 0.0107(4) 0.0022(3) 0.0048(3) 0.0043(3) C5 0.0103(4) 0.0121(4) 0.0099(3) 0.0039(3) 0.0052(3) 0.0042(3) C6 0.0103(4) 0.0098(3) 0.0111(4) 0.0021(3) 0.0053(3) 0.0044(3) C7 0.0144(4) 0.0136(4) 0.0164(4) 0.0027(3) 0.0085(3) 0.0050(3) C8 0.0150(4) 0.0178(4) 0.0140(4) 0.0018(3) 0.0085(3) 0.0055(3) C9 0.0144(4) 0.0138(4) 0.0173(4) 0.0032(3) 0.0092(3) 0.0053(3) C10 0.0139(4) 0.0158(4) 0.0130(4) 0.0036(3) 0.0072(3) 0.0072(3) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7306(8) . ? Cl2 C5 1.7244(8) . ? O1 C1 1.2277(10) . ? O2 C3 1.2994(10) . ? O2 H2 0.825(16) . ? O3 C4 1.2201(10) . ? O4 C6 1.2930(10) . ? O4 H4 0.836(19) . ? O5 C8 1.4281(11) . ? O5 C9 1.4296(11) . ? N1 C10 1.4940(12) . ? N1 C7 1.5033(12) . ? N1 H1A 0.908(16) . ? N1 H1B 0.892(15) . ? C1 C2 1.4433(11) . ? C1 C3 1.5248(12) 2_767 ? C2 C3 1.3606(11) . ? C3 C1 1.5248(12) 2_767 ? C4 C5 1.4423(11) . ? C4 C6 1.5242(12) 2_556 ? C5 C6 1.3613(11) . ? C6 C4 1.5242(12) 2_556 ? C7 C8 1.5104(13) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5145(12) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O2 H2 117.0(16) . . ? C6 O4 H4 108(3) . . ? C8 O5 C9 110.32(7) . . ? C10 N1 C7 111.27(7) . . ? C10 N1 H1A 109.3(10) . . ? C7 N1 H1A 110.1(10) . . ? C10 N1 H1B 109.1(10) . . ? C7 N1 H1B 108.9(9) . . ? H1A N1 H1B 108.0(13) . . ? O1 C1 C2 123.08(8) . . ? O1 C1 C3 118.62(7) . 2_767 ? C2 C1 C3 118.30(7) . 2_767 ? C3 C2 C1 121.53(8) . . ? C3 C2 Cl1 121.45(6) . . ? C1 C2 Cl1 116.98(6) . . ? O2 C3 C2 127.33(8) . . ? O2 C3 C1 112.54(7) . 2_767 ? C2 C3 C1 120.12(7) . 2_767 ? O3 C4 C5 123.71(8) . . ? O3 C4 C6 118.35(7) . 2_556 ? C5 C4 C6 117.94(7) . 2_556 ? C6 C5 C4 122.91(7) . . ? C6 C5 Cl2 119.27(6) . . ? C4 C5 Cl2 117.82(6) . . ? O4 C6 C5 123.93(8) . . ? O4 C6 C4 116.92(7) . 2_556 ? C5 C6 C4 119.15(7) . 2_556 ? N1 C7 C8 109.41(7) . . ? N1 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N1 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? O5 C8 C7 111.33(7) . . ? O5 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? O5 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? O5 C9 C10 110.88(7) . . ? O5 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? N1 C10 C9 108.95(7) . . ? N1 C10 H10A 109.9 . . ? C9 C10 H10A 109.9 . . ? N1 C10 H10B 109.9 . . ? C9 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -177.95(8) . . . . ? C3 C1 C2 C3 2.47(13) 2_767 . . . ? O1 C1 C2 Cl1 -0.35(11) . . . . ? C3 C1 C2 Cl1 -179.92(6) 2_767 . . . ? C1 C2 C3 O2 177.13(8) . . . . ? Cl1 C2 C3 O2 -0.37(13) . . . . ? C1 C2 C3 C1 -2.52(13) . . . 2_767 ? Cl1 C2 C3 C1 179.98(6) . . . 2_767 ? O3 C4 C5 C6 178.08(9) . . . . ? C6 C4 C5 C6 -0.89(14) 2_556 . . . ? O3 C4 C5 Cl2 -1.60(12) . . . . ? C6 C4 C5 Cl2 179.43(6) 2_556 . . . ? C4 C5 C6 O4 -179.98(8) . . . . ? Cl2 C5 C6 O4 -0.31(12) . . . . ? C4 C5 C6 C4 0.90(14) . . . 2_556 ? Cl2 C5 C6 C4 -179.43(6) . . . 2_556 ? C10 N1 C7 C8 -53.55(10) . . . . ? C9 O5 C8 C7 -61.23(10) . . . . ? N1 C7 C8 O5 56.47(10) . . . . ? C8 O5 C9 C10 62.08(9) . . . . ? C7 N1 C10 C9 54.33(9) . . . . ? O5 C9 C10 N1 -58.30(9) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.551 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.058 # Attachment '- 120K.cif' data_120K _database_code_depnum_ccdc_archive 'CCDC 876321' _chemical_name_common 'morpholinium hydrogen chloranilete' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Cl2 N O5' _chemical_formula_weight 296.10 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.62043(16) _cell_length_b 9.10670(16) _cell_length_c 9.19145(17) _cell_angle_alpha 91.9171(7) _cell_angle_beta 116.6737(7) _cell_angle_gamma 114.0287(7) _cell_volume 567.849(19) _cell_formula_units_Z 2 _cell_measurement_temperature 120(1) _cell_measurement_reflns_used 15975 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 30.1 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_preparation ; Single crystals suitable for X-ray diffraction were prepared by slow evaporation from an acetonitrile solution of chloranilic acid with morpholine (molar ration 1:1). ; _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.732 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.585 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; (NUMABS; Higashi, 1999) ; _exptl_absorpt_correction_T_min 0.826 _exptl_absorpt_correction_T_max 0.900 _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16851 _diffrn_reflns_av_R_equivalents 0.0147 _diffrn_reflns_av_sigmaI/netI 0.0083 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 30.03 _reflns_number_total 3305 _reflns_number_gt 3205 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+0.2012P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3305 _refine_ls_number_parameters 178 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0232 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0618 _refine_ls_wR_factor_gt 0.0614 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.76399(3) 0.16891(2) 0.70492(3) 0.01386(6) Uani 1 1 d . . . Cl2 Cl -0.00113(3) 0.11692(3) 0.18032(3) 0.01611(6) Uani 1 1 d . . . O1 O 1.17757(10) 0.32538(8) 0.98016(8) 0.01352(12) Uani 1 1 d . . . O2 O 0.61751(9) 0.40887(8) 0.76693(8) 0.01330(12) Uani 1 1 d D . . H2 H 0.544(3) 0.318(2) 0.696(3) 0.020 Uiso 0.63(2) 1 d PD . . O3 O -0.34212(10) -0.07796(9) 0.22402(8) 0.01604(13) Uani 1 1 d . . . O4 O 0.34808(9) 0.18433(8) 0.50809(8) 0.01320(12) Uani 1 1 d D . . H4 H 0.430(5) 0.239(4) 0.609(3) 0.020 Uiso 0.37(2) 1 d PD . . O5 O 0.82758(10) 0.41761(9) 0.26549(9) 0.01646(13) Uani 1 1 d . . . N1 N 0.48571(11) 0.31969(10) 0.29306(10) 0.01357(14) Uani 1 1 d . . . C1 C 1.09083(12) 0.40206(10) 0.98583(10) 0.01026(14) Uani 1 1 d . . . C2 C 0.88678(12) 0.34902(10) 0.86463(10) 0.01058(15) Uani 1 1 d . . . C3 C 0.79679(12) 0.43982(10) 0.87168(10) 0.01050(15) Uani 1 1 d . . . C4 C -0.18300(12) -0.04155(10) 0.34760(11) 0.01094(15) Uani 1 1 d . . . C5 C 0.00317(12) 0.05466(10) 0.35661(10) 0.01134(15) Uani 1 1 d . . . C6 C 0.17960(12) 0.09814(10) 0.49729(11) 0.01094(15) Uani 1 1 d . . . C7 C 0.50787(14) 0.19819(11) 0.19926(12) 0.01556(16) Uani 1 1 d . . . H7A H 0.3771 0.1157 0.1043 0.019 Uiso 1 1 calc R . . H7B H 0.5651 0.1375 0.2759 0.019 Uiso 1 1 calc R . . C8 C 0.64077(14) 0.29152(12) 0.13268(12) 0.01653(17) Uani 1 1 d . . . H8A H 0.6602 0.2121 0.0754 0.020 Uiso 1 1 calc R . . H8B H 0.5771 0.3435 0.0484 0.020 Uiso 1 1 calc R . . C9 C 0.80365(14) 0.53738(12) 0.34584(12) 0.01573(16) Uani 1 1 d . . . H9A H 0.7380 0.5882 0.2614 0.019 Uiso 1 1 calc R . . H9B H 0.9347 0.6271 0.4335 0.019 Uiso 1 1 calc R . . C10 C 0.68179(13) 0.45648(12) 0.42614(11) 0.01451(16) Uani 1 1 d . . . H10A H 0.7502 0.4106 0.5150 0.017 Uiso 1 1 calc R . . H10B H 0.6641 0.5404 0.4790 0.017 Uiso 1 1 calc R . . H1A H 0.415(2) 0.2658(19) 0.3422(19) 0.026(4) Uiso 1 1 d . . . H1B H 0.420(2) 0.3639(18) 0.2200(19) 0.022(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01225(10) 0.01178(10) 0.01340(10) -0.00023(7) 0.00426(8) 0.00494(8) Cl2 0.01284(10) 0.02054(11) 0.01202(10) 0.00754(8) 0.00608(8) 0.00541(8) O1 0.0129(3) 0.0152(3) 0.0143(3) 0.0041(2) 0.0065(2) 0.0087(2) O2 0.0082(3) 0.0138(3) 0.0133(3) 0.0012(2) 0.0025(2) 0.0048(2) O3 0.0101(3) 0.0201(3) 0.0132(3) 0.0051(2) 0.0036(2) 0.0056(2) O4 0.0081(3) 0.0154(3) 0.0115(3) 0.0021(2) 0.0045(2) 0.0023(2) O5 0.0119(3) 0.0180(3) 0.0188(3) 0.0018(2) 0.0087(3) 0.0056(2) N1 0.0115(3) 0.0173(3) 0.0150(3) 0.0070(3) 0.0080(3) 0.0078(3) C1 0.0101(3) 0.0107(3) 0.0099(3) 0.0040(3) 0.0054(3) 0.0044(3) C2 0.0093(3) 0.0102(3) 0.0096(3) 0.0014(3) 0.0038(3) 0.0035(3) C3 0.0093(3) 0.0111(3) 0.0103(3) 0.0034(3) 0.0051(3) 0.0039(3) C4 0.0102(3) 0.0105(3) 0.0110(4) 0.0023(3) 0.0050(3) 0.0045(3) C5 0.0106(4) 0.0123(4) 0.0101(3) 0.0040(3) 0.0053(3) 0.0044(3) C6 0.0106(4) 0.0101(3) 0.0113(4) 0.0021(3) 0.0054(3) 0.0045(3) C7 0.0148(4) 0.0140(4) 0.0167(4) 0.0027(3) 0.0087(3) 0.0052(3) C8 0.0155(4) 0.0183(4) 0.0145(4) 0.0020(3) 0.0088(3) 0.0057(3) C9 0.0146(4) 0.0143(4) 0.0181(4) 0.0033(3) 0.0095(3) 0.0054(3) C10 0.0144(4) 0.0164(4) 0.0135(4) 0.0037(3) 0.0075(3) 0.0075(3) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7308(8) . ? Cl2 C5 1.7243(8) . ? O1 C1 1.2277(10) . ? O2 C3 1.2984(10) . ? O2 H2 0.822(16) . ? O3 C4 1.2195(10) . ? O4 C6 1.2932(10) . ? O4 H4 0.838(19) . ? O5 C8 1.4273(11) . ? O5 C9 1.4295(11) . ? N1 C10 1.4940(12) . ? N1 C7 1.5034(12) . ? N1 H1A 0.914(16) . ? N1 H1B 0.891(15) . ? C1 C2 1.4426(11) . ? C1 C3 1.5251(12) 2_767 ? C2 C3 1.3615(11) . ? C3 C1 1.5251(12) 2_767 ? C4 C5 1.4425(11) . ? C4 C6 1.5241(12) 2_556 ? C5 C6 1.3607(11) . ? C6 C4 1.5241(12) 2_556 ? C7 C8 1.5102(13) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5143(13) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O2 H2 117.4(16) . . ? C6 O4 H4 108(3) . . ? C8 O5 C9 110.34(7) . . ? C10 N1 C7 111.27(7) . . ? C10 N1 H1A 109.2(10) . . ? C7 N1 H1A 110.1(10) . . ? C10 N1 H1B 109.0(10) . . ? C7 N1 H1B 108.9(9) . . ? H1A N1 H1B 108.3(13) . . ? O1 C1 C2 123.10(8) . . ? O1 C1 C3 118.59(7) . 2_767 ? C2 C1 C3 118.30(7) . 2_767 ? C3 C2 C1 121.56(8) . . ? C3 C2 Cl1 121.42(6) . . ? C1 C2 Cl1 116.98(6) . . ? O2 C3 C2 127.31(8) . . ? O2 C3 C1 112.59(7) . 2_767 ? C2 C3 C1 120.09(7) . 2_767 ? O3 C4 C5 123.71(8) . . ? O3 C4 C6 118.38(8) . 2_556 ? C5 C4 C6 117.90(7) . 2_556 ? C6 C5 C4 122.91(7) . . ? C6 C5 Cl2 119.28(6) . . ? C4 C5 Cl2 117.81(6) . . ? O4 C6 C5 123.91(8) . . ? O4 C6 C4 116.90(7) . 2_556 ? C5 C6 C4 119.19(7) . 2_556 ? N1 C7 C8 109.39(7) . . ? N1 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N1 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? O5 C8 C7 111.33(7) . . ? O5 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? O5 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? O5 C9 C10 110.86(7) . . ? O5 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? N1 C10 C9 108.94(7) . . ? N1 C10 H10A 109.9 . . ? C9 C10 H10A 109.9 . . ? N1 C10 H10B 109.9 . . ? C9 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -177.96(8) . . . . ? C3 C1 C2 C3 2.51(13) 2_767 . . . ? O1 C1 C2 Cl1 -0.39(11) . . . . ? C3 C1 C2 Cl1 -179.92(6) 2_767 . . . ? C1 C2 C3 O2 177.12(8) . . . . ? Cl1 C2 C3 O2 -0.34(13) . . . . ? C1 C2 C3 C1 -2.56(13) . . . 2_767 ? Cl1 C2 C3 C1 179.98(6) . . . 2_767 ? O3 C4 C5 C6 178.09(9) . . . . ? C6 C4 C5 C6 -0.88(14) 2_556 . . . ? O3 C4 C5 Cl2 -1.61(12) . . . . ? C6 C4 C5 Cl2 179.42(6) 2_556 . . . ? C4 C5 C6 O4 -179.97(8) . . . . ? Cl2 C5 C6 O4 -0.27(12) . . . . ? C4 C5 C6 C4 0.89(14) . . . 2_556 ? Cl2 C5 C6 C4 -179.41(6) . . . 2_556 ? C10 N1 C7 C8 -53.55(10) . . . . ? C9 O5 C8 C7 -61.25(10) . . . . ? N1 C7 C8 O5 56.47(10) . . . . ? C8 O5 C9 C10 62.11(9) . . . . ? C7 N1 C10 C9 54.34(9) . . . . ? O5 C9 C10 N1 -58.31(10) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.531 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.057 # Attachment '- 130K.cif' data_130K _database_code_depnum_ccdc_archive 'CCDC 876322' _chemical_name_common 'morpholinium hydrogen chloranilete' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Cl2 N O5' _chemical_formula_weight 296.10 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.62156(16) _cell_length_b 9.11162(16) _cell_length_c 9.19374(17) _cell_angle_alpha 91.9362(7) _cell_angle_beta 116.6690(7) _cell_angle_gamma 113.9804(7) _cell_volume 568.635(19) _cell_formula_units_Z 2 _cell_measurement_temperature 130(1) _cell_measurement_reflns_used 15908 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 30.1 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_preparation ; Single crystals suitable for X-ray diffraction were prepared by slow evaporation from an acetonitrile solution of chloranilic acid with morpholine (molar ration 1:1). ; _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.729 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.584 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; (NUMABS; Higashi, 1999) ; _exptl_absorpt_correction_T_min 0.832 _exptl_absorpt_correction_T_max 0.900 _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(1) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16863 _diffrn_reflns_av_R_equivalents 0.0147 _diffrn_reflns_av_sigmaI/netI 0.0083 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 30.03 _reflns_number_total 3310 _reflns_number_gt 3186 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+0.1944P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3310 _refine_ls_number_parameters 178 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0235 _refine_ls_R_factor_gt 0.0227 _refine_ls_wR_factor_ref 0.0631 _refine_ls_wR_factor_gt 0.0624 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.76414(3) 0.16907(2) 0.70515(3) 0.01479(6) Uani 1 1 d . . . Cl2 Cl -0.00132(3) 0.11689(3) 0.18041(3) 0.01720(6) Uani 1 1 d . . . O1 O 1.17765(10) 0.32535(8) 0.98029(8) 0.01434(13) Uani 1 1 d . . . O2 O 0.61776(9) 0.40893(8) 0.76701(8) 0.01414(12) Uani 1 1 d D . . H2 H 0.545(3) 0.318(2) 0.696(3) 0.021 Uiso 0.62(3) 1 d PD . . O3 O -0.34194(10) -0.07807(9) 0.22421(9) 0.01713(13) Uani 1 1 d . . . O4 O 0.34777(9) 0.18437(8) 0.50803(8) 0.01400(12) Uani 1 1 d D . . H4 H 0.429(5) 0.239(4) 0.609(3) 0.021 Uiso 0.38(3) 1 d PD . . O5 O 0.82721(10) 0.41732(9) 0.26541(9) 0.01756(14) Uani 1 1 d . . . N1 N 0.48559(11) 0.31986(10) 0.29285(10) 0.01453(14) Uani 1 1 d . . . C1 C 1.09081(12) 0.40203(10) 0.98589(10) 0.01081(15) Uani 1 1 d . . . C2 C 0.88690(12) 0.34916(10) 0.86477(10) 0.01113(15) Uani 1 1 d . . . C3 C 0.79695(12) 0.43991(10) 0.87169(10) 0.01100(15) Uani 1 1 d . . . C4 C -0.18280(12) -0.04161(10) 0.34776(11) 0.01154(15) Uani 1 1 d . . . C5 C 0.00312(12) 0.05469(11) 0.35666(10) 0.01196(15) Uani 1 1 d . . . C6 C 0.17939(12) 0.09817(10) 0.49733(11) 0.01155(15) Uani 1 1 d . . . C7 C 0.50763(14) 0.19835(12) 0.19902(12) 0.01662(17) Uani 1 1 d . . . H7A H 0.3770 0.1160 0.1040 0.020 Uiso 1 1 calc R . . H7B H 0.5647 0.1376 0.2755 0.020 Uiso 1 1 calc R . . C8 C 0.64057(14) 0.29160(12) 0.13261(12) 0.01759(17) Uani 1 1 d . . . H8A H 0.6600 0.2123 0.0753 0.021 Uiso 1 1 calc R . . H8B H 0.5770 0.3437 0.0485 0.021 Uiso 1 1 calc R . . C9 C 0.80333(14) 0.53700(12) 0.34580(12) 0.01678(17) Uani 1 1 d . . . H9A H 0.7378 0.5879 0.2615 0.020 Uiso 1 1 calc R . . H9B H 0.9343 0.6266 0.4335 0.020 Uiso 1 1 calc R . . C10 C 0.68150(13) 0.45635(12) 0.42599(11) 0.01539(16) Uani 1 1 d . . . H10A H 0.7497 0.4104 0.5148 0.018 Uiso 1 1 calc R . . H10B H 0.6638 0.5402 0.4789 0.018 Uiso 1 1 calc R . . H1A H 0.415(2) 0.2662(19) 0.342(2) 0.027(4) Uiso 1 1 d . . . H1B H 0.419(2) 0.3645(18) 0.2192(19) 0.023(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01306(10) 0.01251(10) 0.01435(10) -0.00026(7) 0.00451(8) 0.00527(8) Cl2 0.01367(10) 0.02195(11) 0.01279(10) 0.00810(8) 0.00642(8) 0.00573(8) O1 0.0136(3) 0.0161(3) 0.0152(3) 0.0042(2) 0.0068(2) 0.0091(2) O2 0.0085(3) 0.0148(3) 0.0141(3) 0.0013(2) 0.0025(2) 0.0051(2) O3 0.0106(3) 0.0215(3) 0.0141(3) 0.0055(2) 0.0038(2) 0.0059(2) O4 0.0086(3) 0.0165(3) 0.0121(3) 0.0023(2) 0.0047(2) 0.0024(2) O5 0.0127(3) 0.0193(3) 0.0202(3) 0.0021(3) 0.0094(3) 0.0061(3) N1 0.0125(3) 0.0185(4) 0.0163(3) 0.0078(3) 0.0088(3) 0.0085(3) C1 0.0106(3) 0.0114(3) 0.0107(3) 0.0043(3) 0.0059(3) 0.0048(3) C2 0.0098(3) 0.0107(3) 0.0103(3) 0.0014(3) 0.0042(3) 0.0038(3) C3 0.0098(3) 0.0116(3) 0.0109(3) 0.0036(3) 0.0055(3) 0.0041(3) C4 0.0109(3) 0.0112(3) 0.0114(4) 0.0025(3) 0.0051(3) 0.0048(3) C5 0.0111(4) 0.0131(4) 0.0105(3) 0.0040(3) 0.0055(3) 0.0046(3) C6 0.0110(4) 0.0106(3) 0.0120(4) 0.0021(3) 0.0055(3) 0.0047(3) C7 0.0157(4) 0.0151(4) 0.0177(4) 0.0030(3) 0.0092(3) 0.0054(3) C8 0.0164(4) 0.0196(4) 0.0154(4) 0.0020(3) 0.0094(3) 0.0060(3) C9 0.0155(4) 0.0152(4) 0.0192(4) 0.0035(3) 0.0100(3) 0.0057(3) C10 0.0153(4) 0.0177(4) 0.0142(4) 0.0041(3) 0.0080(3) 0.0082(3) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7314(8) . ? Cl2 C5 1.7241(8) . ? O1 C1 1.2283(10) . ? O2 C3 1.2981(10) . ? O2 H2 0.823(16) . ? O3 C4 1.2199(10) . ? O4 C6 1.2937(10) . ? O4 H4 0.838(19) . ? O5 C8 1.4268(11) . ? O5 C9 1.4292(11) . ? N1 C10 1.4939(12) . ? N1 C7 1.5032(12) . ? N1 H1A 0.912(16) . ? N1 H1B 0.902(15) . ? C1 C2 1.4425(11) . ? C1 C3 1.5256(12) 2_767 ? C2 C3 1.3606(11) . ? C3 C1 1.5256(12) 2_767 ? C4 C5 1.4423(12) . ? C4 C6 1.5229(12) 2_556 ? C5 C6 1.3604(11) . ? C6 C4 1.5229(12) 2_556 ? C7 C8 1.5101(13) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5136(13) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O2 H2 117.0(17) . . ? C6 O4 H4 107(3) . . ? C8 O5 C9 110.33(7) . . ? C10 N1 C7 111.31(7) . . ? C10 N1 H1A 109.1(10) . . ? C7 N1 H1A 110.1(10) . . ? C10 N1 H1B 109.1(9) . . ? C7 N1 H1B 109.1(9) . . ? H1A N1 H1B 108.1(13) . . ? O1 C1 C2 123.13(8) . . ? O1 C1 C3 118.59(7) . 2_767 ? C2 C1 C3 118.27(7) . 2_767 ? C3 C2 C1 121.58(8) . . ? C3 C2 Cl1 121.39(6) . . ? C1 C2 Cl1 116.98(6) . . ? O2 C3 C2 127.30(8) . . ? O2 C3 C1 112.60(7) . 2_767 ? C2 C3 C1 120.10(7) . 2_767 ? O3 C4 C5 123.68(8) . . ? O3 C4 C6 118.35(8) . 2_556 ? C5 C4 C6 117.96(7) . 2_556 ? C6 C5 C4 122.83(8) . . ? C6 C5 Cl2 119.32(6) . . ? C4 C5 Cl2 117.85(6) . . ? O4 C6 C5 123.85(8) . . ? O4 C6 C4 116.94(7) . 2_556 ? C5 C6 C4 119.20(7) . 2_556 ? N1 C7 C8 109.34(7) . . ? N1 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N1 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? O5 C8 C7 111.35(7) . . ? O5 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? O5 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? O5 C9 C10 110.89(8) . . ? O5 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.0 . . ? N1 C10 C9 108.91(7) . . ? N1 C10 H10A 109.9 . . ? C9 C10 H10A 109.9 . . ? N1 C10 H10B 109.9 . . ? C9 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -177.92(8) . . . . ? C3 C1 C2 C3 2.54(13) 2_767 . . . ? O1 C1 C2 Cl1 -0.35(11) . . . . ? C3 C1 C2 Cl1 -179.89(6) 2_767 . . . ? C1 C2 C3 O2 177.17(8) . . . . ? Cl1 C2 C3 O2 -0.29(13) . . . . ? C1 C2 C3 C1 -2.59(13) . . . 2_767 ? Cl1 C2 C3 C1 179.95(6) . . . 2_767 ? O3 C4 C5 C6 178.07(9) . . . . ? C6 C4 C5 C6 -0.85(14) 2_556 . . . ? O3 C4 C5 Cl2 -1.66(12) . . . . ? C6 C4 C5 Cl2 179.41(6) 2_556 . . . ? C4 C5 C6 O4 179.98(8) . . . . ? Cl2 C5 C6 O4 -0.29(12) . . . . ? C4 C5 C6 C4 0.86(14) . . . 2_556 ? Cl2 C5 C6 C4 -179.41(6) . . . 2_556 ? C10 N1 C7 C8 -53.56(10) . . . . ? C9 O5 C8 C7 -61.27(10) . . . . ? N1 C7 C8 O5 56.48(10) . . . . ? C8 O5 C9 C10 62.11(10) . . . . ? C7 N1 C10 C9 54.34(9) . . . . ? O5 C9 C10 N1 -58.29(10) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.511 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.057 # Attachment '- 145K.cif' data_145K _database_code_depnum_ccdc_archive 'CCDC 876323' _chemical_name_common 'morpholinium hydrogen chloranilete' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Cl2 N O5' _chemical_formula_weight 296.10 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.62366(16) _cell_length_b 9.11968(17) _cell_length_c 9.19716(17) _cell_angle_alpha 91.9817(7) _cell_angle_beta 116.6494(7) _cell_angle_gamma 113.9058(7) _cell_volume 569.92(2) _cell_formula_units_Z 2 _cell_measurement_temperature 145(1) _cell_measurement_reflns_used 15898 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 30.1 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_preparation ; Single crystals suitable for X-ray diffraction were prepared by slow evaporation from an acetonitrile solution of chloranilic acid with morpholine (molar ration 1:1). ; _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.583 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; (NUMABS; Higashi, 1999) ; _exptl_absorpt_correction_T_min 0.829 _exptl_absorpt_correction_T_max 0.901 _exptl_special_details ; ? ; _diffrn_ambient_temperature 145(1) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16941 _diffrn_reflns_av_R_equivalents 0.0143 _diffrn_reflns_av_sigmaI/netI 0.0082 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 30.03 _reflns_number_total 3327 _reflns_number_gt 3171 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+0.1977P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3327 _refine_ls_number_parameters 178 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0238 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0627 _refine_ls_wR_factor_gt 0.0617 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.76437(3) 0.16933(3) 0.70551(3) 0.01632(6) Uani 1 1 d . . . Cl2 Cl -0.00158(3) 0.11683(3) 0.18059(3) 0.01894(6) Uani 1 1 d . . . O1 O 1.17762(10) 0.32529(8) 0.98045(8) 0.01560(13) Uani 1 1 d . . . O2 O 0.61822(9) 0.40910(8) 0.76713(8) 0.01543(13) Uani 1 1 d D . . H2 H 0.546(3) 0.318(2) 0.697(3) 0.023 Uiso 0.61(3) 1 d PD . . O3 O -0.34174(10) -0.07820(9) 0.22444(9) 0.01876(14) Uani 1 1 d . . . O4 O 0.34730(9) 0.18450(8) 0.50794(8) 0.01538(13) Uani 1 1 d D . . H4 H 0.430(4) 0.238(4) 0.609(3) 0.023 Uiso 0.39(3) 1 d PD . . O5 O 0.82667(10) 0.41691(9) 0.26525(9) 0.01930(14) Uani 1 1 d . . . N1 N 0.48538(12) 0.32002(10) 0.29267(10) 0.01586(15) Uani 1 1 d . . . C1 C 1.09074(12) 0.40197(10) 0.98594(10) 0.01168(15) Uani 1 1 d . . . C2 C 0.88716(12) 0.34931(10) 0.86496(10) 0.01213(15) Uani 1 1 d . . . C3 C 0.79707(12) 0.44002(10) 0.87183(10) 0.01199(15) Uani 1 1 d . . . C4 C -0.18274(12) -0.04170(10) 0.34786(11) 0.01261(15) Uani 1 1 d . . . C5 C 0.00304(12) 0.05464(11) 0.35678(10) 0.01301(15) Uani 1 1 d . . . C6 C 0.17907(12) 0.09823(10) 0.49729(11) 0.01263(15) Uani 1 1 d . . . C7 C 0.50736(14) 0.19870(12) 0.19873(12) 0.01825(17) Uani 1 1 d . . . H7A H 0.3768 0.1167 0.1037 0.022 Uiso 1 1 calc R . . H7B H 0.5642 0.1378 0.2751 0.022 Uiso 1 1 calc R . . C8 C 0.64020(14) 0.29164(12) 0.13244(12) 0.01934(18) Uani 1 1 d . . . H8A H 0.6595 0.2123 0.0750 0.023 Uiso 1 1 calc R . . H8B H 0.5768 0.3439 0.0485 0.023 Uiso 1 1 calc R . . C9 C 0.80279(14) 0.53643(12) 0.34562(12) 0.01842(17) Uani 1 1 d . . . H9A H 0.7374 0.5874 0.2614 0.022 Uiso 1 1 calc R . . H9B H 0.9336 0.6258 0.4333 0.022 Uiso 1 1 calc R . . C10 C 0.68105(14) 0.45602(12) 0.42574(12) 0.01681(16) Uani 1 1 d . . . H10A H 0.7491 0.4100 0.5144 0.020 Uiso 1 1 calc R . . H10B H 0.6634 0.5399 0.4787 0.020 Uiso 1 1 calc R . . H1A H 0.415(2) 0.2669(19) 0.343(2) 0.029(4) Uiso 1 1 d . . . H1B H 0.419(2) 0.3642(18) 0.2192(19) 0.026(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01433(10) 0.01385(10) 0.01580(10) -0.00031(7) 0.00488(8) 0.00582(8) Cl2 0.01504(10) 0.02420(12) 0.01398(10) 0.00892(8) 0.00695(8) 0.00628(8) O1 0.0147(3) 0.0176(3) 0.0166(3) 0.0046(2) 0.0073(2) 0.0100(2) O2 0.0094(3) 0.0161(3) 0.0155(3) 0.0016(2) 0.0028(2) 0.0057(2) O3 0.0114(3) 0.0239(3) 0.0152(3) 0.0063(3) 0.0040(2) 0.0064(3) O4 0.0095(3) 0.0181(3) 0.0134(3) 0.0027(2) 0.0053(2) 0.0027(2) O5 0.0139(3) 0.0214(3) 0.0221(3) 0.0023(3) 0.0104(3) 0.0066(3) N1 0.0135(3) 0.0204(4) 0.0177(4) 0.0087(3) 0.0095(3) 0.0093(3) C1 0.0112(3) 0.0126(3) 0.0117(3) 0.0048(3) 0.0063(3) 0.0053(3) C2 0.0105(3) 0.0118(3) 0.0113(3) 0.0017(3) 0.0045(3) 0.0041(3) C3 0.0105(3) 0.0127(3) 0.0121(3) 0.0040(3) 0.0059(3) 0.0046(3) C4 0.0116(4) 0.0123(3) 0.0126(4) 0.0029(3) 0.0055(3) 0.0052(3) C5 0.0118(4) 0.0144(4) 0.0113(4) 0.0043(3) 0.0057(3) 0.0050(3) C6 0.0120(4) 0.0118(3) 0.0127(4) 0.0023(3) 0.0058(3) 0.0051(3) C7 0.0168(4) 0.0167(4) 0.0194(4) 0.0033(3) 0.0098(3) 0.0058(3) C8 0.0179(4) 0.0217(4) 0.0170(4) 0.0023(3) 0.0103(3) 0.0066(3) C9 0.0169(4) 0.0168(4) 0.0209(4) 0.0039(3) 0.0108(3) 0.0061(3) C10 0.0169(4) 0.0195(4) 0.0156(4) 0.0046(3) 0.0089(3) 0.0092(3) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7314(9) . ? Cl2 C5 1.7242(9) . ? O1 C1 1.2284(10) . ? O2 C3 1.2969(10) . ? O2 H2 0.821(17) . ? O3 C4 1.2195(11) . ? O4 C6 1.2944(10) . ? O4 H4 0.835(19) . ? O5 C8 1.4267(12) . ? O5 C9 1.4281(12) . ? N1 C10 1.4932(12) . ? N1 C7 1.5024(12) . ? N1 H1A 0.917(16) . ? N1 H1B 0.897(15) . ? C1 C2 1.4416(11) . ? C1 C3 1.5258(12) 2_767 ? C2 C3 1.3613(11) . ? C3 C1 1.5258(12) 2_767 ? C4 C5 1.4428(12) . ? C4 C6 1.5227(12) 2_556 ? C5 C6 1.3594(11) . ? C6 C4 1.5227(12) 2_556 ? C7 C8 1.5092(13) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5133(13) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O2 H2 116.9(17) . . ? C6 O4 H4 108(3) . . ? C8 O5 C9 110.28(7) . . ? C10 N1 C7 111.29(7) . . ? C10 N1 H1A 108.6(10) . . ? C7 N1 H1A 110.4(10) . . ? C10 N1 H1B 109.3(10) . . ? C7 N1 H1B 108.8(9) . . ? H1A N1 H1B 108.3(13) . . ? O1 C1 C2 123.16(8) . . ? O1 C1 C3 118.55(7) . 2_767 ? C2 C1 C3 118.29(7) . 2_767 ? C3 C2 C1 121.61(8) . . ? C3 C2 Cl1 121.31(6) . . ? C1 C2 Cl1 117.03(6) . . ? O2 C3 C2 127.25(8) . . ? O2 C3 C1 112.69(7) . 2_767 ? C2 C3 C1 120.05(7) . 2_767 ? O3 C4 C5 123.71(8) . . ? O3 C4 C6 118.37(8) . 2_556 ? C5 C4 C6 117.91(7) . 2_556 ? C6 C5 C4 122.84(8) . . ? C6 C5 Cl2 119.33(7) . . ? C4 C5 Cl2 117.82(6) . . ? O4 C6 C5 123.84(8) . . ? O4 C6 C4 116.92(7) . 2_556 ? C5 C6 C4 119.24(7) . 2_556 ? N1 C7 C8 109.38(8) . . ? N1 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N1 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? O5 C8 C7 111.34(8) . . ? O5 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? O5 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? O5 C9 C10 110.91(8) . . ? O5 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.0 . . ? N1 C10 C9 108.90(7) . . ? N1 C10 H10A 109.9 . . ? C9 C10 H10A 109.9 . . ? N1 C10 H10B 109.9 . . ? C9 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -177.98(8) . . . . ? C3 C1 C2 C3 2.45(13) 2_767 . . . ? O1 C1 C2 Cl1 -0.32(12) . . . . ? C3 C1 C2 Cl1 -179.90(6) 2_767 . . . ? C1 C2 C3 O2 177.12(8) . . . . ? Cl1 C2 C3 O2 -0.43(13) . . . . ? C1 C2 C3 C1 -2.49(13) . . . 2_767 ? Cl1 C2 C3 C1 179.95(6) . . . 2_767 ? O3 C4 C5 C6 178.02(9) . . . . ? C6 C4 C5 C6 -0.93(14) 2_556 . . . ? O3 C4 C5 Cl2 -1.65(12) . . . . ? C6 C4 C5 Cl2 179.40(6) 2_556 . . . ? C4 C5 C6 O4 179.98(8) . . . . ? Cl2 C5 C6 O4 -0.35(13) . . . . ? C4 C5 C6 C4 0.94(14) . . . 2_556 ? Cl2 C5 C6 C4 -179.39(6) . . . 2_556 ? C10 N1 C7 C8 -53.54(10) . . . . ? C9 O5 C8 C7 -61.29(10) . . . . ? N1 C7 C8 O5 56.49(10) . . . . ? C8 O5 C9 C10 62.16(10) . . . . ? C7 N1 C10 C9 54.30(10) . . . . ? O5 C9 C10 N1 -58.33(10) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.475 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.055 # Attachment '- 160K.cif' data_160K _database_code_depnum_ccdc_archive 'CCDC 876324' _chemical_name_common 'morpholinium hydrogen chloranilete' _chemical_melting_point ? _chemical_formula_moiety 'C4 H10 N O, C6 H2 Cl2 O4' _chemical_formula_sum 'C10 H11 Cl2 N O5' _chemical_formula_weight 296.10 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.62499(16) _cell_length_b 9.12773(17) _cell_length_c 9.20087(17) _cell_angle_alpha 92.0011(7) _cell_angle_beta 116.6392(7) _cell_angle_gamma 113.8619(7) _cell_volume 571.01(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 15910 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 30.2 _cell_measurement_temperature 160(1) _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_preparation ; Single crystals suitable for X-ray diffraction were prepared by slow evaporation from an acetonitrile solution of chloranilic acid with morpholine (molar ration 1:1). ; _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.722 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.581 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; (NUMABS; Higashi, 1999) ; _exptl_absorpt_correction_T_min 0.834 _exptl_absorpt_correction_T_max 0.901 _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(1) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16945 _diffrn_reflns_av_R_equivalents 0.0141 _diffrn_reflns_av_sigmaI/netI 0.0080 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 30.03 _reflns_number_total 3334 _reflns_number_gt 3180 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+0.2004P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3334 _refine_ls_number_parameters 178 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0240 _refine_ls_R_factor_gt 0.0230 _refine_ls_wR_factor_ref 0.0632 _refine_ls_wR_factor_gt 0.0623 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.76459(3) 0.16961(3) 0.70582(3) 0.01787(6) Uani 1 1 d . . . Cl2 Cl -0.00185(3) 0.11679(3) 0.18076(3) 0.02073(6) Uani 1 1 d . . . O1 O 1.17765(10) 0.32532(8) 0.98069(8) 0.01700(13) Uani 1 1 d . . . O2 O 0.61855(9) 0.40915(8) 0.76715(9) 0.01678(13) Uani 1 1 d D . . H2 H 0.546(3) 0.319(2) 0.697(3) 0.025 Uiso 0.59(3) 1 d PD . . O3 O -0.34155(10) -0.07827(9) 0.22476(9) 0.02047(14) Uani 1 1 d . . . O4 O 0.34689(9) 0.18457(8) 0.50784(8) 0.01676(13) Uani 1 1 d D . . H4 H 0.430(4) 0.237(4) 0.609(3) 0.025 Uiso 0.41(3) 1 d PD . . O5 O 0.82620(10) 0.41658(9) 0.26511(9) 0.02117(14) Uani 1 1 d . . . N1 N 0.48521(12) 0.32015(10) 0.29249(10) 0.01724(15) Uani 1 1 d . . . C1 C 1.09076(12) 0.40193(10) 0.98607(10) 0.01266(15) Uani 1 1 d . . . C2 C 0.88734(12) 0.34938(10) 0.86520(10) 0.01315(15) Uani 1 1 d . . . C3 C 0.79725(12) 0.44014(10) 0.87184(10) 0.01298(15) Uani 1 1 d . . . C4 C -0.18264(12) -0.04170(10) 0.34796(11) 0.01369(15) Uani 1 1 d . . . C5 C 0.00287(12) 0.05470(11) 0.35682(11) 0.01411(15) Uani 1 1 d . . . C6 C 0.17887(12) 0.09829(10) 0.49731(11) 0.01368(15) Uani 1 1 d . . . C7 C 0.50705(14) 0.19888(12) 0.19854(12) 0.01989(17) Uani 1 1 d . . . H7A H 0.3766 0.1171 0.1036 0.024 Uiso 1 1 calc R . . H7B H 0.5638 0.1380 0.2748 0.024 Uiso 1 1 calc R . . C8 C 0.63991(14) 0.29164(13) 0.13231(12) 0.02112(18) Uani 1 1 d . . . H8A H 0.6592 0.2124 0.0749 0.025 Uiso 1 1 calc R . . H8B H 0.5767 0.3440 0.0484 0.025 Uiso 1 1 calc R . . C9 C 0.80235(14) 0.53597(12) 0.34546(13) 0.02012(18) Uani 1 1 d . . . H9A H 0.7370 0.5870 0.2613 0.024 Uiso 1 1 calc R . . H9B H 0.9331 0.6251 0.4331 0.024 Uiso 1 1 calc R . . C10 C 0.68066(14) 0.45581(12) 0.42548(12) 0.01832(17) Uani 1 1 d . . . H10A H 0.7486 0.4097 0.5141 0.022 Uiso 1 1 calc R . . H10B H 0.6631 0.5397 0.4784 0.022 Uiso 1 1 calc R . . H1A H 0.417(2) 0.2680(19) 0.343(2) 0.030(4) Uiso 1 1 d . . . H1B H 0.419(2) 0.3646(18) 0.2183(19) 0.026(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01564(10) 0.01516(10) 0.01735(11) -0.00032(7) 0.00529(8) 0.00638(8) Cl2 0.01644(10) 0.02648(12) 0.01525(10) 0.00979(8) 0.00756(8) 0.00684(9) O1 0.0159(3) 0.0191(3) 0.0180(3) 0.0049(2) 0.0078(2) 0.0109(2) O2 0.0103(3) 0.0175(3) 0.0168(3) 0.0016(2) 0.0030(2) 0.0062(2) O3 0.0124(3) 0.0261(3) 0.0164(3) 0.0070(3) 0.0042(2) 0.0069(3) O4 0.0104(3) 0.0199(3) 0.0142(3) 0.0029(2) 0.0056(2) 0.0030(2) O5 0.0151(3) 0.0237(3) 0.0243(3) 0.0027(3) 0.0115(3) 0.0073(3) N1 0.0146(3) 0.0224(4) 0.0193(4) 0.0096(3) 0.0104(3) 0.0101(3) C1 0.0121(3) 0.0135(3) 0.0128(3) 0.0053(3) 0.0068(3) 0.0058(3) C2 0.0115(3) 0.0128(3) 0.0123(3) 0.0019(3) 0.0049(3) 0.0046(3) C3 0.0113(3) 0.0137(3) 0.0130(4) 0.0043(3) 0.0063(3) 0.0050(3) C4 0.0126(4) 0.0135(3) 0.0133(4) 0.0030(3) 0.0057(3) 0.0058(3) C5 0.0130(4) 0.0155(4) 0.0124(4) 0.0048(3) 0.0062(3) 0.0057(3) C6 0.0131(4) 0.0127(3) 0.0137(4) 0.0025(3) 0.0062(3) 0.0055(3) C7 0.0181(4) 0.0183(4) 0.0211(4) 0.0038(3) 0.0105(4) 0.0061(3) C8 0.0197(4) 0.0238(4) 0.0184(4) 0.0027(3) 0.0112(4) 0.0075(4) C9 0.0182(4) 0.0184(4) 0.0229(4) 0.0043(3) 0.0116(4) 0.0067(3) C10 0.0184(4) 0.0214(4) 0.0170(4) 0.0052(3) 0.0097(3) 0.0102(3) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7315(9) . ? Cl2 C5 1.7235(9) . ? O1 C1 1.2280(10) . ? O2 C3 1.2962(10) . ? O2 H2 0.821(17) . ? O3 C4 1.2186(11) . ? O4 C6 1.2943(10) . ? O4 H4 0.837(19) . ? O5 C8 1.4264(12) . ? O5 C9 1.4276(12) . ? N1 C10 1.4927(12) . ? N1 C7 1.5020(12) . ? N1 H1A 0.910(16) . ? N1 H1B 0.904(15) . ? C1 C2 1.4413(11) . ? C1 C3 1.5263(12) 2_767 ? C2 C3 1.3615(12) . ? C3 C1 1.5263(12) 2_767 ? C4 C5 1.4422(12) . ? C4 C6 1.5226(12) 2_556 ? C5 C6 1.3599(11) . ? C6 C4 1.5226(12) 2_556 ? C7 C8 1.5095(13) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5127(13) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O2 H2 116.8(18) . . ? C6 O4 H4 108(2) . . ? C8 O5 C9 110.30(7) . . ? C10 N1 C7 111.33(7) . . ? C10 N1 H1A 108.2(10) . . ? C7 N1 H1A 110.6(10) . . ? C10 N1 H1B 109.4(9) . . ? C7 N1 H1B 108.7(9) . . ? H1A N1 H1B 108.6(13) . . ? O1 C1 C2 123.18(8) . . ? O1 C1 C3 118.56(7) . 2_767 ? C2 C1 C3 118.26(7) . 2_767 ? C3 C2 C1 121.63(8) . . ? C3 C2 Cl1 121.26(6) . . ? C1 C2 Cl1 117.07(6) . . ? O2 C3 C2 127.20(8) . . ? O2 C3 C1 112.73(7) . 2_767 ? C2 C3 C1 120.06(7) . 2_767 ? O3 C4 C5 123.74(8) . . ? O3 C4 C6 118.33(8) . 2_556 ? C5 C4 C6 117.93(7) . 2_556 ? C6 C5 C4 122.81(8) . . ? C6 C5 Cl2 119.35(7) . . ? C4 C5 Cl2 117.84(6) . . ? O4 C6 C5 123.78(8) . . ? O4 C6 C4 116.95(7) . 2_556 ? C5 C6 C4 119.25(7) . 2_556 ? N1 C7 C8 109.36(8) . . ? N1 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N1 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? O5 C8 C7 111.31(8) . . ? O5 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? O5 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? O5 C9 C10 110.93(8) . . ? O5 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.0 . . ? N1 C10 C9 108.89(8) . . ? N1 C10 H10A 109.9 . . ? C9 C10 H10A 109.9 . . ? N1 C10 H10B 109.9 . . ? C9 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -177.91(8) . . . . ? C3 C1 C2 C3 2.52(13) 2_767 . . . ? O1 C1 C2 Cl1 -0.36(12) . . . . ? C3 C1 C2 Cl1 -179.92(6) 2_767 . . . ? C1 C2 C3 O2 177.13(8) . . . . ? Cl1 C2 C3 O2 -0.31(13) . . . . ? C1 C2 C3 C1 -2.57(13) . . . 2_767 ? Cl1 C2 C3 C1 179.98(6) . . . 2_767 ? O3 C4 C5 C6 178.03(9) . . . . ? C6 C4 C5 C6 -0.92(14) 2_556 . . . ? O3 C4 C5 Cl2 -1.71(12) . . . . ? C6 C4 C5 Cl2 179.35(6) 2_556 . . . ? C4 C5 C6 O4 179.95(8) . . . . ? Cl2 C5 C6 O4 -0.32(13) . . . . ? C4 C5 C6 C4 0.93(14) . . . 2_556 ? Cl2 C5 C6 C4 -179.34(6) . . . 2_556 ? C10 N1 C7 C8 -53.53(10) . . . . ? C9 O5 C8 C7 -61.29(10) . . . . ? N1 C7 C8 O5 56.47(11) . . . . ? C8 O5 C9 C10 62.18(10) . . . . ? C7 N1 C10 C9 54.30(10) . . . . ? O5 C9 C10 N1 -58.32(10) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.459 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.055 # Attachment '- 180K.cif' data_180K _database_code_depnum_ccdc_archive 'CCDC 876325' #TrackingRef '- 180K.cif' _audit_update_record ; 2012-04-16 # Formatted by publCIF ; _chemical_name_common 'morpholinium hydrogen chloranilete' _chemical_melting_point ? _chemical_formula_moiety ' C4 H10 N O, 0.5(C6 H1.18 Cl2 O4), 0.5(C6 H0.82 Cl2 O4)' _chemical_formula_sum 'C10 H11 Cl2 N O5' _chemical_formula_weight 296.10 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.62739(16) _cell_length_b 9.13846(17) _cell_length_c 9.20609(17) _cell_angle_alpha 92.0264(7) _cell_angle_beta 116.6211(7) _cell_angle_gamma 113.8289(7) _cell_volume 572.40(2) _cell_formula_units_Z 2 _cell_measurement_temperature 180(1) _cell_measurement_reflns_used 15822 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 30.1 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_preparation ; Single crystals suitable for X-ray diffraction were prepared by slow evaporation from an acetonitrile solution of chloranilic acid with morpholine (molar ration 1:1). ; _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.718 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.580 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; (NUMABS; Higashi, 1999) ; _exptl_absorpt_correction_T_min 0.824 _exptl_absorpt_correction_T_max 0.901 _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16984 _diffrn_reflns_av_R_equivalents 0.0141 _diffrn_reflns_av_sigmaI/netI 0.0081 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 30.03 _reflns_number_total 3342 _reflns_number_gt 3167 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.1931P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3342 _refine_ls_number_parameters 178 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0246 _refine_ls_R_factor_gt 0.0234 _refine_ls_wR_factor_ref 0.0642 _refine_ls_wR_factor_gt 0.0631 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.76485(3) 0.16995(3) 0.70614(3) 0.01968(6) Uani 1 1 d . . . Cl2 Cl -0.00212(3) 0.11675(3) 0.18100(3) 0.02282(7) Uani 1 1 d . . . O1 O 1.17767(10) 0.32533(9) 0.98097(9) 0.01862(13) Uani 1 1 d . . . O2 O 0.61898(9) 0.40927(9) 0.76725(9) 0.01832(13) Uani 1 1 d D . . H2 H 0.547(3) 0.319(2) 0.697(3) 0.027 Uiso 0.59(3) 1 d PD . . O3 O -0.34138(10) -0.07839(9) 0.22511(9) 0.02245(15) Uani 1 1 d . . . O4 O 0.34648(9) 0.18467(9) 0.50774(8) 0.01830(13) Uani 1 1 d D . . H4 H 0.430(4) 0.237(4) 0.608(3) 0.027 Uiso 0.41(3) 1 d PD . . O5 O 0.82566(10) 0.41625(9) 0.26494(10) 0.02338(15) Uani 1 1 d . . . N1 N 0.48500(12) 0.32028(11) 0.29237(11) 0.01892(15) Uani 1 1 d . . . C1 C 1.09066(12) 0.40189(10) 0.98617(10) 0.01371(15) Uani 1 1 d . . . C2 C 0.88759(12) 0.34958(10) 0.86542(10) 0.01426(15) Uani 1 1 d . . . C3 C 0.79741(12) 0.44027(10) 0.87186(10) 0.01406(15) Uani 1 1 d . . . C4 C -0.18257(12) -0.04173(11) 0.34819(11) 0.01497(15) Uani 1 1 d . . . C5 C 0.00278(12) 0.05466(11) 0.35692(11) 0.01531(15) Uani 1 1 d . . . C6 C 0.17857(12) 0.09830(10) 0.49724(11) 0.01489(15) Uani 1 1 d . . . C7 C 0.50672(15) 0.19914(12) 0.19833(13) 0.02183(18) Uani 1 1 d . . . H7A H 0.3763 0.1176 0.1034 0.026 Uiso 1 1 calc R . . H7B H 0.5633 0.1381 0.2744 0.026 Uiso 1 1 calc R . . C8 C 0.63960(15) 0.29168(13) 0.13225(13) 0.02318(19) Uani 1 1 d . . . H8A H 0.6589 0.2125 0.0749 0.028 Uiso 1 1 calc R . . H8B H 0.5765 0.3440 0.0485 0.028 Uiso 1 1 calc R . . C9 C 0.80191(15) 0.53549(12) 0.34532(13) 0.02208(18) Uani 1 1 d . . . H9A H 0.7368 0.5866 0.2613 0.026 Uiso 1 1 calc R . . H9B H 0.9325 0.6244 0.4330 0.026 Uiso 1 1 calc R . . C10 C 0.68019(14) 0.45554(12) 0.42513(12) 0.02010(17) Uani 1 1 d . . . H10A H 0.7480 0.4095 0.5137 0.024 Uiso 1 1 calc R . . H10B H 0.6626 0.5393 0.4780 0.024 Uiso 1 1 calc R . . H1A H 0.416(2) 0.2672(19) 0.342(2) 0.033(4) Uiso 1 1 d . . . H1B H 0.418(2) 0.3647(18) 0.2188(19) 0.027(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01715(10) 0.01668(10) 0.01907(11) -0.00039(8) 0.00568(8) 0.00701(8) Cl2 0.01796(11) 0.02924(12) 0.01672(11) 0.01083(8) 0.00822(8) 0.00743(9) O1 0.0172(3) 0.0210(3) 0.0197(3) 0.0053(2) 0.0083(3) 0.0120(3) O2 0.0111(3) 0.0193(3) 0.0186(3) 0.0019(2) 0.0033(2) 0.0068(2) O3 0.0133(3) 0.0288(4) 0.0179(3) 0.0078(3) 0.0044(3) 0.0074(3) O4 0.0113(3) 0.0217(3) 0.0155(3) 0.0032(2) 0.0060(2) 0.0033(2) O5 0.0166(3) 0.0264(3) 0.0267(4) 0.0031(3) 0.0127(3) 0.0081(3) N1 0.0160(3) 0.0245(4) 0.0213(4) 0.0107(3) 0.0115(3) 0.0111(3) C1 0.0130(3) 0.0148(3) 0.0139(4) 0.0056(3) 0.0073(3) 0.0064(3) C2 0.0123(3) 0.0140(3) 0.0135(4) 0.0022(3) 0.0054(3) 0.0051(3) C3 0.0119(3) 0.0151(4) 0.0141(4) 0.0047(3) 0.0066(3) 0.0053(3) C4 0.0136(4) 0.0149(4) 0.0145(4) 0.0034(3) 0.0061(3) 0.0063(3) C5 0.0139(4) 0.0170(4) 0.0134(4) 0.0052(3) 0.0066(3) 0.0061(3) C6 0.0141(4) 0.0142(4) 0.0147(4) 0.0026(3) 0.0066(3) 0.0060(3) C7 0.0197(4) 0.0200(4) 0.0231(4) 0.0040(3) 0.0114(4) 0.0066(3) C8 0.0218(4) 0.0263(5) 0.0202(4) 0.0029(4) 0.0125(4) 0.0084(4) C9 0.0199(4) 0.0204(4) 0.0252(5) 0.0047(3) 0.0129(4) 0.0073(3) C10 0.0205(4) 0.0237(4) 0.0186(4) 0.0059(3) 0.0108(3) 0.0115(4) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7320(9) . ? Cl2 C5 1.7232(9) . ? O1 C1 1.2287(10) . ? O2 C3 1.2951(10) . ? O2 H2 0.820(17) . ? O3 C4 1.2183(11) . ? O4 C6 1.2946(10) . ? O4 H4 0.835(19) . ? O5 C8 1.4257(12) . ? O5 C9 1.4270(12) . ? N1 C10 1.4914(13) . ? N1 C7 1.5018(13) . ? N1 H1A 0.910(16) . ? N1 H1B 0.901(15) . ? C1 C2 1.4401(11) . ? C1 C3 1.5269(12) 2_767 ? C2 C3 1.3619(12) . ? C3 C1 1.5269(12) 2_767 ? C4 C5 1.4427(12) . ? C4 C6 1.5218(12) 2_556 ? C5 C6 1.3590(12) . ? C6 C4 1.5218(12) 2_556 ? C7 C8 1.5092(14) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5120(13) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O2 H2 117.0(18) . . ? C6 O4 H4 109(2) . . ? C8 O5 C9 110.31(7) . . ? C10 N1 C7 111.34(7) . . ? C10 N1 H1A 108.7(10) . . ? C7 N1 H1A 110.1(10) . . ? C10 N1 H1B 109.4(9) . . ? C7 N1 H1B 108.9(9) . . ? H1A N1 H1B 108.5(13) . . ? O1 C1 C2 123.23(8) . . ? O1 C1 C3 118.51(7) . 2_767 ? C2 C1 C3 118.26(7) . 2_767 ? C3 C2 C1 121.67(8) . . ? C3 C2 Cl1 121.19(7) . . ? C1 C2 Cl1 117.09(6) . . ? O2 C3 C2 127.19(8) . . ? O2 C3 C1 112.79(7) . 2_767 ? C2 C3 C1 120.02(7) . 2_767 ? O3 C4 C5 123.72(8) . . ? O3 C4 C6 118.36(8) . 2_556 ? C5 C4 C6 117.92(7) . 2_556 ? C6 C5 C4 122.77(8) . . ? C6 C5 Cl2 119.38(7) . . ? C4 C5 Cl2 117.85(6) . . ? O4 C6 C5 123.77(8) . . ? O4 C6 C4 116.92(7) . 2_556 ? C5 C6 C4 119.30(7) . 2_556 ? N1 C7 C8 109.37(8) . . ? N1 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N1 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? O5 C8 C7 111.32(8) . . ? O5 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? O5 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? O5 C9 C10 110.94(8) . . ? O5 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.0 . . ? N1 C10 C9 108.94(8) . . ? N1 C10 H10A 109.9 . . ? C9 C10 H10A 109.9 . . ? N1 C10 H10B 109.9 . . ? C9 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -177.90(8) . . . . ? C3 C1 C2 C3 2.49(13) 2_767 . . . ? O1 C1 C2 Cl1 -0.33(12) . . . . ? C3 C1 C2 Cl1 -179.94(6) 2_767 . . . ? C1 C2 C3 O2 177.17(8) . . . . ? Cl1 C2 C3 O2 -0.30(13) . . . . ? C1 C2 C3 C1 -2.54(14) . . . 2_767 ? Cl1 C2 C3 C1 179.99(6) . . . 2_767 ? O3 C4 C5 C6 178.03(9) . . . . ? C6 C4 C5 C6 -1.02(14) 2_556 . . . ? O3 C4 C5 Cl2 -1.63(13) . . . . ? C6 C4 C5 Cl2 179.33(6) 2_556 . . . ? C4 C5 C6 O4 180.00(8) . . . . ? Cl2 C5 C6 O4 -0.36(13) . . . . ? C4 C5 C6 C4 1.03(14) . . . 2_556 ? Cl2 C5 C6 C4 -179.32(6) . . . 2_556 ? C10 N1 C7 C8 -53.46(10) . . . . ? C9 O5 C8 C7 -61.26(11) . . . . ? N1 C7 C8 O5 56.42(11) . . . . ? C8 O5 C9 C10 62.15(10) . . . . ? C7 N1 C10 C9 54.23(10) . . . . ? O5 C9 C10 N1 -58.27(10) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.440 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.055 # Attachment '- 200K.cif' data_200K _database_code_depnum_ccdc_archive 'CCDC 876326' #TrackingRef '- 200K.cif' _audit_update_record ; 2012-04-16 # Formatted by publCIF ; _chemical_name_common 'morpholinium hydrogen chloranilete' _chemical_melting_point ? _chemical_formula_moiety 'C4 H10 N O, 0.5(C6 H1.18 Cl2 O4), 0.5(C6 H0.82 Cl2 O4)' _chemical_formula_sum 'C10 H11 Cl2 N O5' _chemical_formula_weight 296.10 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.62930(16) _cell_length_b 9.15077(17) _cell_length_c 9.21274(17) _cell_angle_alpha 92.0613(7) _cell_angle_beta 116.6008(7) _cell_angle_gamma 113.7992(7) _cell_volume 573.91(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200(1) _cell_measurement_reflns_used 15792 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 30.1 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_preparation ; Single crystals suitable for X-ray diffraction were prepared by slow evaporation from an acetonitrile solution of chloranilic acid with morpholine (molar ration 1:1). ; _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.713 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.578 _exptl_absorpt_correction_T_min 0.824 _exptl_absorpt_correction_T_max 0.901 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; (NUMABS; Higashi, 1999) ; _diffrn_ambient_temperature 200(1) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17031 _diffrn_reflns_av_R_equivalents 0.0146 _diffrn_reflns_av_sigmaI/netI 0.0083 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 30.02 _reflns_number_total 3346 _reflns_number_gt 3185 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+0.1816P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3346 _refine_ls_number_parameters 178 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0254 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0659 _refine_ls_wR_factor_gt 0.0651 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.76513(3) 0.17033(3) 0.70648(3) 0.02201(6) Uani 1 1 d . . . Cl2 Cl -0.00246(3) 0.11669(3) 0.18128(3) 0.02542(7) Uani 1 1 d . . . O1 O 1.17755(10) 0.32538(9) 0.98132(9) 0.02070(14) Uani 1 1 d . . . O2 O 0.61940(10) 0.40944(9) 0.76722(9) 0.02034(13) Uani 1 1 d D . . H2 H 0.547(3) 0.320(2) 0.698(3) 0.031 Uiso 0.59(3) 1 d PD . . O3 O -0.34123(10) -0.07847(10) 0.22563(9) 0.02504(15) Uani 1 1 d . . . O4 O 0.34606(10) 0.18478(9) 0.50760(9) 0.02032(13) Uani 1 1 d D . . H4 H 0.430(4) 0.234(4) 0.608(3) 0.030 Uiso 0.41(3) 1 d PD . . O5 O 0.82500(11) 0.41597(10) 0.26467(10) 0.02596(15) Uani 1 1 d . . . N1 N 0.48482(12) 0.32041(11) 0.29217(11) 0.02102(16) Uani 1 1 d . . . C1 C 1.09053(12) 0.40180(10) 0.98630(11) 0.01518(15) Uani 1 1 d . . . C2 C 0.88784(12) 0.34981(10) 0.86557(11) 0.01587(15) Uani 1 1 d . . . C3 C 0.79756(12) 0.44040(11) 0.87191(11) 0.01559(15) Uani 1 1 d . . . C4 C -0.18239(13) -0.04175(11) 0.34843(11) 0.01665(15) Uani 1 1 d . . . C5 C 0.00261(13) 0.05466(11) 0.35700(11) 0.01710(16) Uani 1 1 d . . . C6 C 0.17829(12) 0.09833(10) 0.49715(11) 0.01649(16) Uani 1 1 d . . . C7 C 0.50641(15) 0.19935(13) 0.19819(13) 0.02420(19) Uani 1 1 d . . . H7A H 0.3761 0.1180 0.1033 0.029 Uiso 1 1 calc R . . H7B H 0.5629 0.1384 0.2741 0.029 Uiso 1 1 calc R . . C8 C 0.63917(15) 0.29169(13) 0.13223(13) 0.0258(2) Uani 1 1 d . . . H8A H 0.6585 0.2126 0.0748 0.031 Uiso 1 1 calc R . . H8B H 0.5761 0.3440 0.0486 0.031 Uiso 1 1 calc R . . C9 C 0.80135(15) 0.53503(13) 0.34507(13) 0.02450(19) Uani 1 1 d . . . H9A H 0.7363 0.5861 0.2612 0.029 Uiso 1 1 calc R . . H9B H 0.9319 0.6238 0.4326 0.029 Uiso 1 1 calc R . . C10 C 0.67981(15) 0.45530(13) 0.42488(12) 0.02237(18) Uani 1 1 d . . . H10A H 0.7475 0.4092 0.5133 0.027 Uiso 1 1 calc R . . H10B H 0.6623 0.5390 0.4778 0.027 Uiso 1 1 calc R . . H1A H 0.415(2) 0.2678(19) 0.341(2) 0.034(4) Uiso 1 1 d . . . H1B H 0.418(2) 0.3653(19) 0.2184(19) 0.031(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01907(11) 0.01870(11) 0.02133(11) -0.00042(8) 0.00630(9) 0.00779(8) Cl2 0.01993(11) 0.03258(13) 0.01857(11) 0.01202(9) 0.00907(9) 0.00818(9) O1 0.0188(3) 0.0234(3) 0.0219(3) 0.0057(3) 0.0090(3) 0.0131(3) O2 0.0124(3) 0.0215(3) 0.0205(3) 0.0022(2) 0.0037(2) 0.0077(2) O3 0.0147(3) 0.0323(4) 0.0197(3) 0.0087(3) 0.0048(3) 0.0080(3) O4 0.0125(3) 0.0241(3) 0.0171(3) 0.0037(2) 0.0066(2) 0.0036(2) O5 0.0186(3) 0.0294(4) 0.0299(4) 0.0038(3) 0.0144(3) 0.0092(3) N1 0.0176(3) 0.0276(4) 0.0238(4) 0.0123(3) 0.0130(3) 0.0125(3) C1 0.0144(3) 0.0167(4) 0.0153(4) 0.0062(3) 0.0081(3) 0.0072(3) C2 0.0136(3) 0.0158(4) 0.0152(4) 0.0028(3) 0.0061(3) 0.0058(3) C3 0.0131(4) 0.0170(4) 0.0154(4) 0.0053(3) 0.0072(3) 0.0060(3) C4 0.0149(4) 0.0165(4) 0.0161(4) 0.0036(3) 0.0065(3) 0.0067(3) C5 0.0154(4) 0.0188(4) 0.0150(4) 0.0056(3) 0.0072(3) 0.0067(3) C6 0.0153(4) 0.0157(4) 0.0159(4) 0.0028(3) 0.0069(3) 0.0063(3) C7 0.0215(4) 0.0223(4) 0.0258(5) 0.0046(4) 0.0124(4) 0.0073(4) C8 0.0243(5) 0.0293(5) 0.0226(4) 0.0034(4) 0.0139(4) 0.0094(4) C9 0.0219(4) 0.0226(4) 0.0280(5) 0.0052(4) 0.0141(4) 0.0079(4) C10 0.0229(4) 0.0266(4) 0.0208(4) 0.0067(3) 0.0121(4) 0.0131(4) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7321(9) . ? Cl2 C5 1.7226(9) . ? O1 C1 1.2278(10) . ? O2 C3 1.2942(10) . ? O2 H2 0.812(17) . ? O3 C4 1.2181(11) . ? O4 C6 1.2947(10) . ? O4 H4 0.832(19) . ? O5 C8 1.4247(13) . ? O5 C9 1.4262(12) . ? N1 C10 1.4908(13) . ? N1 C7 1.5012(13) . ? N1 H1A 0.904(16) . ? N1 H1B 0.909(16) . ? C1 C2 1.4390(11) . ? C1 C3 1.5275(12) 2_767 ? C2 C3 1.3624(12) . ? C3 C1 1.5275(12) 2_767 ? C4 C5 1.4418(12) . ? C4 C6 1.5217(12) 2_556 ? C5 C6 1.3587(12) . ? C6 C4 1.5217(12) 2_556 ? C7 C8 1.5083(14) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5115(14) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O2 H2 117.5(19) . . ? C6 O4 H4 108(3) . . ? C8 O5 C9 110.33(8) . . ? C10 N1 C7 111.37(7) . . ? C10 N1 H1A 109.0(10) . . ? C7 N1 H1A 110.1(10) . . ? C10 N1 H1B 109.3(10) . . ? C7 N1 H1B 109.1(9) . . ? H1A N1 H1B 107.9(13) . . ? O1 C1 C2 123.29(8) . . ? O1 C1 C3 118.46(7) . 2_767 ? C2 C1 C3 118.25(7) . 2_767 ? C3 C2 C1 121.72(8) . . ? C3 C2 Cl1 121.15(7) . . ? C1 C2 Cl1 117.09(6) . . ? O2 C3 C2 127.15(8) . . ? O2 C3 C1 112.85(7) . 2_767 ? C2 C3 C1 119.99(7) . 2_767 ? O3 C4 C5 123.74(8) . . ? O3 C4 C6 118.29(8) . 2_556 ? C5 C4 C6 117.97(7) . 2_556 ? C6 C5 C4 122.72(8) . . ? C6 C5 Cl2 119.40(7) . . ? C4 C5 Cl2 117.88(6) . . ? O4 C6 C5 123.75(8) . . ? O4 C6 C4 116.94(7) . 2_556 ? C5 C6 C4 119.31(7) . 2_556 ? N1 C7 C8 109.32(8) . . ? N1 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N1 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? O5 C8 C7 111.35(8) . . ? O5 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? O5 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? O5 C9 C10 110.94(8) . . ? O5 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.0 . . ? N1 C10 C9 108.88(8) . . ? N1 C10 H10A 109.9 . . ? C9 C10 H10A 109.9 . . ? N1 C10 H10B 109.9 . . ? C9 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -177.95(8) . . . . ? C3 C1 C2 C3 2.34(13) 2_767 . . . ? O1 C1 C2 Cl1 -0.25(12) . . . . ? C3 C1 C2 Cl1 -179.96(6) 2_767 . . . ? C1 C2 C3 O2 177.19(8) . . . . ? Cl1 C2 C3 O2 -0.41(13) . . . . ? C1 C2 C3 C1 -2.38(14) . . . 2_767 ? Cl1 C2 C3 C1 -179.99(6) . . . 2_767 ? O3 C4 C5 C6 177.99(9) . . . . ? C6 C4 C5 C6 -1.01(14) 2_556 . . . ? O3 C4 C5 Cl2 -1.68(13) . . . . ? C6 C4 C5 Cl2 179.33(6) 2_556 . . . ? C4 C5 C6 O4 180.00(8) . . . . ? Cl2 C5 C6 O4 -0.34(13) . . . . ? C4 C5 C6 C4 1.02(14) . . . 2_556 ? Cl2 C5 C6 C4 -179.32(6) . . . 2_556 ? C10 N1 C7 C8 -53.51(11) . . . . ? C9 O5 C8 C7 -61.25(11) . . . . ? N1 C7 C8 O5 56.41(11) . . . . ? C8 O5 C9 C10 62.14(11) . . . . ? C7 N1 C10 C9 54.30(10) . . . . ? O5 C9 C10 N1 -58.29(11) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.448 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.058 data_338K _database_code_depnum_ccdc_archive 'CCDC 887991' _chemical_name_common 'morpholinium hydrogen chloranilete' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Cl2 N O5' _chemical_formula_weight 296.10 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.66982(18) _cell_length_b 9.21282(19) _cell_length_c 9.26605(19) _cell_angle_alpha 92.6113(7) _cell_angle_beta 116.6498(7) _cell_angle_gamma 113.4563(7) _cell_volume 583.72(2) _cell_formula_units_Z 2 _cell_measurement_temperature 338(1) _cell_measurement_reflns_used 15246 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 30.1 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_preparation ; Single crystals suitable for X-ray diffraction were prepared by slow evaporation from an acetonitrile solution of chloranilic acid with morpholine (molar ration 1:1). ; _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.685 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.569 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; (NUMABS; Higashi, 1999) ; _exptl_absorpt_correction_T_min 0.791 _exptl_absorpt_correction_T_max 0.843 _exptl_special_details ; ? ; _diffrn_ambient_temperature 338(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17198 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0147 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 30.03 _reflns_number_total 3389 _reflns_number_gt 3131 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku/MSC, 2004)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+0.1179P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3389 _refine_ls_number_parameters 177 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0984 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.76731(4) 0.17347(4) 0.70884(4) 0.03902(10) Uani 1 1 d . . . Cl2 Cl -0.00488(5) 0.11616(5) 0.18356(4) 0.04441(11) Uani 1 1 d . . . O1 O 1.17689(13) 0.32611(11) 0.98439(12) 0.03566(19) Uani 1 1 d . . . O2 O 0.62227(12) 0.41032(11) 0.76674(11) 0.03496(19) Uani 1 1 d D . . H2 H 0.550(5) 0.318(3) 0.705(5) 0.052 Uiso 0.50 1 d PD . . O3 O -0.34065(13) -0.07931(14) 0.22928(12) 0.0438(2) Uani 1 1 d . . . O4 O 0.34317(12) 0.18506(12) 0.50649(11) 0.03509(19) Uani 1 1 d D . . H4 H 0.425(5) 0.223(5) 0.607(3) 0.053 Uiso 0.50 1 d PD . . O5 O 0.82061(15) 0.41472(14) 0.26307(14) 0.0457(2) Uani 1 1 d . . . N1 N 0.48338(16) 0.32093(15) 0.29181(15) 0.0361(2) Uani 1 1 d . . . C1 C 1.09027(15) 0.40226(13) 0.98789(13) 0.02513(19) Uani 1 1 d . . . C2 C 0.88910(15) 0.35118(13) 0.86671(13) 0.0265(2) Uani 1 1 d . . . C3 C 0.79900(14) 0.44124(13) 0.87150(13) 0.0256(2) Uani 1 1 d . . . C4 C -0.18193(16) -0.04190(13) 0.35038(13) 0.0280(2) Uani 1 1 d . . . C5 C 0.00150(16) 0.05459(14) 0.35800(13) 0.0281(2) Uani 1 1 d . . . C6 C 0.17662(15) 0.09834(13) 0.49649(13) 0.0273(2) Uani 1 1 d . . . C7 C 0.5042(2) 0.20122(18) 0.19762(19) 0.0420(3) Uani 1 1 d . . . H7A H 0.3769 0.1222 0.1046 0.050 Uiso 1 1 calc R . . H7B H 0.5591 0.1417 0.2710 0.050 Uiso 1 1 calc R . . C8 C 0.6361(2) 0.2918(2) 0.13225(19) 0.0451(3) Uani 1 1 d . . . H8A H 0.6542 0.2140 0.0757 0.054 Uiso 1 1 calc R . . H8B H 0.5744 0.3424 0.0508 0.054 Uiso 1 1 calc R . . C9 C 0.7976(2) 0.53234(18) 0.3432(2) 0.0426(3) Uani 1 1 d . . . H9A H 0.7341 0.5819 0.2617 0.051 Uiso 1 1 calc R . . H9B H 0.9251 0.6187 0.4291 0.051 Uiso 1 1 calc R . . C10 C 0.6769(2) 0.45415(18) 0.42252(17) 0.0387(3) Uani 1 1 d . . . H10A H 0.7433 0.4097 0.5086 0.046 Uiso 1 1 calc R . . H10B H 0.6607 0.5364 0.4748 0.046 Uiso 1 1 calc R . . H1A H 0.414(3) 0.262(3) 0.341(3) 0.061(6) Uiso 1 1 d . . . H1B H 0.414(3) 0.364(2) 0.215(3) 0.053(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.03306(16) 0.03288(16) 0.03774(17) -0.00095(12) 0.01043(12) 0.01365(12) Cl2 0.03436(16) 0.0571(2) 0.03194(16) 0.02138(14) 0.01519(13) 0.01387(14) O1 0.0312(4) 0.0396(5) 0.0378(4) 0.0089(4) 0.0138(4) 0.0225(4) O2 0.0202(4) 0.0371(4) 0.0352(4) 0.0035(3) 0.0057(3) 0.0131(3) O3 0.0234(4) 0.0583(6) 0.0331(4) 0.0167(4) 0.0068(3) 0.0129(4) O4 0.0212(4) 0.0425(5) 0.0286(4) 0.0072(3) 0.0110(3) 0.0059(3) O5 0.0324(5) 0.0526(6) 0.0532(6) 0.0076(5) 0.0262(4) 0.0166(4) N1 0.0300(5) 0.0481(6) 0.0416(6) 0.0227(5) 0.0226(4) 0.0222(5) C1 0.0223(4) 0.0281(4) 0.0259(4) 0.0103(4) 0.0124(4) 0.0121(4) C2 0.0221(4) 0.0272(5) 0.0257(5) 0.0052(4) 0.0102(4) 0.0101(4) C3 0.0195(4) 0.0292(5) 0.0253(4) 0.0086(4) 0.0105(4) 0.0099(4) C4 0.0231(5) 0.0284(5) 0.0261(5) 0.0065(4) 0.0093(4) 0.0104(4) C5 0.0241(5) 0.0307(5) 0.0244(5) 0.0088(4) 0.0107(4) 0.0101(4) C6 0.0236(5) 0.0269(5) 0.0261(5) 0.0047(4) 0.0104(4) 0.0101(4) C7 0.0356(6) 0.0394(6) 0.0443(7) 0.0087(5) 0.0198(6) 0.0128(5) C8 0.0435(7) 0.0529(8) 0.0390(7) 0.0062(6) 0.0246(6) 0.0190(6) C9 0.0359(6) 0.0394(6) 0.0495(7) 0.0090(5) 0.0236(6) 0.0131(5) C10 0.0402(6) 0.0476(7) 0.0347(6) 0.0120(5) 0.0205(5) 0.0246(6) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7191(11) . ? Cl2 C5 1.7222(11) . ? O1 C1 1.2233(13) . ? O2 C3 1.2901(12) . ? O2 H2 0.807(19) . ? O3 C4 1.2138(14) . ? O4 C6 1.2988(13) . ? O4 H4 0.823(19) . ? O5 C9 1.4131(18) . ? O5 C8 1.4154(18) . ? N1 C10 1.4801(19) . ? N1 C7 1.4908(19) . ? N1 H1A 0.93(2) . ? N1 H1B 0.92(2) . ? C1 C2 1.4372(14) . ? C1 C3 1.5175(15) 2_767 ? C2 C3 1.3580(15) . ? C3 C1 1.5175(15) 2_767 ? C4 C5 1.4465(15) . ? C4 C6 1.5211(15) 2_556 ? C5 C6 1.3536(14) . ? C6 C4 1.5211(15) 2_556 ? C7 C8 1.510(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.5138(19) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O2 H2 116(3) . . ? C6 O4 H4 106(3) . . ? C9 O5 C8 110.04(11) . . ? C10 N1 C7 111.00(10) . . ? C10 N1 H1A 110.3(14) . . ? C7 N1 H1A 107.0(13) . . ? C10 N1 H1B 110.4(13) . . ? C7 N1 H1B 107.2(12) . . ? H1A N1 H1B 110.9(18) . . ? O1 C1 C2 123.61(10) . . ? O1 C1 C3 118.18(9) . 2_767 ? C2 C1 C3 118.20(9) . 2_767 ? C3 C2 C1 122.07(10) . . ? C3 C2 Cl1 120.69(8) . . ? C1 C2 Cl1 117.19(8) . . ? O2 C3 C2 127.34(10) . . ? O2 C3 C1 112.98(9) . 2_767 ? C2 C3 C1 119.68(9) . 2_767 ? O3 C4 C5 123.86(11) . . ? O3 C4 C6 117.77(10) . 2_556 ? C5 C4 C6 118.36(9) . 2_556 ? C6 C5 C4 122.58(10) . . ? C6 C5 Cl2 119.12(8) . . ? C4 C5 Cl2 118.30(8) . . ? O4 C6 C5 123.73(10) . . ? O4 C6 C4 117.22(9) . 2_556 ? C5 C6 C4 119.04(9) . 2_556 ? N1 C7 C8 109.62(12) . . ? N1 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? N1 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? O5 C8 C7 111.73(12) . . ? O5 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? O5 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? O5 C9 C10 111.10(12) . . ? O5 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? O5 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? N1 C10 C9 109.38(11) . . ? N1 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? N1 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -178.03(11) . . . . ? C3 C1 C2 C3 2.33(17) 2_767 . . . ? O1 C1 C2 Cl1 -0.36(15) . . . . ? C3 C1 C2 Cl1 180.00(7) 2_767 . . . ? C1 C2 C3 O2 177.49(11) . . . . ? Cl1 C2 C3 O2 -0.10(17) . . . . ? C1 C2 C3 C1 -2.36(17) . . . 2_767 ? Cl1 C2 C3 C1 -179.95(7) . . . 2_767 ? O3 C4 C5 C6 178.12(12) . . . . ? C6 C4 C5 C6 -1.05(18) 2_556 . . . ? O3 C4 C5 Cl2 -1.65(17) . . . . ? C6 C4 C5 Cl2 179.19(8) 2_556 . . . ? C4 C5 C6 O4 -179.89(11) . . . . ? Cl2 C5 C6 O4 -0.13(16) . . . . ? C4 C5 C6 C4 1.05(18) . . . 2_556 ? Cl2 C5 C6 C4 -179.18(8) . . . 2_556 ? C10 N1 C7 C8 -52.90(15) . . . . ? C9 O5 C8 C7 -60.94(17) . . . . ? N1 C7 C8 O5 56.26(17) . . . . ? C8 O5 C9 C10 61.75(16) . . . . ? C7 N1 C10 C9 53.85(15) . . . . ? O5 C9 C10 N1 -58.33(15) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.353 _refine_diff_density_min -0.696 _refine_diff_density_rms 0.125