#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/02/2010269.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2010269 loop_ _publ_author_name 'Garcia, J.G.' 'Fronzek, F.R.' 'Gandour, R.D.' _publ_section_title ; Two dimethylmorpholinium bromides ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2022 _journal_page_last 2025 _journal_paper_doi 10.1107/S0108270194004518 _journal_volume 50 _journal_year 1994 _chemical_formula_moiety 'C13 H20 N1 O2 1+,Br1 1-,nH2 O1' _chemical_formula_sum 'C13 H22 Br N O3' _chemical_formula_weight 308.2 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_type_scat_source IntTabIV _cell_angle_alpha 90 _cell_angle_beta 93.38(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.451(3) _cell_length_b 13.535(2) _cell_length_c 12.915(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298 _cell_measurement_theta_max 25 _cell_measurement_theta_min 1 _cell_volume 1474.7(6) _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method \w-2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 2889 _diffrn_reflns_theta_max 25 _diffrn_standards_decay_% -3.4 _diffrn_standards_interval_time 177 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.8 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_correction_T_min 0.914 _exptl_absorpt_correction_type empirical _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.388 _exptl_crystal_description Needle _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.43 _refine_diff_density_min -0.18 _refine_ls_goodness_of_fit_obs 1.388 _refine_ls_number_parameters 244 _refine_ls_number_reflns 1705 _refine_ls_R_factor_obs 0.044 _refine_ls_shift/esd_max 0.03 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 4F~o~^2^[\s^2^(F^2^) + (0.02F~o~^2^)^2^]^-1^' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.033 _reflns_number_observed 1705 _reflns_number_total 2583 _reflns_observed_criterion I>1\s(I) _cod_data_source_file cr1117.cif _cod_data_source_block cr1117b _cod_depositor_comments ; Marking attached hydrogen atoms. Antanas Vaitkus, 2017-03-24 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value ' w = 4F~o~^2^[\s^2^(F^2^) + (0.02F~o~^2^)^2^]^-1^' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 4F~o~^2^[\s^2^(F^2^) + (0.02F~o~^2^)^2^]^-1^'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1474.8(9) _cod_original_sg_symbol_H-M 'P 21/n' _cod_original_formula_sum 'C13 H22 Br N1 O3' _cod_database_code 2010269 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,1/2-y,1/2+z -x,-y,-z 1/2-x,1/2+y,1/2-z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_attached_hydrogens Br .71862(5) .67662(4) .09612(3) 0 O1 .7140(3) .7343(2) .5168(2) 0 O2 .5427(3) .8658(2) .4807(2) 0 N .8453(4) .8648(2) .3673(2) 0 C1 .8171(4) .8951(3) .4766(3) 0 C2 .6897(4) .8372(3) .5285(3) 0 C3 .7317(5) .7021(3) .4127(3) 0 C4 .8676(5) .7545(3) .3667(3) 0 C5 .9943(5) .9145(4) .3358(3) 0 C6 .7126(5) .8957(3) .2918(3) 0 C7 .7016(4) .8594(3) .6434(3) 0 C8 .6472(5) .9481(3) .6793(3) 0 C9 .6632(5) .9714(3) .7836(3) 0 C10 .7313(5) .9052(4) .8530(3) 0 C11 .7885(5) .8173(3) .8184(3) 0 C12 .7741(5) .7946(3) .7142(3) 0 C13 .7581(7) .5918(3) .4170(4) 0 O1W .9490(10) .8705(8) .0874(7) 2 H20H .478(3) .853(2) .509(2) 0 H1a .789(3) .965(2) .476(2) 0 H1b .913(3) .884(2) .519(2) 0 H3 .636(3) .718(2) .373(2) 0 H4a .963(3) .743(2) .408(2) 0 H4b .879(4) .730(3) .296(2) 0 H5a 1.078(4) .895(2) .382(2) 0 H5b 1.010(4) .894(3) .268(3) 0 H5c .971(5) .989(3) .338(3) 0 H6a .604(4) .861(3) .305(3) 0 H6b .700(3) .965(2) .294(2) 0 H6c .729(4) .872(2) .216(2) 0 H8 .605(4) .990(2) .632(2) 0 H9 .627(4) 1.033(2) .801(3) 0 H10 .748(4) .921(3) .923(3) 0 H11 .833(4) .772(3) .871(3) 0 H12 .815(3) .741(2) .690(2) 0 H13a .660(6) .563(4) .453(4) 0 H13b .762(4) .576(3) .351(3) 0 H13c .839(4) .579(3) .453(3) 0 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 O1 C3 115.1(3) yes C1 N C4 107.6(3) yes C1 N C5 108.3(3) yes C1 N C6 112.4(3) yes C4 N C5 109.6(3) yes C4 N C6 111.2(3) yes C5 N C6 107.8(3) yes N C1 C2 115.4(3) yes O1 C2 O2 110.7(3) yes O1 C2 C1 110.4(3) yes O1 C2 C7 107.4(3) yes O2 C2 C1 107.1(3) yes O2 C2 C7 112.4(3) yes C1 C2 C7 108.9(3) yes O1 C3 C4 110.7(3) yes O1 C3 C13 106.8(3) yes C4 C3 C13 111.5(4) yes N C4 C3 111.5(3) yes C2 C7 C8 120.0(3) yes C2 C7 C12 121.6(3) yes C8 C7 C12 118.3(3) yes C7 C8 C9 120.8(4) yes C8 C9 C10 120.1(4) yes C9 C10 C11 119.8(4) yes C10 C11 C12 120.0(4) yes C7 C12 C11 120.9(4) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 . . 1.417(4) yes O1 C3 . . 1.429(5) yes O2 C2 . . 1.409(4) yes N C1 . . 1.502(5) yes N C4 . . 1.504(5) yes N C5 . . 1.505(5) yes N C6 . . 1.501(5) yes C1 C2 . . 1.519(5) yes C2 C7 . . 1.511(5) yes C3 C4 . . 1.502(6) yes C3 C13 . . 1.511(6) yes C7 C8 . . 1.376(5) yes C7 C12 . . 1.384(5) yes C8 C9 . . 1.382(6) yes C9 C10 . . 1.369(9) yes C10 C11 . . 1.369(7) yes C11 C12 . . 1.379(5) yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C2 O1 C3 C4 57.8(4) yes C4 N C1 C2 -50.5(4) yes N C1 C2 O1 49.4(4) yes N C1 C2 O2 -71.2(4) yes O2 C2 C7 C8 -42.9(5) yes H20H O2 C2 O1 76(2) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139057425