#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/02/2010268.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_2010268 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 'C14 H22 N1 O3 1+,Br1 1-' _chemical_formula_sum 'C14 H22 Br N O3' _chemical_formula_weight 332.3 _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_type_scat_source IntTabIV _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.341(4) _cell_length_b 15.692(6) _cell_length_c 8.479(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 295 _cell_measurement_theta_max 13 _cell_measurement_theta_min 10 _cell_volume 1508.9(9) _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 'no redundant data' _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1604 _diffrn_reflns_theta_max 25 _diffrn_standards_decay_% <2 _diffrn_standards_interval_time 167 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.7 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_correction_T_min 0.738 _exptl_absorpt_correction_type empirical _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.462 _exptl_crystal_description Prism _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.24 _refine_diff_density_max 0.87 _refine_diff_density_min -0.28 _refine_ls_extinction_coef 8.7E-8(6) _refine_ls_extinction_method '(1 + gI~c~)^-1^ applied to F~c~' _refine_ls_goodness_of_fit_obs 2.176 _refine_ls_number_parameters 176 _refine_ls_number_reflns 1159 _refine_ls_R_factor_obs 0.0464 _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 0.0468 _reflns_number_observed 1159 _reflns_number_total 1418 _reflns_observed_criterion I>1\s(I) _cod_data_source_file cr1117.cif _cod_data_source_block cr1117a _cod_depositor_comments ; 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 1509(2) _cod_original_formula_sum 'C14 H22 Br1 N1 O3' _cod_database_code 2010268 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,1/2+z 1/2+x,1/2-y,z 1/2-x,1/2+y,1/2+z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z Br .67054(6) .88346(5) .0 O1 .6600(4) .5983(3) .2187(6) O2 .7691(4) .6780(3) .0378(6) O3 .9940(5) .8035(3) .6793(6) N .8130(4) .4881(3) .0355(7) C1 .8581(6) .5544(4) .1504(8) C2 .7730(6) .6288(4) .1769(9) C3 .6116(7) .5414(4) .1049(9) C4 .6913(6) .4635(4) .0847(9) C5 .8190(7) .5174(5) -.1300(10) C6 .8914(7) .4098(5) .0520(10) C7 .8227(6) .6799(4) .3151(9) C8 .7861(6) .6658(4) .4669(8) C9 .8372(6) .7077(5) .5932(9) C10 .9322(6) .7625(4) .5626(8) C11 .9681(6) .7756(5) .4108(8) C12 .9148(6) .7355(4) .2890(9) C13 .4909(7) .5172(5) .1590(10) C14 .9673(7) .7852(5) .8390(10) H2OH .712(8) .704(6) .070(10) H1a .9301 .5766 .1106 H1b .8718 .5274 .2489 H3 .6063 .5678 .0044 H4a .6954 .4338 .1821 H4b .6583 .4273 .0064 H5a .7706 .5662 -.1430 H5b .8982 .5313 -.1559 H5c .7921 .4732 -.1980 H6a .8888 .3899 .1575 H6b .8641 .3663 -.0170 H6c .9702 .4244 .0250 H8 .7242 .6263 .4858 H9 .8086 .6995 .6974 H11 1.0316 .8135 .3904 H12 .9409 .7458 .1843 H13a .4441 .5670 .1704 H13b .4556 .4802 .0839 H13c .4962 .4887 .2580 H14a 1.0168 .8180 .9060 H14b .8871 .7988 .8598 H14c .9801 .7262 .8590 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 113.1(5) yes C10 O3 C14 119.0(6) yes C1 N C4 108.1(5) yes C1 N C5 112.4(5) yes C1 N C6 107.4(6) yes C4 N C5 112.8(5) yes C4 N C6 107.9(5) yes C5 N C6 108.0(6) yes N C1 C2 114.0(5) yes O1 C2 O2 111.5(5) yes O1 C2 C1 110.4(5) yes O1 C2 C7 108.7(6) yes O2 C2 C1 108.3(6) yes O2 C2 C7 111.5(5) yes C1 C2 C7 106.3(6) yes O1 C3 C4 110.4(6) yes O1 C3 C13 107.7(6) yes C4 C3 C13 111.9(6) yes N C4 C3 111.8(5) yes C2 C7 C8 121.7(6) yes C2 C7 C12 119.2(6) yes C8 C7 C12 118.8(7) yes C7 C8 C9 121.6(6) yes C8 C9 C10 118.0(7) yes O3 C10 C9 123.1(6) yes O3 C10 C11 117.2(6) yes C9 C10 C11 119.7(6) yes C10 C11 C12 121.1(7) yes C7 C12 C11 120.7(7) 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 . . 1.414(8) yes O1 C3 . . 1.425(9) yes O2 C2 . . 1.410(9) yes O3 C10 . . 1.372(8) yes O3 C14 . . 1.420(10) yes N C1 . . 1.514(9) yes N C4 . . 1.493(9) yes N C5 . . 1.480(10) yes N C6 . . 1.522(9) yes C1 C2 . . 1.530(10) yes C2 C7 . . 1.530(10) yes C3 C4 . . 1.530(10) yes C3 C13 . . 1.490(10) yes C7 C8 . . 1.370(10) yes C7 C12 . . 1.380(10) yes C8 C9 . . 1.380(10) yes C9 C10 . . 1.400(10) yes C10 C11 . . 1.370(10) yes C11 C12 . . 1.350(10) 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 60.1(7) yes C4 N C1 C2 -50.5(7) yes N C1 C2 O1 52.6(8) yes N C1 C2 O2 -69.8(7) yes O2 C2 C7 C12 -38.5(8) yes H2OH O2 C2 O1 46(6) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139057423