#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/06/2010644.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_2010644 loop_ _publ_author_name 'Batsanov, Andrei S.' 'Howard, Judith A. K.' _publ_section_title ; Morpholine--\b-iodophenylacetylene (1/1) revisited: an exceptionally short I···N contact ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 252 _journal_page_last 253 _journal_paper_doi 10.1107/S0108270199014705 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C8 H5 I,C4 H9 N O' _chemical_formula_sum 'C12 H14 I N O' _chemical_formula_weight 315.14 _chemical_melting_point 348(5) _chemical_name_systematic ; morpholine \b-iodophenylacetylene complex (1:1) ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 96.050(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.8670(10) _cell_length_b 4.8579(2) _cell_length_c 29.390(2) _cell_measurement_reflns_used 470 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 23 _cell_measurement_theta_min 12 _cell_volume 1258.92(18) _computing_cell_refinement SMART _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL ' _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1995)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full .990 _diffrn_measured_fraction_theta_max .990 _diffrn_measurement_device 'Siemens SMART 1K CCD area detector diffractometer' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0267 _diffrn_reflns_av_sigmaI/netI .0213 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_number 10880 _diffrn_reflns_theta_full 29.00 _diffrn_reflns_theta_max 29.00 _diffrn_reflns_theta_min 1.39 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 2.519 _exptl_absorpt_correction_T_max .7517 _exptl_absorpt_correction_T_min .5202 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(XPREP in SHELXTL; Sheldrick, 1995), before correction R~int~ = 0.080' _exptl_crystal_colour 'colourless ' _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'plate ' _exptl_crystal_F_000 616 _exptl_crystal_size_max .32 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .12 _refine_diff_density_max .603 _refine_diff_density_min -.832 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.295 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 3316 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.295 _refine_ls_R_factor_all .0320 _refine_ls_R_factor_gt .0286 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0062P)^2^+1.8187P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .0583 _reflns_number_gt 3136 _reflns_number_total 3316 _reflns_threshold_expression I>2\s(I) _cod_data_source_file na1436.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_chemical_melting_point' value '343-353 K' was changed to '348(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '343-353 K' was changed to '348(5)' - the average value was taken and precision was estimated. '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0062P)^2^+1.8187P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0062P)^2^+1.8187P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1258.9(2) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2010644 _cod_database_fobs_code 2010644 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol I .241246(19) .58943(4) .468957(6) .02788(6) Uani d . 1 . . I O1 .2882(2) 1.2521(4) .61565(7) .0349(4) Uani d . 1 . . O C2 .4176(3) 1.0834(8) .61074(10) .0383(6) Uani d . 1 . . C H21 .4271 .9413 .6350 .050 Uiso d R 1 . . H H22 .5105 1.1980 .6142 .050 Uiso d R 1 . . H C3 .4027(3) .9453(7) .56413(10) .0321(6) Uani d . 1 . . C H31 .4034 1.0878 .5401 .042 Uiso d R 1 . . H H32 .4912 .8235 .5619 .042 Uiso d R 1 . . H N4 .2625(3) .7821(5) .55599(8) .0303(5) Uani d . 1 . . N H4 .2686 .6334 .5760 .039 Uiso d R 1 . . H C5 .1310(3) .9520(7) .56448(10) .0330(6) Uani d . 1 . . C H51 .0394 .8344 .5628 .043 Uiso d R 1 . . H H52 .1145 1.0939 .5403 .043 Uiso d R 1 . . H C6 .1524(3) 1.0917(7) .61086(10) .0357(6) Uani d . 1 . . C H61 .0643 1.2122 .6144 .046 Uiso d R 1 . . H H62 .1574 .9506 .6353 .046 Uiso d R 1 . . H C11 .2439(3) .2693(8) .31857(10) .0374(7) Uani d . 1 . . C C12 .3382(6) .3976(11) .29077(15) .0755(15) Uani d . 1 . . C H12 .4017 .5440 .3026 .091 Uiso d R 1 . . H C13 .3414(7) .3153(11) .24561(15) .0820(16) Uani d . 1 . . C H13 .4089 .4033 .2272 .098 Uiso d R 1 . . H C14 .2492(5) .1101(11) .22743(12) .0651(13) Uani d . 1 . . C H14 .2477 .0627 .1960 .078 Uiso d R 1 . . H C15 .1587(6) -.0271(12) .25492(15) .0756(15) Uani d . 1 . . C H15 .0977 -.1764 .2429 .091 Uiso d R 1 . . H C16 .1559(5) .0513(11) .30045(13) .0632(12) Uani d . 1 . . C H16 .0931 -.0454 .3193 .076 Uiso d R 1 . . H C17 .2375(3) .3592(7) .36494(10) .0346(6) Uani d . 1 . . C C18 .2338(3) .4460(7) .40305(10) .0333(6) Uani d . 1 . . C loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I .02880(9) .03156(9) .02374(9) .00131(8) .00498(6) -.00052(8) O1 .0427(11) .0279(10) .0352(11) -.0019(9) .0091(9) -.0044(9) C2 .0321(14) .0518(18) .0299(14) -.0028(14) -.0007(11) -.0034(14) C3 .0236(12) .0423(16) .0305(13) .0053(11) .0036(10) -.0024(12) N4 .0387(12) .0251(11) .0275(11) .0002(10) .0054(9) .0009(9) C5 .0258(12) .0406(16) .0331(14) -.0043(12) .0053(10) -.0041(12) C6 .0340(14) .0409(16) .0343(14) .0008(13) .0131(11) -.0021(13) C11 .0349(14) .0524(19) .0247(13) .0135(14) .0027(10) .0014(13) C12 .114(4) .075(3) .044(2) -.022(3) .039(2) -.015(2) C13 .133(5) .080(3) .041(2) -.002(3) .046(3) .000(2) C14 .085(3) .087(3) .0236(15) .036(3) .0068(17) -.0041(19) C15 .074(3) .113(4) .040(2) -.009(3) .0064(19) -.030(2) C16 .060(2) .097(3) .0347(18) -.013(2) .0126(16) -.020(2) C17 .0313(13) .0438(17) .0289(14) .0087(12) .0039(10) .0031(12) C18 .0307(13) .0430(16) .0265(13) .0037(12) .0040(10) .0015(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C18 I N4 177.84(10) yes C6 O1 C2 110.8(2) yes O1 C2 C3 110.5(2) yes O1 C2 H21 109.6 ? C3 C2 H21 109.6 ? O1 C2 H22 109.6 ? C3 C2 H22 109.6 ? H21 C2 H22 108.1 ? N4 C3 C2 112.1(2) yes N4 C3 H31 109.2 ? C2 C3 H31 109.2 ? N4 C3 H32 109.2 ? C2 C3 H32 109.2 ? H31 C3 H32 107.9 ? C5 N4 C3 110.0(2) yes C5 N4 I 112.09(17) yes C3 N4 I 108.20(16) yes C5 N4 H4 108.8 ? C3 N4 H4 108.8 ? I N4 H4 108.8 ? N4 C5 C6 112.2(2) ? N4 C5 H51 109.2 ? C6 C5 H51 109.2 ? N4 C5 H52 109.2 ? C6 C5 H52 109.2 ? H51 C5 H52 107.9 ? O1 C6 C5 110.9(2) ? O1 C6 H61 109.5 ? C5 C6 H61 109.5 ? O1 C6 H62 109.5 ? C5 C6 H62 109.5 ? H61 C6 H62 108.0 ? C12 C11 C16 118.0(3) ? C12 C11 C17 120.8(4) ? C16 C11 C17 121.3(3) ? C11 C12 C13 120.7(5) ? C11 C12 H12 119.6 ? C13 C12 H12 119.6 ? C14 C13 C12 120.9(4) ? C14 C13 H13 119.6 ? C12 C13 H13 119.6 ? C13 C14 C15 119.3(4) ? C13 C14 H14 120.3 ? C15 C14 H14 120.3 ? C14 C15 C16 120.2(5) ? C14 C15 H15 119.9 ? C16 C15 H15 119.9 ? C11 C16 C15 120.7(4) ? C11 C16 H16 119.6 ? C15 C16 H16 119.6 ? C18 C17 C11 177.0(4) ? C17 C18 I 176.5(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag I C18 . 2.053(3) yes I N4 . 2.712(2) yes O1 C6 . 1.429(4) yes O1 C2 . 1.430(4) yes C2 C3 . 1.518(4) yes C2 H21 . .9900 ? C2 H22 . .9900 ? C3 N4 . 1.473(4) yes C3 H31 . .9900 ? C3 H32 . .9900 ? N4 C5 . 1.471(4) yes N4 H4 . .9300 ? C5 C6 . 1.517(4) yes C5 H51 . .9900 ? C5 H52 . .9900 ? C6 H61 . .9900 ? C6 H62 . .9900 ? C11 C12 . 1.378(5) ? C11 C16 . 1.388(6) ? C11 C17 . 1.438(4) yes C12 C13 . 1.390(6) ? C12 H12 . .9500 ? C13 C14 . 1.362(7) ? C13 H13 . .9500 ? C14 C15 . 1.370(7) ? C14 H14 . .9500 ? C15 C16 . 1.394(5) ? C15 H15 . .9500 ? C16 H16 . .9500 ? C17 C18 . 1.201(4) 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 O1 C2 C3 N4 -56.5(3) C2 C3 N4 C5 52.2(3) C3 N4 C5 C6 -51.7(3) N4 C5 C6 O1 55.7(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21135917 2 PubChem 139057566