#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/64/2006499.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_2006499 loop_ _publ_author_name 'Mague, Joel T.' 'Ensley, Harry E.' 'Ling, Jing' _publ_section_title ; Intermediates for the Convenient Synthesis of Bicyclic Aziridinocarbamates ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1347 _journal_page_last 1350 _journal_paper_doi 10.1107/S0108270197006070 _journal_volume 53 _journal_year 1997 _chemical_formula_structural 'C9 H16 I1 N1 O2' _chemical_formula_sum 'C9 H16 I N O2' _chemical_formula_weight 297.14 _chemical_name_systematic ; 5-iodo-6-(n-pentyl)-2-oxazineone ; _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_type_scat_source International_Tables_for_Xray_Crystallography_(Vol._IV) _cell_angle_alpha 90 _cell_angle_beta 102.160(10) _cell_angle_gamma 90 _cell_formula_units_Z 16 _cell_length_a 42.768(9) _cell_length_b 11.338(2) _cell_length_c 10.1230(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 17 _cell_measurement_theta_min 12 _cell_volume 4798.5(14) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'PROCESS MolEN (Fair, 1990)' _computing_molecular_graphics 'ORTEPII (Johnson,_1976)' _computing_publication_material 'CIF VAX MolEN' _computing_structure_refinement 'LSFM MolEN' _computing_structure_solution 'MULTAN (Main et al., 1980) (direct methods)' _diffrn_ambient_temperature 293 _diffrn_measurement_device Enraf_Nonius_CAD4 _diffrn_measurement_method \q/2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_limit_h_max 50 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4511 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.86 _diffrn_standards_decay_% -9.9 _diffrn_standards_interval_time 120 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 2.64 _exptl_absorpt_correction_T_max 0.593 _exptl_absorpt_correction_T_min 0.332 _exptl_absorpt_correction_type \y_scans_(North,_Phillips_&_Mathews,_1968) _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.64 _exptl_crystal_density_method none _exptl_crystal_description Plate _exptl_crystal_F_000 2336 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.74 _refine_diff_density_min -0.17 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.86 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 2840 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.086 _refine_ls_R_factor_obs .039 _refine_ls_shift/esd_max 0.039 _refine_ls_structure_factor_coef F _refine_ls_weighting_details '4Fo^2^/[\s^2^(Fo^2^) + 0.0009Fo^4^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs .050 _reflns_number_observed 2840 _reflns_number_total 4210 _reflns_observed_criterion >2.0\s(I) _cod_data_source_file fr1050.cif _cod_data_source_block 3 _cod_depositor_comments ; Updating space group information and adding the symmetry operation list. Antanas Vaitkus, 2018-06-14 Marking attached hydrogen atoms. Antanas Vaitkus, 2017-03-27 ; _cod_original_cell_volume 4799.0(10) _cod_original_sg_symbol_H-M 'C 2/c' _cod_original_formula_sum 'C9 H16 I1 N1 O2' _cod_database_code 2006499 _cod_database_fobs_code 2006499 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,y,-z+1/2 3 -x,-y,-z 4 x,-y,z+1/2 5 x+1/2,y+1/2,z 6 -x+1/2,y+1/2,-z+1/2 7 -x+1/2,-y+1/2,-z 8 x+1/2,-y+1/2,z+1/2 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 I1 .0723(3) .0840(3) .0823(3) .0330(2) .0058(2) .0022(2) O1 .047(2) .048(2) .048(2) -.010(2) .0170(10) -.009(2) O2 .048(2) .060(2) .059(2) -.003(2) .020(2) -.005(2) N1 .050(2) .042(2) .047(2) -.013(2) .011(2) -.002(2) C1 .045(3) .055(3) .038(2) .006(2) .012(2) .003(2) C2 .053(3) .050(3) .043(3) -.006(3) .007(2) -.004(2) C3 .034(2) .040(3) .049(3) .001(2) .007(2) .004(2) C4 .044(3) .053(3) .039(2) -.005(2) .008(2) .001(2) C5 .055(3) .064(4) .065(3) -.016(3) .020(3) -.002(3) C6 .075(4) .096(5) .082(4) -.030(4) .028(3) .002(4) C7 .105(5) .142(6) .149(6) -.071(4) .073(4) -.036(6) C8 .179(9) .29(2) .230(10) -.070(10) .113(7) -.030(10) C9 .059(5) .40(2) .42(2) -.085(8) .036(9) -.16(2) I2 .0639(2) .0659(2) .0740(2) .0054(2) .0228(2) .0200(2) O3 .034(2) .045(2) .062(2) -.006(2) .0120(10) -.011(2) O4 .050(2) .040(2) .075(2) -.003(2) .022(2) -.013(2) N2 .032(2) .045(2) .071(3) .003(2) .009(2) -.010(2) C10 .049(3) .043(3) .050(3) -.003(2) .014(2) -.010(2) C11 .049(3) .050(3) .051(3) -.010(3) .005(2) -.011(2) C12 .045(3) .036(2) .047(2) .000(2) .014(2) .005(2) C13 .043(3) .049(3) .039(2) .003(2) .013(2) -.005(2) C14 .049(3) .056(3) .066(3) .004(3) .024(2) -.001(3) C15 .050(3) .072(4) .071(3) .005(3) .022(3) .002(3) C16 .052(3) .070(4) .075(3) -.003(3) .025(3) -.012(3) C17 .068(4) .101(5) .106(5) -.015(4) .038(3) .002(4) C18 .050(4) .180(10) .220(10) -.007(6) .039(5) .026(8) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_attached_hydrogens I1 .597630(10) .21956(5) .48094(5) .08100(10) Uani ? 0 O1 .64972(8) .0041(3) .4206(3) .0463(9) Uani ? 0 O2 .68758(8) .0834(3) .3354(3) .0540(10) Uani ? 0 N1 .67940(10) .1559(4) .5335(4) .0460(10) Uani ? 0 C1 .63090(10) .1000(5) .6048(5) .0450(10) Uani ? 0 C2 .66320(10) .1573(5) .6446(5) .0490(10) Uani ? 0 C3 .67350(10) .0821(4) .4277(5) .0410(10) Uani ? 0 C4 .63420(10) -.0136(5) .5350(5) .0450(10) Uani ? 0 C5 .60390(10) -.0817(6) .4782(5) .060(2) Uani ? 0 C6 .5839(2) -.1078(7) .5784(7) .083(2) Uani ? 0 C7 .5525(2) -.1703(8) .5157(8) .125(3) Uani ? 0 C8 .5289(3) -.181(2) .5950(10) .223(6) Uani ? 0 C9 .4985(3) -.237(2) .508(2) .295(9) Uani ? 3 I2 .200570(10) .23385(4) .52132(4) .06670(10) Uani ? 0 O3 .19346(8) -.0374(3) .6555(3) .0469(9) Uani ? 0 O4 .22470(8) -.1600(3) .5734(4) .0540(10) Uani ? 0 N2 .24777(9) -.0004(4) .6853(4) .0500(10) Uani ? 0 C10 .21280(10) .1606(4) .7237(5) .0470(10) Uani ? 0 C11 .24650(10) .1122(5) .7533(5) .0500(10) Uani ? 0 C12 .22280(10) -.0700(4) .6358(5) .0420(10) Uani ? 0 C13 .19020(10) .0622(5) .7421(4) .0430(10) Uani ? 0 C14 .15530(10) .0927(5) .7146(6) .055(2) Uani ? 0 C15 .13480(10) .0013(5) .7699(6) .063(2) Uani ? 0 C16 .09970(10) .0227(5) .7291(6) .064(2) Uani ? 0 C17 .0800(2) -.0596(7) .7930(7) .089(2) Uani ? 0 C18 .0436(2) -.0340(10) .7550(10) .149(4) Uani ? 3 H1n .6917 .2192 .5060 .0547 Uiso calc 0 H1 .6228 .0821 .6912 .0547 Uiso calc 0 H2n .2676 -.0355 .6653 .0608 Uiso calc 0 H10 .2087 .2311 .7775 .0469 Uiso calc 0 H2a .6605 .2367 .6703 .0588 Uiso calc 0 H2b .6756 .1157 .7187 .0588 Uiso calc 0 H4 .6463 -.0589 .6069 .0544 Uiso calc 0 H5a .6097 -.1544 .4435 .0720 Uiso calc 0 H5b .5915 -.0367 .4069 .0720 Uiso calc 0 H6a .5790 -.0356 .6171 .0990 Uiso calc 0 H6b .5958 -.1568 .6471 .0990 Uiso calc 0 H7a .5578 -.2480 .4927 .1502 Uiso calc 0 H7b .5431 -.1286 .4358 .1502 Uiso calc 0 H8a .5239 -.1045 .6238 .2673 Uiso calc 0 H8b .5367 -.2288 .6712 .2673 Uiso calc 0 H11a .2603 .1667 .7227 .0606 Uiso calc 0 H11b .2534 .1012 .8481 .0606 Uiso calc 0 H13 .1965 .0447 .8357 .0518 Uiso calc 0 H14a .1477 .0986 .6196 .0666 Uiso calc 0 H14b .1529 .1668 .7554 .0666 Uiso calc 0 H15a .1406 .0024 .8657 .0755 Uiso calc 0 H15b .1392 -.0744 .7378 .0755 Uiso calc 0 H16a .0935 .0143 .6338 .0769 Uiso calc 0 H16b .0955 .1010 .7538 .0769 Uiso calc 0 H17a .0868 -.0536 .8884 .1065 Uiso calc 0 H17b .0834 -.1376 .7653 .1065 Uiso calc 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 C3 O1 C4 121.0(4) yes C2 N1 C3 126.2(4) yes C2 N1 H1n 127.0(10) yes C3 N1 H1n 105.0(10) yes I1 C1 C2 109.8(4) ? I1 C1 C4 112.5(3) ? I1 C1 H1 109.0(10) ? C2 C1 C4 109.1(4) yes C2 C1 H1 108.0(10) ? C4 C1 H1 108.0(10) ? N1 C2 C1 110.7(4) yes O1 C3 O2 117.5(5) yes O1 C3 N1 117.8(5) yes O2 C3 N1 124.7(5) yes O1 C4 C1 111.1(4) yes O1 C4 C5 105.3(4) yes C1 C4 C5 117.6(5) yes C4 C5 C6 114.3(5) ? C5 C6 C7 112.9(6) ? C6 C7 C8 118.0(10) ? C7 C8 C9 109.0(10) ? C12 O3 C13 120.5(4) yes C11 N2 C12 126.0(4) yes C11 N2 H2n 124.0(10) yes C12 N2 H2n 110.0(10) yes I2 C10 C11 111.0(4) ? I2 C10 C13 111.4(3) ? I2 C10 H10 100.0(10) ? C11 C10 C13 108.4(4) yes C11 C10 H10 117.0(10) ? C13 C10 H10 109.0(10) ? N2 C11 C10 110.7(4) yes O3 C12 O4 118.0(5) yes O3 C12 N2 118.2(4) yes O4 C12 N2 123.8(5) yes O3 C13 C10 110.7(4) yes O3 C13 C14 106.6(4) yes C10 C13 C14 116.4(5) yes C13 C14 C15 113.5(5) ? C14 C15 C16 114.1(5) ? C15 C16 C17 114.0(6) ? C16 C17 C18 113.8(8) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag I1 C1 2.164(5) ? O1 C3 1.340(6) yes O1 C4 1.466(6) yes O2 C3 1.212(6) yes N1 C2 1.440(7) yes N1 C3 1.341(6) yes N1 H1n .96(4) yes C1 C2 1.503(7) yes C1 C4 1.490(7) yes C1 H1 1.03(3) ? C4 C5 1.512(7) ? C5 C6 1.488(9) ? C6 C7 1.530(10) ? C7 C8 1.420(10) ? C8 C9 1.55(2) ? I2 C10 2.170(5) ? O3 C12 1.362(6) yes O3 C13 1.455(6) yes O4 C12 1.212(6) yes N2 C11 1.457(7) yes N2 C12 1.337(6) yes N2 H2n 1.00(4) yes C10 C11 1.510(8) yes C10 C13 1.514(8) yes C10 H10 1.00(4) ? C13 C14 1.500(7) ? C14 C15 1.538(8) ? C15 C16 1.491(8) ? C16 C17 1.493(9) ? C17 C18 1.550(10) ? 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 C4 O1 C3 O2 172.3(4) yes C4 O1 C3 N1 -10.1(6) yes C3 O1 C4 C1 37.5(6) yes C3 O1 C4 C5 165.8(4) yes C3 N1 C2 C1 -22.2(7) yes C2 N1 C3 O1 2.3(7) yes C2 N1 C3 O2 179.8(5) yes C4 C1 C2 N1 46.8(5) yes C2 C1 C4 O1 -54.7(5) yes C2 C1 C4 C5 -176.0(4) yes C13 O3 C12 O4 173.1(4) yes C13 O3 C12 N2 -7.4(6) yes C12 O3 C13 C10 38.6(6) yes C12 O3 C13 C14 166.1(4) yes C12 N2 C11 C10 -18.0(7) yes C11 N2 C12 O3 -3.6(7) yes C11 N2 C12 O4 175.9(4) yes C13 C10 C11 N2 46.6(5) yes C11 C10 C13 O3 -57.1(5) yes C11 C10 C13 C14 -179.0(4) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139055660