#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/69/2006950.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_2006950 loop_ _publ_author_name 'Thalladi, Venkat R.' 'Katz, Amy K.' 'Carrell, H. L.' 'Nangia, Ashwini' 'Desiraju, Gautam R.' _publ_section_title ; Trimethyl Isocyanurate and Triethyl Isocyanurate ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 86 _journal_page_last 89 _journal_paper_doi 10.1107/S010827019701384X _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C6 H9 N3 O3' _chemical_formula_sum 'C6 H9 N3 O3' _chemical_formula_weight 171.155 _chemical_melting_point 449 _chemical_name_common 'Trimethyl isocyanurate' _chemical_name_systematic ; 1,3,5-Trimethyl-1,3,5-triazine(1H,3H,5H)-2,4,6-trione ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _cell_angle_alpha 90.00 _cell_angle_beta 100.88(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 8.1420(10) _cell_length_b 13.3930(10) _cell_length_c 14.8220(10) _cell_measurement_reflns_used 50 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25 _cell_measurement_theta_min 2 _cell_volume 1587.2(4) _computing_cell_refinement 'CAD4 Software' _computing_data_collection 'CAD4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'CAD4 Software' _computing_molecular_graphics 'ORTEP (Johnson, 1976) and PLUTO (Motherwell & Clegg, 1978)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2754 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_min 2.07 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type none _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.241 _refine_diff_density_min -0.188 _refine_ls_extinction_coef 0.058(5) _refine_ls_extinction_method SHELXL93 _refine_ls_goodness_of_fit_all 1.088 _refine_ls_goodness_of_fit_obs 1.211 _refine_ls_hydrogen_treatment 'H atoms riding' _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 2508 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.088 _refine_ls_restrained_S_obs 1.211 _refine_ls_R_factor_all 0.074 _refine_ls_R_factor_obs .053 _refine_ls_shift/esd_max -0.007 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0967P)^2^+0.3347P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.163 _refine_ls_wR_factor_obs .152 _reflns_number_observed 1814 _reflns_number_total 2508 _reflns_observed_criterion >2sigma(I) _cod_data_source_file oa1038.cif _cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '449 K' was changed to '449' - the value should be numeric and without a unit designator. 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 '449 K' was changed to '449' - the value should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0967P)^2^+0.3347P] 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^)+(0.0967P)^2^+0.3347P] 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 1587.2(3) _cod_original_sg_symbol_H-M 'P 21/a' _cod_database_code 2006950 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' 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 C11 .0495(15) .059(2) .0434(13) .0102(13) .0117(12) .0108(11) C12 .055(2) .0411(14) .0487(14) -.0025(11) -.0004(12) .0045(11) C13 .0448(14) .0486(14) .0485(14) -.0045(12) .0103(11) -.0005(11) C14 .096(2) .043(2) .074(2) .0014(15) .007(2) -.0086(14) C15 .063(2) .109(3) .104(3) -.026(2) .026(2) .020(2) C16 .072(2) .069(2) .096(2) .018(2) .028(2) -.013(2) N11 .0510(12) .0420(11) .0454(11) .0005(9) .0057(9) -.0022(9) N12 .0455(11) .0542(13) .0515(12) -.0063(10) .0096(10) .0110(10) N13 .0452(11) .0456(12) .0534(12) .0053(9) .0104(10) -.0023(9) O11 .085(2) .087(2) .085(2) .0271(12) .0449(13) .0069(12) O12 .092(2) .0487(12) .0881(15) -.0149(11) .0057(12) -.0074(11) O13 .0691(13) .079(2) .103(2) -.0232(11) .0380(13) -.0087(12) C21 .051(2) .052(2) .068(2) .0009(13) .0046(14) .0113(13) C22 .077(2) .053(2) .054(2) .0008(14) .0198(15) -.0004(13) C23 .054(2) .059(2) .048(2) .0011(13) .0098(13) .0026(12) C24 .085(2) .123(3) .077(2) .025(2) .042(2) .015(2) C25 .127(3) .095(3) .052(2) .005(2) -.014(2) .018(2) C26 .058(2) .132(3) .087(2) .026(2) .018(2) .002(2) N21 .0524(12) .0660(14) .0523(13) .0052(11) .0160(10) .0092(11) N22 .0698(15) .0581(14) .0458(12) -.0030(12) .0006(11) .0054(10) N23 .0513(13) .070(2) .0501(12) .0071(11) .0125(10) .0042(11) O21 .0588(13) .096(2) .108(2) .0132(12) .0044(12) .0261(14) O22 .119(2) .101(2) .0638(14) .0155(15) .0429(14) -.0040(12) O23 .0775(15) .117(2) .0455(11) .0137(13) .0024(10) .0096(12) 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_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol C11 .2058(3) .9458(2) .0761(2) .0504(7) Uani d . 1 . C C12 .1263(3) 1.0959(2) .1485(2) .0497(6) Uani d . 1 . C C13 -.0500(3) .9489(2) .1376(2) .0471(6) Uani d . 1 . C C14 .0353(4) .7962(2) .0687(2) .0724(9) Uani d . 1 . C H141 -.0695(4) .7745(2) .0826(2) .109 Uiso calc R 1 . H H142 .1245(4) .7579(2) .1039(2) .109 Uiso calc R 1 . H H143 .0343(4) .7868(2) .0044(2) .109 Uiso calc R 1 . H C15 .3891(4) 1.0903(3) .0914(3) .0907(12) Uani d . 1 . C H151 .4500(4) 1.0450(3) .0598(3) .136 Uiso calc R 1 . H H152 .4555(4) 1.1067(3) .1501(3) .136 Uiso calc R 1 . H H153 .3642(4) 1.1501(3) .0557(3) .136 Uiso calc R 1 . H C16 -.1365(4) 1.1013(2) .2046(2) .0775(9) Uani d . 1 . C H161 -.2295(4) 1.0587(2) .2087(2) .116 Uiso calc R 1 . H H162 -.1755(4) 1.1593(2) .1688(2) .116 Uiso calc R 1 . H H163 -.0831(4) 1.1216(2) .2652(2) .116 Uiso calc R 1 . H N11 .0604(3) .90258(14) .09186(13) .0466(5) Uani d . 1 . N N12 .2322(2) 1.0430(2) .10445(14) .0504(6) Uani d . 1 . N N13 -.0160(2) 1.04696(15) .16055(14) .0479(5) Uani d . 1 . N O11 .3032(3) .9010(2) .0384(2) .0820(7) Uani d . 1 . O O12 .1548(3) 1.18093(14) .1748(2) .0777(7) Uani d . 1 . O O13 -.1714(3) .9062(2) .1550(2) .0806(7) Uani d . 1 . O C21 .5950(3) .8468(2) .4674(2) .0580(7) Uani d . 1 . C C22 .3399(4) .8932(2) .5208(2) .0600(7) Uani d . 1 . C C23 .3468(3) .8935(2) .3577(2) .0532(7) Uani d . 1 . C C24 .6057(5) .8549(3) .3038(2) .0917(12) Uani d . 1 . C H241 .7185(5) .8350(3) .3284(2) .137 Uiso calc R 1 . H H242 .6065(5) .9177(3) .2727(2) .137 Uiso calc R 1 . H H243 .5531(5) .8053(3) .2612(2) .137 Uiso calc R 1 . H C25 .5839(5) .8374(3) .6309(2) .0956(12) Uani d . 1 . C H251 .5070(5) .8513(3) .6711(2) .143 Uiso calc R 1 . H H252 .6827(5) .8773(3) .6487(2) .143 Uiso calc R 1 . H H253 .6136(5) .7680(3) .6351(2) .143 Uiso calc R 1 . H C26 .0891(4) .9351(3) .4102(3) .0919(12) Uani d . 1 . C H261 .0493(4) .9426(3) .4668(3) .138 Uiso calc R 1 . H H262 .0263(4) .8837(3) .3739(3) .138 Uiso calc R 1 . H H263 .0754(4) .9970(3) .3770(3) .138 Uiso calc R 1 . H N21 .5115(3) .8653(2) .37963(15) .0561(6) Uani d . 1 . N N22 .5049(3) .8616(2) .53563(15) .0592(6) Uani d . 1 . N N23 .2673(3) .9076(2) .43016(15) .0569(6) Uani d . 1 . N O21 .7396(3) .8198(2) .4835(2) .0889(8) Uani d . 1 . O O22 .2655(3) .9076(2) .58233(15) .0912(8) Uani d . 1 . O O23 .2770(3) .9076(2) .27945(14) .0813(7) Uani d . 1 . O 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' N N 0.0061 0.0033 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O11 C11 N11 121.9(3) O11 C11 N12 122.1(3) N11 C11 N12 115.9(2) O12 C12 N13 121.5(3) O12 C12 N12 122.6(3) N13 C12 N12 115.9(2) O13 C13 N13 122.2(2) O13 C13 N11 122.0(2) N13 C13 N11 115.8(2) N11 C14 H141 109.5(2) N11 C14 H142 109.47(15) H141 C14 H142 109.5 N11 C14 H143 109.47(15) H141 C14 H143 109.5 H142 C14 H143 109.5 N12 C15 H151 109.5(2) N12 C15 H152 109.5(2) H151 C15 H152 109.5 N12 C15 H153 109.5(2) H151 C15 H153 109.5 H152 C15 H153 109.5 N13 C16 H161 109.5(2) N13 C16 H162 109.5(2) H161 C16 H162 109.5 N13 C16 H163 109.5(2) H161 C16 H163 109.5 H162 C16 H163 109.5 C11 N11 C13 123.9(2) C11 N11 C14 117.0(2) C13 N11 C14 118.5(2) C12 N12 C11 124.0(2) C12 N12 C15 118.7(3) C11 N12 C15 117.2(3) C12 N13 C13 124.1(2) C12 N13 C16 118.2(2) C13 N13 C16 117.7(2) O21 C21 N22 122.2(3) O21 C21 N21 122.0(3) N22 C21 N21 115.8(2) O22 C22 N23 122.2(3) O22 C22 N22 122.7(3) N23 C22 N22 115.1(2) O23 C23 N23 121.8(3) O23 C23 N21 122.2(3) N23 C23 N21 116.0(2) N21 C24 H241 109.5(2) N21 C24 H242 109.5(2) H241 C24 H242 109.5 N21 C24 H243 109.5(2) H241 C24 H243 109.5 H242 C24 H243 109.5 N22 C25 H251 109.5(2) N22 C25 H252 109.5(2) H251 C25 H252 109.5 N22 C25 H253 109.5(2) H251 C25 H253 109.5 H252 C25 H253 109.5 N23 C26 H261 109.5(2) N23 C26 H262 109.5(2) H261 C26 H262 109.5 N23 C26 H263 109.5(2) H261 C26 H263 109.5 H262 C26 H263 109.5 C23 N21 C21 124.1(2) C23 N21 C24 118.0(2) C21 N21 C24 117.9(2) C21 N22 C22 124.4(2) C21 N22 C25 118.5(3) C22 N22 C25 117.0(3) C23 N23 C22 124.6(2) C23 N23 C26 118.2(2) C22 N23 C26 117.2(3) 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 C11 O11 . 1.212(3) ? C11 N11 . 1.376(3) ? C11 N12 . 1.373(3) ? C12 O12 . 1.212(3) ? C12 N13 . 1.372(3) ? C12 N12 . 1.372(3) ? C13 O13 . 1.211(3) ? C13 N13 . 1.372(3) ? C13 N11 . 1.372(3) ? C14 N11 . 1.470(3) ? C14 H141 . .96 ? C14 H142 . .96 ? C14 H143 . .96 ? C15 N12 . 1.471(3) ? C15 H151 . .96 ? C15 H152 . .96 ? C15 H153 . .96 ? C16 N13 . 1.470(3) ? C16 H161 . .96 ? C16 H162 . .96 ? C16 H163 . .96 ? C21 O21 . 1.211(3) ? C21 N22 . 1.371(4) ? C21 N21 . 1.372(4) ? C22 O22 . 1.203(3) ? C22 N23 . 1.375(4) ? C22 N22 . 1.386(4) ? C23 O23 . 1.206(3) ? C23 N23 . 1.368(3) ? C23 N21 . 1.372(3) ? C24 N21 . 1.482(4) ? C24 H241 . .96 ? C24 H242 . .96 ? C24 H243 . .96 ? C25 N22 . 1.473(4) ? C25 H251 . .96 ? C25 H252 . .96 ? C25 H253 . .96 ? C26 N23 . 1.472(4) ? C26 H261 . .96 ? C26 H262 . .96 ? C26 H263 . .96 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C14 H141 O11 4_575 0.96 2.602(4) 3.229(4) 123.2(3) C14 H142 O13 4_675 0.96 2.773(4) 3.679(4) 157.7(3) C14 H143 O12 3_575 0.96 2.841(4) 3.662(4) 144.0(3) C15 H151 O11 3_675 0.96 2.790(4) 3.437(4) 125.5(4) C16 H162 O12 4_585 0.96 2.558(4) 3.362(4) 141.4(4) C16 H163 O22 3_576 0.96 2.955(5) 3.513(5) 118.3(3) C24 H242 O13 1_655 0.96 2.744(5) 3.185(5) 108.8(4) C25 H252 O12 3_676 0.96 2.808(4) 3.251(4) 109.0(3) C25 H253 O22 4_675 0.96 2.836(5) 3.725(5) 154.6(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 12670 2 PubChem 139055864