#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/69/2006951.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_2006951 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 'C9 H15 N3 O3' _chemical_formula_sum 'C9 H15 N3 O3' _chemical_formula_weight 213.24 _chemical_melting_point 370 _chemical_name_common 'Triethyl isocyanurate' _chemical_name_systematic ; 1,3,5-Triethyl-1,3,5-triazine(1H,3H,5H)-2,4,6-trione ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.835(2) _cell_length_b 8.1440(10) _cell_length_c 16.820(5) _cell_measurement_reflns_used 750 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.81 _cell_measurement_theta_min 2.78 _cell_volume 1073.3(4) _computing_cell_refinement MADNES _computing_data_collection 'MADNES Pflugrath & Messerschmidt, 1989)' _computing_data_reduction MADNES _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 121 _diffrn_measurement_device 'Enraf-Nonius FAST area detector' _diffrn_measurement_method 'rotation scans' _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 0.000 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1568 _diffrn_reflns_theta_max 28.81 _diffrn_reflns_theta_min 2.78 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.296 _refine_diff_density_min -0.227 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 8.4(16) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.074 _refine_ls_goodness_of_fit_obs 1.041 _refine_ls_hydrogen_treatment 'H atoms riding' _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 1568 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.074 _refine_ls_restrained_S_obs 1.041 _refine_ls_R_factor_all 0.044 _refine_ls_R_factor_obs .038 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.1546P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.107 _refine_ls_wR_factor_obs .096 _reflns_number_observed 1380 _reflns_number_total 1568 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file oa1038.cif _[local]_cod_data_source_block 2 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '370 K' was changed to '370' - 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 '370 K' was changed to '370' - 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^)+(0.0629P)^2^+0.1546P] 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^)+(0.0629P)^2^+0.1546P] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2006951 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' '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 O1 .0230(8) .0155(6) .0322(8) .0035(6) -.0050(6) -.0003(6) O2 .0150(7) .0244(7) .0201(6) .0043(6) -.0026(6) .0027(6) O3 .0197(7) .0277(7) .0235(7) -.0025(6) -.0043(6) -.0103(6) N1 .0098(7) .0178(7) .0123(7) .0013(6) -.0012(6) .0006(6) N2 .0133(8) .0149(7) .0147(7) -.0023(6) -.0046(6) -.0011(6) N3 .0129(8) .0106(7) .0151(7) .0021(6) .0008(6) -.0018(6) C1 .0136(9) .0155(8) .0159(8) -.0021(7) .0019(7) .0032(7) C2 .0119(8) .0165(8) .0103(8) .0002(7) .0014(7) -.0002(7) C3 .0113(9) .0186(9) .0115(8) -.0003(7) .0039(7) -.0015(6) C4 .0136(9) .0270(10) .0146(8) .0030(8) -.0033(7) .0053(7) C5 .0150(9) .0201(9) .0198(9) -.0062(8) -.0045(8) -.0042(7) C6 .0201(10) .0119(8) .0237(9) .0043(8) .0058(8) -.0037(7) C7 .0144(10) .0437(14) .0254(10) .0031(10) -.0003(9) .0121(10) C8 .0242(11) .0240(10) .0236(10) -.0036(10) -.0024(9) -.0035(8) C9 .0253(11) .0301(10) .0254(10) .0047(10) .0075(9) -.0068(9) 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 O1 .2536(2) 1.1599(2) .91522(9) .0236(4) Uani d . 1 . O O2 .6076(2) .7366(2) .97900(8) .0199(3) Uani d . 1 . O O3 .1740(2) .6586(2) .80296(8) .0236(4) Uani d . 1 . O N1 .2114(2) .9124(2) .85599(9) .0133(3) Uani d . 1 . N N2 .4379(2) .9539(2) .94531(9) .0143(3) Uani d . 1 . N N3 .3949(2) .6942(2) .88883(9) .0129(3) Uani d . 1 . N C1 .2963(2) 1.0180(2) .90691(11) .0150(4) Uani d . 1 . C C2 .4878(2) .7909(2) .94091(10) .0129(4) Uani d . 1 . C C3 .2537(2) .7480(2) .84659(10) .0138(4) Uani d . 1 . C C4 .0590(2) .9754(3) .81446(11) .0184(4) Uani d . 1 . C H41 .0435(2) .9150(3) .76527(11) .022 Uiso calc R 1 . H H42 .0767(2) 1.0900(3) .80108(11) .022 Uiso calc R 1 . H C5 .5277(3) 1.0634(2) 1.00183(11) .0183(4) Uani d . 1 . C H51 .5393(3) 1.1716(2) .97836(11) .022 Uiso calc R 1 . H H52 .6414(3) 1.0208(2) 1.01164(11) .022 Uiso calc R 1 . H C6 .4438(3) .5207(2) .87904(12) .0186(4) Uani d . 1 . C H61 .3417(3) .4536(2) .87684(12) .022 Uiso calc R 1 . H H62 .5101(3) .4860(2) .92478(12) .022 Uiso calc R 1 . H C7 -.1009(3) .9595(3) .86479(13) .0278(5) Uani d . 1 . C H71 -.1970(3) 1.0016(3) .83580(13) .042 Uiso calc R 1 . H H72 -.0869(3) 1.0208(3) .91310(13) .042 Uiso calc R 1 . H H73 -.1201(3) .8460(3) .87731(13) .042 Uiso calc R 1 . H C8 .4334(3) 1.0774(3) 1.07954(12) .0239(5) Uani d . 1 . C H81 .4949(3) 1.1490(3) 1.11464(12) .036 Uiso calc R 1 . H H82 .4236(3) .9707(3) 1.10337(12) .036 Uiso calc R 1 . H H83 .3215(3) 1.1214(3) 1.07013(12) .036 Uiso calc R 1 . H C9 .5478(3) .4937(3) .80407(12) .0269(5) Uani d . 1 . C H91 .5773(3) .3797(3) .79968(12) .040 Uiso calc R 1 . H H92 .6501(3) .5584(3) .80650(12) .040 Uiso calc R 1 . H H93 .4818(3) .5260(3) .75860(12) .040 Uiso calc R 1 . H 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 C1 N1 C3 123.7(2) C1 N1 C4 117.8(2) C3 N1 C4 118.3(2) C2 N2 C1 124.2(2) C2 N2 C5 118.5(2) C1 N2 C5 116.9(2) C2 N3 C3 124.34(15) C2 N3 C6 118.6(2) C3 N3 C6 117.0(2) O1 C1 N1 122.1(2) O1 C1 N2 121.8(2) N1 C1 N2 116.0(2) O2 C2 N2 122.5(2) O2 C2 N3 122.0(2) N2 C2 N3 115.5(2) O3 C3 N3 122.3(2) O3 C3 N1 121.8(2) N3 C3 N1 115.9(2) N1 C4 C7 112.0(2) N1 C4 H41 109.21(10) C7 C4 H41 109.21(12) N1 C4 H42 109.21(10) C7 C4 H42 109.21(13) H41 C4 H42 107.9 N2 C5 C8 111.7(2) N2 C5 H51 109.28(10) C8 C5 H51 109.28(12) N2 C5 H52 109.28(10) C8 C5 H52 109.28(12) H51 C5 H52 107.9 N3 C6 C9 111.8(2) N3 C6 H61 109.25(11) C9 C6 H61 109.25(12) N3 C6 H62 109.25(11) C9 C6 H62 109.25(12) H61 C6 H62 107.9 C4 C7 H71 109.47(11) C4 C7 H72 109.47(12) H71 C7 H72 109.5 C4 C7 H73 109.47(13) H71 C7 H73 109.5 H72 C7 H73 109.5 C5 C8 H81 109.47(11) C5 C8 H82 109.47(12) H81 C8 H82 109.5 C5 C8 H83 109.47(12) H81 C8 H83 109.5 H82 C8 H83 109.5 C6 C9 H91 109.47(11) C6 C9 H92 109.47(12) H91 C9 H92 109.5 C6 C9 H93 109.47(12) H91 C9 H93 109.5 H92 C9 H93 109.5 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 O1 C1 . 1.211(2) ? O2 C2 . 1.220(2) ? O3 C3 . 1.207(2) ? N1 C1 . 1.384(2) ? N1 C3 . 1.388(2) ? N1 C4 . 1.475(2) ? N2 C2 . 1.385(2) ? N2 C1 . 1.386(2) ? N2 C5 . 1.481(2) ? N3 C2 . 1.385(2) ? N3 C3 . 1.385(2) ? N3 C6 . 1.473(2) ? C4 C7 . 1.518(3) ? C4 H41 . .97 ? C4 H42 . .97 ? C5 C8 . 1.506(3) ? C5 H51 . .97 ? C5 H52 . .97 ? C6 C9 . 1.517(3) ? C6 H61 . .97 ? C6 H62 . .97 ? C7 H71 . .96 ? C7 H72 . .96 ? C7 H73 . .96 ? C8 H81 . .96 ? C8 H82 . .96 ? C8 H83 . .96 ? C9 H91 . .96 ? C9 H92 . .96 ? C9 H93 . .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 C6 H61 O1 1_545 0.97 2.572(2) 3.350(2) 137.4(2) C7 H71 O3 3_556 0.96 2.667(3) 3.305(3) 124.3(2) C7 H73 O2 1_455 0.96 2.876(3) 3.493(3) 123.0(2) C8 H81 O1 4_577 0.96 2.604(3) 3.299(3) 129.5(2) C8 H82 O3 4_567 0.96 2.728(3) 3.340(3) 122.2(2)