#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/24/2012438.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_2012438 loop_ _publ_author_name 'Usman, Anwar' 'Chantrapromma, Suchada' 'Fun, Hoong-Kun' 'Poh, Bo-Long' 'Karalai, Chatchanok' _publ_section_title ; Hexamethylenetetraminium 2,4,6-trinitrophenolate ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o46 _journal_page_last o47 _journal_paper_doi 10.1107/S0108270101018571 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C6 H13 N4 1+, C6 H2 N3 O7 1-' _chemical_formula_sum 'C12 H15 N7 O7' _chemical_formula_weight 369.31 _chemical_name_systematic ; Hexamethylenetetramine-2,4,6-trinitrophenol ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 107.0220(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.4995(2) _cell_length_b 6.63440(10) _cell_length_c 18.6203(2) _cell_measurement_reflns_used 6652 _cell_measurement_temperature 183(2) _cell_measurement_theta_max 28.33 _cell_measurement_theta_min 3.23 _cell_volume 1476.48(4) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 183(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full .975 _diffrn_measured_fraction_theta_max .975 _diffrn_measurement_device_type ; Siemens SMART 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 .0690 _diffrn_reflns_av_sigmaI/netI .0961 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 8504 _diffrn_reflns_theta_full 28.29 _diffrn_reflns_theta_max 28.29 _diffrn_reflns_theta_min 3.23 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .139 _exptl_absorpt_correction_T_max .9570 _exptl_absorpt_correction_T_min .9466 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 768 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .40 _exptl_crystal_size_min .32 _refine_diff_density_max .425 _refine_diff_density_min -.430 _refine_ls_extinction_coef .033(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_ref .951 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 240 _refine_ls_number_reflns 3575 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .951 _refine_ls_R_factor_all .0689 _refine_ls_R_factor_gt .0580 _refine_ls_shift/su_max .000 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0807P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .1474 _refine_ls_wR_factor_ref .1539 _reflns_number_gt 2697 _reflns_number_total 3575 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file ln1125.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: '_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 ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2012438 _cod_database_fobs_code 2012438 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 O1 .60294(10) .5516(2) .07795(8) .0320(3) Uani d . 1 . . O O2 .45903(14) .8527(2) .04912(12) .0550(5) Uani d . 1 . . O O3 .29116(13) .7894(3) .04515(12) .0615(6) Uani d . 1 . . O O4 .18616(10) .2220(2) .15681(8) .0312(4) Uani d . 1 . . O O5 .30662(12) -.0030(2) .21338(10) .0438(4) Uani d . 1 . . O O6 .67789(12) .0254(2) .20283(10) .0431(4) Uani d . 1 . . O O7 .73586(11) .2486(2) .14037(10) .0408(4) Uani d . 1 . . O N3 .66203(12) .1781(2) .16407(9) .0223(3) Uani d . 1 . . N N2 .28268(12) .1539(2) .17746(8) .0227(3) Uani d . 1 . . N N1 .38972(12) .7422(2) .06093(9) .0243(3) Uani d . 1 . . N N4 .81992(11) .61547(19) .09625(7) .0149(3) Uani d . 1 . . N N5 .97556(10) .7577(2) .19366(7) .0157(3) Uani d . 1 . . N N6 1.00739(11) .59303(19) .08449(8) .0160(3) Uani d . 1 . . N N7 .91067(11) .91728(19) .07003(8) .0151(3) Uani d . 1 . . N C1 .53481(13) .4662(2) .10504(9) .0182(3) Uani d . 1 . . C C2 .42297(13) .5466(2) .09739(9) .0171(3) Uani d . 1 . . C C3 .34367(13) .4483(2) .12158(9) .0168(3) Uani d . 1 . . C H3A .2733 .5054 .1143 .020 Uiso calc R 1 . . H C4 .36892(13) .2631(2) .15695(9) .0170(3) Uani d . 1 . . C C5 .47419(13) .1785(2) .17098(9) .0175(3) Uani d . 1 . . C H5A .4908 .0567 .1966 .021 Uiso calc R 1 . . H C6 .55404(13) .2770(2) .14654(9) .0176(3) Uani d . 1 . . C C7 .86933(13) .6544(2) .17982(9) .0167(3) Uani d . 1 . . C H7A .8181 .7361 .1978 .020 Uiso calc R 1 . . H H7B .8802 .5274 .2068 .020 Uiso calc R 1 . . H C8 .90167(14) .4883(2) .06953(9) .0174(3) Uani d . 1 . . C H8A .9127 .3597 .0954 .021 Uiso calc R 1 . . H H8B .8717 .4629 .0161 .021 Uiso calc R 1 . . H C9 .80422(13) .8160(2) .05523(9) .0162(3) Uani d . 1 . . C H9A .7730 .7938 .0017 .019 Uiso calc R 1 . . H H9B .7524 .8994 .0720 .019 Uiso calc R 1 . . H C10 1.05185(13) .6316(2) .16567(9) .0181(3) Uani d . 1 . . C H10A 1.1237 .6986 .1758 .022 Uiso calc R 1 . . H H10B 1.0635 .5042 .1924 .022 Uiso calc R 1 . . H C11 .98830(13) .7876(2) .04477(9) .0173(3) Uani d . 1 . . C H11A .9580 .7635 -.0087 .021 Uiso calc R 1 . . H H11B 1.0593 .8568 .0532 .021 Uiso calc R 1 . . H C12 .95718(13) .9492(2) .15161(9) .0169(3) Uani d . 1 . . C H12A .9062 1.0326 .1691 .020 Uiso calc R 1 . . H H12B 1.0277 1.0207 .1615 .020 Uiso calc R 1 . . H H1N4 .751(2) .550(3) .0879(14) .046(7) Uiso d . 1 . . H 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 .0130(6) .0422(8) .0414(8) -.0030(5) .0087(6) .0185(6) O2 .0472(10) .0246(8) .1038(16) -.0003(7) .0387(10) .0197(8) O3 .0211(8) .0479(10) .1066(16) .0081(7) .0046(9) .0446(10) O4 .0117(6) .0399(8) .0434(8) .0009(5) .0104(6) .0099(6) O5 .0277(8) .0465(9) .0591(10) .0008(6) .0156(7) .0337(8) O6 .0261(8) .0465(9) .0603(11) .0174(6) .0181(7) .0281(8) O7 .0222(7) .0264(7) .0838(13) .0037(5) .0310(8) .0089(7) N3 .0146(7) .0219(7) .0309(8) .0009(5) .0074(6) -.0016(6) N2 .0145(7) .0314(8) .0226(7) -.0016(6) .0062(6) .0078(6) N1 .0219(8) .0202(7) .0281(8) -.0014(6) .0032(6) .0033(6) N4 .0103(6) .0165(6) .0183(7) -.0016(5) .0048(5) .0009(5) N5 .0119(6) .0188(6) .0160(6) .0006(5) .0033(5) .0012(5) N6 .0148(7) .0172(6) .0183(7) .0019(5) .0082(5) .0020(5) N7 .0143(6) .0144(6) .0175(6) .0007(5) .0058(5) .0019(5) C1 .0115(7) .0242(8) .0181(8) -.0041(6) .0030(6) -.0002(6) C2 .0139(8) .0174(7) .0184(8) -.0014(6) .0022(6) .0011(6) C3 .0117(7) .0219(8) .0165(7) .0001(6) .0035(6) -.0013(6) C4 .0116(8) .0229(8) .0176(8) -.0023(6) .0062(6) .0021(6) C5 .0143(8) .0190(7) .0181(8) .0000(6) .0031(6) .0012(6) C6 .0099(7) .0218(8) .0204(8) .0006(6) .0033(6) -.0016(6) C7 .0158(8) .0218(8) .0145(7) -.0005(6) .0078(6) .0019(6) C8 .0188(8) .0142(7) .0208(8) .0001(6) .0083(6) -.0020(6) C9 .0118(7) .0185(7) .0166(7) .0026(5) .0016(6) .0020(6) C10 .0124(7) .0223(8) .0189(8) .0044(6) .0034(6) .0039(6) C11 .0164(8) .0193(8) .0192(8) .0014(6) .0099(6) .0031(6) C12 .0159(7) .0141(7) .0204(8) -.0018(5) .0049(6) -.0023(6) 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' 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 O6 N3 O7 121.20(15) yes O6 N3 C6 119.06(14) ? O7 N3 C6 119.74(14) ? O5 N2 O4 122.60(14) yes O5 N2 C4 119.32(14) ? O4 N2 C4 118.07(14) ? O2 N1 O3 121.94(16) yes O2 N1 C2 120.14(15) ? O3 N1 C2 117.89(14) ? C8 N4 C9 108.82(12) ? C8 N4 C7 108.64(12) ? C9 N4 C7 108.69(12) ? C8 N4 H1N4 111.3(14) ? C9 N4 H1N4 110.2(15) ? C7 N4 H1N4 109.2(15) ? C7 N5 C10 108.83(12) ? C7 N5 C12 108.73(12) ? C10 N5 C12 108.51(12) ? C8 N6 C11 108.66(12) ? C8 N6 C10 109.30(12) ? C11 N6 C10 108.68(12) ? C9 N7 C11 108.89(12) ? C9 N7 C12 109.09(12) ? C11 N7 C12 108.35(12) ? O1 C1 C6 125.47(15) ? O1 C1 C2 122.79(15) ? C6 C1 C2 111.73(13) ? C3 C2 C1 123.88(15) ? C3 C2 N1 116.08(14) ? C1 C2 N1 120.03(14) ? C2 C3 C4 119.52(15) ? C2 C3 H3A 120.2 ? C4 C3 H3A 120.2 ? C5 C4 C3 121.41(14) ? C5 C4 N2 119.35(14) ? C3 C4 N2 119.21(14) ? C6 C5 C4 119.11(15) ? C6 C5 H5A 120.4 ? C4 C5 H5A 120.4 ? C5 C6 N3 115.37(14) ? C5 C6 C1 124.14(14) ? N3 C6 C1 120.49(14) ? N5 C7 N4 109.83(12) ? N5 C7 H7A 109.7 ? N4 C7 H7A 109.7 ? N5 C7 H7B 109.7 ? N4 C7 H7B 109.7 ? H7A C7 H7B 108.2 ? N6 C8 N4 109.58(12) ? N6 C8 H8A 109.8 ? N4 C8 H8A 109.8 ? N6 C8 H8B 109.8 ? N4 C8 H8B 109.8 ? H8A C8 H8B 108.2 ? N7 C9 N4 109.62(12) ? N7 C9 H9A 109.7 ? N4 C9 H9A 109.7 ? N7 C9 H9B 109.7 ? N4 C9 H9B 109.7 ? H9A C9 H9B 108.2 ? N6 C10 N5 111.90(12) ? N6 C10 H10A 109.2 ? N5 C10 H10A 109.2 ? N6 C10 H10B 109.2 ? N5 C10 H10B 109.2 ? H10A C10 H10B 107.9 ? N6 C11 N7 112.14(12) ? N6 C11 H11A 109.2 ? N7 C11 H11A 109.2 ? N6 C11 H11B 109.2 ? N7 C11 H11B 109.2 ? H11A C11 H11B 107.9 ? N7 C12 N5 112.13(12) ? N7 C12 H12A 109.2 ? N5 C12 H12A 109.2 ? N7 C12 H12B 109.2 ? N5 C12 H12B 109.2 ? H12A C12 H12B 107.9 ? 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 . 1.2456(19) yes O2 N1 . 1.2037(19) yes O3 N1 . 1.221(2) yes O4 N2 . 1.2393(18) yes O5 N2 . 1.2258(19) yes O6 N3 . 1.226(2) yes O7 N3 . 1.2262(18) yes N3 C6 . 1.449(2) ? N2 C4 . 1.4403(19) ? N1 C2 . 1.467(2) ? N4 C8 . 1.517(2) yes N4 C9 . 1.5181(19) yes N4 C7 . 1.519(2) yes N4 H1N4 . .94(3) ? N5 C7 . 1.4488(19) yes N5 C10 . 1.4737(19) yes N5 C12 . 1.474(2) yes N6 C8 . 1.446(2) yes N6 C11 . 1.4719(19) yes N6 C10 . 1.472(2) yes N7 C9 . 1.4431(19) yes N7 C11 . 1.4733(19) yes N7 C12 . 1.474(2) yes C1 C6 . 1.457(2) ? C1 C2 . 1.464(2) ? C2 C3 . 1.368(2) ? C3 C4 . 1.386(2) ? C3 H3A . .9300 ? C4 C5 . 1.383(2) ? C5 C6 . 1.377(2) ? C5 H5A . .9300 ? C7 H7A . .9700 ? C7 H7B . .9700 ? C8 H8A . .9700 ? C8 H8B . .9700 ? C9 H9A . .9700 ? C9 H9B . .9700 ? C10 H10A . .9700 ? C10 H10B . .9700 ? C11 H11A . .9700 ? C11 H11B . .9700 ? C12 H12A . .9700 ? C12 H12B . .9700 ? 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 _geom_hbond_publ_flag N4 H14N O1 1_555 .94(2) 1.81(3) 2.666(2) 152(2) yes N4 H14N O7 1_555 .94(2) 2.26(2) 2.865(2) 122(2) yes C12 H12A O7 1_565 .97 2.49 3.362(2) 149 yes C12 H12B O4 1_665 .97 2.41 3.364(2) 167 yes C5 H5A Cg 2_645 .93 3.30 4.07 142 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 C1 C2 C3 174.80(16) C6 C1 C2 C3 -4.4(2) O1 C1 C2 N1 -4.2(3) C6 C1 C2 N1 176.62(14) O2 N1 C2 C3 167.90(18) O3 N1 C2 C3 -10.3(2) O2 N1 C2 C1 -13.0(3) O3 N1 C2 C1 168.81(18) C1 C2 C3 C4 1.3(3) N1 C2 C3 C4 -179.67(14) C2 C3 C4 C5 2.5(2) C2 C3 C4 N2 -175.61(15) O5 N2 C4 C5 6.9(2) O4 N2 C4 C5 -172.03(15) O5 N2 C4 C3 -174.93(17) O4 N2 C4 C3 6.1(2) C3 C4 C5 C6 -2.6(3) N2 C4 C5 C6 175.49(14) C4 C5 C6 N3 179.64(14) C4 C5 C6 C1 -1.0(3) O6 N3 C6 C5 -4.9(2) O7 N3 C6 C5 175.43(17) O6 N3 C6 C1 175.74(16) O7 N3 C6 C1 -3.9(3) O1 C1 C6 C5 -174.91(17) C2 C1 C6 C5 4.3(2) O1 C1 C6 N3 4.4(3) C2 C1 C6 N3 -176.45(14) C10 N5 C7 N4 -59.11(16) C12 N5 C7 N4 58.91(15) C8 N4 C7 N5 59.14(15) C9 N4 C7 N5 -59.12(15) C11 N6 C8 N4 -59.31(16) C10 N6 C8 N4 59.14(16) C9 N4 C8 N6 59.25(16) C7 N4 C8 N6 -58.93(15) C11 N7 C9 N4 58.91(16) C12 N7 C9 N4 -59.16(15) C8 N4 C9 N7 -59.03(16) C7 N4 C9 N7 59.12(15) C8 N6 C10 N5 -60.44(16) C11 N6 C10 N5 57.99(16) C7 N5 C10 N6 60.22(16) C12 N5 C10 N6 -57.94(16) C8 N6 C11 N7 60.76(16) C10 N6 C11 N7 -58.08(16) C9 N7 C11 N6 -60.66(17) C12 N7 C11 N6 57.88(16) C9 N7 C12 N5 60.49(16) C11 N7 C12 N5 -57.92(16) C7 N5 C12 N7 -60.16(16) C10 N5 C12 N7 58.06(16)