#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/24/2012439.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_2012439 loop_ _publ_author_name 'Usman, Anwar' 'Chantrapromma, Suchada' 'Fun, Hoong-Kun' 'Poh, Bo-Long' 'Karalai, Chatchanok' _publ_section_title ; A 1:1 adduct of hexamethylenetetramine and 4-hydroxy-3-methoxybenzaldehyde ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o48 _journal_page_last o50 _journal_paper_doi 10.1107/S0108270101020194 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C6 H12 N4, C8 H8 O3' _chemical_formula_moiety 'C6 H12 N4, C8 H8 O3' _chemical_formula_sum 'C14 H20 N4 O3' _chemical_formula_weight 292.34 _chemical_melting_point 352 _chemical_name_systematic ; Hexamethylenetetramine-4-hydroxy-3-methoxybenzaldehyde ; _space_group_IT_number 29 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 27.1214(3) _cell_length_b 7.13270(10) _cell_length_c 7.47760(10) _cell_measurement_reflns_used 4976 _cell_measurement_temperature 183(2) _cell_measurement_theta_max 28.30 _cell_measurement_theta_min 2.86 _cell_volume 1446.53(3) _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 .966 _diffrn_measured_fraction_theta_max .966 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _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 .0765 _diffrn_reflns_av_sigmaI/netI .0714 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 8042 _diffrn_reflns_theta_full 28.30 _diffrn_reflns_theta_max 28.30 _diffrn_reflns_theta_min 2.86 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .097 _exptl_absorpt_correction_T_max .9885 _exptl_absorpt_correction_T_min .9697 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 624 _exptl_crystal_size_max .32 _exptl_crystal_size_mid .24 _exptl_crystal_size_min .12 _refine_diff_density_max .243 _refine_diff_density_min -.264 _refine_ls_extinction_coef .030(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 .943 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 1870 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all .943 _refine_ls_R_factor_all .0631 _refine_ls_R_factor_gt .0486 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0562P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .1071 _refine_ls_wR_factor_ref .1134 _reflns_number_gt 1441 _reflns_number_total 1870 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ln1127.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 'Orthorhombic' changed to 'orthorhombic' 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_database_code 2012439 _cod_database_fobs_code 2012439 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, 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 N1 .47535(8) .3756(3) .6221(3) .0304(5) Uani d . 1 . . N N2 .40811(8) .3651(3) .8404(4) .0303(5) Uani d . 1 . . N N3 .47249(7) .1258(3) .8451(4) .0313(5) Uani d . 1 . . N N4 .41215(7) .1310(3) .6020(3) .0245(5) Uani d . 1 . . N C1 .50360(9) .2521(4) .7393(5) .0338(6) Uani d . 1 . . C H1A .5233 .3280 .8198 .041 Uiso calc R 1 . . H H1B .5260 .1778 .6672 .041 Uiso calc R 1 . . H C2 .44119(11) .4846(3) .7354(4) .0343(6) Uani d . 1 . . C H2A .4602 .5629 .8160 .041 Uiso calc R 1 . . H H2B .4216 .5664 .6599 .041 Uiso calc R 1 . . H C3 .44570(10) .2580(4) .5021(4) .0299(6) Uani d . 1 . . C H3A .4675 .1837 .4277 .036 Uiso calc R 1 . . H H3B .4263 .3379 .4242 .036 Uiso calc R 1 . . H C4 .37993(8) .2472(4) .7168(4) .0294(6) Uani d . 1 . . C H4A .3595 .3265 .6417 .035 Uiso calc R 1 . . H H4B .3582 .1660 .7849 .035 Uiso calc R 1 . . H C5 .44293(10) .0138(3) .7209(4) .0300(6) Uani d . 1 . . C H5A .4218 -.0697 .7887 .036 Uiso calc R 1 . . H H5B .4647 -.0628 .6485 .036 Uiso calc R 1 . . H C6 .43873(10) .2436(4) .9518(4) .0332(7) Uani d . 1 . . C H6A .4176 .1633 1.0231 .040 Uiso calc R 1 . . H H6B .4579 .3204 1.0332 .040 Uiso calc R 1 . . H O2 .24422(11) -.7869(3) .4360(4) .0626(8) Uani d . 1 . . O O3 .32498(6) -.1490(3) .6078(3) .0324(5) Uani d . 1 . . O O1 .38307(7) -.0747(3) .3227(3) .0375(5) Uani d . 1 . . O C7 .35748(8) -.2367(3) .3297(4) .0269(6) Uani d . 1 . . C C8 .36169(9) -.3623(4) .1876(4) .0336(7) Uani d . 1 . . C H8 .3820 -.3339 .0911 .040 Uiso calc R 1 . . H C9 .33566(9) -.5292(4) .1902(4) .0331(6) Uani d . 1 . . C H9 .3394 -.6140 .0966 .040 Uiso calc R 1 . . H C10 .30433(8) -.5712(4) .3297(4) .0277(6) Uani d . 1 . . C C11 .29899(8) -.4437(4) .4721(4) .0247(5) Uani d . 1 . . C H11 .2774 -.4701 .5653 .030 Uiso calc R 1 . . H C12 .32581(8) -.2799(3) .4733(4) .0237(5) Uani d . 1 . . C C13 .27700(11) -.7489(4) .3307(5) .0372(7) Uani d . 1 . . C C14 .29172(11) -.1858(5) .7514(4) .0434(8) Uani d . 1 . . C H14A .2915 -.0812 .8321 .065 Uiso calc R 1 . . H H14B .3021 -.2964 .8141 .065 Uiso calc R 1 . . H H14C .2591 -.2046 .7046 .065 Uiso calc R 1 . . H H13 .2876(10) -.843(4) .230(4) .033(8) Uiso d . 1 . . H H1 .3848(16) -.004(6) .439(8) .092(15) 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 N1 .0330(11) .0260(12) .0321(12) -.0085(9) .0009(11) .0014(10) N2 .0335(11) .0262(11) .0311(12) .0049(9) .0017(11) -.0092(10) N3 .0310(11) .0280(12) .0349(13) .0033(9) -.0046(11) .0055(11) N4 .0268(10) .0200(10) .0265(12) -.0038(8) .0031(10) -.0026(9) C1 .0221(12) .0379(14) .0413(16) -.0022(11) -.0032(13) .0014(12) C2 .0471(16) .0173(12) .0385(16) -.0017(12) -.0063(13) -.0032(13) C3 .0391(15) .0281(14) .0225(13) -.0055(11) .0022(12) .0013(11) C4 .0243(12) .0301(13) .0339(15) .0032(11) -.0013(13) -.0058(11) C5 .0325(13) .0188(12) .0387(17) .0023(11) .0028(12) .0033(13) C6 .0397(15) .0363(16) .0236(14) -.0048(12) -.0014(12) -.0004(12) O2 .0854(18) .0466(13) .0557(16) -.0291(13) .0236(15) -.0217(13) O3 .0345(10) .0301(10) .0325(11) -.0067(8) .0142(9) -.0122(8) O1 .0379(10) .0424(11) .0321(12) -.0170(9) .0072(10) -.0108(10) C7 .0188(11) .0340(14) .0278(14) -.0027(10) -.0020(11) -.0072(12) C8 .0267(12) .0467(17) .0274(15) -.0059(12) .0047(12) -.0130(13) C9 .0279(13) .0402(15) .0311(15) .0010(12) -.0017(13) -.0148(13) C10 .0235(11) .0277(13) .0318(14) .0034(9) -.0054(12) -.0094(12) C11 .0197(11) .0268(13) .0277(14) .0024(9) -.0008(11) -.0040(11) C12 .0198(11) .0256(12) .0258(14) .0043(9) -.0018(10) -.0086(11) C13 .0428(16) .0333(15) .0356(17) -.0032(12) -.0021(15) -.0100(14) C14 .0520(18) .0375(16) .0406(18) -.0097(14) .0250(15) -.0179(14) 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 C1 N1 C3 108.0(2) C1 N1 C2 107.6(2) C3 N1 C2 107.9(2) C6 N2 C4 108.4(2) C6 N2 C2 107.6(2) C4 N2 C2 108.4(2) C5 N3 C1 107.9(2) C5 N3 C6 108.29(19) C1 N3 C6 107.4(2) C5 N4 C4 107.6(2) C5 N4 C3 107.54(19) C4 N4 C3 108.16(19) N1 C1 N3 113.13(18) N1 C1 H1A 109.0 N3 C1 H1A 109.0 N1 C1 H1B 109.0 N3 C1 H1B 109.0 H1A C1 H1B 107.8 N2 C2 N1 112.66(18) N2 C2 H2A 109.1 N1 C2 H2A 109.1 N2 C2 H2B 109.1 N1 C2 H2B 109.1 H2A C2 H2B 107.8 N1 C3 N4 112.1(2) N1 C3 H3A 109.2 N4 C3 H3A 109.2 N1 C3 H3B 109.2 N4 C3 H3B 109.2 H3A C3 H3B 107.9 N2 C4 N4 112.31(18) N2 C4 H4A 109.1 N4 C4 H4A 109.1 N2 C4 H4B 109.1 N4 C4 H4B 109.1 H4A C4 H4B 107.9 N3 C5 N4 112.44(18) N3 C5 H5A 109.1 N4 C5 H5A 109.1 N3 C5 H5B 109.1 N4 C5 H5B 109.1 H5A C5 H5B 107.8 N2 C6 N3 112.4(2) N2 C6 H6A 109.1 N3 C6 H6A 109.1 N2 C6 H6B 109.1 N3 C6 H6B 109.1 H6A C6 H6B 107.9 C12 O3 C14 115.9(2) C7 O1 H1 115(3) O1 C7 C8 118.6(3) O1 C7 C12 122.0(2) C8 C7 C12 119.4(2) C9 C8 C7 120.0(3) C9 C8 H8 120.0 C7 C8 H8 120.0 C10 C9 C8 120.8(3) C10 C9 H9 119.6 C8 C9 H9 119.6 C9 C10 C11 119.7(2) C9 C10 C13 120.2(3) C11 C10 C13 120.1(3) C12 C11 C10 119.9(2) C12 C11 H11 120.0 C10 C11 H11 120.0 O3 C12 C11 125.0(2) O3 C12 C7 114.8(2) C11 C12 C7 120.2(2) O2 C13 C10 124.3(3) O2 C13 H13 121.4(16) C10 C13 H13 114.3(16) O3 C14 H14A 109.5 O3 C14 H14B 109.5 H14A C14 H14B 109.5 O3 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 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 N1 C1 . 1.460(4) ? N1 C3 . 1.468(3) ? N1 C2 . 1.477(4) ? N2 C6 . 1.461(4) ? N2 C4 . 1.465(3) ? N2 C2 . 1.465(4) ? N3 C5 . 1.464(4) ? N3 C1 . 1.466(4) ? N3 C6 . 1.477(4) ? N4 C5 . 1.479(3) ? N4 C4 . 1.479(3) ? N4 C3 . 1.486(3) ? C1 H1A . .9700 ? C1 H1B . .9700 ? C2 H2A . .9700 ? C2 H2B . .9700 ? C3 H3A . .9700 ? C3 H3B . .9700 ? C4 H4A . .9700 ? C4 H4B . .9700 ? C5 H5A . .9700 ? C5 H5B . .9700 ? C6 H6A . .9700 ? C6 H6B . .9700 ? O1 C7 . 1.349(3) yes O2 C13 . 1.218(4) yes O3 C12 . 1.372(3) yes O3 C14 . 1.426(3) yes O1 H1 . 1.00(5) ? C7 C8 . 1.395(4) ? C7 C12 . 1.409(4) ? C8 C9 . 1.384(4) ? C8 H8 . .9300 ? C9 C10 . 1.379(4) ? C9 H9 . .9300 ? C10 C11 . 1.408(4) ? C10 C13 . 1.468(4) ? C11 C12 . 1.376(3) ? C11 H11 . .9300 ? C13 H13 . 1.05(3) ? C14 H14A . .9600 ? C14 H14B . .9600 ? C14 H14C . .9600 ? 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 O1 H1 O3 1_555 1.01(6) 2.30(5) 2.703(3) 102(3) yes O1 H1 N4 1_555 1.01(6) 1.72(5) 2.671(3) 156(4) yes C13 H13 O2 4_554 1.05(3) 2.40(3) 3.019(5) 117(2) yes C14 H14A O2 4_565 .96 2.44 3.309(4) 151 yes C3 H3B Cg 1_565 .96 3.26 4.147(3) 153 yes C14 H14C Cg 4_555 .96 2.97 3.713(3) 135 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 C3 N1 C1 N3 -58.4(3) C2 N1 C1 N3 57.9(3) C5 N3 C1 N1 58.3(3) C6 N3 C1 N1 -58.3(3) C6 N2 C2 N1 58.6(3) C4 N2 C2 N1 -58.5(3) C1 N1 C2 N2 -57.8(3) C3 N1 C2 N2 58.5(3) C1 N1 C3 N4 58.1(3) C2 N1 C3 N4 -58.0(3) C5 N4 C3 N1 -58.1(3) C4 N4 C3 N1 57.8(3) C6 N2 C4 N4 -58.6(3) C2 N2 C4 N4 57.9(3) C5 N4 C4 N2 58.3(3) C3 N4 C4 N2 -57.6(3) C1 N3 C5 N4 -58.1(3) C6 N3 C5 N4 57.9(3) C4 N4 C5 N3 -58.1(3) C3 N4 C5 N3 58.2(3) C4 N2 C6 N3 58.0(3) C2 N2 C6 N3 -59.0(3) C5 N3 C6 N2 -57.7(3) C1 N3 C6 N2 58.6(3) O1 C7 C8 C9 -179.6(3) C12 C7 C8 C9 -1.3(4) C7 C8 C9 C10 1.8(4) C8 C9 C10 C11 -.5(4) C8 C9 C10 C13 -179.9(3) C9 C10 C11 C12 -1.4(4) C13 C10 C11 C12 178.0(2) C14 O3 C12 C11 -3.0(4) C14 O3 C12 C7 177.6(2) C10 C11 C12 O3 -177.5(2) C10 C11 C12 C7 1.9(3) O1 C7 C12 O3 -2.9(3) C8 C7 C12 O3 178.8(2) O1 C7 C12 C11 177.6(2) C8 C7 C12 C11 -.6(4) C9 C10 C13 O2 -170.4(3) C11 C10 C13 O2 10.2(5)