#------------------------------------------------------------------------------ #$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/49/2104949.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_2104949 loop_ _publ_author_name 'Lemmerer, Andreas' _publ_section_title ; Seven hexamethylenetetramine (HMTA) complexes with mono- and dicarboxylic acids: analysis of packing modes of HMTA complexes in the literature ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 177 _journal_page_last 192 _journal_volume 67 _journal_year 2011 _chemical_formula_moiety 'C8 H12 O4, C6 H12 N4' _chemical_formula_sum 'C14 H24 N4 O4' _chemical_formula_weight 312.37 _chemical_name_systematic ; (cis-cyclohexane-1,4-dicarboxylic acid).(hexamethylenetetramine) ; _space_group_IT_number 11 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yb' _symmetry_space_group_name_H-M 'P 1 21/m 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 108.0280(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.9169(4) _cell_length_b 21.6383(15) _cell_length_c 6.1135(4) _cell_measurement_reflns_used 4457 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.2 _cell_measurement_theta_min 3.5 _cell_volume 744.29(9) _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 7732 _diffrn_reflns_theta_full 28 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_min 1.88 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 336 _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.384 _refine_diff_density_min -0.192 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 1834 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.135 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0383 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0462P)^2^+0.2047P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0982 _refine_ls_wR_factor_ref 0.1007 _reflns_number_gt 1671 _reflns_number_total 1834 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file so5048.cif _[local]_cod_data_source_block 6 _[local]_cod_cif_authors_sg_H-M P2(1)/m _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 1555 2011-01-17 13:19:09Z saulius ; _cod_database_code 2104949 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' loop_ _atom_site_type_symbol _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 C C1 0.0028(2) 0.30493(5) 0.4874(2) 0.0255(2) Uani d . 1 . . H H1A 0.0134 0.3054 0.6522 0.031 Uiso calc R 1 . . H H1B -0.0849 0.3423 0.4147 0.031 Uiso calc R 1 . . C C2 -0.1383(3) 0.25 0.1349(3) 0.0301(4) Uani d S 1 . . H H2A -0.2268 0.213 0.0587 0.036 Uiso calc PR 0.5 . . H H2B -0.2268 0.287 0.0587 0.036 Uiso calc PR 0.5 . . C C3 0.2259(2) 0.30464(5) 0.2190(2) 0.0278(3) Uani d . 1 . . H H3A 0.1422 0.3422 0.1426 0.033 Uiso calc R 1 . . H H3B 0.3874 0.3048 0.2029 0.033 Uiso calc R 1 . . C C4 0.3699(3) 0.25 0.5758(3) 0.0285(3) Uani d S 1 . . H H4A 0.5332 0.25 0.5646 0.034 Uiso calc SR 1 . . H H4B 0.3818 0.25 0.7409 0.034 Uiso calc SR 1 . . N N1 0.24521(16) 0.30643(4) 0.46634(16) 0.0238(2) Uani d . 1 . . N N2 -0.1276(2) 0.25 0.3783(2) 0.0246(3) Uani d S 1 . . N N3 0.0980(3) 0.25 0.1048(2) 0.0264(3) Uani d S 1 . . C C5 0.76810(17) 0.47070(4) 0.88665(17) 0.0191(2) Uani d . 1 . . H H5 0.6764 0.5083 0.8158 0.023 Uiso calc R 1 . . C C6 0.97720(19) 0.46367(5) 0.79008(17) 0.0213(2) Uani d . 1 . . H H6A 1.0675 0.4257 0.8529 0.026 Uiso calc R 1 . . H H6B 0.9162 0.4596 0.6206 0.026 Uiso calc R 1 . . C C7 0.85884(18) 0.48038(5) 1.14611(18) 0.0211(2) Uani d . 1 . . H H7A 0.946 0.443 1.2204 0.025 Uiso calc R 1 . . H H7B 0.722 0.4863 1.2048 0.025 Uiso calc R 1 . . C C8 0.60253(19) 0.41565(5) 0.82252(19) 0.0225(2) Uani d . 1 . . O O1 0.50330(19) 0.40969(5) 0.59859(15) 0.0403(3) Uani d . 1 . . H H1 0.413(3) 0.3753(10) 0.565(3) 0.06 Uiso d . 1 . . O O2 0.56245(17) 0.38095(4) 0.96001(16) 0.0370(2) Uani d . 1 . . 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 C1 0.0293(5) 0.0191(5) 0.0317(6) 0.0011(4) 0.0148(5) -0.0038(4) C2 0.0244(8) 0.0298(8) 0.0272(8) 0 -0.0048(6) 0 C3 0.0362(6) 0.0247(5) 0.0261(5) -0.0056(4) 0.0148(5) 0.0028(4) C4 0.0200(7) 0.0373(9) 0.0238(7) 0 0.0001(6) 0 N1 0.0246(5) 0.0233(4) 0.0233(5) -0.0075(3) 0.0073(4) -0.0046(3) N2 0.0176(6) 0.0218(6) 0.0348(7) 0 0.0087(5) 0 N3 0.0361(7) 0.0246(6) 0.0177(6) 0 0.0075(5) 0 C5 0.0196(5) 0.0167(4) 0.0208(5) -0.0031(4) 0.0058(4) -0.0007(4) C6 0.0250(5) 0.0208(5) 0.0197(5) -0.0043(4) 0.0094(4) -0.0039(4) C7 0.0233(5) 0.0215(5) 0.0210(5) -0.0041(4) 0.0103(4) -0.0016(4) C8 0.0209(5) 0.0182(5) 0.0279(5) -0.0027(4) 0.0068(4) -0.0015(4) O1 0.0519(6) 0.0368(5) 0.0274(5) -0.0269(4) 0.0053(4) -0.0053(4) O2 0.0432(5) 0.0310(5) 0.0348(5) -0.0161(4) 0.0092(4) 0.0053(4) 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 2 -1 -1 0.34 -2 1 1 0.35 0 -1 0 0.25 0 1 0 0.17 0 0 1 0.08 0 0 -1 0.03 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 C1 N1 . . 111.55(9) ? N2 C1 H1A . . 109.3 ? N1 C1 H1A . . 109.3 ? N2 C1 H1B . . 109.3 ? N1 C1 H1B . . 109.3 ? H1A C1 H1B . . 108 ? N3 C2 N2 . . 112.51(12) ? N3 C2 H2A . . 109.1 ? N2 C2 H2A . . 109.1 ? N3 C2 H2B . . 109.1 ? N2 C2 H2B . . 109.1 ? H2A C2 H2B . . 107.8 ? N3 C3 N1 . . 111.96(9) ? N3 C3 H3A . . 109.2 ? N1 C3 H3A . . 109.2 ? N3 C3 H3B . . 109.2 ? N1 C3 H3B . . 109.2 ? H3A C3 H3B . . 107.9 ? N1 C4 N1 4_565 . 111.69(12) ? N1 C4 H4A 4_565 . 109.3 ? N1 C4 H4A . . 109.3 ? N1 C4 H4B 4_565 . 109.3 ? N1 C4 H4B . . 109.3 ? H4A C4 H4B . . 107.9 ? C4 N1 C1 . . 107.71(9) ? C4 N1 C3 . . 108.12(10) ? C1 N1 C3 . . 108.54(9) ? C1 N2 C1 . 4_565 108.87(12) ? C1 N2 C2 . . 108.28(8) ? C1 N2 C2 4_565 . 108.28(8) ? C3 N3 C3 . 4_565 108.18(13) ? C3 N3 C2 . . 108.29(8) ? C3 N3 C2 4_565 . 108.29(8) ? C8 C5 C7 . . 111.65(8) ? C8 C5 C6 . . 110.88(8) ? C7 C5 C6 . . 110.36(8) ? C8 C5 H5 . . 107.9 ? C7 C5 H5 . . 107.9 ? C6 C5 H5 . . 107.9 ? C7 C6 C5 3_767 . 110.35(8) ? C7 C6 H6A 3_767 . 109.6 ? C5 C6 H6A . . 109.6 ? C7 C6 H6B 3_767 . 109.6 ? C5 C6 H6B . . 109.6 ? H6A C6 H6B . . 108.1 ? C5 C7 C6 . 3_767 111.53(8) ? C5 C7 H7A . . 109.3 ? C6 C7 H7A 3_767 . 109.3 ? C5 C7 H7B . . 109.3 ? C6 C7 H7B 3_767 . 109.3 ? H7A C7 H7B . . 108 ? O2 C8 O1 . . 122.91(10) ? O2 C8 C5 . . 124.13(10) ? O1 C8 C5 . . 112.96(9) ? C8 O1 H1 . . 111.0(12) ? 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 C1 N2 . 1.4610(13) ? C1 N1 . 1.4794(14) ? C1 H1A . 0.99 ? C1 H1B . 0.99 ? C2 N3 . 1.466(2) ? C2 N2 . 1.470(2) ? C2 H2A . 0.99 ? C2 H2B . 0.99 ? C3 N3 . 1.4597(14) ? C3 N1 . 1.4816(14) ? C3 H3A . 0.99 ? C3 H3B . 0.99 ? C4 N1 4_565 1.4757(13) ? C4 N1 . 1.4757(13) ? C4 H4A . 0.99 ? C4 H4B . 0.99 ? N2 C1 4_565 1.4610(13) ? N3 C3 4_565 1.4597(14) ? C5 C8 . 1.5148(13) ? C5 C7 . 1.5235(14) ? C5 C6 . 1.5345(14) ? C5 H5 . 1 ? C6 C7 3_767 1.5247(14) ? C6 H6A . 0.99 ? C6 H6B . 0.99 ? C7 C6 3_767 1.5247(14) ? C7 H7A . 0.99 ? C7 H7B . 0.99 ? C8 O2 . 1.2041(14) ? C8 O1 . 1.3183(14) ? O1 H1 . 0.90(2) ? 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 O1 H1 N1 . 0.90(2) 1.79(2) 2.6859(12) 173(2) C1 H1A N3 1_556 0.99 2.91 3.8288(17) 154 C2 H2A O2 4_464 0.99 2.36 3.3368(13) 167 C4 H4A N2 1_655 0.99 2.6 3.539(2) 159 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N1 C4 N1 C1 4_565 . . . 59.21(15) ? N1 C4 N1 C3 4_565 . . . -57.90(15) ? N2 C1 N1 C4 . . . . -58.83(12) ? N2 C1 N1 C3 . . . . 58.00(12) ? N3 C3 N1 C4 . . . . 58.75(12) ? N3 C3 N1 C1 . . . . -57.82(12) ? N1 C1 N2 C1 . . . 4_565 59.23(15) ? N1 C1 N2 C2 . . . . -58.30(12) ? N3 C2 N2 C1 . . . . 58.95(8) ? N3 C2 N2 C1 . . . 4_565 -58.95(8) ? N1 C3 N3 C3 . . . 4_565 -59.43(15) ? N1 C3 N3 C2 . . . . 57.73(13) ? N2 C2 N3 C3 . . . . -58.54(8) ? N2 C2 N3 C3 . . . 4_565 58.54(8) ? C8 C5 C6 C7 . . . 3_767 179.47(8) ? C7 C5 C6 C7 . . . 3_767 -56.29(12) ? C8 C5 C7 C6 . . . 3_767 -179.24(9) ? C6 C5 C7 C6 . . . 3_767 56.97(12) ? C7 C5 C8 O2 . . . . -5.50(15) ? C6 C5 C8 O2 . . . . 118.01(12) ? C7 C5 C8 O1 . . . . 173.85(9) ? C6 C5 C8 O1 . . . . -62.65(12) ?