#------------------------------------------------------------------------------ #$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/49/2104948.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_2104948 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 'C6 H12 N4, 2(C7 H5 N O4), 2(H2 O)' _chemical_formula_sum 'C20 H26 N6 O10' _chemical_formula_weight 510.47 _chemical_name_systematic ; bis(4-nitrobenzoic acid).(hexamethylenetetramine) dihydrate ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 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 98.9090(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.0807(4) _cell_length_b 7.4730(2) _cell_length_c 25.0633(7) _cell_measurement_reflns_used 6174 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.27 _cell_measurement_theta_min 3.22 _cell_volume 2235.39(11) _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.0287 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 16252 _diffrn_reflns_theta_full 28 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_min 1.64 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1072 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.325 _refine_diff_density_min -0.283 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2697 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.014 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0358 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0746P)^2^+0.5453P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1042 _refine_ls_wR_factor_ref 0.1097 _reflns_number_gt 2336 _reflns_number_total 2697 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file so5048.cif _[local]_cod_data_source_block 5 _[local]_cod_cif_authors_sg_H-M C2/c _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 2104948 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 0.63894(8) 0.20671(14) 0.24788(4) 0.0225(2) Uani d . 1 . . H H1A 0.678 0.1312 0.2242 0.027 Uiso calc R 1 . . H H1B 0.6958 0.2821 0.2701 0.027 Uiso calc R 1 . . C C2 0.52603(9) 0.20649(15) 0.31804(4) 0.0230(2) Uani d . 1 . . H H2A 0.5817 0.2819 0.341 0.028 Uiso calc R 1 . . H H2B 0.4882 0.1307 0.3422 0.028 Uiso calc R 1 . . C C3 0.5 -0.0203(2) 0.25 0.0240(3) Uani d S 1 . . H H3A 0.4623 -0.0982 0.2736 0.029 Uiso calc PR 0.5 . . H H3B 0.5377 -0.0982 0.2264 0.029 Uiso calc PR 0.5 . . C C4 0.5 0.4335(2) 0.25 0.0245(3) Uani d S 1 . . H H4A 0.4447 0.5114 0.2278 0.029 Uiso calc PR 0.5 . . H H4B 0.5553 0.5114 0.2722 0.029 Uiso calc PR 0.5 . . N N1 0.55785(7) 0.32295(12) 0.21416(3) 0.0220(2) Uani d . 1 . . N N2 0.58459(7) 0.09067(12) 0.28372(3) 0.0210(2) Uani d . 1 . . C C5 0.64857(7) 1.00770(13) 0.04469(4) 0.0180(2) Uani d . 1 . . C C6 0.63945(8) 0.94181(14) -0.00781(4) 0.0193(2) Uani d . 1 . . H H6 0.6483 0.8174 -0.0138 0.023 Uiso calc R 1 . . C C7 0.61751(8) 1.05742(14) -0.05131(4) 0.0211(2) Uani d . 1 . . H H7 0.6119 1.0144 -0.0873 0.025 Uiso calc R 1 . . C C8 0.60386(8) 1.23785(13) -0.04100(4) 0.0199(2) Uani d . 1 . . C C9 0.61289(8) 1.30719(13) 0.01042(4) 0.0209(2) Uani d . 1 . . H H9 0.6034 1.4316 0.0161 0.025 Uiso calc R 1 . . C C10 0.63624(8) 1.19054(13) 0.05374(4) 0.0202(2) Uani d . 1 . . H H10 0.6439 1.2351 0.0896 0.024 Uiso calc R 1 . . C C11 0.67147(8) 0.88629(13) 0.09262(4) 0.0198(2) Uani d . 1 . . N N3 0.57974(7) 1.36026(13) -0.08743(4) 0.0257(2) Uani d . 1 . . O O1 0.66848(7) 0.71520(10) 0.07904(3) 0.02437(19) Uani d . 1 . . H H1 0.6819(12) 0.6422(19) 0.1096(6) 0.037 Uiso d . 1 . . O O2 0.69003(8) 0.94056(11) 0.13859(3) 0.0322(2) Uani d . 1 . . O O3 0.56430(9) 1.29658(13) -0.13271(4) 0.0398(2) Uani d . 1 . . O O4 0.57552(8) 1.52114(11) -0.07795(4) 0.0362(2) Uani d . 1 . . O O1W 0.70875(6) 0.48453(11) 0.15381(3) 0.0251(2) Uani d D 1 . . H H1W 0.6606(10) 0.4486(19) 0.1720(5) 0.038 Uiso d D 1 . . H H2W 0.7722(8) 0.4976(18) 0.1734(5) 0.038 Uiso d 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 0.0186(5) 0.0286(5) 0.0204(5) 0.0000(4) 0.0030(4) -0.0008(4) C2 0.0239(5) 0.0300(6) 0.0148(5) 0.0021(4) 0.0022(4) -0.0005(4) C3 0.0267(7) 0.0191(7) 0.0256(8) 0 0.0018(6) 0 C4 0.0275(7) 0.0193(7) 0.0263(8) 0 0.0028(6) 0 N1 0.0227(4) 0.0246(4) 0.0188(4) -0.0028(3) 0.0030(3) 0.0025(3) N2 0.0207(4) 0.0231(4) 0.0185(4) 0.0024(3) 0.0012(3) 0.0012(3) C5 0.0132(4) 0.0211(5) 0.0200(5) -0.0008(3) 0.0037(3) 0.0000(4) C6 0.0162(4) 0.0195(5) 0.0223(5) -0.0005(3) 0.0035(4) -0.0023(4) C7 0.0176(4) 0.0257(5) 0.0202(5) -0.0016(4) 0.0033(4) -0.0019(4) C8 0.0139(4) 0.0231(5) 0.0227(5) -0.0007(4) 0.0027(4) 0.0046(4) C9 0.0171(4) 0.0182(5) 0.0279(5) -0.0011(3) 0.0049(4) -0.0005(4) C10 0.0182(4) 0.0220(5) 0.0208(5) -0.0020(4) 0.0046(4) -0.0028(4) C11 0.0171(4) 0.0221(5) 0.0208(5) -0.0002(4) 0.0050(4) -0.0003(4) N3 0.0207(4) 0.0296(5) 0.0270(5) 0.0008(4) 0.0046(4) 0.0082(4) O1 0.0323(4) 0.0197(4) 0.0210(4) 0.0010(3) 0.0034(3) 0.0020(3) O2 0.0472(5) 0.0293(4) 0.0192(4) 0.0016(4) 0.0025(3) -0.0016(3) O3 0.0509(6) 0.0445(5) 0.0227(4) 0.0026(4) 0.0012(4) 0.0065(4) O4 0.0426(5) 0.0265(4) 0.0405(5) 0.0049(4) 0.0093(4) 0.0105(4) O1W 0.0249(4) 0.0291(4) 0.0205(4) -0.0069(3) 0.0010(3) 0.0047(3) 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 0 1 0 0.18 0 -1 0 0.19 1 1 -1 0.18 -1 -1 1 0.18 0 0 -1 0.07 0 0 1 0.02 1 0 -1 0.15 -1 0 1 0.12 -2 2 1 0.15 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 . . 112.15(8) ? N2 C1 H1A . . 109.2 ? N1 C1 H1A . . 109.2 ? N2 C1 H1B . . 109.2 ? N1 C1 H1B . . 109.2 ? H1A C1 H1B . . 107.9 ? N2 C2 N1 . 2_655 112.16(8) ? N2 C2 H2A . . 109.2 ? N1 C2 H2A 2_655 . 109.2 ? N2 C2 H2B . . 109.2 ? N1 C2 H2B 2_655 . 109.2 ? H2A C2 H2B . . 107.9 ? N2 C3 N2 . 2_655 111.64(12) ? N2 C3 H3A . . 109.3 ? N2 C3 H3A 2_655 . 109.3 ? N2 C3 H3B . . 109.3 ? N2 C3 H3B 2_655 . 109.3 ? H3A C3 H3B . . 108 ? N1 C4 N1 . 2_655 111.82(12) ? N1 C4 H4A . . 109.3 ? N1 C4 H4A 2_655 . 109.3 ? N1 C4 H4B . . 109.3 ? N1 C4 H4B 2_655 . 109.3 ? H4A C4 H4B . . 107.9 ? C4 N1 C1 . . 108.47(7) ? C4 N1 C2 . 2_655 108.26(7) ? C1 N1 C2 . 2_655 107.75(8) ? C1 N2 C3 . . 108.41(7) ? C1 N2 C2 . . 108.01(8) ? C3 N2 C2 . . 108.13(7) ? C6 C5 C10 . . 120.29(9) ? C6 C5 C11 . . 121.44(9) ? C10 C5 C11 . . 118.28(9) ? C7 C6 C5 . . 120.05(9) ? C7 C6 H6 . . 120 ? C5 C6 H6 . . 120 ? C6 C7 C8 . . 118.27(10) ? C6 C7 H7 . . 120.9 ? C8 C7 H7 . . 120.9 ? C9 C8 C7 . . 123.04(10) ? C9 C8 N3 . . 118.86(9) ? C7 C8 N3 . . 118.09(9) ? C8 C9 C10 . . 118.23(9) ? C8 C9 H9 . . 120.9 ? C10 C9 H9 . . 120.9 ? C9 C10 C5 . . 120.11(10) ? C9 C10 H10 . . 119.9 ? C5 C10 H10 . . 119.9 ? O2 C11 O1 . . 124.28(10) ? O2 C11 C5 . . 123.06(9) ? O1 C11 C5 . . 112.66(9) ? O3 N3 O4 . . 123.91(10) ? O3 N3 C8 . . 118.45(9) ? O4 N3 C8 . . 117.64(9) ? C11 O1 H1 . . 111.1(9) ? H1W O1W H2W . . 111.3(13) ? 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 . 1.4739(13) ? C1 N1 . 1.4737(13) ? C1 H1A . 0.99 ? C1 H1B . 0.99 ? C2 N2 . 1.4758(13) ? C2 N1 2_655 1.4773(13) ? C2 H2A . 0.99 ? C2 H2B . 0.99 ? C3 N2 . 1.4760(12) ? C3 N2 2_655 1.4760(12) ? C3 H3A . 0.99 ? C3 H3B . 0.99 ? C4 N1 . 1.4738(12) ? C4 N1 2_655 1.4738(12) ? C4 H4A . 0.99 ? C4 H4B . 0.99 ? N1 C2 2_655 1.4773(13) ? C5 C6 . 1.3932(14) ? C5 C10 . 1.3968(14) ? C5 C11 . 1.4967(14) ? C6 C7 . 1.3842(15) ? C6 H6 . 0.95 ? C7 C8 . 1.3875(15) ? C7 H7 . 0.95 ? C8 C9 . 1.3778(15) ? C8 N3 . 1.4734(13) ? C9 C10 . 1.3868(15) ? C9 H9 . 0.95 ? C10 H10 . 0.95 ? C11 O2 . 1.2092(13) ? C11 O1 . 1.3222(13) ? N3 O3 . 1.2179(14) ? N3 O4 . 1.2281(13) ? O1 H1 . 0.933(15) ? O1W H1W . 0.838(8) ? O1W H2W . 0.849(9) ? 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 O1W . 0.933(15) 1.616(15) 2.5373(11) 168.0(10) O1W H1W N1 . 0.838(8) 1.986(9) 2.8148(11) 170.0(10) O1W H2W N2 4_655 0.849(9) 2.014(9) 2.8465(11) 166.0(10) C1 H1A O2 1_545 0.99 2.6 3.5162(13) 154 C2 H2B O2 2_645 0.99 2.69 3.5809(14) 151 C2 H2A O4 6_576 0.99 2.52 3.2883(14) 134 C9 H9 O1 1_565 0.95 2.69 3.5139(13) 146 C10 H10 O1W 1_565 0.95 2.51 3.3474(13) 147 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 2_655 . . . -58.38(6) ? N1 C4 N1 C2 2_655 . . 2_655 58.28(6) ? N2 C1 N1 C4 . . . . 58.50(10) ? N2 C1 N1 C2 . . . 2_655 -58.48(10) ? N1 C1 N2 C3 . . . . 58.74(11) ? N1 C1 N2 C2 . . . . -58.21(10) ? N2 C3 N2 C1 2_655 . . . -58.43(6) ? N2 C3 N2 C2 2_655 . . . 58.43(6) ? N1 C2 N2 C1 2_655 . . . 58.24(11) ? N1 C2 N2 C3 2_655 . . . -58.89(11) ? C10 C5 C6 C7 . . . . -0.33(14) ? C11 C5 C6 C7 . . . . 179.59(8) ? C5 C6 C7 C8 . . . . -0.73(14) ? C6 C7 C8 C9 . . . . 1.06(15) ? C6 C7 C8 N3 . . . . -179.59(8) ? C7 C8 C9 C10 . . . . -0.29(15) ? N3 C8 C9 C10 . . . . -179.64(8) ? C8 C9 C10 C5 . . . . -0.81(14) ? C6 C5 C10 C9 . . . . 1.12(14) ? C11 C5 C10 C9 . . . . -178.80(8) ? C6 C5 C11 O2 . . . . 173.01(10) ? C10 C5 C11 O2 . . . . -7.06(15) ? C6 C5 C11 O1 . . . . -7.34(13) ? C10 C5 C11 O1 . . . . 172.59(8) ? C9 C8 N3 O3 . . . . -175.05(10) ? C7 C8 N3 O3 . . . . 5.57(14) ? C9 C8 N3 O4 . . . . 4.34(13) ? C7 C8 N3 O4 . . . . -175.04(9) ?