#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:53:41 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/39/2103906.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_2103906 loop_ _publ_author_name 'Pinheiro, Carlos Bas\'ilio' 'Gardon, Manuel' 'Chapuis, Gervais' _publ_section_title ; Structural changes of hexamethylenetetramine and undecanedioic acid co-crystal (HMT-C11) as a function of the temperature ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 416 _journal_page_last 427 _journal_paper_doi 10.1107/S0108768103007754 _journal_volume 59 _journal_year 2003 _chemical_formula_sum 'C17 H32 N4 O4' _chemical_formula_weight 356.47 _chemical_name_systematic ; ? ; _space_group_IT_number 63 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-B 2b 2' _symmetry_space_group_name_H-M 'B m m b' _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 9.3593(19) _cell_length_b 29.257(6) _cell_length_c 7.2982(15) _cell_measurement_reflns_used 3000 _cell_measurement_temperature 323(2) _cell_measurement_theta_max 25 _cell_measurement_theta_min 3.54 _cell_volume 1998.4(7) _computing_cell_refinement 'kM4 - Oxford Diffraction' _computing_data_collection 'kM4 - Oxford Diffraction' _computing_data_reduction Xprep _computing_molecular_graphics XP _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 323(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Oxford CCD' _diffrn_measurement_method oscillation _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 0.1360 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 10013 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 3.54 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_crystal_colour transparent _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_description platelets _exptl_crystal_F_000 776 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.5 _refine_diff_density_max 0.144 _refine_diff_density_min -0.129 _refine_ls_extinction_coef 0.0029(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.193 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 107 _refine_ls_number_reflns 958 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.193 _refine_ls_R_factor_all 0.0857 _refine_ls_R_factor_gt 0.0727 _refine_ls_shift/su_max 0.043 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1351P)^2^+0.2969P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2296 _refine_ls_wR_factor_ref 0.2438 _reflns_number_gt 741 _reflns_number_total 958 _reflns_threshold_expression >2sigma(I) _cod_data_source_file na0146.cif _cod_data_source_block 324K _cod_original_sg_symbol_H-M Bmmb _cod_database_code 2103906 _cod_database_fobs_code 2103906 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y+1/2, z' 'x, -y, -z' 'x+1/2, y, z+1/2' '-x+1/2, y+1/2, -z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z' 'x, y-1/2, -z' '-x, y, z' '-x+1/2, -y, -z+1/2' 'x+1/2, -y-1/2, z+1/2' 'x+1/2, y-1/2, -z+1/2' '-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_type_symbol C1 0.5000 0.371596(11) 0.80134(5) 0.09573(10) Uani d S 1 C C2 0.42607(4) 0.404443(15) 0.93067(6) 0.09901(14) Uani d P 0.50 C H2A 0.3878 0.4299 0.8608 0.119 Uiso calc PR 0.50 H H2B 0.3466 0.3889 0.9892 0.119 Uiso calc PR 0.50 H C3 0.52513(5) 0.422557(11) 1.07573(5) 0.09726(14) Uani d P 0.50 C H3A 0.5988 0.4410 1.0185 0.117 Uiso calc PR 0.50 H H3B 0.5713 0.3972 1.1374 0.117 Uiso calc PR 0.50 H C4 0.44503(5) 0.451433(16) 1.21617(6) 0.11112(18) Uani d P 0.50 C H4A 0.3931 0.4752 1.1515 0.133 Uiso calc PR 0.50 H H4B 0.3752 0.4322 1.2769 0.133 Uiso calc PR 0.50 H C5 0.53681(4) 0.473711(14) 1.36043(6) 0.10317(19) Uani d P 0.50 C H5B 0.5919 0.4503 1.4225 0.124 Uiso calc PR 0.50 H H5A 0.6037 0.4943 1.3010 0.124 Uiso calc PR 0.50 H C6 0.45305(7) 0.5000 1.5000 0.1168(3) Uani d SP 0.50 C H6A 0.3916 0.5213 1.4355 0.140 Uiso calc PR 0.25 H H6B 0.3916 0.4787 1.5645 0.140 Uiso calc PR 0.25 H O2A 0.60501(6) 0.35606(3) 0.79683(10) 0.1952(3) Uani d P 0.33320(10) O O2B 0.55348(8) 0.34038(3) 0.87000(10) 0.1106(3) Uani d P 0.16720(10) O O1 0.41227(4) 0.363430(13) 0.65917(5) 0.13111(13) Uani d P 0.50 O H1 0.4484 0.3442 0.5917 0.197 Uiso calc PR 0.50 H N1 0.5000 0.291349(7) 0.44775(3) 0.07734(7) Uani d S 1 N N2 0.36998(2) 0.2500 0.21342(3) 0.08721(8) Uani d S 1 N CC 0.37194(2) 0.289798(8) 0.32924(3) 0.09373(7) Uani d . 1 C HCA 0.2871 0.2899 0.4055 0.112 Uiso calc R 1 H HCB 0.3695 0.3170 0.2533 0.112 Uiso calc R 1 H CD 0.5000 0.2500 0.10196(5) 0.09886(16) Uani d S 1 C HDB 0.5000 0.2768 0.0237 0.119 Uiso calc SPR 0.50 H HDA 0.5000 0.2232 0.0237 0.119 Uiso calc SPR 0.50 H CE 0.5000 0.2500 0.56189(4) 0.07275(11) Uani d S 1 C HEA 0.4161 0.2500 0.6400 0.087 Uiso calc SPR 0.50 H HEB 0.5839 0.2500 0.6400 0.087 Uiso calc SPR 0.50 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 C1 0.1044(2) 0.08211(16) 0.10072(18) 0.000 0.000 -0.01110(16) C2 0.1071(3) 0.0808(2) 0.1091(3) 0.02006(19) -0.0095(2) -0.0186(2) C3 0.0912(3) 0.0892(2) 0.1114(2) -0.0004(2) -0.0037(2) -0.01360(19) C4 0.1125(4) 0.0992(3) 0.1216(3) 0.00641(19) -0.0017(3) -0.0313(2) C5 0.1032(5) 0.0908(2) 0.1155(2) 0.00305(19) -0.0017(2) -0.0155(2) C6 0.1155(7) 0.1128(4) 0.1220(4) 0.000 0.000 -0.0441(3) O2A 0.1135(3) 0.3100(6) 0.1620(4) 0.1112(3) -0.0175(3) -0.0893(4) O2B 0.1308(6) 0.1083(4) 0.0928(4) 0.0791(3) -0.0061(4) -0.0233(4) O1 0.1395(2) 0.1295(2) 0.1243(2) 0.03303(18) -0.0331(2) -0.0308(2) N1 0.07649(12) 0.08541(13) 0.07013(11) 0.000 0.000 -0.00442(11) N2 0.05588(11) 0.14328(18) 0.06247(10) 0.000 -0.00861(9) 0.000 CC 0.06907(10) 0.12585(14) 0.08627(11) 0.02730(10) -0.00174(9) 0.01482(11) CD 0.0822(2) 0.1614(4) 0.05297(17) 0.000 0.000 0.000 CE 0.06181(17) 0.1045(2) 0.05197(15) 0.000 0.000 0.000 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle O2A C1 O2A 12_655 . 130.24(9) O2A C1 O2B 12_655 12_655 44.66(5) O2A C1 O2B . 12_655 94.27(6) O2A C1 O2B 12_655 . 94.27(6) O2A C1 O2B . . 44.66(5) O2B C1 O2B 12_655 . 51.33(7) O2A C1 O1 12_655 . 49.31(4) O2A C1 O1 . . 117.13(5) O2B C1 O1 12_655 . 85.97(4) O2B C1 O1 . . 117.30(5) O2A C1 O1 12_655 12_655 117.13(5) O2A C1 O1 . 12_655 49.31(4) O2B C1 O1 12_655 12_655 117.30(5) O2B C1 O1 . 12_655 85.97(4) O1 C1 O1 . 12_655 75.28(4) O2A C1 C2 12_655 12_655 134.41(5) O2A C1 C2 . 12_655 82.57(5) O2B C1 C2 12_655 12_655 115.41(5) O2B C1 C2 . 12_655 91.91(5) O1 C1 C2 . 12_655 150.78(3) O1 C1 C2 12_655 12_655 108.34(3) O2A C1 C2 12_655 . 82.57(5) O2A C1 C2 . . 134.41(5) O2B C1 C2 12_655 . 91.91(5) O2B C1 C2 . . 115.41(5) O1 C1 C2 . . 108.34(3) O1 C1 C2 12_655 . 150.78(3) C2 C1 C2 12_655 . 54.38(4) C3 C2 C1 . . 112.38(3) C2 C3 C4 . . 111.43(4) C5 C4 C3 . . 115.40(4) C6 C5 C4 . . 113.51(4) C5 C6 C5 4_568 . 116.89(5) O2B O2A O1 . 12_655 128.90(9) O2B O2A C1 . . 72.17(7) O1 O2A C1 12_655 . 78.54(5) O2B O2A O2B . 12_655 30.19(6) O1 O2A O2B 12_655 12_655 103.39(5) C1 O2A O2B . 12_655 44.58(4) O2B O2A C2 . 12_655 89.52(8) O1 O2A C2 12_655 12_655 110.28(6) C1 O2A C2 . 12_655 59.41(4) O2B O2A C2 12_655 12_655 83.91(4) O2A O2B O2B . 12_655 124.42(6) O2A O2B C1 . . 63.17(7) O2B O2B C1 12_655 . 64.34(4) O2A O2B O2A . 12_655 99.03(9) O2B O2B O2A 12_655 12_655 25.39(4) C1 O2B O2A . 12_655 41.15(4) O2A O2B O1 . 12_655 28.25(5) O2B O2B O1 12_655 12_655 100.80(3) C1 O2B O1 . 12_655 51.65(4) O2A O2B O1 12_655 12_655 76.50(4) CE N1 CC . . 107.846(16) CE N1 CC . 12_655 107.842(16) CC N1 CC . 12_655 108.29(3) CC N2 CC 10_565 . 108.03(3) CC N2 CD 10_565 . 108.413(15) CC N2 CD . . 108.412(15) N2 CC N1 . . 112.256(19) N2 CD N2 . 3_655 112.48(3) N1 CE N1 . 10_565 110.90(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance C1 O2A 12_655 1.0834(6) C1 O2A . 1.0834(6) C1 O2B 12_655 1.1557(8) C1 O2B . 1.1557(8) C1 O1 . 1.3446(5) C1 O1 12_655 1.3446(5) C1 C2 12_655 1.5143(6) C1 C2 . 1.5143(6) C2 C3 . 1.5037(6) C3 C4 . 1.5252(6) C4 C5 . 1.5070(7) C5 C6 . 1.4978(6) C6 C5 4_568 1.4978(6) O2A O2B . 0.8533(10) O2A O1 12_655 1.0402(8) O2A O2B 12_655 1.6418(10) O2A C2 12_655 1.7443(9) O2B O2B 12_655 1.0010(14) O2B O2A 12_655 1.6418(10) O2B O1 12_655 1.7102(9) N1 CE . 1.4688(4) N1 CC . 1.4788(3) N1 CC 12_655 1.4788(3) N2 CC 10_565 1.4388(3) N2 CC . 1.4389(3) N2 CD . 1.4638(4) CD N2 3_655 1.4638(4) CE N1 10_565 1.4688(4) 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 . 0.82 1.93 2.7390(6) 168.1 CC HCA O2A 5_454 0.97 2.70 3.1710(8) 110.5 CC HCA O2B 5_454 0.97 2.65 3.3410(9) 128.3 CD HDB O2B 1_554 0.97 2.23 3.1794(9) 166.1 C2 H2B O1 16 0.97 2.82 3.7747(8) 167.2 CC HCA N2 7 0.97 2.93 3.7873(6) 148.3 CE HEB N2 5 0.97 2.73 3.6350(7) 155.3 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 C3 C2 C1 O1 . . . . -169.36(3) C3 C2 C1 O2A . . . . 6.38(8) C3 C2 C1 O2B . . . . 56.81(5) C1 C2 C3 C4 . . . . -173.88(3) C2 C3 C4 C5 . . . . -176.14(4) C3 C4 C5 C6 . . . . -177.46(3) C4 C5 C6 C5 . . . 4_568 -175.26(4) C5 C6 C5 C4 . . 4_568 4_568 -175.26(4) C6 C5 C4 C3 . 4_568 4_568 4_568 -177.46(3) C5 C4 C3 C2 4_568 4_568 4_568 4_568 -176.14(4) C4 C3 C2 C1 4_568 4_568 4_568 4_568 -173.88(3)