#------------------------------------------------------------------------------ #$Date: 2017-10-13 07:09:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201973 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202199.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_2202199 loop_ _publ_author_name 'Dale, Sophie H.' 'Elsegood, Mark R. J.' _publ_section_title ; Trimesic acid bis(N,N-dimethylformamide) solvate at 150K ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o127 _journal_page_last o128 _journal_paper_doi 10.1107/S160053680300076X _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C15 H20 N2 O8' _chemical_formula_moiety 'C15 H20 N2 O8' _chemical_formula_sum 'C15 H20 N2 O8' _chemical_formula_weight 356.33 _chemical_name_systematic ; Trimesic acid bis(N,N-dimethylformamide) solvate ; _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 except OH coords freely refined' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'All non-H atoms found by direct methods' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.719(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 16.6529(18) _cell_length_b 14.4143(16) _cell_length_c 7.2310(8) _cell_measurement_reflns_used 1416 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 26.42 _cell_measurement_theta_min 2.45 _cell_volume 1735.6(3) _computing_cell_refinement 'SAINT (Siemens, 1994)' _computing_data_collection 'SMART (Siemens, 1994)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and local programs' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0740 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 8644 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.87 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2001)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 752 _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.234 _refine_diff_density_min -0.219 _refine_ls_extinction_coef 0.0005(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 1.025 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 240 _refine_ls_number_reflns 3064 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.025 _refine_ls_R_factor_all 0.1204 _refine_ls_R_factor_gt 0.0514 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0475P)^2^+0.6362P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1048 _refine_ls_wR_factor_ref 0.1338 _reflns_number_gt 1664 _reflns_number_total 3064 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6132.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2202199 _cod_database_fobs_code 2202199 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 C1 0.33564(17) 0.6428(2) -0.0696(4) 0.0220(7) Uani d . 1 . . C C2 0.27185(17) 0.6966(2) -0.0084(4) 0.0208(7) Uani d . 1 . . C H2 0.2242 0.6673 0.0326 0.025 Uiso calc R 1 . . H C3 0.27729(17) 0.7922(2) -0.0067(4) 0.0206(7) Uani d . 1 . . C C4 0.34667(17) 0.8353(2) -0.0695(4) 0.0234(7) Uani d . 1 . . C H4 0.3502 0.9010 -0.0704 0.028 Uiso calc R 1 . . H C5 0.41113(18) 0.7819(2) -0.1313(4) 0.0223(7) Uani d . 1 . . C C6 0.40506(17) 0.6859(2) -0.1303(4) 0.0220(7) Uani d . 1 . . C H6 0.4488 0.6493 -0.1715 0.026 Uiso calc R 1 . . H C7 0.33008(18) 0.5389(2) -0.0747(4) 0.0251(8) Uani d . 1 . . C O1 0.38163(13) 0.48977(15) -0.1405(3) 0.0345(6) Uani d . 1 . . O O2 0.26379(13) 0.50821(15) -0.0014(3) 0.0316(6) Uani d . 1 . . O H2A 0.260(2) 0.455(3) -0.019(5) 0.047 Uiso d . 1 . . H C8 0.21036(18) 0.8513(2) 0.0593(4) 0.0238(8) Uani d . 1 . . C O3 0.14420(13) 0.80494(16) 0.0989(3) 0.0328(6) Uani d . 1 . . O H3 0.105(2) 0.839(3) 0.135(5) 0.049 Uiso d . 1 . . H O4 0.21653(13) 0.93499(15) 0.0756(3) 0.0319(6) Uani d . 1 . . O C9 0.48552(19) 0.8249(2) -0.2024(4) 0.0270(8) Uani d . 1 . . C O5 0.48175(14) 0.91764(16) -0.2115(3) 0.0375(6) Uani d . 1 . . O H5 0.527(2) 0.936(3) -0.252(5) 0.056 Uiso d . 1 . . H O6 0.54328(13) 0.78065(16) -0.2484(3) 0.0418(7) Uani d . 1 . . O O7 0.23200(13) 0.33931(16) -0.0409(3) 0.0399(7) Uani d . 1 . . O C10 0.2856(2) 0.2795(2) -0.0544(5) 0.0332(9) Uani d . 1 . . C H10 0.3399 0.2995 -0.0583 0.040 Uiso calc R 1 . . H N1 0.27062(16) 0.18998(18) -0.0638(4) 0.0321(7) Uani d . 1 . . N C11 0.3350(2) 0.1219(2) -0.0824(5) 0.0428(10) Uani d . 1 . . C H11A 0.3861 0.1542 -0.0996 0.064 Uiso calc R 1 . . H H11B 0.3238 0.0822 -0.1897 0.064 Uiso calc R 1 . . H H11C 0.3382 0.0837 0.0295 0.064 Uiso calc R 1 . . H C12 0.1889(2) 0.1561(3) -0.0598(6) 0.0538(11) Uani d . 1 . . C H12A 0.1556 0.1995 0.0100 0.081 Uiso calc R 1 . . H H12B 0.1878 0.0951 -0.0002 0.081 Uiso calc R 1 . . H H12C 0.1678 0.1508 -0.1866 0.081 Uiso calc R 1 . . H O8 0.02931(13) 0.91508(17) 0.2006(3) 0.0419(7) Uani d . 1 . . O C13 0.0486(2) 0.9956(3) 0.2403(5) 0.0366(9) Uani d . 1 . . C H13 0.1039 1.0114 0.2333 0.044 Uiso calc R 1 . . H N2 -0.00169(16) 1.0615(2) 0.2917(4) 0.0336(7) Uani d . 1 . . N C14 -0.0872(2) 1.0426(3) 0.3040(6) 0.0569(12) Uani d . 1 . . C H14A -0.1149 1.0677 0.1947 0.085 Uiso calc R 1 . . H H14B -0.1084 1.0718 0.4156 0.085 Uiso calc R 1 . . H H14C -0.0958 0.9754 0.3100 0.085 Uiso calc R 1 . . H C15 0.0248(3) 1.1553(3) 0.3322(6) 0.0626(13) Uani d . 1 . . C H15A 0.0836 1.1580 0.3287 0.094 Uiso calc R 1 . . H H15B 0.0066 1.1732 0.4555 0.094 Uiso calc R 1 . . H H15C 0.0021 1.1979 0.2398 0.094 Uiso calc R 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 C1 0.0220(17) 0.0214(18) 0.0225(18) 0.0018(14) 0.0016(14) 0.0002(15) C2 0.0224(17) 0.0224(18) 0.0177(17) -0.0023(14) 0.0015(14) -0.0012(14) C3 0.0232(17) 0.0190(18) 0.0197(17) -0.0005(14) 0.0051(14) 0.0010(14) C4 0.0296(18) 0.0192(18) 0.0212(17) -0.0024(15) -0.0016(14) -0.0006(15) C5 0.0221(17) 0.0243(19) 0.0203(17) -0.0015(14) -0.0007(14) 0.0001(15) C6 0.0222(17) 0.0249(19) 0.0191(18) 0.0036(15) 0.0029(14) -0.0041(15) C7 0.0229(18) 0.0251(19) 0.0274(19) -0.0006(15) 0.0045(15) -0.0029(16) O1 0.0295(12) 0.0233(13) 0.0510(15) 0.0017(11) 0.0133(11) -0.0098(12) O2 0.0335(13) 0.0161(12) 0.0455(15) 0.0001(11) 0.0133(11) -0.0016(12) C8 0.0249(18) 0.023(2) 0.0235(19) -0.0002(16) -0.0004(14) 0.0003(16) O3 0.0258(13) 0.0240(13) 0.0490(16) 0.0010(11) 0.0150(12) -0.0027(12) O4 0.0333(13) 0.0178(14) 0.0448(15) 0.0011(11) 0.0041(11) 0.0000(11) C9 0.0252(18) 0.027(2) 0.029(2) -0.0030(16) 0.0042(15) -0.0014(17) O5 0.0307(14) 0.0258(14) 0.0562(17) -0.0071(12) 0.0125(12) 0.0020(13) O6 0.0300(14) 0.0351(15) 0.0608(17) -0.0037(12) 0.0180(13) -0.0018(13) O7 0.0386(14) 0.0196(13) 0.0619(18) -0.0030(12) 0.0142(12) -0.0018(13) C10 0.032(2) 0.026(2) 0.041(2) -0.0041(18) 0.0091(17) -0.0013(18) N1 0.0368(17) 0.0194(16) 0.0403(18) -0.0025(13) 0.0030(14) 0.0032(14) C11 0.054(3) 0.024(2) 0.050(2) 0.0022(18) 0.003(2) 0.0005(19) C12 0.045(2) 0.029(2) 0.087(3) -0.0134(19) 0.004(2) 0.002(2) O8 0.0334(14) 0.0361(16) 0.0565(17) 0.0044(12) 0.0088(12) -0.0096(14) C13 0.034(2) 0.035(2) 0.040(2) 0.0037(19) 0.0128(17) 0.0026(19) N2 0.0332(16) 0.0341(18) 0.0336(17) 0.0077(14) 0.0074(13) -0.0021(15) C14 0.033(2) 0.065(3) 0.072(3) 0.018(2) -0.011(2) -0.030(2) C15 0.069(3) 0.030(2) 0.090(3) 0.002(2) 0.037(3) -0.005(2) 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 C6 C1 C2 119.5(3) C6 C1 C7 119.3(3) C2 C1 C7 121.1(3) C3 C2 C1 120.6(3) C3 C2 H2 119.7 C1 C2 H2 119.7 C2 C3 C4 119.8(3) C2 C3 C8 121.7(3) C4 C3 C8 118.6(3) C3 C4 C5 120.2(3) C3 C4 H4 119.9 C5 C4 H4 119.9 C6 C5 C4 119.4(3) C6 C5 C9 118.6(3) C4 C5 C9 122.0(3) C1 C6 C5 120.6(3) C1 C6 H6 119.7 C5 C6 H6 119.7 O1 C7 O2 124.4(3) O1 C7 C1 123.2(3) O2 C7 C1 112.3(3) C7 O2 H2A 109(3) O4 C8 O3 123.3(3) O4 C8 C3 122.4(3) O3 C8 C3 114.3(3) C8 O3 H3 115(2) O6 C9 O5 123.5(3) O6 C9 C5 123.3(3) O5 C9 C5 113.2(3) C9 O5 H5 106(3) O7 C10 N1 123.2(3) O7 C10 H10 118.4 N1 C10 H10 118.4 C10 N1 C12 120.5(3) C10 N1 C11 121.7(3) C12 N1 C11 117.9(3) N1 C11 H11A 109.5 N1 C11 H11B 109.5 H11A C11 H11B 109.5 N1 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 N1 C12 H12A 109.5 N1 C12 H12B 109.5 H12A C12 H12B 109.5 N1 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 O8 C13 N2 125.1(3) O8 C13 H13 117.5 N2 C13 H13 117.5 C13 N2 C15 122.2(3) C13 N2 C14 120.5(3) C15 N2 C14 117.3(3) N2 C14 H14A 109.5 N2 C14 H14B 109.5 H14A C14 H14B 109.5 N2 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 N2 C15 H15A 109.5 N2 C15 H15B 109.5 H15A C15 H15B 109.5 N2 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 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 C1 C6 . 1.388(4) ? C1 C2 . 1.392(4) ? C1 C7 . 1.500(4) ? C2 C3 . 1.382(4) ? C2 H2 . 0.9500 ? C3 C4 . 1.393(4) ? C3 C8 . 1.486(4) ? C4 C5 . 1.398(4) ? C4 H4 . 0.9500 ? C5 C6 . 1.388(4) ? C5 C9 . 1.483(4) ? C6 H6 . 0.9500 ? C7 O1 . 1.215(4) ? C7 O2 . 1.308(4) ? O2 H2A . 0.79(4) ? C8 O4 . 1.217(4) ? C8 O3 . 1.323(4) ? O3 H3 . 0.85(4) ? C9 O6 . 1.204(4) ? C9 O5 . 1.340(4) ? O5 H5 . 0.86(4) ? O7 C10 . 1.245(4) ? C10 N1 . 1.316(4) ? C10 H10 . 0.9500 ? N1 C12 . 1.447(4) ? N1 C11 . 1.460(4) ? C11 H11A . 0.9800 ? C11 H11B . 0.9800 ? C11 H11C . 0.9800 ? C12 H12A . 0.9800 ? C12 H12B . 0.9800 ? C12 H12C . 0.9800 ? O8 C13 . 1.238(4) ? C13 N2 . 1.323(4) ? C13 H13 . 0.9500 ? N2 C15 . 1.451(5) ? N2 C14 . 1.453(4) ? C14 H14A . 0.9800 ? C14 H14B . 0.9800 ? C14 H14C . 0.9800 ? C15 H15A . 0.9800 ? C15 H15B . 0.9800 ? C15 H15C . 0.9800 ? 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 O2 H2A O7 . 0.79(4) 1.73(4) 2.507(3) 168(4) O3 H3 O8 . 0.85(4) 1.75(4) 2.599(3) 176(4) O5 H5 O1 2_654 0.86(4) 1.88(4) 2.732(3) 171(4) 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 C6 C1 C2 C3 -0.4(5) C7 C1 C2 C3 -179.1(3) C1 C2 C3 C4 1.0(5) C1 C2 C3 C8 -179.5(3) C2 C3 C4 C5 -1.0(5) C8 C3 C4 C5 179.5(3) C3 C4 C5 C6 0.4(4) C3 C4 C5 C9 178.9(3) C2 C1 C6 C5 -0.3(5) C7 C1 C6 C5 178.4(3) C4 C5 C6 C1 0.3(5) C9 C5 C6 C1 -178.3(3) C6 C1 C7 O1 -4.7(5) C2 C1 C7 O1 174.0(3) C6 C1 C7 O2 175.5(3) C2 C1 C7 O2 -5.8(4) C2 C3 C8 O4 174.0(3) C4 C3 C8 O4 -6.5(5) C2 C3 C8 O3 -5.8(4) C4 C3 C8 O3 173.6(3) C6 C5 C9 O6 -5.0(5) C4 C5 C9 O6 176.5(3) C6 C5 C9 O5 174.6(3) C4 C5 C9 O5 -4.0(4) O7 C10 N1 C12 0.5(5) O7 C10 N1 C11 179.1(3) O8 C13 N2 C15 -178.5(4) O8 C13 N2 C14 -0.5(6) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21131938