#------------------------------------------------------------------------------ #$Date: 2011-01-03 14:48:23 +0200 (Mon, 03 Jan 2011) $ #$Revision: 5312 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/7203593.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7203593 loop_ _publ_author_name 'Haynes, Delia A.' 'Jones, William' 'Motherwell, W. D. Samuel' _publ_section_title ; Cocrystallisation of succinic and fumaric acids with lutidines: a systematic study ; _journal_issue 11 _journal_name_full CrystEngComm _journal_page_first 830 _journal_volume 8 _journal_year 2006 _chemical_formula_moiety 'C7 H10 N 1+,0.5(C4 H2 O4 2-),C4 H4 O4' _chemical_formula_sum 'C13 H15 N O6' _chemical_formula_weight 281.26 _chemical_name_common '3,4 lutidine fumarate' _chemical_name_systematic ; ? ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 102.305(2) _cell_angle_beta 104.584(2) _cell_angle_gamma 107.975(2) _cell_formula_units_Z 2 _cell_length_a 7.0478(2) _cell_length_b 10.0870(3) _cell_length_c 10.8570(3) _cell_measurement_reflns_used 3656 _cell_measurement_temperature 180(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 1.00 _cell_volume 674.12(4) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _diffrn_ambient_temperature 180(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6479 _diffrn_reflns_theta_full 27.45 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_min 3.53 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_correction_T_min 0.907 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.278 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 189 _refine_ls_number_reflns 3049 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0421 _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^)+(0.0302P)^2^+0.3119P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0944 _refine_ls_wR_factor_ref 0.1015 _reflns_number_gt 2565 _reflns_number_total 3049 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file b610294h.txt _[local]_cod_data_source_block wj0324 _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 ; _cod_original_cell_volume 674.12(3) _cod_database_code 7203593 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.20706(19) 0.20194(13) 0.40151(12) 0.0271(3) Uani 1 1 d . . . H11N H 0.1133 0.2009 0.4421 0.032 Uiso 1 1 calc R . . C11 C 0.1509(2) 0.09657(16) 0.28507(15) 0.0270(3) Uani 1 1 d . . . H11 H 0.0123 0.0220 0.2488 0.032 Uiso 1 1 calc R . . C12 C 0.2925(2) 0.09517(16) 0.21714(14) 0.0255(3) Uani 1 1 d . . . C13 C 0.4950(2) 0.20926(16) 0.27226(15) 0.0260(3) Uani 1 1 d . . . C14 C 0.5458(2) 0.31398(16) 0.39362(15) 0.0292(3) Uani 1 1 d . . . H14 H 0.6827 0.3906 0.4329 0.035 Uiso 1 1 calc R . . C15 C 0.4002(2) 0.30810(16) 0.45772(15) 0.0294(3) Uani 1 1 d . . . H15 H 0.4369 0.3793 0.5417 0.035 Uiso 1 1 calc R . . C16 C 0.2314(3) -0.02772(19) 0.09203(16) 0.0399(4) Uani 1 1 d . . . H16A H 0.0849 -0.0953 0.0702 0.060 Uiso 1 1 calc R . . H16B H 0.3265 -0.0806 0.1056 0.060 Uiso 1 1 calc R . . H16C H 0.2427 0.0120 0.0181 0.060 Uiso 1 1 calc R . . C17 C 0.6558(3) 0.2140(2) 0.20310(18) 0.0398(4) Uani 1 1 d . . . H17A H 0.7908 0.2951 0.2592 0.060 Uiso 1 1 calc R . . H17B H 0.6047 0.2291 0.1165 0.060 Uiso 1 1 calc R . . H17C H 0.6768 0.1211 0.1886 0.060 Uiso 1 1 calc R . . C21 C 0.7711(2) 0.08890(14) 0.47855(13) 0.0197(3) Uani 1 1 d . . . C22 C 0.5920(2) 0.05604(14) 0.53269(13) 0.0204(3) Uani 1 1 d . . . H22 H 0.6114 0.1184 0.6177 0.025 Uiso 1 1 calc R . . O21 O 0.92674(15) 0.21056(10) 0.53914(10) 0.0253(2) Uani 1 1 d . . . O22 O 0.76103(16) -0.00068(11) 0.37568(10) 0.0295(2) Uani 1 1 d . . . C31 C 0.0748(2) 0.53480(16) 0.19180(15) 0.0270(3) Uani 1 1 d . . . C32 C 0.0337(2) 0.47078(16) 0.04635(14) 0.0275(3) Uani 1 1 d . . . H32 H 0.0570 0.3831 0.0180 0.033 Uiso 1 1 calc R . . O31 O 0.01917(17) 0.64843(12) 0.21885(11) 0.0347(3) Uani 1 1 d D . . H31 H 0.049(3) 0.693(2) 0.3172(15) 0.042 Uiso 1 1 d D . . O32 O 0.15194(19) 0.48558(13) 0.27476(11) 0.0383(3) Uani 1 1 d . . . C41 C -0.3961(2) 0.68900(15) 0.13213(13) 0.0237(3) Uani 1 1 d . . . C42 C -0.4862(2) 0.52797(15) 0.06400(14) 0.0237(3) Uani 1 1 d . . . H42 H -0.5251 0.4634 0.1136 0.028 Uiso 1 1 calc R . . O41 O -0.41013(17) 0.72113(11) 0.25343(10) 0.0316(3) Uani 1 1 d D . . H41 H -0.348(3) 0.8259(16) 0.2969(17) 0.038 Uiso 1 1 d D . . O42 O -0.32139(18) 0.77960(11) 0.08213(11) 0.0345(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0292(6) 0.0320(7) 0.0308(7) 0.0137(5) 0.0181(5) 0.0168(5) C11 0.0235(7) 0.0294(7) 0.0302(8) 0.0121(6) 0.0102(6) 0.0103(6) C12 0.0290(7) 0.0286(7) 0.0238(7) 0.0117(6) 0.0115(6) 0.0132(6) C13 0.0264(7) 0.0332(8) 0.0300(7) 0.0187(6) 0.0151(6) 0.0164(6) C14 0.0270(7) 0.0270(7) 0.0341(8) 0.0133(6) 0.0103(6) 0.0087(6) C15 0.0362(8) 0.0255(7) 0.0293(8) 0.0093(6) 0.0124(6) 0.0140(6) C16 0.0490(10) 0.0409(9) 0.0291(8) 0.0069(7) 0.0152(7) 0.0177(8) C17 0.0340(8) 0.0592(11) 0.0430(10) 0.0276(8) 0.0250(7) 0.0228(8) C21 0.0207(6) 0.0196(6) 0.0192(6) 0.0052(5) 0.0073(5) 0.0085(5) C22 0.0234(6) 0.0206(6) 0.0189(6) 0.0046(5) 0.0097(5) 0.0096(5) O21 0.0213(5) 0.0237(5) 0.0240(5) -0.0009(4) 0.0101(4) 0.0035(4) O22 0.0318(5) 0.0238(5) 0.0275(5) -0.0020(4) 0.0172(4) 0.0048(4) C31 0.0186(6) 0.0274(7) 0.0257(7) -0.0004(6) 0.0072(5) 0.0027(5) C32 0.0203(7) 0.0264(7) 0.0272(7) -0.0032(6) 0.0086(5) 0.0051(5) O31 0.0365(6) 0.0396(6) 0.0221(5) -0.0033(5) 0.0070(4) 0.0180(5) O32 0.0429(7) 0.0384(6) 0.0299(6) 0.0085(5) 0.0101(5) 0.0141(5) C41 0.0210(6) 0.0244(7) 0.0213(7) 0.0024(5) 0.0050(5) 0.0081(5) C42 0.0210(6) 0.0227(7) 0.0247(7) 0.0039(5) 0.0072(5) 0.0078(5) O41 0.0403(6) 0.0216(5) 0.0258(5) -0.0013(4) 0.0165(5) 0.0043(4) O42 0.0469(7) 0.0256(5) 0.0265(6) 0.0073(4) 0.0128(5) 0.0086(5) 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' O O 0.0106 0.0060 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 N11 C11 122.09(12) . . ? C15 N11 H11N 119.0 . . ? C11 N11 H11N 119.0 . . ? N11 C11 C12 120.84(13) . . ? N11 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C13 118.03(13) . . ? C11 C12 C16 119.99(13) . . ? C13 C12 C16 121.94(13) . . ? C14 C13 C12 118.75(12) . . ? C14 C13 C17 120.63(14) . . ? C12 C13 C17 120.58(14) . . ? C15 C14 C13 120.59(13) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? N11 C15 C14 119.64(14) . . ? N11 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O22 C21 O21 122.49(12) . . ? O22 C21 C22 120.04(11) . . ? O21 C21 C22 117.45(11) . . ? C22 C22 C21 122.92(15) 2_656 . ? C22 C22 H22 118.5 2_656 . ? C21 C22 H22 118.5 . . ? O32 C31 O31 124.71(13) . . ? O32 C31 C32 122.09(14) . . ? O31 C31 C32 113.20(13) . . ? C32 C32 C31 123.80(17) 2_565 . ? C32 C32 H32 118.1 2_565 . ? C31 C32 H32 118.1 . . ? C31 O31 H31 113.1(11) . . ? O42 C41 O41 124.28(13) . . ? O42 C41 C42 124.08(13) . . ? O41 C41 C42 111.63(12) . . ? C42 C42 C41 121.69(17) 2_465 . ? C42 C42 H42 119.2 2_465 . ? C41 C42 H42 119.2 . . ? C41 O41 H41 110.5(11) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C15 1.3325(19) . ? N11 C11 1.3418(19) . ? N11 H11N 0.8800 . ? C11 C12 1.3837(19) . ? C11 H11 0.9500 . ? C12 C13 1.408(2) . ? C12 C16 1.492(2) . ? C13 C14 1.384(2) . ? C13 C17 1.5036(19) . ? C14 C15 1.371(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C21 O22 1.2488(16) . ? C21 O21 1.2665(16) . ? C21 C22 1.4990(17) . ? C22 C22 1.324(3) 2_656 ? C22 H22 0.9500 . ? C31 O32 1.2099(19) . ? C31 O31 1.3213(19) . ? C31 C32 1.4880(19) . ? C32 C32 1.331(3) 2_565 ? C32 H32 0.9500 . ? O31 H31 1.005(14) . ? C41 O42 1.2105(17) . ? C41 O41 1.3240(16) . ? C41 C42 1.4844(19) . ? C42 C42 1.323(3) 2_465 ? C42 H42 0.9500 . ? O41 H41 0.964(14) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11N O21 0.88 1.89 2.7715(14) 175.9 1_455 O31 H31 O21 1.005(14) 1.591(15) 2.5769(14) 166.0(18) 2_666 O41 H41 O22 0.964(14) 1.607(14) 2.5706(14) 177.3(18) 1_465 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N11 C11 C12 -0.8(2) . . . . ? N11 C11 C12 C13 -1.4(2) . . . . ? N11 C11 C12 C16 176.43(14) . . . . ? C11 C12 C13 C14 2.4(2) . . . . ? C16 C12 C13 C14 -175.45(14) . . . . ? C11 C12 C13 C17 -179.90(14) . . . . ? C16 C12 C13 C17 2.3(2) . . . . ? C12 C13 C14 C15 -1.1(2) . . . . ? C17 C13 C14 C15 -178.90(14) . . . . ? C11 N11 C15 C14 2.1(2) . . . . ? C13 C14 C15 N11 -1.1(2) . . . . ? O22 C21 C22 C22 -9.0(3) . . . 2_656 ? O21 C21 C22 C22 169.48(17) . . . 2_656 ? O32 C31 C32 C32 -174.04(17) . . . 2_565 ? O31 C31 C32 C32 5.9(2) . . . 2_565 ? O42 C41 C42 C42 -8.1(3) . . . 2_465 ? O41 C41 C42 C42 171.07(16) . . . 2_465 ?