#------------------------------------------------------------------------------ #$Date: 2014-11-28 02:47:18 +0200 (Fri, 28 Nov 2014) $ #$Revision: 127953 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/89/7218924.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_7218924 loop_ _publ_author_name 'Venkatesan, Perumal' 'Thamotharan, Subbiah' 'Ganesh Kumar, Rajendran' 'Ilangovan, Andivelu' _publ_section_title ; Invariant and variable intermolecular interactions in functionalized malonic acid half-esters: X-ray, Hirshfeld surfaces and PIXEL energy analyses† ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C4CE02125H _journal_year 2014 _chemical_formula_sum 'C12 H13 N O4' _chemical_formula_weight 235.23 _chemical_name_systematic ; (2E)-2-(ethoxycarbonyl)-3-(phenylamino)prop-2-enoic acid ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2013 _audit_update_record ; 2014-11-18 deposited with the CCDC. 2014-11-25 downloaded from the CCDC. ; _cell_angle_alpha 84.212(9) _cell_angle_beta 75.935(9) _cell_angle_gamma 82.835(9) _cell_formula_units_Z 2 _cell_length_a 7.0418(13) _cell_length_b 7.5275(14) _cell_length_c 11.444(2) _cell_measurement_reflns_used 4539 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 31.67 _cell_measurement_theta_min 2.73 _cell_volume 582.26(19) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 296 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.875 _diffrn_measurement_device_type MoK\a _diffrn_measurement_method 'phi and omega scans' _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 0.0283 _diffrn_reflns_av_unetI/netI 0.0259 _diffrn_reflns_laue_measured_fraction_full 1.000 _diffrn_reflns_laue_measured_fraction_max 0.875 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 14267 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.875 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 33.583 _diffrn_reflns_theta_min 1.839 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_T_max 0.9859 _exptl_absorpt_correction_T_min 0.9780 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.342 _exptl_crystal_description prism _exptl_crystal_F_000 248 _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.249 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 4021 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0473 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0799P)^2^+0.0408P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1314 _refine_ls_wR_factor_ref 0.1492 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2736 _reflns_number_total 4021 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file c4ce02125h2.cif _[local]_cod_data_source_block MHE-1 _cod_original_cell_volume 582.28(19) _cod_database_code 7218924 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.978 _shelx_estimated_absorpt_t_max 0.986 _shelxl_version_number 2013-3 _shelx_res_file ; TITL 371 in P -1 /C12 H13 N O4/ CELL 0.71073 7.0418 7.5275 11.4443 84.212 75.935 82.835 ZERR 2.00 0.0013 0.0014 0.0020 0.009 0.009 0.009 LATT 1 SFAC C H N O UNIT 24 26 2 8 MERG 2 TEMP 23 SIZE 0.14 0.16 0.22 MORE 2 ACTA 50 L.S. 5 BOND $H FMAP 2 PLAN -20 HTAB 2 HTAB N1 O2 HTAB O1 O3 HTAB N1 O2_$1 htab c2 o2_$1 htab c12 c2_$2 htab c5 c12_$3 wpdb -1 EQIV $1 -x+1, -y+1, -z+1 eqiv $2 -1+x,y,z eqiv $3 -x-1,-y+1,-z+2 CONF MPLA 7 N1 C1 C2 C3 C4 C5 C6 MPLA 7 C7 C8 C9 O1 O2 O3 O4 WGHT 0.079900 0.040800 FVAR 1.00937 MOLE 1 O1 4 0.162148 0.771584 0.350144 11.00000 0.04779 0.07833 = 0.03802 0.01011 -0.00935 0.00291 H1O 2 0.040751 0.828089 0.373372 11.00000 0.09747 O2 4 0.352262 0.598919 0.451744 11.00000 0.04152 0.08531 = 0.04773 0.00852 -0.00626 0.00982 O3 4 -0.182549 0.880746 0.460938 11.00000 0.04856 0.06992 = 0.04281 0.01134 -0.01394 0.00877 O4 4 -0.288776 0.799544 0.657094 11.00000 0.04335 0.05559 = 0.03966 0.00305 -0.00974 0.00983 N1 3 0.210747 0.496723 0.687473 11.00000 0.04133 0.04665 = 0.03422 0.00336 -0.00979 0.00407 H1N 2 0.317373 0.489550 0.629914 11.00000 0.06269 C1 1 0.216557 0.400203 0.800016 11.00000 0.04655 0.04042 = 0.03366 -0.00080 -0.01049 0.00692 C2 1 0.392487 0.376163 0.836289 11.00000 0.04906 0.06253 = 0.04453 0.00341 -0.01522 0.00560 AFIX 43 H2 2 0.504783 0.420025 0.786792 11.00000 -1.20000 AFIX 0 C3 1 0.399296 0.285946 0.947253 11.00000 0.06979 0.07901 = 0.04859 0.00388 -0.02640 0.01145 AFIX 43 H3 2 0.516948 0.269870 0.972143 11.00000 -1.20000 AFIX 0 C4 1 0.234632 0.220100 1.020784 11.00000 0.08712 0.07009 = 0.03615 0.00598 -0.01434 0.01404 AFIX 43 H4 2 0.240405 0.160911 1.095396 11.00000 -1.20000 AFIX 0 C5 1 0.061136 0.242073 0.983600 11.00000 0.06952 0.06346 = 0.04349 0.00823 0.00182 0.00311 AFIX 43 H5 2 -0.050271 0.196762 1.033155 11.00000 -1.20000 AFIX 0 C6 1 0.050684 0.331376 0.872635 11.00000 0.05074 0.05511 = 0.04459 0.00343 -0.00862 0.00110 AFIX 43 H6 2 -0.066607 0.344766 0.847412 11.00000 -1.20000 AFIX 0 C7 1 0.053266 0.598131 0.666750 11.00000 0.04140 0.03955 = 0.03609 -0.00180 -0.01095 0.00135 AFIX 43 H7 2 -0.056083 0.606720 0.731405 11.00000 -1.20000 AFIX 0 C8 1 0.032991 0.692577 0.560024 11.00000 0.03893 0.04033 = 0.03648 0.00032 -0.01227 0.00079 C9 1 0.193075 0.683848 0.452230 11.00000 0.04041 0.05068 = 0.03865 0.00252 -0.01167 -0.00280 C10 1 -0.151997 0.798016 0.553945 11.00000 0.04150 0.04231 = 0.03880 0.00137 -0.01208 0.00116 C11 1 -0.478930 0.895779 0.649006 11.00000 0.04081 0.05941 = 0.04796 0.00591 -0.01120 0.00698 AFIX 23 H11A 2 -0.534511 0.840556 0.593686 11.00000 -1.20000 H11B 2 -0.463293 1.019718 0.619433 11.00000 -1.20000 AFIX 0 C12 1 -0.610911 0.887518 0.772132 11.00000 0.05366 0.06385 = 0.05112 0.00082 -0.00459 0.00998 AFIX 137 H12A 2 -0.619350 0.764376 0.802375 11.00000 -1.50000 H12B 2 -0.739704 0.943633 0.768563 11.00000 -1.50000 H12C 2 -0.558840 0.949213 0.824907 11.00000 -1.50000 AFIX 0 HKLF 4 REM 371 in P -1 /C12 H13 N O4/ REM R1 = 0.0473 for 2736 Fo > 4sig(Fo) and 0.0692 for all 4021 data REM 163 parameters refined using 0 restraints END WGHT 0.0799 0.0408 REM Instructions for potential hydrogen bonds HTAB O1 O3 HTAB N1 O2 HTAB N1 O2_$1 REM Highest difference peak 0.249, deepest hole -0.240, 1-sigma level 0.049 Q1 1 0.3925 0.3247 0.8963 11.00000 0.05 0.25 Q2 1 0.0508 0.6365 0.6059 11.00000 0.05 0.23 Q3 1 0.0750 0.2692 0.9197 11.00000 0.05 0.22 Q4 1 0.1361 0.3868 0.8401 11.00000 0.05 0.21 Q5 1 0.2907 0.3956 0.8340 11.00000 0.05 0.20 Q6 1 0.1062 0.6939 0.5130 11.00000 0.05 0.20 Q7 1 0.1974 0.4436 0.7429 11.00000 0.05 0.20 Q8 1 0.2986 0.2857 0.9835 11.00000 0.05 0.19 Q9 1 0.0483 0.3102 0.9369 11.00000 0.05 0.19 Q10 1 -0.0451 0.7506 0.5559 11.00000 0.05 0.19 Q11 1 -0.2203 0.8717 0.6802 11.00000 0.05 0.16 Q12 1 -0.5455 0.8975 0.7156 11.00000 0.05 0.14 Q13 1 0.1549 0.1937 1.0033 11.00000 0.05 0.14 Q14 1 0.0638 0.8401 0.6218 11.00000 0.05 0.14 Q15 1 -0.2362 0.8056 0.6122 11.00000 0.05 0.13 Q16 1 -0.1496 0.9067 0.5040 11.00000 0.05 0.13 Q17 1 -0.4475 0.9694 0.6963 11.00000 0.05 0.13 Q18 1 -0.5388 0.7524 0.5994 11.00000 0.05 0.13 Q19 1 0.0010 0.3131 0.8579 11.00000 0.05 0.13 Q20 1 0.2227 0.8041 0.5988 11.00000 0.05 0.12 ; _shelx_res_checksum 71974 loop_ _space_group_symop_operation_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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp O1 O 0.16215(14) 0.77158(14) 0.35014(7) 0.0567(2) Uani 1 1 d . . H1O H 0.041(3) 0.828(3) 0.373(2) 0.097(6) Uiso 1 1 d . . O2 O 0.35226(13) 0.59892(14) 0.45174(8) 0.0613(3) Uani 1 1 d . . O3 O -0.18255(12) 0.88075(13) 0.46094(7) 0.0556(2) Uani 1 1 d . . O4 O -0.28878(11) 0.79954(11) 0.65709(7) 0.0480(2) Uani 1 1 d . . N1 N 0.21075(14) 0.49672(12) 0.68747(8) 0.0418(2) Uani 1 1 d . . H1N H 0.317(2) 0.490(2) 0.6299(15) 0.063(4) Uiso 1 1 d . . C1 C 0.21656(16) 0.40020(14) 0.80002(9) 0.0411(2) Uani 1 1 d . . C2 C 0.39249(18) 0.37616(18) 0.83629(11) 0.0528(3) Uani 1 1 d . . H2 H 0.5048 0.4200 0.7868 0.063 Uiso 1 1 calc R U C3 C 0.3993(2) 0.2859(2) 0.94725(12) 0.0659(4) Uani 1 1 d . . H3 H 0.5169 0.2699 0.9721 0.079 Uiso 1 1 calc R U C4 C 0.2346(2) 0.2201(2) 1.02078(11) 0.0671(4) Uani 1 1 d . . H4 H 0.2404 0.1609 1.0954 0.081 Uiso 1 1 calc R U C5 C 0.0611(2) 0.24207(19) 0.98360(12) 0.0632(4) Uani 1 1 d . . H5 H -0.0503 0.1968 1.0332 0.076 Uiso 1 1 calc R U C6 C 0.05068(19) 0.33138(17) 0.87263(11) 0.0516(3) Uani 1 1 d . . H6 H -0.0666 0.3448 0.8474 0.062 Uiso 1 1 calc R U C7 C 0.05327(15) 0.59813(13) 0.66675(9) 0.0392(2) Uani 1 1 d . . H7 H -0.0561 0.6067 0.7314 0.047 Uiso 1 1 calc R U C8 C 0.03299(15) 0.69258(13) 0.56002(9) 0.0386(2) Uani 1 1 d . . C9 C 0.19307(16) 0.68385(15) 0.45223(10) 0.0434(2) Uani 1 1 d . . C10 C -0.15200(15) 0.79802(14) 0.55394(9) 0.0412(2) Uani 1 1 d . . C11 C -0.47893(16) 0.89578(18) 0.64901(11) 0.0510(3) Uani 1 1 d . . H11A H -0.5345 0.8406 0.5937 0.061 Uiso 1 1 calc R U H11B H -0.4633 1.0197 0.6194 0.061 Uiso 1 1 calc R U C12 C -0.6109(2) 0.88752(19) 0.77213(12) 0.0593(3) Uani 1 1 d . . H12A H -0.6194 0.7644 0.8024 0.089 Uiso 1 1 calc R U H12B H -0.7397 0.9436 0.7686 0.089 Uiso 1 1 calc R U H12C H -0.5588 0.9492 0.8249 0.089 Uiso 1 1 calc R U 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 O1 0.0478(5) 0.0783(6) 0.0380(4) 0.0101(4) -0.0093(3) 0.0029(4) O2 0.0415(4) 0.0853(7) 0.0477(5) 0.0085(4) -0.0063(3) 0.0098(4) O3 0.0486(4) 0.0699(6) 0.0428(4) 0.0113(4) -0.0139(3) 0.0088(4) O4 0.0434(4) 0.0556(5) 0.0397(4) 0.0031(3) -0.0097(3) 0.0098(3) N1 0.0413(5) 0.0467(5) 0.0342(4) 0.0034(3) -0.0098(3) 0.0041(4) C1 0.0466(5) 0.0404(5) 0.0337(5) -0.0008(4) -0.0105(4) 0.0069(4) C2 0.0491(6) 0.0625(7) 0.0445(6) 0.0034(5) -0.0152(5) 0.0056(5) C3 0.0698(9) 0.0790(9) 0.0486(7) 0.0039(6) -0.0264(6) 0.0114(7) C4 0.0871(10) 0.0701(9) 0.0362(6) 0.0060(5) -0.0143(6) 0.0140(7) C5 0.0695(8) 0.0635(8) 0.0435(6) 0.0082(5) 0.0018(6) 0.0031(6) C6 0.0507(6) 0.0551(7) 0.0446(6) 0.0034(5) -0.0086(5) 0.0011(5) C7 0.0414(5) 0.0396(5) 0.0361(5) -0.0018(4) -0.0110(4) 0.0014(4) C8 0.0389(5) 0.0403(5) 0.0365(5) 0.0003(4) -0.0123(4) 0.0008(4) C9 0.0404(5) 0.0507(6) 0.0386(5) 0.0025(4) -0.0117(4) -0.0028(4) C10 0.0415(5) 0.0423(5) 0.0388(5) 0.0014(4) -0.0121(4) 0.0012(4) C11 0.0408(6) 0.0594(7) 0.0480(6) 0.0059(5) -0.0112(4) 0.0070(5) C12 0.0537(7) 0.0639(8) 0.0511(7) 0.0008(6) -0.0046(5) 0.0100(6) 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 C9 O1 H1O 103.1(14) C10 O4 C11 115.10(8) C7 N1 C1 123.40(9) C7 N1 H1N 118.8(10) C1 N1 H1N 117.8(10) C6 C1 C2 120.27(10) C6 C1 N1 121.14(10) C2 C1 N1 118.59(10) C1 C2 C3 119.26(12) C1 C2 H2 120.4 C3 C2 H2 120.4 C4 C3 C2 120.84(13) C4 C3 H3 119.6 C2 C3 H3 119.6 C3 C4 C5 119.66(11) C3 C4 H4 120.2 C5 C4 H4 120.2 C4 C5 C6 120.60(13) C4 C5 H5 119.7 C6 C5 H5 119.7 C1 C6 C5 119.35(12) C1 C6 H6 120.3 C5 C6 H6 120.3 N1 C7 C8 127.30(9) N1 C7 H7 116.4 C8 C7 H7 116.4 C7 C8 C10 119.70(9) C7 C8 C9 120.81(9) C10 C8 C9 119.47(9) O2 C9 O1 119.20(10) O2 C9 C8 122.60(9) O1 C9 C8 118.20(9) O3 C10 O4 121.61(9) O3 C10 C8 123.20(10) O4 C10 C8 115.19(9) O4 C11 C12 107.73(9) O4 C11 H11A 110.2 C12 C11 H11A 110.2 O4 C11 H11B 110.2 C12 C11 H11B 110.2 H11A C11 H11B 108.5 C11 C12 H12A 109.5 C11 C12 H12B 109.5 H12A C12 H12B 109.5 C11 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C9 1.3344(13) O1 H1O 0.90(2) O2 C9 1.2183(14) O3 C10 1.2293(12) O4 C10 1.3299(14) O4 C11 1.4598(13) N1 C7 1.3224(13) N1 C1 1.4205(12) N1 H1N 0.870(17) C1 C6 1.3841(17) C1 C2 1.3852(16) C2 C3 1.3870(16) C2 H2 0.9300 C3 C4 1.372(2) C3 H3 0.9300 C4 C5 1.374(2) C4 H4 0.9300 C5 C6 1.3896(16) C5 H5 0.9300 C6 H6 0.9300 C7 C8 1.3791(13) C7 H7 0.9300 C8 C10 1.4514(14) C8 C9 1.4556(15) C11 C12 1.4877(17) C11 H11A 0.9700 C11 H11B 0.9700 C12 H12A 0.9600 C12 H12B 0.9600 C12 H12C 0.9600 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 N1 H1N O2 0.870(17) 2.089(16) 2.7072(13) 127.4(13) . O1 H1O O3 0.90(2) 1.67(2) 2.5281(13) 159(2) . N1 H1N O2 0.870(17) 2.326(17) 3.1340(14) 154.5(13) 2_666 C2 H2 O2 0.93 2.68 3.3483(16) 129.2 2_666 C12 H12A C2 0.96 2.90 3.843(2) 166.9 1_455 C5 H5 C12 0.93 2.93 3.838(2) 166.7 2_467 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 C7 N1 C1 C6 32.44(16) C7 N1 C1 C2 -147.45(11) C6 C1 C2 C3 -1.43(19) N1 C1 C2 C3 178.47(11) C1 C2 C3 C4 0.2(2) C2 C3 C4 C5 0.7(2) C3 C4 C5 C6 -0.4(2) C2 C1 C6 C5 1.66(19) N1 C1 C6 C5 -178.22(11) C4 C5 C6 C1 -0.7(2) C1 N1 C7 C8 -178.30(10) N1 C7 C8 C10 -179.82(10) N1 C7 C8 C9 1.94(17) C7 C8 C9 O2 -2.36(18) C10 C8 C9 O2 179.40(11) C7 C8 C9 O1 177.06(10) C10 C8 C9 O1 -1.18(16) C11 O4 C10 O3 3.87(17) C11 O4 C10 C8 -176.13(9) C7 C8 C10 O3 -177.59(10) C9 C8 C10 O3 0.68(18) C7 C8 C10 O4 2.41(16) C9 C8 C10 O4 -179.33(9) C10 O4 C11 C12 -178.63(10)