#------------------------------------------------------------------------------ #$Date: 2016-03-26 22:50:16 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180520 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/89/7218925.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_7218925 loop_ _publ_author_name 'Venkatesan, Perumal' 'Thamotharan, Subbiah' 'Kumar, Rajendran Ganesh' 'Ilangovan, Andivelu' _publ_section_title ; Invariant and variable intermolecular interactions in functionalized malonic acid half-esters: X-ray, Hirshfeld surface and PIXEL energy analyses ; _journal_issue 4 _journal_name_full CrystEngComm _journal_page_first 904 _journal_paper_doi 10.1039/C4CE02125H _journal_volume 17 _journal_year 2015 _chemical_formula_sum 'C13 H15 N O4' _chemical_formula_weight 249.26 _chemical_name_systematic ; (2E)-2-(ethoxycarbonyl)-3-[(4-methylphenyl)amino]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-2014 _audit_update_record ; 2014-11-18 deposited with the CCDC. 2014-11-25 downloaded from the CCDC. ; _cell_angle_alpha 93.415(2) _cell_angle_beta 104.473(2) _cell_angle_gamma 95.382(2) _cell_formula_units_Z 2 _cell_length_a 6.8768(2) _cell_length_b 7.5092(3) _cell_length_c 12.8653(4) _cell_measurement_reflns_used 2013 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 22.10 _cell_measurement_theta_min 2.73 _cell_volume 638.06(4) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.9000 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_unetI/netI 0.0257 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 9589 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 24.321 _diffrn_reflns_theta_min 1.641 _exptl_absorpt_coefficient_mu 0.097 _exptl_crystal_colour COLORLESS _exptl_crystal_density_diffrn 1.297 _exptl_crystal_description PRISM _exptl_crystal_F_000 264 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.151 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.032 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 2078 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.022 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0393 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.0895P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0961 _refine_ls_wR_factor_ref 0.1081 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1479 _reflns_number_total 2078 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c4ce02125h2.cif _cod_data_source_block MHE-2 _cod_depositor_comments 'Adding full bibliography for 7218923--7218927.cif.' _cod_database_code 7218925 #BEGIN Tags that were not found in dictionaries: _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. ; _shelxl_version_number 2014-3 _shelx_res_file ; TITL shelxl P-1 R = 0.04 CELL 0.71073 6.8768 7.5092 12.8653 93.415 104.473 95.382 ZERR 2 0.0002 0.0003 0.0004 0.002 0.002 0.002 LATT 1 SFAC C 2.31000 20.84392 1.02000 10.20751 1.58860 0.56870 0.86500 = 51.65125 0.21560 0.00330 0.00160 11.500 0.68000 12.01000 SFAC H 0.49300 10.51091 0.32291 26.12573 0.14019 3.14236 0.04081 = 57.79977 0.00304 0.00000 0.00000 0.624 0.35000 1.00800 SFAC N 12.21261 0.00570 3.13220 9.89331 2.01250 28.99754 1.16630 = 0.58260 -11.52901 0.00610 0.00330 19.600 0.68000 14.01000 SFAC O 3.04850 13.27711 2.28680 5.70111 1.54630 0.32390 0.86700 = 32.90894 0.25080 0.01060 0.00600 32.500 0.68000 16.00000 UNIT 26 30 2 8 TEMP 23 L.S. 5 FMAP 2 PLAN -20 ACTA BOND $H CONF WGHT 0.052000 0.089500 FVAR 0.93061 O1 4 0.030798 0.235040 0.364110 11.00000 0.05350 0.07571 = 0.05134 -0.00666 0.01001 -0.00731 AFIX 3 H1O 2 -0.079002 0.174040 0.384190 11.00000 -1.50000 AFIX 0 O2 4 0.310304 0.401015 0.455040 11.00000 0.05081 0.08155 = 0.06039 -0.00297 0.01833 -0.01340 O3 4 -0.221379 0.123008 0.466052 11.00000 0.04837 0.06950 = 0.05991 -0.00801 0.00641 -0.01628 O4 4 -0.159438 0.196934 0.643331 11.00000 0.04626 0.05519 = 0.05806 0.00307 0.01282 -0.01385 N1 3 0.370270 0.493139 0.668849 11.00000 0.04387 0.04986 = 0.04773 0.00071 0.01124 -0.00737 AFIX 3 H1N 2 0.426870 0.499939 0.612709 11.00000 -1.20000 AFIX 0 C1 1 0.474813 0.580144 0.771275 11.00000 0.04684 0.04463 = 0.04413 0.00408 0.00825 -0.00688 C2 1 0.683646 0.596745 0.800635 11.00000 0.04650 0.06486 = 0.05534 0.00096 0.01304 -0.00858 AFIX 43 H2 2 0.753890 0.553446 0.753187 11.00000 -1.20000 AFIX 0 C3 1 0.787150 0.677737 0.900517 11.00000 0.04901 0.07604 = 0.05912 0.00512 0.00396 -0.01303 AFIX 43 H3 2 0.927664 0.688627 0.919235 11.00000 -1.20000 AFIX 0 C4 1 0.689651 0.743244 0.973734 11.00000 0.06626 0.06263 = 0.04766 0.00627 0.00790 -0.01228 C5 1 0.480843 0.726490 0.941983 11.00000 0.06818 0.07590 = 0.05381 -0.00525 0.01977 -0.00665 AFIX 43 H5 2 0.410412 0.769743 0.989350 11.00000 -1.20000 AFIX 0 C6 1 0.374174 0.647385 0.841987 11.00000 0.04846 0.06837 = 0.05843 -0.00337 0.01258 -0.00482 AFIX 43 H6 2 0.233792 0.639540 0.822376 11.00000 -1.20000 AFIX 0 C7 1 0.192313 0.394582 0.649545 11.00000 0.04112 0.04155 = 0.05291 0.00645 0.01124 -0.00143 AFIX 43 H7 2 0.136747 0.383889 0.708082 11.00000 -1.20000 AFIX 0 C8 1 0.080401 0.306528 0.553567 11.00000 0.03978 0.03947 = 0.04825 0.00260 0.00767 0.00021 C9 1 0.149481 0.318151 0.456214 11.00000 0.04216 0.04831 = 0.05175 0.00026 0.00821 0.00158 C10 1 -0.111429 0.201743 0.549162 11.00000 0.04356 0.04321 = 0.05276 0.00309 0.00935 -0.00006 C11 1 -0.354924 0.097120 0.639119 11.00000 0.04244 0.05620 = 0.07400 0.00087 0.01763 -0.01102 AFIX 23 H11A 2 -0.362923 -0.023342 0.605458 11.00000 -1.20000 H11B 2 -0.463697 0.156803 0.597237 11.00000 -1.20000 AFIX 0 C12 1 -0.373173 0.089596 0.752136 11.00000 0.06806 0.07086 = 0.07992 0.01338 0.02547 -0.01494 AFIX 137 H12A 2 -0.269342 0.024552 0.791780 11.00000 -1.50000 H12B 2 -0.503323 0.030028 0.751435 11.00000 -1.50000 H12C 2 -0.358580 0.209375 0.785802 11.00000 -1.50000 AFIX 0 C13 1 0.806938 0.832735 1.082902 11.00000 0.09384 0.11181 = 0.05613 -0.00567 0.00103 -0.02001 AFIX 137 H13A 2 0.915054 0.764218 1.113426 11.00000 -1.50000 H13B 2 0.718337 0.838802 1.129725 11.00000 -1.50000 H13C 2 0.861759 0.951904 1.074744 11.00000 -1.50000 AFIX 0 HKLF 4 REM shelxl P-1 R = 0.04 REM R1 = 0.0393 for 1479 Fo > 4sig(Fo) and 0.0618 for all 2078 data REM 165 parameters refined using 0 restraints END WGHT 0.0522 0.0920 REM Highest difference peak 0.151, deepest hole -0.150, 1-sigma level 0.032 Q1 1 0.9796 0.8810 1.0728 11.00000 0.05 0.15 Q2 1 0.7455 0.6459 0.9599 11.00000 0.05 0.12 Q3 1 0.3637 0.8540 0.9625 11.00000 0.05 0.11 Q4 1 0.7971 0.7278 1.1364 11.00000 0.05 0.11 Q5 1 0.0023 0.2413 0.2822 11.00000 0.05 0.10 Q6 1 0.9627 0.6011 0.9329 11.00000 0.05 0.10 Q7 1 0.1850 0.2602 0.6002 11.00000 0.05 0.10 Q8 1 -0.4768 0.2447 0.6032 11.00000 0.05 0.10 Q9 1 0.7417 1.0280 1.1208 11.00000 0.05 0.09 Q10 1 0.2254 0.7619 0.7961 11.00000 0.05 0.09 Q11 1 0.7685 0.4648 0.7409 11.00000 0.05 0.09 Q12 1 -0.4376 0.0404 0.5478 11.00000 0.05 0.09 Q13 1 0.5587 0.5311 0.8033 11.00000 0.05 0.09 Q14 1 -0.0677 0.2446 0.7191 11.00000 0.05 0.09 Q15 1 -0.2838 0.1594 0.8315 11.00000 0.05 0.09 Q16 1 0.3317 0.3750 0.3606 11.00000 0.05 0.09 Q17 1 0.4732 0.3302 0.6668 11.00000 0.05 0.08 Q18 1 0.1184 0.2876 0.5198 11.00000 0.05 0.08 Q19 1 0.6800 0.9935 1.0612 11.00000 0.05 0.08 Q20 1 -0.0011 0.3219 0.2250 11.00000 0.05 0.08 ; _shelx_res_checksum 52863 #END Tags that were not found in dictionaries 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 0.03080(18) 0.23504(18) 0.36411(10) 0.0623(4) Uani 1 1 d . . H1O H -0.0790 0.1740 0.3842 0.093 Uiso 1 1 d R U O2 O 0.31030(19) 0.40102(19) 0.45504(10) 0.0653(4) Uani 1 1 d . . O3 O -0.22138(18) 0.12301(18) 0.46605(11) 0.0627(4) Uani 1 1 d . . O4 O -0.15944(17) 0.19693(16) 0.64333(10) 0.0546(4) Uani 1 1 d . . N1 N 0.3703(2) 0.49314(19) 0.66885(11) 0.0482(4) Uani 1 1 d . . H1N H 0.4269 0.4999 0.6127 0.058 Uiso 1 1 d R U C1 C 0.4748(3) 0.5801(2) 0.77127(14) 0.0466(5) Uani 1 1 d . . C2 C 0.6836(3) 0.5967(3) 0.80064(15) 0.0567(5) Uani 1 1 d . . H2 H 0.7539 0.5534 0.7532 0.068 Uiso 1 1 calc R U C3 C 0.7872(3) 0.6777(3) 0.90052(16) 0.0645(6) Uani 1 1 d . . H3 H 0.9277 0.6886 0.9192 0.077 Uiso 1 1 calc R U C4 C 0.6897(3) 0.7432(3) 0.97373(15) 0.0613(6) Uani 1 1 d . . C5 C 0.4808(3) 0.7265(3) 0.94198(16) 0.0666(6) Uani 1 1 d . . H5 H 0.4104 0.7697 0.9893 0.080 Uiso 1 1 calc R U C6 C 0.3742(3) 0.6474(3) 0.84199(16) 0.0597(5) Uani 1 1 d . . H6 H 0.2338 0.6395 0.8224 0.072 Uiso 1 1 calc R U C7 C 0.1923(2) 0.3946(2) 0.64955(14) 0.0456(5) Uani 1 1 d . . H7 H 0.1367 0.3839 0.7081 0.055 Uiso 1 1 calc R U C8 C 0.0804(2) 0.3065(2) 0.55357(14) 0.0435(4) Uani 1 1 d . . C9 C 0.1495(3) 0.3182(2) 0.45621(15) 0.0485(5) Uani 1 1 d . . C10 C -0.1114(3) 0.2017(2) 0.54916(15) 0.0474(5) Uani 1 1 d . . C11 C -0.3549(3) 0.0971(3) 0.63912(16) 0.0584(5) Uani 1 1 d . . H11A H -0.3629 -0.0233 0.6055 0.070 Uiso 1 1 calc R U H11B H -0.4637 0.1568 0.5972 0.070 Uiso 1 1 calc R U C12 C -0.3732(3) 0.0896(3) 0.75214(17) 0.0730(6) Uani 1 1 d . . H12A H -0.2693 0.0246 0.7918 0.109 Uiso 1 1 calc R U H12B H -0.5033 0.0300 0.7514 0.109 Uiso 1 1 calc R U H12C H -0.3586 0.2094 0.7858 0.109 Uiso 1 1 calc R U C13 C 0.8069(4) 0.8327(4) 1.08290(18) 0.0931(8) Uani 1 1 d . . H13A H 0.9151 0.7642 1.1134 0.140 Uiso 1 1 calc R U H13B H 0.7183 0.8388 1.1297 0.140 Uiso 1 1 calc R U H13C H 0.8618 0.9519 1.0747 0.140 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 0.0535(8) 0.0757(9) 0.0513(8) -0.0067(7) 0.0100(6) -0.0073(7) O2 0.0508(8) 0.0816(10) 0.0604(9) -0.0030(7) 0.0183(6) -0.0134(7) O3 0.0484(7) 0.0695(9) 0.0599(9) -0.0080(7) 0.0064(6) -0.0163(6) O4 0.0463(7) 0.0552(8) 0.0581(8) 0.0031(6) 0.0128(6) -0.0139(6) N1 0.0439(8) 0.0499(9) 0.0477(9) 0.0007(7) 0.0112(7) -0.0074(7) C1 0.0468(10) 0.0446(10) 0.0441(11) 0.0041(8) 0.0083(8) -0.0069(8) C2 0.0465(11) 0.0649(13) 0.0553(12) 0.0010(10) 0.0130(9) -0.0086(9) C3 0.0490(11) 0.0760(15) 0.0591(13) 0.0051(11) 0.0040(10) -0.0130(10) C4 0.0663(13) 0.0626(13) 0.0477(12) 0.0063(10) 0.0079(10) -0.0123(10) C5 0.0682(13) 0.0759(15) 0.0538(13) -0.0052(11) 0.0198(10) -0.0066(11) C6 0.0485(11) 0.0684(13) 0.0584(13) -0.0034(10) 0.0126(9) -0.0048(9) C7 0.0411(9) 0.0415(10) 0.0529(11) 0.0064(8) 0.0112(8) -0.0014(8) C8 0.0398(9) 0.0395(10) 0.0483(11) 0.0026(8) 0.0077(8) 0.0002(7) C9 0.0422(10) 0.0483(11) 0.0518(12) 0.0003(9) 0.0082(9) 0.0016(8) C10 0.0436(10) 0.0432(10) 0.0528(12) 0.0031(9) 0.0094(9) -0.0001(8) C11 0.0424(10) 0.0562(12) 0.0740(14) 0.0009(10) 0.0176(9) -0.0110(9) C12 0.0681(13) 0.0709(15) 0.0799(16) 0.0134(12) 0.0255(12) -0.0149(11) C13 0.0938(17) 0.112(2) 0.0561(14) -0.0057(14) 0.0010(13) -0.0200(15) 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 104.8 C10 O4 C11 115.28(14) C7 N1 C1 123.85(15) C7 N1 H1N 116.2 C1 N1 H1N 119.9 C6 C1 C2 119.21(17) C6 C1 N1 121.84(16) C2 C1 N1 118.95(16) C3 C2 C1 119.65(19) C3 C2 H2 120.2 C1 C2 H2 120.2 C2 C3 C4 122.27(19) C2 C3 H3 118.9 C4 C3 H3 118.9 C3 C4 C5 116.92(18) C3 C4 C13 121.3(2) C5 C4 C13 121.8(2) C6 C5 C4 121.8(2) C6 C5 H5 119.1 C4 C5 H5 119.1 C1 C6 C5 120.15(18) C1 C6 H6 119.9 C5 C6 H6 119.9 N1 C7 C8 127.84(17) N1 C7 H7 116.1 C8 C7 H7 116.1 C7 C8 C9 120.85(15) C7 C8 C10 119.59(16) C9 C8 C10 119.55(15) O2 C9 O1 119.01(17) O2 C9 C8 122.67(16) O1 C9 C8 118.31(15) O3 C10 O4 121.91(16) O3 C10 C8 123.24(17) O4 C10 C8 114.86(15) O4 C11 C12 107.78(15) O4 C11 H11A 110.2 C12 C11 H11A 110.1 O4 C11 H11B 110.1 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 C4 C13 H13A 109.5 C4 C13 H13B 109.5 H13A C13 H13B 109.5 C4 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C9 1.339(2) O1 H1O 0.9452 O2 C9 1.2210(19) O3 C10 1.225(2) O4 C10 1.335(2) O4 C11 1.4634(19) N1 C7 1.3279(19) N1 C1 1.420(2) N1 H1N 0.9039 C1 C6 1.374(3) C1 C2 1.382(2) C2 C3 1.377(3) C2 H2 0.9300 C3 C4 1.379(3) C3 H3 0.9300 C4 C5 1.383(3) C4 C13 1.515(3) C5 C6 1.379(3) C5 H5 0.9300 C6 H6 0.9300 C7 C8 1.373(2) C7 H7 0.9300 C8 C9 1.451(2) C8 C10 1.458(2) C11 C12 1.494(3) C11 H11A 0.9700 C11 H11B 0.9700 C12 H12A 0.9600 C12 H12B 0.9600 C12 H12C 0.9600 C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 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 -33.3(3) C7 N1 C1 C2 146.45(18) C6 C1 C2 C3 0.9(3) N1 C1 C2 C3 -178.77(17) C1 C2 C3 C4 0.3(3) C2 C3 C4 C5 -0.9(3) C2 C3 C4 C13 -179.7(2) C3 C4 C5 C6 0.3(3) C13 C4 C5 C6 179.0(2) C2 C1 C6 C5 -1.6(3) N1 C1 C6 C5 178.15(17) C4 C5 C6 C1 1.0(3) C1 N1 C7 C8 179.75(17) N1 C7 C8 C9 -1.8(3) N1 C7 C8 C10 178.91(16) C7 C8 C9 O2 2.1(3) C10 C8 C9 O2 -178.64(17) C7 C8 C9 O1 -177.58(16) C10 C8 C9 O1 1.7(3) C11 O4 C10 O3 -2.2(3) C11 O4 C10 C8 178.02(15) C7 C8 C10 O3 178.33(17) C9 C8 C10 O3 -1.0(3) C7 C8 C10 O4 -1.9(2) C9 C8 C10 O4 178.84(16) C10 O4 C11 C12 174.12(17)